Episodes

9h ago

Why do most investors fail at the exact moments when staying invested matters most—and how can options help fix that? In this episode, I talk with Hamilton Reiner, Managing Director at J.P. Morgan Asset Management and CIO of the U.S. Core Equity Team, about how options can be used not for speculation, but to create discipline, manage risk, and help investors stay invested through market volatility. Hamilton shares lessons from more than three decades managing equities and derivatives, explains why volatility is misunderstood, and breaks down how hedged strategies, rebalancing, and risk-based portfolio construction can dramatically improve long-term outcomes—without requiring heroic market timing. Highlights: Why options are about precision, not leverage Hedging vs. income: the two primary institutional use cases for options How downside buffers help investors stay invested during drawdowns Why volatility is a feature of equities, not a flaw The biggest behavioral mistakes investors make in up and down markets Why missing the best days destroys long-term returns How rebalancing quietly outperforms market timing The role of options inside a modern 60/40 portfolio Why risk tolerance—not asset allocation—should come first Lessons from 2008, 2020, and decades of market cycles The underrated power of compounding and staying in the game Guest Bio: Hamilton Reiner, managing director, is CIO of the U.S. Core Equity Team, Head of U.S. Equity Derivatives for J.P. Morgan Equity Asset Management, and a portfolio manager. He has been managing U.S. equities and U.S. equity derivatives for over 30 years, at firms such as Barclays Capital, Lehman Brothers, and Deutsche Bank. He started his career at the options investing firm O’Connor and Associates, where he developed his passion for derivatives investing. Hamilton obtained a B.S.E. in Finance from the Wharton School of the University of Pennsylvania. Our Podcast now receives more than 300,000 downloads a month. Are you interested in Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Hamilton Reiner: LinkedIn: https://www.linkedin.com/in/hamilton-reiner-7033594b/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (0:32) Understanding Options: Strategies and Historical Use (4:20) Managing Stock Gains and Behavioral Biases in Investing (8:16) The Importance of Risk Tolerance and Market Timing (18:27) Decision-Making Challenges in Institutional Investment (22:17) Market Uncertainty and the Role of the VIX (24:14) Volatility, Investment Sizing, and Portfolio Integration (30:18) Market Cycles, Behavioral Biases, and Career Advice (38:23) Key Investment Lessons and the Power of Compounding (43:09) Closing remarks

1d ago

Why do the most successful investors and founders still miss their best opportunities—and how much of that comes down to poor relationship management? In this episode, I talk with Patrick Ewers, founder of Mindmaven, about why relationships—not intelligence or effort—are the true limiting factor in professional success. Patrick shares lessons from being an early employee at LinkedIn under Reid Hoffman, coaching partners at top firms like Sequoia and Andreessen Horowitz, and building a systemized approach to relationship management that scales. We break down why important things lose to urgent ones, how delegation and leverage unlock effectiveness, and why small, consistent actions compound into billion-dollar outcomes. Highlights: Why relationships are the highest-leverage asset in investing and leadership The “importance vs. urgency” trap that causes missed opportunities How poor follow-up—not bad judgment—creates most investing regrets Practical delegation systems that free up 10–12 hours per week Why dictating follow-ups is more thoughtful than typing them Inbox shadowing and decision triage for leaders How to make people feel valued without fake niceness Why efficiency enables deeper, more authentic relationships The role of thinking time (“white space”) in elite performance Why relationship management is the CEO’s final job Guest Bio: Patrick Ewers is the founder of Mindmaven, an executive coaching firm focused on helping leaders unlock their full potential through relationship management. He was one of the earliest employees at LinkedIn, working closely under Reid Hoffman, and later became one of Silicon Valley’s most sought-after relationship coaches. Over the past 15 years, Patrick has coached hundreds of founders, executives, and investors, including leaders from firms such as Sequoia Capital, Andreessen Horowitz, Benchmark, and First Round Capital, as well as companies like Reddit, Roblox, and Thumbtack. He is the author of Radical Delegation and has been recognized by Forbes as one of Silicon Valley’s top relationship management experts. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Patrick Ewers: LinkedIn: https://www.linkedin.com/in/patrick/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (1:00) Early career and importance of relationships in business (2:40) Challenges and consequences of neglecting relationships (6:50) Best practices for managing and delegating relationships (10:48) Techniques for efficient business communication (18:25) Balancing transactional and thoughtful relationships (24:29) Strategies for effective meetings and scheduling (27:08) Principles and tools for effective delegation (35:59) Psychological aspects and predictability in email management (41:07) Democratizing executive-level efficiency and avoiding micromanagement (44:26) Leveraging recruiting for sustainable advantages (47:32) Role of relationship management in founding a company (49:09) Best practices for unstructured thinking and managing time (54:19) Overcoming work ambiguity and optimizing thinking environments (55:47) How to collaborate with industry experts (57:36) Closing remarks

2d ago

How do the best venture investors consistently spot unicorn founders before the rest of the market even knows they exist? In this episode, I talk with Jamie Lee, Co-Founder and Managing Partner of Tamarack Global, about sourcing asymmetric deal flow in deep tech and why founder referrals are the single strongest signal of future breakout companies. Jamie explains how Tamarack applies hedge-fund-level diligence at the seed stage, why intuition and pattern recognition matter as much as data, and how concentrated conviction—combined with relentless research—drives their unusually high unicorn hit rate. We also explore humanoid robotics, labor automation, and why the next industrial revolution is already underway. Highlights: Why founder referrals outperform every other sourcing channel Venture beta vs. true asymmetric alpha Applying hedge fund diligence to pre-seed and seed investing Why most early-stage investors under-diligence founders The power of intuition and “gut scores” in decision-making Lessons Jamie learned from Philippe Laffont at Coatue Why long-term time horizons matter more than near-term metrics The humanoid robotics market and the $40T global labor opportunity Playing offense by preempting rounds in breakout companies Why conviction beats caution early in an investing career Guest Bio: Jamie Lee is the Co-Founder and Managing Partner of Tamarack Global, an early-stage deep-tech venture capital firm investing across defense, aerospace, robotics, advanced manufacturing, AI, and the energy transition. He began his career in derivatives at Goldman Sachs, advised technology companies in special situations at JPMorgan, and later managed a $1.5 billion long/short equity portfolio at Coatue Management. Jamie holds a B.A. in Economics from Williams College and an MBA from Columbia Business School, where he also completed the school’s Deep Value Investing program. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Jamie Lee: LinkedIn: https://www.linkedin.com/in/jamie-lee-77430382/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (0:11) Jamie Lee's sourcing strategy and founder referrals (4:19) Winning competitive investment rounds and the role of due diligence (10:07) Insights from SpaceX and the humanoid robot space (15:34) Learnings from venture funds and lessons from Philippe Lafont (24:19) The interplay of gut instinct and social psychology in investing (30:12) The importance of diligence and pattern matching in manager selection (33:04) Advice for younger investors and predicting high-value outcomes (37:50) Confidence in investment picks and closing remarks (38:05) Closing remarks

3d ago

How do you scale a growth equity firm from a $52M first fund to $5B across six funds—without losing discipline or trust? In this episode, I talk with Brian Neider, Managing Partner at Lead Edge Capital, about building a durable growth equity platform by combining rigorous metrics with deep relationship-building. Brian shares how Lead Edge created a differentiated LP model centered on high-net-worth individuals who actively support portfolio companies, why communication and education compound trust over decades, and how a strict investment framework helps avoid negative alpha as the firm scales. We also discuss why exits matter more than paper gains, how to think about “walking dead” portfolio companies, and what truly energizes long-term investing. Highlights: Why Lead Edge raised its first fund from individuals, not institutions How 700+ LPs became a competitive advantage, not a liability The importance of disciplined metrics before falling in love with founders How structured LP engagement improves deal sourcing and outcomes Why communication, education, and transparency compound trust The danger of “negative alpha” and unstructured decision-making How pattern recognition scales exponentially—but portfolio work does not Why exit planning should start on day one The hardest part of growth equity: managing the “walking dead” What motivates Brian most after more than a decade of investing Guest Bio: Brian Neider is a Managing Partner at Lead Edge Capital, where he helps oversee the firm’s investment strategy, portfolio management, and operations. He is a member of the firm’s Investment, Disposition, and Management Committees and has led or co-led investments in companies including Toast, Asana, Duo Security, Lucid, Amplitude, and Workhuman. Prior to joining Lead Edge in 2012, Brian invested at Bessemer Venture Partners and FTV Capital, focusing on mid-market growth opportunities across software, internet, and business services. He holds a B.S. in Economics from the Wharton School and an MBA from Columbia Business School and is based in New York. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Brian Neider: LinkedIn: https://www.linkedin.com/in/brian-neider-7774041/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (1:20) The first fund, early advice, and challenges with institutional investors (5:33) Building and managing relationships with investors (12:06) The role of LP dinners, NextGen events, and full-time engagement teams (17:01) Key metrics and strategies for investment selection (21:32) Competitive market strategies and the value of LP introductions (25:35) Utilizing introductions, advice, and understanding growth factors (32:40) Addressing challenges with portfolio companies and LP feedback (38:14) People-centric opportunity filtering and advice for early-stage LeadEdge (42:37) Comprehensive framework and strategies around exits (45:16) Closing remarks

4d ago

How do you build portfolios that survive liquidity crises, inflation shocks, and the most volatile market regimes in modern history? In this episode, I talk with Alfred Lee, Deputy Chief Investment Officer at Q Wealth Partners and one of Canada’s most experienced multi-asset portfolio architects. Alfred previously managed over $75 billion across equities, fixed income, commodities, factor strategies, and thematic ETFs at BMO—while also spending a year at the Bank of Canada running part of its quantitative easing program during the pandemic. He shares what he learned from overseeing $25B in fixed income and $50B in equities, how ETFs transformed the public markets, why alpha is harder to generate than ever, and why alternatives, real assets, CTAs, and discretionary macro strategies must anchor the next generation of portfolios. Highlights: Lessons from overseeing $75B across fixed income, equities & commodities What Alfred learned managing QE operations at the Bank of Canada Why generating alpha in public markets is harder than at any point in history How Q Wealth Partners serves as Canada’s version of a modern RIA aggregator Building model portfolios using open architecture while staying within regulatory guardrails The “debasement regime”: why inflation will appear in bursts for years Why CPI understates real-world cost of living and what that means for investors How to allocate to Bitcoin, gold, and real assets through one-ticket solutions 60/40 is outdated: Alfred’s 50/30/20 framework for the next decade Behavioral finance as the biggest driver of investor outcomes Why illiquidity is a feature, not a bug—and the “virtue of staying invested” How to evaluate private credit, private equity, and alternative strategies Why liquidity collapses cause correlations to spike across asset classes How to run “portfolio war games”: preparing for the next crisis The single greatest lesson Alfred learned from 2008 and 2020: never assume liquidity Guest Bio: Alfred Lee is the Deputy Chief Investment Officer at Q Wealth Partners, where he oversees portfolio construction, asset allocation, and investment platform design for one of Canada’s fastest-growing wealth platforms. Before joining Q Wealth, Alfred spent over a decade at BMO, where he helped grow its ETF franchise to $100 billion in assets and managed more than $75 billion across fixed income, equities, commodities, and factor strategies. He previously completed a one-year secondment at the Bank of Canada, where he ran part of the central bank’s quantitative easing program during the pandemic, helping restore liquidity and functionality to the provincial bond and funding markets. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startupsuccess #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Alfred Lee: LinkedIn: https://www.linkedin.com/in/alfred-lee-cfa-cmt-dms-b329025/ Q Wealth Partners: https://www.qwealth.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (0:39) Influence of mentors in Alfred's career & building an asset management firm (2:23) Launching a gold bullion fund & overview of Q Wealth Partners (4:38) Portfolio allocation strategies and views on alternatives (8:49) Inflation, purchasing power, and philosophy on Bitcoin and gold (11:55) Behavioral finance and modernizing the 60/40 portfolio (18:19) Mapping portfolio construction with privates and diversification (23:26) Addressing the J-curve effect and interval funds usage (27:44) Handling unique investment opportunities and avoiding deworsification (32:13) Adding investments and the importance of uncorrelated returns (39:05) Timeless advice and managing liquidity during crises (41:51) War games and crisis preparation for asset managers (44:14) Closing remarks

Dec 12

What does it take to build a sovereign wealth fund from scratch—and still outperform in some of the hardest markets in decades? In this episode, I talk with Peter Madsen, Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), one of the most quietly sophisticated sovereign wealth funds in the United States. Peter shares how he went from running hedge fund portfolios in London to becoming the first investment hire tasked with modernizing Utah’s endowment. We break down SITFO’s philosophy on mean reversion, factor-based investing, public vs. private markets, active vs. passive strategy, and how a small CIO team competes with far larger institutions. Peter also explains why small caps are broken, how he shifted capital into private equity, why micro-VC funds outperform mega-funds, and how SITFO uses AI and collaborative models to underwrite managers in a world of overwhelming information. Highlights: Why Peter left London to build a sovereign wealth fund with permanent capital The decline of fund-of-funds—and how it shaped his CIO philosophy Why mean reversion still matters, even when markets feel one-sided Active vs. passive: why benchmarks themselves are an “active decision” Why small caps are structurally different today—and no longer reliably outperform The “equal-weighted portfolio” origin story and how SITFO built asset allocation from scratch Why SITFO shifted capital from small caps into private equity How micro-VC funds outperform large venture funds mathematically Why SITFO partners with seed funds, super angels, and Fund I/Fund II managers The collaborative LP model: revenue-sharing, co-invest structures, and research leverage How SITFO built a zero-and-zero co-invest platform to recapture fee drag Using AI to screen manager decks, extract underwriting criteria, and systematize memo writing Why sovereign wealth fund investing differs from pensions and endowments Managing cashflows from land revenues while protecting K–12 distributions Why Sharpe ratio optimization is misleading for long-horizon investors Factor modeling, Venn by Two Sigma, and designing purpose-driven portfolios Guest Bio: Peter Madsen is the Director and Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), where he has led the state’s sovereign wealth fund since 2015. He previously served as a Managing Director at Cube Capital in London and as a Partner at RVK, advising large institutional investors on global portfolios, governance, and asset allocation. At SITFO, Peter has overseen the evolution of the fund from a more traditional portfolio into a globally diversified allocator across public and private markets, grounded in mean reversion, factor-based risk management, and long-term stewardship for Utah’s public education system. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement #interview #podcast Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Peter Madsen: LinkedIn: https://www.linkedin.com/in/pmads/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (2:02) Assessing fund managers and market conditions; Active vs. passive investing (7:22) Shift from small cap to private equity; Diversification and asset allocation (11:46) Factor exposure and tools for analysis in investment strategies (16:08) Investment strategy and evaluation in venture capital (23:03) Collaborative model and structuring co-invest accounts for better returns (27:10) Utilizing AI tools in investment screening (31:51) Sovereign wealth fund investing insights (32:55) Closing remarks

Dec 11

How do you turn distressed opportunities into structural alpha—again and again—in an asset class most investors still misunderstand? In this episode, I’m joined by Philip Benjamin, Co-Founder and Managing Partner of Colzen Capital, about how he built a differentiated pre-exit liquidity strategy that serves founders, executives, and investors simultaneously. Philip shares how his fourth-generation real estate background and the 2008 financial crisis shaped his investing worldview, how he applies a distressed-real-estate mindset to late-stage ventures, and why Colzen’s structured equity financing model creates downside protection, aligned incentives, and access to elite companies long before IPO. We also discuss portfolio construction, expected return math, founder psychology, and why this emerging asset class is quietly becoming massive. Highlights: How the global financial crisis shaped Philip’s investment philosophy The real-estate insight that led to Colzen’s equity financing model How Philip helped create a solution for executives facing the 90-day exercise deadline Why founders want liquidity without selling—and how Colzen solves that The investor’s advantage: downside protection, PIK interest, and equity participation Why late-stage venture outcomes cluster between 0.7x–3x—and how to systematize that Understanding structural alpha vs. manager alpha in Colzen’s model How to underwrite companies past binary risk and still outperform The psychology of founders choosing Colzen over selling secondary Why pre-exit liquidity is already a $60B asset class Education as the bottleneck—and why this market will become mainstream Why diversification across industries matters even within structured finance Building long-term LP relationships and evolving from Fund I to Fund II Creating win-win transactions: non-zero-sum liquidity for founders and investors The family-office analogy of planting, harvesting, and replanting new seeds Guest Bio: Philip Benjamin is the Co-Founder and Managing Partner of Colzen Capital, where he leads one of the most innovative structured equity financing strategies in the late-stage venture ecosystem. Philip’s investment philosophy is informed by his fourth-generation real estate family background and by experiencing the 2008 financial crisis just as he graduated college. His family’s timely liquidity event before the crash enabled him to explore private alternatives and eventually develop a distinctive approach to venture risk. Before launching Colzen, Philip invested across fund managers, direct deals, and special situations, eventually partnering with Sam Buleau to refine a pre-exit liquidity model that supports founders and executives without forcing them to sell shares. Philip applies a distressed-real-estate mindset to venture—focused on downside protection, valuation discipline, and structured upside—and has become a leading voice in the growing pre-exit liquidity asset class. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startupsuccess #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Philip Benjamin: LinkedIn: https://www.linkedin.com/in/philip-h-benjamin/ Colzen Capital: https://www.linkedin.com/company/colzen/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (1:12) Transitioning to private alternatives and founding Colson (2:16) Mentorship and early real estate investment strategies (4:17) Creation of the equity financing model and navigating market crashes (6:34) Fund formation, strategy, and comparison to private equity (8:03) Value proposition for founders and executives (11:22) Investment strategy, decision-making, and expected returns (18:01) Evolution from Fund One to Fund Two and structural alpha (21:48) Expanding investor access and synergy in the venture space (24:10) Trends in pre-exit liquidity solutions and staying private (27:36) LP feedback and the importance of diversification (33:55) Relationship management and collaboration opportunities (37:50) The family office business and value creation (40:49) Decision-making and planning for future generations (41:32) Closing remarks

Dec 10

What does it take to build four top-decile crypto funds in one of the most volatile asset classes on earth? In this episode, I talk with Rennick Palley, Founder of Stratos, about how he approaches crypto investing with a disciplined, mathematically grounded framework. We break down how Stratos constructs top-performing venture and liquid portfolios, why crypto is shifting from momentum-driven trends to fundamentals, how to size positions without blowing up, and why Bitcoin and gold are behaving the way they are in today’s macro environment. Rennick also shares his philosophy on decisiveness, conviction, and avoiding the costly mistakes investors make when they hesitate. Highlights: How Stratos generated four top-decile crypto venture funds Why fund size matters more than most crypto investors admit Crypto’s evolution from momentum to fundamentals-driven investing How to size early-stage positions and avoid portfolio blowups Why the smartest investors focus on: “Just don’t screw this up” The future of Bitcoin as digital gold Why gold is outperforming Bitcoin this year — and why that may change What on-chain data reveals about global truth systems Why most crypto VC funds underperform the benchmark (just like traditional VC vs. Nasdaq) How institutions should think about crypto allocation and volatility The behavioral cost of hesitation and the danger of inaction Why crypto provides “free leverage” — and why that makes risk management essential Thoughts on government seizure scenarios, custody, and ETF risk Meme coins, debasement psychology, and the role of speculation How investors can compound returns across cycles without blowing up Guest Bio: Rennick Palley is the Founder of Stratos, an investment firm he launched in 2016 after entering the crypto markets. Under his leadership, Stratos has built multiple top-decile venture funds and a liquid strategy designed to compound capital across highly volatile cycles. Before founding Stratos, Rennick worked as a Research Associate at Sanders Capital, a $75 billion global equity manager known for its fundamental, value-driven approach. He holds dual Bachelor’s degrees in Applied Mathematics and Mechanical Engineering from Southern Methodist University and a Master’s in Quantitative Finance from the Massachusetts Institute of Technology. Rennick blends value-investing discipline, quantitative rigor, and crypto-native insight, making him one of the most analytical and thoughtful investors in digital assets today. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startupsuccess #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Rennick Palley: X/Twitter: https://x.com/RennickPalley Stratos: https://www.stratos.xyz/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (2:00) Key principles in crypto venture investing (4:18) Analyzing large outcome clustering in crypto (5:12) Momentum vs. value in evaluating crypto wins (8:14) The future of information and crypto as a hedge (12:22) Historical parallels and Bitcoin's potential challenges (17:45) Strategies for a potential Bitcoin confiscation scenario (21:01) Debating Bitcoin's future valuation and effects of forced sales (27:10) Insights from Rennick Palley and liquid crypto strategies (31:34) Comparing crypto to traditional endowment strategies (33:06) Sector importance and risk management in crypto (39:47) Systematic decision-making and the role of an engineering background (43:43) Portfolio construction and institutional crypto allocation (45:52) Transitioning from venture to liquid crypto investments (49:08) The benefits of illiquidity in alternative investments (50:31) Fund liquidity and managing investor relationships (53:10) Determining the optimal portfolio size for Bitcoin (54:13) Utilizing leverage in crypto investing (57:12) Guidance for newcomers to crypto investing (59:45) Closing remarks

Dec 9

How do you build a $10B real estate empire by turning yourself into a media company—and why is vulnerability the ultimate competitive advantage? In this episode, I talk with Ryan Serhant, founder and CEO of SERHANT., one of the most influential real estate brokerages in the world and a pioneer at the intersection of real estate, media, entertainment, and technology. Ryan breaks down the turning points that shaped his career—from selling a $13M townhouse through YouTube a decade ago, to betting everything on social media before anyone believed in it, to building a fast-growing real estate ecosystem powered by content, authenticity, and scale. We dive into Season 2 of Netflix’s Owning Manhattan, the biggest highs and lows of his year, the reality of leading a thousand-agent organization, and why the future of real estate is screenless, human-centric, and powered by creators. Highlights: How a YouTube video led to Ryan’s first $13M sale and changed his career Why he bet his entire future on social media long before agents believed in it The balance between going viral and preserving luxury brand credibility The power of authenticity online—and why the internet detects B.S. instantly How Season 2 of Owning Manhattan became his most raw and emotional year on TV The behind-the-scenes reality of office fights, breakdowns, and $60M deals Why vulnerability drives more business than perfection ever could The moment he realized he had to evolve from broker-friend to CEO-leader What broke at SERHANT. as the company scaled from 500 to 1,500 agents The difference between respect vs. trust—and why employees must earn both Ryan’s four rules for every new hire, including “perform magic” Why culture is defined by the behaviors you allow, not what you write on paper The future of content: micro-dramas, interactive media, and 5-minute emotional arcs How SERHANT. is building a screenless, AI-powered real estate transaction Advice for new agents: join a team, do the work no one wants to do, and get reps Guest Bio: Ryan Serhant is one of the most recognized and successful real estate brokers on the planet. He is the founder and CEO of SERHANT., a modern multidimensional real estate brokerage operating at the intersection of media, entertainment, education, and technology. Ryan has closed nearly $10 billion in sales and has represented clients in some of the most record-breaking transactions across New York and South Florida. Before launching his firm, he became a global personality as the star of Bravo’s Million Dollar Listing New York and now serves as Executive Producer and lead star of Netflix’s Owning Manhattan. Beyond real estate, Ryan is an entrepreneur, creator, bestselling author, and philanthropist whose content reaches over six million people. SERHANT. has grown rapidly under his leadership, expanding across multiple states and pioneering LISTED, a dedicated YouTube network focused on real estate and lifestyle. Ryan actively supports organizations including City Harvest, Feeding America, the Ali Forney Center, the NYC Sanitation Foundation, the American Cancer Society, and Project Sunshine. He lives in Brooklyn with his wife, Emilia, and their daughter, Zena. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ ###Stay Connected with Ryan Serhant: LinkedIn: https://www.linkedin.com/in/ryanserhant/ Website: https://serhant.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Preview (1:12) Selling a $13 million home via YouTube and the impact of social media (5:40) Authenticity, vulnerability, and balancing content in luxury real estate (12:02) High and low moments, scaling challenges, and leadership (22:29) Special guest insights on season two highlights (24:38) Real-time CEO moments and a major deal gone wrong (27:02) Season two highlights: Miami, Mercedes Benz, and narrative arcs (29:08) Learning from mistakes across seasons one and two (32:06) Discussing the future of content creation and media convergence (34:08) Ryan Serhant's vision for the future of his company (35:53) Advice for new real estate agents and industry insights (37:26) Closing remarks

Dec 8

Why do the world’s best CIOs make investment decisions based on gut — not spreadsheets? In this episode, I’m joined by Julia Rees Toader, CFA, Founding Partner at PrinCap and former Global Head of Portfolio Strategy at Goldman Sachs Asset Management. Julia spent a decade advising sovereign wealth funds, pensions, private banks, and ultra-wealthy families on portfolio construction, risk management, and asset allocation. She shares the biggest lessons she learned from working with the world’s top CIOs — from why diversification rarely drives behavior, to where the smartest allocators take idiosyncratic risk, to how emotions secretly influence the most sophisticated investment decisions. Highlights: What Julia learned rising from intern to global head at Goldman Sachs The surprising truth: top CIOs make decisions based on emotions + gut, not just models Why diversification rarely changes behavior — and why portfolios still converge to “vibes” Where the best allocators take idiosyncratic risk without blowing up the portfolio Why ultra-wealthy families succeed by leaning into their operating-business advantages Home country bias: the hidden 10x overweight that destroys returns How to avoid behavioral traps using blind comparisons and rotating devil’s advocates Options-based hedging vs. fixed income — and why 60/40 is outdated Why avoiding losers matters as much as picking winners Why volatility is emotional, not mathematical — and how Julia coaches clients through drawdowns The biggest risk mistakes she saw in sovereign wealth funds & global pensions The seductive danger of storytelling in investing — from thematic equity bubbles to VC pitches How AI will reshape diligence, bias detection, and decision-making Guest Bio: Julia Rees Toader, CFA, is the Founding Partner at PrinCap, an independent investment portfolio strategy firm advising institutions, family offices, and high-net-worth individuals on asset allocation, manager selection, and strategic portfolio design. Before founding PrinCap, Julia served as Head of Portfolio Strategy and Head of Relationship Management at Heritage Holdings, a multifamily office. She previously spent over a decade at Goldman Sachs Asset Management, where she rose from founding intern to Global Head of Portfolio Strategy, advising CIOs of sovereign wealth funds, pensions, private banks, and other large allocators around the world. Julia began her career in M&A and business development for an early-stage medical device biotech company. She holds a degree in Mechanical Engineering and Computer Science from Princeton University and is a CFA charterholder. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Julie Rees Toader: LinkedIn: https://www.linkedin.com/in/julia-rees-toader-cfa-22871030/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Introduction (2:55) Emotional and qualitative considerations in taking idiosyncratic risks in portfolios (6:04) Flexibility and unique strengths of allocators (7:15) Building meaningful portfolios with high returns (8:30) Options-based hedging strategies (11:29) Overcoming behavioral biases and market timing (14:01) Addressing home country bias in investment committees (17:02) Dynamics and size of effective investment committees (19:12) Role of tax strategy and alpha in investment (22:00) Strategic value and managing portfolio fluctuations (25:18) Tools and client risk tolerance in portfolio risk assessment (28:07) Lessons from transitioning to a family office (30:40) Family office investment strategies and perspectives on risk (34:24) Outsourcing tasks and addressing personal liability in decisions (37:01) Evaluating family office dynamics and resource advantages (39:04) Incorporating AI in investment management (41:04) Timeless advice for new investors and thought experiments with AI (45:22) Market timing and asset class favorability (46:09) Closing remarks

Dec 5

What does it take to build the most dominant FinTech investment bank in the world—starting from a $99 incorporation and a used laptop? In this episode, I speak with Steve McLaughlin, Founder, CEO, and Managing Partner of FT Partners, widely regarded as the leading investment bank in FinTech. Steve has personally closed hundreds of the biggest M&A, capital raise, and IPO advisory transactions in the industry—while pioneering a completely different approach to value creation in investment banking. We cover everything from the humble beginnings of FT Partners, to Steve’s philosophy of “never die,” to his groundbreaking thesis on AI, tokenization, defensibility in FinTech, and why he believes we’re entering a new era of trillion-dollar global financial technology companies. We also dive into the incentives model Steve built that has generated some of the largest fees in the history of investment banking—and why clients keep coming back. Highlights: How Steve left Goldman to launch FT Partners during the dot-com crash—with no brand, employees, or clients. The “never die” mindset and why consistency compounds in markets. FT Partners’ deep-work model: 500-page decks, long-term models, and internal data science. How the firm differentiates from Goldman/Morgan Stanley and attracts elite talent. The incentives behind nine-figure fees—and why Steve thinks bankers should be paid like PE/VC when they create real value. Inside FT Partners’ $25M investment in Model ML and how AI will reshape investment banking. Tokenization, stablecoins, and where the next trillion-dollar FinTech giants will emerge. Why the strongest FinTech companies embed AI across every function. How AI will change deal sourcing, buyer mapping, and global transaction execution. The future of FinTech over the next decade—post-AI and fully digital. Steve’s views on money, charity, family, and why he still personally handles major client calls. Guest Bio: Steve McLaughlin is the Founder, CEO, and Managing Partner of Financial Technology Partners (FT Partners), the leading investment bank focused exclusively on FinTech. Since launching in 2001, Steve has built FT Partners into a globally recognized advisory powerhouse, completing hundreds of the most important transactions across payments, digital banking, crypto, wealth & capital markets tech, InsurTech, healthcare payments, and more. He has been ranked #1 on Institutional Investor’s “Most Influential Dealmakers in FinTech,” named Investment Banker of the Year, and recognized as the #1 FinTech banker in Silicon Valley by The Information. FT Partners has also won Investment Banking Firm of the Year four times since 2004. Before founding FT Partners, Steve led the Global Financial Technology Group at Goldman Sachs. He earned his BSBA from Villanova University and his MBA from Wharton. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Steve McLaughlin: LinkedIn: https://www.linkedin.com/in/stevemclaughlinftpartners/ FT Partners: https://www.ftpartners.com Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are solely their own and do not represent the views of Weisburd Capital or its affiliates. Participants may hold positions or have other financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are based solely on the opinions of the speaker and are subject to risks and uncertainties. Information discussed in this episode may include third-party data or opinions; while believed to be reliable, such information has not been independently verified. Listeners should conduct their own research and consult their own professional advisors before making any investment decisions. Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introductions (0:04) FD Partners origin story, early challenges, and current scale (1:49) Lessons from market downturns and economic cycles on fintech (3:48) Long-term strategy, resilience, and talent strategy (6:34) Innovations in AI and fintech (7:58) Teamwork and the F1 racing analogy (9:47) Traditional banks vs. fintech and value-added roles (15:15) Private markets and client engagement strategies (19:28) Being labeled the world's richest banker and fintech trends (24:58) The future of fintech and AI's impact (29:06) AI's defensibility and pricing in the fintech market (32:07) Competitive differentiation with AI in fintech (33:24) Closing remarks

Dec 4

What does it take to recruit the top 0.1% of engineers in the world — and why has talent become the ultimate constraint in AI? In this episode, I’m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density—not headcount—is the strongest predictor of outcomes in today’s startup environment. Highlights: Why AI founders are “at war” — and recruiting firms are the arms dealers. Defining S-tier talent: clear evidence of greatness, spiky abilities, and proven complexity-handling. Capital is abundant; talent is the true constraint in modern AI company building. Why companies must tell a compelling story if they lack high-signal founders or top-tier backers. How AI’s rapid improvement reshapes recruiting needs — fewer engineers, but far more specialized ones. The Sequoia-backed company that failed to hire until they raised their comp bands. (7 declines vs. 17 hires after fixing comp.) Why founders should overpay strategically for the roles that matter most. Key signals elite engineers look for: founding team quality, investor pedigree, mission clarity, and market upside. Why “experience with greatness” de-risks execution in early-stage teams. The #1 heuristic Chris wishes he learned earlier: “If you wouldn’t hire 100 of that person, don’t hire one.” Guest Bio: Chris Vasquez is the Founder & CEO of Quantum Talent, a specialized recruiting firm focused on placing elite technical talent into leading AI, frontier-tech, and enterprise software startups. Quantum works with hundreds of venture-backed companies and has partnered with 80% of Tier 1 VC firms, helping founders build high-density engineering teams capable of shipping breakthrough products. With deep expertise in identifying the top 0.1% of engineers, researchers, and product leaders, Chris and his team have become one of the most trusted upstream partners in the AI ecosystem — operating at the intersection of talent, technology, and high-velocity company building. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Chris Vasquez: LinkedIn: https://www.linkedin.com/in/chris-vasquez-66137553/ Quantum: https://www.quantumtalent.io/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . david@weisburdcapital.com . (0:00) Introduction (2:38) Talent Density and the Shift from Capital to Talent in Startups (5:16) AI's Impact on Talent Recruitment and Compensation Strategies (9:45) What S Tier Engineers Seek in Companies (11:14) Establishing Talent Density by Overpaying Initial Hires (14:28) The Role of Talent in Product-Market Fit (17:21) Strategies for Recruiting Top AI Talent (24:01) The Distinction Between Good and S-tier Recruiters (27:43) Effective Recruiting Heuristics and Compensation Tactics (30:23) Managing Internal Politics for High Compensation Hires (31:48) Timeless Advice for Recruiters (34:34) Closing remarks

Dec 3

How do you balance power-law outcomes with real risk management while building a durable venture franchise? In this episode, I speak with Mark Peter Davis (MPD) — Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York’s most active early-stage investors. We discuss how Mark’s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages. Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest. Highlights: How 20 years in venture reshaped Mark’s thinking on risk, liquidity, and exit timing. Why early VCs get caught in the “TechCrunch punch” and over-index on hope. Power laws vs. portfolio consistency — why vintages swing and how Mark mitigates volatility. How secondaries, tenders, and mid-market PE can drive liquidity for the “middle 80%” of winners. The “tweener rule”: why Interplay often sells ~50% when outcomes are unclear. Incentive alignment between GPs and LPs — and why building a long-term institution changes behavior. Avoiding narrative traps: why founder behavior and fund construction matter more than storytelling. Brokerage-model VC vs. operational-institutional VC — and why the difference is huge. How soft commits, goodwill, and reference strength drive proprietary access. Entrepreneurship patterns: the “500 problems” every startup faces. Why you can’t learn entrepreneurship in a classroom — only through reps. The compounding effect of grit and staying in the game long enough. Guest Bio: Mark Peter Davis is a venture capitalist, serial entrepreneur, author, and startup community organizer. MPD is the Managing Partner of Interplay, a startup ecosystem based in NYC that supports founders and innovation at every stage. The ecosystem comprises a top-performing venture capital fund, an accelerator, a studio, a services platform, and a multi-family office. With over 100 companies funded, incubated, or founded, he ranks among the most active startup founders and investors in New York City. MPD is also an active podcaster, the author of The Fundraising Rules, and the founder of both the Columbia Venture Community and the Blue (Duke) Venture Community. Prior to his current ventures, MPD was a venture capitalist at DFJ Gotham Ventures and Primary Ventures. Before entering VC, he was a M&A advisor to Fortune 1000 acquirers at KPMG and a strategy and operations consultant at Bain & Company. MPD earned his BA from Duke University and his MBA from Columbia Business School. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startupsuccess #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Mark Peter Davis: LinkedIn: https://www.linkedin.com/in/markpeterdavis/ X/Twitter: https://x.com/mpd Interplay: http://interplay.vc/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . david@weisburdcapital.com . (0:00) Introduction (0:31) Evolution and counterintuitive lessons in venture investing (3:25) Reconciling investment worldviews and managing liquidity (7:35) Decision-making and aligning VC incentives with LP interests (12:03) Building an enduring institution and measuring success (18:07) Achieving access to competitive deals and proprietary deal flow (24:24) Competitive tension's impact on investment support (27:19) Integrity and resources in VC partnerships (30:02) Entrepreneurial experience's value in venture capital (32:24) Startups' challenges and the role of pattern recognition (35:24) Unlearning and cognitive restructuring in entrepreneurship (37:23) Mastering the complexities of long-term entrepreneurship (38:11) Timeless advice for aspiring entrepreneurs and enduring success (41:51) Closing remarks

Dec 2

How do the best family offices consistently spot power-law opportunities and avoid the trap of “fake busy” work? In this episode, I’m joined with William (Bill) Brown, CIO of the Terrace Tower Group, about the lessons he learned working for billionaire Leonard Stern, how he helped evolve a legacy real-estate portfolio into a globally diversified family office, and what pattern recognition looks like across trades like the Big Short, crypto, and private credit. We discuss how Bill thinks about decision-making, mental models, productivity, and the mindset required to survive long enough to capture asymmetric upside. Highlights: Lessons from working under Leonard Stern — focus on what truly matters. Why “don’t confuse activity with progress” became a lifelong principle. How Stern gathered insights by walking the office and challenging ideas in real time. The importance of taking leaders on a journey, not presenting decisions once. Batting average vs. slugging percentage — finding your investing style. (Ichiro vs. Aaron Judge) Behind the scenes of the Big Short trade — identifying early signals. Navigating months of drawdowns and conviction challenges. How to know whether you’re the “dumbest person in the room” and avoid confirmation bias. Why the best ideas often come from “other herds” and cross-network pattern recognition. Crypto pattern recognition — spotting the signal when two very different founders agree. How Terrace Tower built a diversified global portfolio from a real-estate foundation. Using private credit to replace income after a major asset sale. “Fake busy” vs. deep work — designing days for real thinking. Staying in the game long enough to benefit from power-law outcomes. Guest Bio: William “Bill” Brown is the Chief Investment Officer of Terrace Tower Group, a global family office originating from the Westfield legacy. Bill oversees the group’s non-real-estate portfolio, spanning public equities, private equity, venture capital, and private credit. Before joining Terrace Tower in 2010, Bill worked in investment banking and spent his early career at Salomon Brothers. His investing philosophy is shaped by decades of experience working with the Stern family and managing multi-asset portfolios across cycles. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Bill Brown: LinkedIn: https://www.linkedin.com/in/william-brown-1a48593/ Terrace Tower Group: https://www.ttgroup.co/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . david@weisburdcapital.com . (0:00) Introduction (0:12) Leonard Stern's investment philosophy and unique work habits (2:16) Leonard Stern's idiosyncratic bets and discussion on risk (4:49) Jeff Bezos and asymmetry in business (5:23) Introduction to and expansion of the big short trade (13:30) Evaluating complex trades as a family office (15:18) Cultivating the right investment mindset (18:53) Early investments in crypto and avoiding busy work (23:02) Energy management and strategic networking (25:10) The importance of not overthinking and perfection in investing (27:03) Resisting the temptation to sell too early (29:13) The importance of staying in the game and imagination in investing (33:19) Terrace Tower Group's current focus and portfolio execution (42:02) Advice for younger self and focusing on what matters (46:42) Closing remarks

Dec 1

How do you scale from a $10M first fund to managing over $1.5B — all in one of the most capacity-constrained asset classes on earth? In this episode, I talk with Eva Shang, Co-founder and General Founder of Legalist, about dropping out of Harvard, getting into Y Combinator, pivoting from legal analytics to litigation finance, and raising their first $10M fund long before they had any track record. We discuss why Legalist chose the fund model over the venture-backed originator model, how they deployed their algorithm to find late-stage cases at scale, why litigation finance is capacity constrained, and how Legalist expanded into adjacent strategies like bankruptcy, mass torts, law-firm lending, and government receivables. Highlights: How Legalist began as a data-driven legal-analytics platform. Why the team shifted from software to asset management. How technology identifies litigation, bankruptcy, and receivables opportunities. The role of public-records sourcing and automated case screening. Why Legalist focuses on uncorrelated, niche credit strategies. How Legalist evaluates risk in litigation finance. How the team structures underwriting across legal and credit factors. Why government receivables and bankruptcy claims require specialized processes. How Legalist works with law firms, claimants, and contractors. Eva’s philosophy on building teams, culture, and long-term systems. Guest Bio: Eva Shang is the Co-founder and General Partner of Legalist, an asset manager specializing in technology-enabled investments across litigation finance, bankruptcy, law-firm lending, mass torts, and government receivables. Eva co-founded the firm in 2016 after leaving Harvard and entering Y Combinator, and has led Legalist from its $10M debut fund to over $1.5B in AUM across multiple strategies. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Eva Shang: LinkedIn: https://www.linkedin.com/in/eshang/ Legalist: https://www.legalist.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (2:20) Y Combinator insights and venture capital decisions (4:51) Emphasizing IRR in building a sustainable business model (6:48) Lessons from early fundraising and growth strategies (9:36) Diversification and understanding capacity-constrained assets (13:33) Fundamentals of litigation finance and sources of alpha (18:08) Exploring the government receivables strategy (20:38) Cultivating long-term vision and independent mindedness in entrepreneurship (24:33) Reflecting on past decisions and the importance of team building (26:14) Closing remarks

Nov 28

What does it actually take for an emerging manager to convince a top LP to invest? In this episode, I’m joined by Alex Edelson, Founder of Slipstream, and one of the most respected LPs backing elite seed funds today. Alex pulls back the curtain on how LPs use AI, what “real talk” references look like, how he evaluates GPs, and why only a tiny percentage of funds ever make it through his screening. We also dive into portfolio construction, picking and winning founders, why deep tech requires more shots on goal, and how Alex builds long-term trust with the world’s top institutions. This conversation is a masterclass in LP underwriting and what separates good managers from truly exceptional ones Highlights: How top seed funds use AI for sourcing, diligence, and market research. Why underwriting venture still comes down to relationships, brand, and founder trust. Why Slipstream screens out ~95% of funds before doing references. What “real talk references” reveal that most LPs never hear. Why deep tech sometimes needs more shots on goal with slightly lower ownership. How Alex developed his “right to win” as an LP after QED. What GPs misunderstand about the bar for raising today. How anti-selling helps LPs filter for long-term partners. Why LP relationships often become deep personal relationships over time. The frontier of the next decade: AI-driven investing and pre-consensus founder identification. Guest Bio: Alex Edelson is the Founder of Slipstream, an LP firm focused on backing top early-stage venture funds. Before launching Slipstream, Alex was part of the leadership team at QED Investors, where he helped shape their approach to portfolio construction, fund strategy, and LP engagement. His legal background and deep relationships across the founder/VC ecosystem have made him one of the most sought-after LP partners for emerging and established seed GPs. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Edelson: https://www.linkedin.com/in/alex-edelson-604767b/ Links Slipstream Investors: https://www.slipstreaminvestors.com/ Weisburd Capital: https://www.weisburdcapital.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:06) Seed funds, AI usage, and diligence processes (1:56) Growing prominence of AI and unique investment approaches (4:00) Constructive GP conversations and Slipstream's strategy (6:11) Comparisons to Palantir and investment beliefs (8:07) Differing views on identifying good GPs (10:55) The importance and role of references in diligence (19:04) Screening out funds and challenges for emerging managers (25:49) Attracting top LPs and building relationships (30:03) The concept of antiselling and excitement for the future (35:17) Closing remarks

Nov 26

What does it really take to raise a venture fund—and why does fundraising never get easier, even at Fund 5 or Fund 6? In this episode, I talk with Yasmine Lacaillade, Founder of Sinefine and one of the most respected capital formation leaders in venture. Yasmine shares her journey from TPG Axon in London to joining Drive Capital at Fund I—years before it became consensus. We discuss why fundraising is always difficult, how LP sentiment shifts every 2–3 years, and why top fundraisers treat the process like enterprise sales rather than relationship maintenance. Yasmine breaks down her market mapping framework, why the top of the funnel must always stay wide, how to qualify LPs quickly, and why “adding value first” is her core operating principle. She also explains how she evaluates new managers, how to identify true LP demand today, and why people, culture, and team cohesion matter more than anything else in venture. Highlights: How moving from London to Columbus led Yasmine into the earliest days of Drive Capital. Why she joined Drive at Fund I—and what she saw before LPs did. Why fundraising never gets easier, even after multiple successful vintages. How LP priorities, liquidity, and macro cycles shift every 2–3 years. The difference between networking vs. honing existing relationships. Why Yasmine treats fundraising like enterprise sales—and why a huge top of funnel is essential. What LPs are actually looking for in a first meeting How to qualify LPs quickly by asking exactly what they’ve invested in over the last 6–12 months. Why the most important skill in fundraising is mapping the market and respecting LPs’ time. How Sinefine structures a new engagement with a GP—from deck narrative to LP segmentation. Why she only works with a handful of managers and how she selects them. How she evaluates team cohesion and founder intensity Why her philosophy is to add value before asking for anything. The psychology of transactional vs. non-transactional relationships and the idea of “goodwill reservoirs.” Why she shut down her fund-of-funds product and how she built Sinefine into a product-oriented platform. How Zoom culture has changed LP behavior, time allocation, and transparency. The importance of story evolution, narrative sharpening, and portfolio math in venture. Guest Bio: Yasmine Lacaillade is the Founder of Sinefine, a capital formation and institutional fundraising advisory firm working with top-tier venture managers. Before launching Sinefine, Yasmine spent over a decade in investment and fundraising roles, including at TPG Axon in London and as an early team member at Drive Capital, where she helped build one of the leading venture franchises in the Midwest from its first fund onward. Yasmine specializes in market mapping, LP strategy, investor relations, and helping emerging and established GPs navigate complex fundraising environments. She is widely recognized for her clarity of thinking, LP intelligence, and ability to guide managers through the entire capital formation journey. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Yasmine Lacaillade: https://www.linkedin.com/in/yasmine-lacaillade-6448888/ Links Sinefine: https://www.sinefine.co/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (3:08) Fundraising challenges in venture capital vs. hedge funds (5:00) Networking and managing relationships in fundraising (9:12) Balancing relationships with the transactional nature of fundraising (13:22) Market mapping and targeting LPs effectively (17:02) Long-term investment decisions and adapting to market conditions (21:58) Building trust in first meetings with LPs (27:36) Transactional relationships and adding value in LP-GP dynamics (31:08) Onboarding a new fund and quick trust-building (34:44) Pursuing relationships with potential managers and the Ashton Kutcher investing principle (38:45) Balancing personal and professional commitments (40:06) Embracing people-pleasing as a strength in investing (42:49) Reputation and value creation in the investment world (44:31) Passion for venture capital and finding excitement in buyouts (49:30) Team cohesion and investment success (50:09) Closing

Nov 25

How do LPs unlock liquidity from private-fund positions without selling at a discount? In this episode, I talk with Alex Simpson, Co-founder of Liquid LP, a platform that provides NAV loans backed by LP and GP interests in private funds. Alex explains how NAV loans work, how lenders underwrite illiquid portfolios, and when borrowing may be preferable to selling in the secondary market. We also discuss how different types of investors—high-net-worth individuals, family offices, and institutions—use these loans for personal liquidity, capital calls, tax needs, portfolio rebalancing, or simply as a liquidity backstop. We also cover underwriting, LTV ranges, recourse structures, timing, advisory boards, and the origin story behind Liquid LP. Highlights: What a NAV loan is and how LP interests serve as collateral. Why some LPs choose a NAV loan rather than selling at a discount. How high-net-worth investors use NAV loans for personal liquidity and taxes. How institutions use NAV loans for portfolio management and capital calls. Differences between Liquid LP and large banks like J.P. Morgan or Goldman Sachs. Underwriting approach: fund quality, diversification, existing pledges, and use of proceeds. Typical LTV ranges (approx. 20–40%) depending on underlying collateral. Loan pricing drivers: asset quality, diversification, and loan structure. Loan timelines: from fast two-week processes to more complex multi-week cases. Recourse vs. non-recourse structures and when each applies. Why purpose of the loan matters for underwriting, even if terms are asset-driven. Standby NAV lending partnerships with funds to support LP liquidity. How GPs sometimes use loans to bridge GP commitments when DPI is slow. How Alex built Liquid LP, beginning with pre-IPO lending before shifting to LP liquidity solutions. Key risks in NAV lending: undisclosed pledges, documentation issues, and thin data on smaller funds. Lessons learned from building an advisory board and aligning incentives. Guest Bio: Alex Simpson is the Co-founder of Liquid LP, a fintech platform that provides NAV-backed lending solutions for LPs, GPs, family offices, and wealth-management clients. Before founding Liquid LP, Alex built and operated companies in South Africa and Australia and worked closely with executives at late-stage and pre-IPO technology companies. His experience in private markets, lending, and alternative-asset liquidity led him to develop a platform focused on helping investors access liquidity without selling long-term positions. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexander Simpson: https://www.linkedin.com/in/alsimpson1/ Links LiquidLP: https://www.linkedin.com/company/liquidlps/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:07) Scale of operations, target clientele, and market rates (2:29) Use cases for institutions and competition with large banks (4:04) Due diligence and factors influencing loan terms (8:15) Recourse vs nonrecourse loans and loan's purpose (10:37) NAV loans for investment stability and GP commit solutions (12:46) Flexibility and risk assessment in lending (15:07) Loan durations, processing times, and standby partnerships (18:22) GP stakes field and LiquidLP's origin and evolution (21:04) NAV loan risks and managing an advisory board (24:34) Advisory board strategy and balancing impact with finance (27:52) Company culture, leveraging finance for impact, and unifying principles (34:25) Closing remarks

Nov 24

What makes a GP interest valuable — and how do you evaluate a manager beyond the fund they’re raising today? In this episode, I talk with Mark Wade, CAIA, Partner at CAZ Investments, about how his team assesses GP interests, private-market managers, partnership structures, and long-term durability. We discuss why GP transactions have evolved, why some firms seek outside capital, and the practical differences between investing as a GP versus an LP. We also touch on evaluating leadership succession, LP base diversification, liquidity considerations, and why sports franchises continue to attract investor interest. Highlights: How GP interest transactions have changed over the past decade. Why private-market firms seek external capital to support growth. Key differences in evaluating a GP interest versus an LP fund commitment. What CAZ looks for in partnership stability and leadership succession. How LP base diversification factors into long-term durability. Liquidity considerations and how secondary/tender processes work. Why sports franchises attract investor attention and how league structures differ. Guest Bio: Mark Wade is a Partner at CAZ Investments, where he leads investment strategy and firm initiatives. Since joining CAZ in 2013, Mark has helped the firm expand its presence across asset classes, with a particular focus on GP stakes, energy, and professional sports. Prior to CAZ, Mark earned his MBA from the University of Chicago Booth School of Business. CAZ is known for its alignment-first model—deploying more than $700 million of insider capital alongside its LPs across a range of alternative investments. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mark Wade: https://www.linkedin.com/in/mark-wade-caia-334b951b/ Links CAZ Investments: https://cazinvestments.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.c (0:00) Introduction (0:14) Mark Wade's background and focus on private markets (2:14) Structuring and capital needs in GP stakes investments (7:15) Key considerations and differences in GP stakes vs LP investments (11:24) Downside protection and alignment of interests in GP stakes (15:01) Base case expectations and liquidity concerns in GP stakes (19:39) Sports investments discussion and value growth (24:15) Comparing sports investments to Bitcoin and impact of AI (25:07) Future trends and investing focus in sports entertainment (26:08) Closing remarks

Nov 21

Is traditional valuation dead for the biggest winners of the AI era? Or have investors simply been looking in the wrong place? In this episode, I talk with Dan Ives, Managing Director and Global Head of Technology Research at Wedbush Securities, and one of Wall Street’s most followed tech analysts. Dan has covered the software and technology sector for 25 years, becoming known for his bold, high-conviction calls on Tesla, Nvidia, Microsoft, and Palantir long before they became consensus. We break down why Dan calls Tesla the world’s leading “physical AI” company, why he thinks AI is the largest tech transformation in 40–50 years, what investors miss when they rely only on spreadsheets, and how his pattern-recognition framework helps him spot multi-baggers years before the herd. Highlights: Why he views Tesla far beyond autos; autonomy, robotics, robo-taxis, and multi-trillion-dollar upside. Why he believes AI is a 40–50 year mega-cycle with second- and third-order winners. Why do great companies look expensive every year until suddenly they don’t. On pattern recognition, global customer conversations, and signals that never show up in models. Lessons from 2008, 2022, and sticking with calls through volatility. Why Nadella, Musk, Karp, and Lisa Su are misunderstood and mispriced by Wall Street. His 1–10 conviction framework and how he sizes up when inflection happens. Where he’s looking for the next multi-baggers in the AI supply chain. How setbacks early in his career reshaped his investing worldview. His role as Chairman of ORBS (EightCo Holdings) and Worldcoin-aligned authentication. Why he partnered with Snow Milk on a fashion collaboration and how “owning who you are” fuels differentiation. Guest Bio: Daniel Ives is the Managing Director and Global Head of Technology Research at Wedbush Securities, where he has been a senior equity research analyst covering the technology sector since 2018. Dan has spent 25 years on Wall Street following software, cloud, cybersecurity, mobile, and the broader enterprise tech ecosystem. He is also the Chairman of EightCo Holdings (ORBS), focused on authentication and digital identity infrastructure aligned with the emerging AI era. Dan is one of the most sought-after tech experts globally, regularly appearing on CNBC, Bloomberg, BBC, Fox Business, ABC, NBC, Sky News, France 24, NPR, and many other global outlets. He is frequently cited in The Wall Street Journal, The New York Times, Financial Times, Barron’s, Time, The Telegraph, and other major publications. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Daniel Ives: https://www.linkedin.com/in/daniel-ives-542321a8/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:17) Dan Ives on the AI revolution, Tesla's market dominance, and valuation methodology (5:10) The importance of long-term vision and global insights in tech investing (10:52) The role of retail investors and the impact of market sentiment (14:25) The significance of true believers and early adopters in investments (16:13) Recognizing when an investment thesis is wrong and adjusting strategies (22:32) Investment sizing, portfolio construction, and utilizing customer feedback (26:16) Psychological biases and their effects on investor confidence (27:06) Leveraging social media and conferences for investment insights (28:31) Understanding power law returns and second/third order effects in the market (32:20) Evaluating investment success: hit rates and the role of outliers (34:09) Influencing stock narratives and decisions at the board level (37:21) Identifying mispriced founder-led companies and embracing failures (43:41) Dan Ives' personal background and approach to maintaining conviction (47:48) Future projects at Wedbush and personal ventures (49:19) Closing remarks

Nov 20

Is private equity still worth it — or has the industry scaled its way into mediocre returns? In this episode, I talk with Nolan Bean, CFA, CAIA, Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, an independent, employee-owned firm advising on $90+ billion in assets for endowments, foundations, healthcare systems, and mission-driven institutions. We dig into the state of OCIOs, interval funds, private equity, and why Nolan believes the lower middle-market still offers the clearest path to real alpha. Nolan also breaks down the coming wave of 401(k) access to private markets, why large-cap buyout is structurally challenged, and how FEG uses a “crisis playbook” to lean into markets without pretending to time them perfectly. Highlights: How FEG advises on $90B+ across 300+ clients, mostly nonprofits. OCIO incentives, risk-taking, and why some firms drift toward being too conservative. Interval funds: easy access, hidden liquidity risks, and “Hotel California” redemptions. Why large buyout PE faces pressure from high entry multiples, rates, and too much capital. Why lower middle-market buyout still works: founder-led deals, ops value-add, less leverage. Main risks in small companies: fragility, client concentration, and key-person exposure. Factor models vs. real alpha: where Fama-French stops explaining PE returns. Shrinking small-cap universe and why public markets may have adverse selection. The coming 401(k) and retail flow into alternatives — and shrinking illiquidity premia. FEG’s VFS (valuation, fundamentals, sentiment) crisis framework for drawdowns. Four key risks: goal risk, market risk, illiquidity risk, and maverick risk. Nolan’s top two lessons: don’t fight the Fed, and relationships compound. Guest Bio: Nolan Bean is the Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, where he has worked since 2004. He leads portfolio construction, research oversight, and investment strategy across FEG’s OCIO and advisory clients. Nolan is both a CFA and CAIA charterholder. He holds a finance and quantitative analysis degree and an MBA from the University of Cincinnati. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Nolan Bean: https://www.linkedin.com/in/nolanbean/ Links FEG Investment Advisors: https://www.feg.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:28) Growth catalysts and criteria for RIAs and investment advisors (2:13) Criticisms of OCIOs and conservative risk-taking (3:59) Discussion on interval funds and private equity buyouts in 2025 (7:39) Challenges in large buyout funds and lower middle market opportunities (16:23) Risks and benchmarking in lower middle market investments (21:45) Democratization of private markets and 401(k) investments (24:36) Illiquidity premium and institutional investors' response (27:06) Identifying opportunities in out-of-favor sectors and portfolio construction (31:07) Managing risk tolerance and market downturn strategies (34:24) Behavioral finance and liquidity in portfolio management (37:18) Evaluating hedge funds and strategies for market downturns (41:21) Diversification benefits and long-term market trends (44:03) Public policy influence on markets and timeless investment advice (47:55) Interest rates' impact on asset prices and politicians' market influence (53:14) Investing during crises and the importance of relationships (56:18) Venture capitalists, reciprocity, and value in relationships (58:22) Closing remarks

Nov 18

How do you build a multibillion-dollar company from scratch, walk away at the peak, and reinvent your life around purpose, generosity, and impact? In this episode, I talk with Pete Kadens, one of America’s most respected first-generation wealth creators and one of the leading philanthropists focused on closing education and opportunity gaps across the U.S. Today. Pete and I dive into how he built Green Thumb Industries (GTI) into a multibillion-dollar cannabis company, the unsexy strategies that made it work, and why choosing overlooked markets and consumers unlocked massive profit. We cover the power of ownership cultures, transparency, discipline frameworks, and why giving equity and education to employees creates extraordinary performance. We also explore the character transformation that led him to retire at 40. Highlights: The unsexy strategy behind scaling GTI into a multibillion-dollar operator Why Pete targeted the 30–50-year-old female consumer long before the market noticed How choosing Toledo instead of Chicago and Erie instead of Philadelphia created monopolistic advantages The power of ownership cultures, ESOP-style alignment, and financial transparency Why employees perform better when they are treated like owners Pete’s shift from business success to a life of impact and philanthropy The emotional toll, guilt, and clarity that led him to retire at 40 How he rebuilt his parenting philosophy: presence, character, and modeling discipline Why “how you do anything is how you do everything” became his family standard The timeless rule he lives by: the gap between “I should” and “I did” Guest Bio: Pete Kadens is a serial entrepreneur and dedicated philanthropist who currently serves as Chairman of The Kadens Family Foundation, a national charitable organization focused on closing education and wealth gaps. He is also the Founder and Co-Chairman of Hope Chicago, which is educating tens of thousands of underserved Chicagoans, and a key supporter of Hope Toledo, now serving more than 300 families with tuition-free college and trade-school pathways. Pete is the Founder & Chairman of Warmer, a new social platform designed to create kind, supportive, and non-toxic peer-to-peer interaction. He also serves as Chairman Emeritus of StreetWise, one of Chicago’s largest homeless assistance organizations, and sits on multiple nonprofit and for-profit boards dedicated to social impact. Pete is a 2019 Henry Crown Fellow at the Aspen Institute, one of the most selective fellowship programs in the world, recognizing leaders who create ventures solving society’s most challenging problems. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Pete Kadens: https://www.linkedin.com/in/petekadens/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:19) Founding Green Thumb Industries and seizing opportunities in the cannabis industry (2:08) Focusing on profit and choosing unsexy locations (4:05) Targeting non-obvious customer segments and building partnerships (7:44) Creating a disciplined framework for employee autonomy and engagement (13:06) The importance and advantages of an employee ownership culture (18:54) Transitioning from business to philanthropy (19:47) Exploring different forms of wealth and personal fulfillment (24:11) Balancing business success with personal life and trade-offs (30:30) Role modeling, parenting philosophies, and teaching kindness (37:40) Pursuing excellence, discipline, and lessons from Aspen Institute fellows (41:41) Importance of suspending assumptions and embracing rest (43:37) Valuing idiosyncratic excellence and embracing neurodivergence (46:28) Turning aspirations into achievements and celebrating progress (49:09) Concept of the minimum lovable product and reflecting on success (50:44) Closing thoughts, gratitude, and how to follow Pete Kadens (51:14) Closing remarks

Nov 17

What separates elite CIOs from everyone else? In this solo-style deep-dive conversation, I sit down with Alan McKnight, Executive Vice President and Chief Investment Officer at Regions Asset Management, to unpack how one of the industry's most respected allocators makes decisions across public and private markets. Alan oversees investment strategy, risk management, and portfolio construction across the firm's full platform — and brings decades of experience from leadership roles at Truist, SunTrust, Equitable, and Morgan Stanley. We get into the realities of managing capital across different client types, how CIOs should think about illiquidity versus opportunity, where structural alpha truly comes from, and the process-driven framework Alan uses to separate skill from luck. If you're an allocator, founder, CIO, or LP, this episode lays out one of the cleanest mental models you'll hear on building durable long-term returns. Highlights: Why liquidity is the most misunderstood variable in portfolio construction How allocators overestimate what they actually need. The barbell playbook Alan uses to balance “hyper-liquid” and “hyper-private” exposures across client types. How to generate structural alpha by lowering fees and accessing co-investments without adding unnecessary risk. Why outcome-based thinking destroys CIO performance How process accountability creates compounding advantages. How to re-underwrite every position with brutal honesty, even when the mark looks terrible in the short term. The alignment problem: why CIO tenures don’t match fund cycles and what it means for long-term returns. The traits that separate world-class allocators from good ones Why the unsexy work often creates the most alpha. Alan’s advice to his younger self and the career decisions that would have accelerated his trajectory even further. Guest Bio: S. Alan McKnight, Jr., CFA is the Executive Vice President and Chief Investment Officer of Regions Asset Management, responsible for overall investment strategy, portfolio and risk management, and portfolio construction across $70BN in assets under management and $150BN in assets under advisement. He is Chairman of the firm’s Investment Working Group and serves on the Asset Liability Committee, regularly representing Regions as its chief spokesperson on markets with outlets including CNBC, Bloomberg, FOX Business, The Wall Street Journal, The New York Times, and CNN Money. Before joining Regions in 2015, Alan served as Head of Institutional Investments for Truist, Chief Investment Officer for SunTrust Institutional Investment Advisors, and held portfolio management roles at Equitable Asset Management and Morgan Stanley Asset Management. He holds a B.A. in Economics from Washington and Lee University, an MBA from the University of Texas at Austin, and the Chartered Financial Analyst designation. Alan has served on boards including the Alliance Theatre, Cherokee Garden Library, The New Normal Society, and the Woodruff Arts Center Investment Committee. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startupsuccess #openlp #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alan McKnight: https://www.linkedin.com/in/s-alan-mcknight-jr-cfa-2b69993/ Links Regions Bank: https://www.regions.com/personal-banking Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:05) Assessing illiquidity: willingness, capacity, and psychological aspects (3:28) Private investment access for smaller investors and alternatives market (6:42) Challenges for small and mid-sized managers in alternatives (8:07) Interval funds: characteristics and practicality (11:06) Liquidity needs and planning across market environments (18:07) Alpha generation, manager selection, and behavioral economics (22:45) Neurobiological and human bias in trading decisions (25:48) Illiquidity benefits and structural alpha in private markets (31:48) Liquidity management strategies and accountability in investing (37:19) Team dynamics and incentive alignment in institutional investing (42:00) Attracting and educating top investment talent (45:03) Leveraging AI in investment research (48:09) Evaluating and interacting with new managers (51:22) Trust and reunderwriting in investment relationships (54:10) Reflective advice and value in foundational tasks (56:21) Closing remarks

Nov 16

What happens when you’re forced to face your biggest fear? In this solo episode, David Weisburd shares a deeply personal reflection on how moments of crisis can become the crucible that forges strength, resilience, and clarity. Drawing inspiration from Lloyd Blankfein’s reflections on the 2008 financial crisis, David explores why confronting your greatest fears—rather than avoiding them—can transform you into a more powerful, anti-fragile version of yourself. From Joe Rogan’s public reckoning to founders who rebuilt stronger after near-death moments, this episode unpacks the paradox of hardship: how the moments that almost break you often become the foundation for your greatest breakthroughs. Highlights: Why your greatest fear may hold the key to your personal and professional growth What Lloyd Blankfein learned from leading Goldman Sachs through the 2008 crisis How Joe Rogan turned public backlash into renewed influence and clarity Why “manufacturing crisis” might reveal what truly limits you How top founders come back stronger from near-death experiences The mindset shift that turns fear into fuel for anti-fragility and leadership growth Host Bio: David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital. Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo). Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies. Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter:@dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.linkedin.com/company/weisburd-capital How I Invest: https://howiinvestpodcast.com/episodes Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:30) Reflection on Lloyd Blankfein's career, antifragility, and confronting challenges (2:42) Closing remarks

Nov 14

Can a 23-year-old Harvard dropout build the next billion-dollar company? In this episode, I talk with Steven Wang, founder and CEO of dub, a U.S. copy-trading platform that lets you automatically mirror the portfolios of real investors and traders. We get into why he thinks most retail investors won’t get good at stock picking, why the future is about picking people, not tickers, and how dub is trying to turn social-media-driven, mimetic trading into better financial outcomes. We also cover the retail trading boom, meme stocks, the “retail army,” what dub’s top creators actually do to generate alpha, and how a creator-led marketplace for strategies could reshape how the next generation builds wealth. Highlights: Why dub is America’s first regulated copy-trading platform and how it works The retail trading boom: meme stocks, FOMO, and 20–35% of daily volume coming from retail How Gen Z thinks about wealth, risk, and becoming a millionaire through investing What dub’s top creators actually do to generate alpha (micro-caps, swing trading, social influence) How momentum trading can become real value (GameStop, Opendoor, AMC) Steven’s founder journey: VR startup at 16, Harvard dropout, and raising $47M Leadership lessons: moving from micromanagement to mission-driven culture The Sisyphus mindset, meditation, and staying grounded during low moments What Steven would tell his 2021 self about reinvention, feedback, and patience Guest Bio: Steven Wang is the founder and CEO of dub, a regulated U.S. copy-trading platform that lets investors follow and automatically mirror the portfolios of real investors and creators. Dub is owned and operated by DASTA Inc., with advisory services provided by dub Advisors, LLC, an SEC-registered investment adviser, and brokerage services provided to retail customers by DASTA Financial, LLC, an SEC-registered broker-dealer and FINRA/SIPC member, with clearing through APEX Clearing Corporation. Dub has raised $47 million in total funding, including a $30 million Series A, and offers access to 200+ crowdsourced Creators with real, transparent track records that users can copy starting from small account sizes. Before founding dub, Steven built and sold a VR startup he began as a teenager, worked briefly at Apple, and attended Harvard before leaving to focus on dub full-time. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Steven Wang: https://www.linkedin.com/in/swangentr/ Links Dub: https://www.dubapp.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:14) Retail investors' underperformance and the thesis behind Dub (0:32) Historical context and explosion of retail trading (1:19) Cultural zeitgeist, social media, and trading during COVID-19 (3:12) Dub's mission post-2022 crash and entrepreneurial journey (5:15) Startups: Timing, market conditions, and young entrepreneurship challenges (7:23) Scaling the business, culture, and hiring practices (12:11) Anti-selling in interviews and wealth transfer to younger generations (14:32) Simplifying investing and the importance of trust in decisions (17:09) Broadening participation in wealth creation and investing habits (19:20) Operationalizing trends and building a marketplace of strategies (23:33) Impact of meme stocks and retail investor strategies (27:11) Legal strategies behind traders' success and building a strong network (35:50) Mindfulness, advice for entrepreneurs, and decision-making (38:23) Balancing ambition, patience, and clarity of vision in startups (41:00) Leadership strategies and the power of compounding efforts (41:28) Closing remarks

Nov 13

How do you turn whiskey barrels into an institutional asset class? In this episode, I sit down with Giuseppe Infusino, Chief Investment Officer and Managing Partner at InvestBev Group, to explore how a real asset like aged whiskey is quietly becoming one of the most uncorrelated and profitable investments in alternative markets. From his early years at RVK advising multi-billion-dollar allocators to managing institutional portfolios in a niche category few understand, Giuseppe shares how InvestBev has built an entirely new asset class from the ground up. We discuss the economics of whiskey aging, how barrel pricing creates asymmetric returns, and why alcohol performs differently across economic cycles. This conversation breaks down incentives, alpha generation, and how to educate LPs on emerging strategies long before they go mainstream. Highlights: The incentives that keep consultants from finding the “best and brightest” managers—and how RVK broke the mold Why 90% of RVK’s fund allocations were self-sourced, and how that approach drives better returns The conversation that led Giuseppe to co-found InvestBev—and how whiskey became a new institutional asset class The real asset characteristics of whiskey barrels—and why they appreciate over time like fine art How InvestBev’s analysis with Kellogg proved near-zero correlation between whiskey and traditional markets Why barrel investments deliver equity-like returns with half the volatility of equities How to educate LPs when creating a new asset class—and what early adopters get right Why InvestBev’s edge comes from deep beverage-industry relationships across Bacardi, Molson, and Coors The scaling lessons from Fund I to Fund V—and how institutional credibility compounds over vintages Why operational excellence, data, and early hiring decisions define fund longevity The best LP advice he ever received: “No investor ever complains about getting their money back.” Guest Bio: Giuseppe Infusino is the Chief Investment Officer and Managing Partner at InvestBev, where he leads the firm’s investment strategy, sourcing, diligence, and structuring processes across consumer brands, beverage services, and hard assets. Prior to InvestBev, he spent over a decade managing institutional investment portfolios for prominent allocators deploying multiple billions in private markets. He holds an MBA in Marketing & Entrepreneurship from the Kellogg School of Management, Northwestern University, and a B.S. in Finance & Real Estate from the University of Wisconsin-Madison. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Giuseppe Infusino: https://www.linkedin.com/in/giuseppe-infusino-331b198/ Links InvestBev: https://www.linkedin.com/company/investbev/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:30) Incentive structures in consulting and investment staff (3:20) Consultants and emerging managers (4:55) Sourcing and transitioning to bourbon investments (7:54) Market dynamics and correlation of bourbon investments (10:27) Asset allocation in bourbon investing (12:05) Educating LPs on bourbon investments (14:15) First mover challenges in new asset classes (16:21) Organizational influence on investment decisions (17:14) Economics of alcohol production (19:07) The three-tiered system in the alcohol industry (19:30) Lessons from starting and scaling a fund manager (21:11) Growth rates and transitioning to private credit (25:43) Operational investments and valuation models (28:27) Best LP advice and perspectives on capital return (31:01) Utilization of AI in investment strategies (33:14) Closing remarks

Nov 11

What separates great investors from generational ones—and how do you actually find the next Elon Musk? In this episode, I sit down with Mike Annunziata, Founder & Managing Partner of Also Capital, a solo GP fund backing the world’s most ambitious hard tech founders. Before launching Also Capital, Mike spent years at the Cornell University Endowment, helping allocate over $1 billion across venture and private equity managers—giving him a front-row seat to what “world-class” really looks like. We talk about how LPs identify the next top-decile fund managers, why the best founders are like amateur pilots, and how to find the tiny behavioral tells that separate the merely ambitious from the truly elite. From identifying credibility under pressure to understanding the physics of hard tech investing, Mike shares a rare, insider’s look at the art of backing outliers. Highlights: How working at the Cornell Endowment shaped Mike’s investor mindset and revealed what “world-class” really looks like The difference between top-quartile and top-decile managers—and why early risk-taking defines greatness Why founders who combine ambition with credibility are the ones who build generational companies What venture investors can learn from Bain Capital Life Sciences and the power of early conviction The “amateur pilot” framework: how to identify founders who take disciplined risks under pressure Why great founders are magnets for talent—and how followership predicts success more than ideas The difference between competitiveness, urgency, and toxic culture in startups How AI is transforming hard tech—from edge computing to design cycles What it takes to spot a breakout hard tech company before anyone else does Why discipline—not deal-chasing—is the real driver of long-term venture success Guest Bio: Mike Annunziata is Managing Partner at Also Capital, where he invests in and supports hard-tech companies solving atomic scale problems—across aerospace, defense, robotics, advanced manufacturing, communications, mobility, and applied AI. Since 2019 he’s seeded companies now valued at over $2 billion including Radiant, Varda Space, K2 Space, and Northwood, which have collectively raised over $500 million. Previously, Mike was Co-Founder & CEO of Farther Farms, a Series B startup out of Cornell University, and spent three years as Senior Investment Analyst at Cornell University’s Investment Office, allocating capital across venture and private funds. He holds a B.S. in Industrial & Labor Relations and an MBA from Cornell University’s Johnson Graduate School of Management. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mike Annunziata: https://www.linkedin.com/in/mike-annunziata-12853bb/ Links Also Capital: https://www.alsocapital.com Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:24) Understanding investment talent and managing risk (0:54) Identifying world-class funds and great managers (2:03) Example of early successful fund: Bain Capital Life Sciences (3:26) Building a brand and competitive advantage in investing (5:00) Traits of successful founders and top decile managers (8:02) Investment edge and volatility in venture strategies (12:27) Focus and diversification of Also Capital investments (16:54) Nonconsensus views and breaking down ambitious projects (19:04) High IQ and EQ in founders and early leadership signs (24:08) Competitiveness, sense of urgency, and mission-driven motivation (31:08) Impact of AI on hard tech startups and identifying big founders (36:08) Attracting top talent and advising young founders (41:10) Dynamics of high RPM vs. high gear in startups (44:20) Timeless advice and understanding pitfalls for new VCs (46:29) Balancing deal volume with founder quality and knowing your founders (52:19) Closing remarks

Nov 10

How do you turn purpose, legacy, and innovation into a single investing philosophy? In this episode, I speak with Sara Crown Star, Venture Partner at FemHealth Ventures and President of SCS Innovations. Sara shares how her experience growing up in one of America’s most prominent families shaped her values as an investor and why she believes the next trillion-dollar opportunity lies in women’s health. We discuss the evolution of FemHealth Ventures’ investment thesis, the creation of the “FemHealth Framework,” and how it’s redefining what women’s health means across drugs, devices, diagnostics, and AI-driven solutions. Sara also shares personal stories from her family’s legacy—how values like integrity, community, and purpose continue to drive generational success. Highlights: How FemHealth Ventures is redefining women’s health through the “FemHealth Framework” How AI and data analytics are transforming fertility outcomes through Cercle, backed by Sheryl Sandberg Why innovation in postpartum depression could save lives—and how Reunion Neuroscience is pioneering new treatment paths The overlooked investment opportunity in women’s health—and how half the population remains underrepresented in clinical trials until 1993 What the Crown family’s story teaches about values, reputation, and resilience across generations The founding lessons of Henry Crown during the Great Depression—and why character still compounds How the Henry Crown Fellows Program at the Aspen Institute turns success into significance Why purpose and meaning unlock the “sixth gear” for investors and founders Advice for future generations: raising independent thinkers, building genuine friendships, and preserving family values Guest Bio: Sara Crown Star is a Venture Partner with FemHealth Ventures, a top-decile VC firm with $100 million in AUM, focused on advancing innovations in women’s health. FemHealth Ventures invests in companies developing drugs, devices, diagnostics, and digital/AI-enabled solutions. Sara is also president of SCS Innovations, which connects entrepreneurs with capital to bring new technologies to market. She serves on the board of 1871 (Chicago’s entrepreneurial hub), is a life trustee of the Erikson Institute, and is President of the Colonel Henry Crown Scholarship Fund. She is also a director of Musicians on Call, the Jewish United Fund of Chicago, the Ortus Foundation, and the Crown Family Foundation. Sara graduated with a B.S. from the University of North Carolina at Chapel Hill and a J.D. from Georgetown University Law Center. She also completed the Wexner Heritage Program and received an Executive M.B.A. from Northwestern’s Kellogg School of Management. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Sara Crown Star: https://www.linkedin.com/in/saracrownstar/ Links FemHealth Ventures: https://www.femhealthventures.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:18) Sara's passion for women's health and career beginnings (2:34) Investment highlights: Gynesonics and Reunion Neuroscience (7:28) Women's exclusion in clinical trials and market potential (9:13) Future trends and family values in women's health investing (14:08) Community impact and the role of purpose in success (22:23) Challenges of prominence and wealth management in the Crown family (25:23) Closing remarks

Nov 9

Why are we wired to chase quick wins instead of lasting breakthroughs—and how can investors reprogram that bias? In this third solo episode, David Weisburd unpacks the neuroscience of decision-making and how understanding dopamine can dramatically change the way you operate as an investor, founder, or builder. Drawing on insights from his conversation with Dave Fontenot of HF0, David explains why long-term rewards (“slow dopamine”) create compounding advantages while short-term hits (“fast dopamine”) destroy focus. He shares tactical strategies for building “monk mode” systems that protect deep work, how to avoid the illusion of productivity, and why the most valuable ideas require discomfort and delay before payoff. This episode is about rewiring your brain for compounding—not con Highlights: How fast dopamine (short-term gratification) undermines long-term focus Why slow dopamine is the neurological key to compounding performance How to structure your day for deep work and “monk mode” productivity Why checking emails or chasing small wins creates addictive behavior loops How to identify the most important, non-urgent tasks that create 10x leverage Why most founders confuse activity with progress—and how to fix it The mental models behind HF0’s ability to 20x ARR in just 12 weeks How to replace short-term dopamine hits with long-term focus triggers What Ryan Hoover’s automation philosophy teaches about time leverage How to act “slow” in a world addicted to fast—and win over decades Host Bio: David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital. Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo). Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies. Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter:@dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.linkedin.com/company/weisburd-capital How I Invest: https://howiinvestpodcast.com/episodes Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (3:50) Aligning business goals with slow dopamine and differentiating career paths (4:59) Ryan Hoover's approach to problem-solving and long-term efficiency (6:53) Dramatic upside of slow thinking and human evolution (7:08) Closing remarks

Nov 7

How do you democratize access to private markets and what happens when everyone can invest like a VC? In this episode, I sit down with Kendrick Nguyen, Co-Founder and CEO of Republic, the global platform that’s opened up private investing to over 3 million people across 150 countries, facilitating more than $2.6+ billion in transactions. We unpack how tokenization, fractionalization, and regulatory innovation are reshaping private markets. Kendrick explains how Republic is bridging the gap between institutions and retail investors, what tokenized SpaceX and OpenAI shares mean for the future of liquidity, and why the next evolution of finance is about participation—not speculation. Highlights: How tokenization creates a faster, cheaper, cross-border infrastructure for capital markets Why retail participation in private markets remains shockingly low—and how Republic is changing that How Robinhood’s tokenized SpaceX and OpenAI campaign boosted stock performance and retail awareness The $150 trillion opportunity in retail capital waiting to enter private markets Inside Republic’s partnership with Hamilton Lane to open institutional funds to everyday investors Why tokenization could make private equity more profitable than public equities How Republic balances legal engineering, regulation, and innovation to stay ahead in fintech The social side of investing: why “return on experience” can be as powerful as ROI How fractional ownership can restore optimism and access to the American Dream Why fintech founders must partner—not fight—with regulators to scale safely Guest Bio: Kendrick Nguyen is the Co-Founder & CEO of Republic, a global platform for investing in private markets. Before launching Republic in 2016, he served as General Counsel at AngelList, leading regulatory affairs and international expansion. He has also co-founded CoinList and held prior roles at The Permal Group and Kanbar Enterprises, and has been a Fellow at Stanford Law School and the Rock Center for Corporate Governance. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Kendrick Nguyen: https://www.linkedin.com/in/kendrick-nguyen-7145bb5/ Links Republic: https://republic.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:45) Retail participation and barriers in private equity (2:51) Access and liquidity issues in private markets (4:25) Social good and gateway products for tokenization (7:25) Robinhood's token giveaway and market impact (11:08) Mirror tokens, regulatory aspects, and partnerships (15:28) Growth in private equity and market disruption comparisons (20:18) Republic's evolution and influencer engagement (26:07) Learning to invest through small investments (31:26) Changing American dream and investment excitement (34:09) Social component and future of crowdfunding (40:52) Legal expertise and regulatory collaboration in fintech (45:44) Launching tokens and long-term investment benefits (50:51) Personal success stories and overcoming obstacles (57:24) Timeless advice and closing remarks (59:39) Closing remarks

Nov 5

Can founders 10x their progress in 12 weeks? In this episode, I speak with Dave Fontenot, Founder of HF0, a groundbreaking startup residency that’s redefining how AI companies are built. HF0’s model—part hacker house, part monastic focus—is based on the idea that startups grow fastest when founders eliminate every distraction and operate in uninterrupted flow. Dave explains how the residency model is helping founders make “two years of progress in 12 weeks,” why the most dangerous distraction is the second most important thing in your business, and how recursive subtraction leads to breakthrough realizations. We discuss what true flow looks like, how competition in AI has changed company-building forever, and why the next generation of founders will work like athletes in training camp. Highlights: How HF0 redefined startup acceleration by replacing addition with subtraction Why the most insidious distraction for founders is the second most important thing in their business How residency-based company building leads to “a year or two of progress in 12 weeks” The psychology behind avoidance—and why even elite founders escape the hardest problems How AI changes the calculus of startup speed by compressing iteration cycles Why “flow compounds” and how context continuity multiplies productivity The secret to building software 10x faster: protect the compound return of uninterrupted work Why empathy and trust—not specs—create products with soul How HF0’s model is spreading globally, spawning a new generation of residencies Practical ways to create “HF0 Lite” in your own life—down to ordering routines and workspace design Guest Bio: Dave Fontenot is the Founder and CEO of HF0, a residency program designed for exceptional founders building the next generation of AI and software companies. At HF0, he helps entrepreneurs compress years of progress into months by creating an environment of deep focus, trust, and accountability. Before HF0, Dave co-founded Backend Capital, an early-stage venture fund backing developers and technical founders, and was one of the key builders behind MHacks, one of the largest collegiate hackathons in the United States. He began his career as a software engineer and community builder, working with some of the world’s most ambitious early-stage founders. Dave’s work sits at the intersection of engineering, psychology, and company building—and he’s become one of the leading voices shaping how high-performing startup teams operate in the AI era. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Dave Fontenot: linkedin.com/in/davefont Links HF0: https://www.hf0.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:32) Historical examples of residency formats in company building (1:01) Overview of the eleventh batch at HF0 (2:21) The principle of subtraction in HF0 (4:01) Role of AI in increasing the rate of realizations (5:21) Practical examples of subtraction in maintaining flow state (7:06) Focusing on the most important business lever (9:01) Success stories and collaboration with investors at HF Zero (12:37) Psychological aspects of task avoidance (17:26) Adaptability of AI-driven startups (18:50) Infinite potential for AI innovation (20:27) The compound return of flow state on productivity (24:02) Flow state comparison to jazz and surfing (27:21) Continuous context in software development (29:07) Identifying valuable AI products (31:09) Building trust and empathy with AI tool users (31:48) Implementing HF0 principles in daily life (34:07) The rise of residencies in early-stage venture (36:03) Auditing interruptions to maintain flow (38:49) Focusing on high-impact tasks (40:13) Competitive nature of AI and residency programs (41:40) Superior company building through residencies (42:43) Practical steps for focus and productivity (43:51) CEO's role in problem-solving (44:21) Closing remarks

Nov 3

How do you train the next generation of allocators—and what separates elite investment offices from the rest? In this episode, I speak with Alex Ambroz, Founder and CEO of the Allocator Training Institute, whose mission is to professionalize allocator education. Alex has spent his career building and leading investment teams across Morgan Creek, J.P. Morgan, Cleveland Clinic, Aberdeen, and now as the founder of Allocator Training Institute. We dive into the evolution of the endowment model, how allocators detect hidden risk, the difference between true alpha and disguised beta, and why collaboration—not competition—is the secret to better portfolio outcomes. Alex also explains how today’s top allocators use data, relationships, and operational excellence to stay ahead of market shifts. Highlights: How Morgan Creek brought the endowment model to the broader OCIO world and scaled to $10 billion AUM Why early adopters of new strategies share the same psychographic traits as elite innovators How allocators spot “fake alpha” hidden behind high beta exposure and factor drift Why most allocators still don’t go beyond CAPM beta—and how that hides systemic risks How the best teams operationalize everything so analysts can focus purely on analysis Why top allocators collaborate instead of compete—and how peer groups share best practices How to build trust through transparency, discretion, and consistency across relationships What allocators really look for in on-site due diligence—down to the parking lot test How great GPs educate allocators by simplifying complexity without dumbing it down Why asking the right questions is a bigger edge than having all the answers Guest Bio: Alex Ambroz is the Founder and CEO of the Allocator Training Institute, the first structured education platform dedicated to developing the next generation of institutional allocators. Before founding ATI, Alex spent two decades in senior investment roles at Morgan Creek Capital, J.P. Morgan, Cleveland Clinic, and Aberdeen Standard Investments, where he built and managed multi-asset portfolios across public and private markets. He has trained hundreds of analysts and investment officers globally and holds deep expertise in portfolio construction, factor modeling, and operational due diligence. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Ambroz: https://www.linkedin.com/in/alexambroz/ Links Allocator Training Institute: https://allocatortraining.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:48) Alex Ambroz's career journey and experience at Morgan Creek (3:16) Endowment model, early adopters, and identifying alpha versus beta (10:30) Fama-French model, factor analysis, and characteristics of forward-thinking LPs (17:50) Collaboration among top allocators and the non-zero-sum nature of asset allocation (25:05) Andy Golden's perspective on allocator influence and fund evaluation (28:10) Operationalizing new asset classes and the importance of asking the right questions (34:02) On-site visits versus Zoom meetings and red flags in operational due diligence (41:47) Effective communication between GPs and LPs and the Allocator Training Institute (49:09) Target audience for Allocator Training Institute and revisiting the infinite game of investing (53:32) Closing remarks

Nov 1

What separates the good investors from the great ones? In this 2nd solo episode, David Weisburd shares the three rules that every world-class investor follows—rules that have nothing to do with IQ, luck, or access, and everything to do with how they think, use time, and define their game. Drawing on hundreds of private conversations with elite fund managers, David breaks down why consistency is overrated, how to buy back your time, and why clarity about your “game” might be the biggest competitive edge of all. If you’re an investor, founder, or builder looking to sharpen your mental model, this episode offers a rare inside look at the mindset of the best in the business. Highlights: Why the best investors don’t care about being consistent—they care about results How cognitive dissonance becomes a superpower in a world that changes daily Why responding to every email is a lie—and what true time management looks like How guarding your time like a hawk directly increases business revenue Why great investors define their “buy box” with boring specificity—and win because of it How clarity about your game protects your time and attracts the right deals What top investors do differently when it comes to decision filters and opportunity flow Host Bio: David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital. Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo). Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies. Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter:@dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.linkedin.com/company/weisburd-capital How I Invest: https://howiinvestpodcast.com/episodes Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:19) Cognitive dissonance and guarding time in top investors (1:39) Specificity and clear investment criteria (2:09) Closing remarks

Oct 31

What happens when an investor treats crypto like software infrastructure, not speculation? In this episode, I sit down with Avichal Garg, Co-Founder and Managing Partner of Electric Capital, to unpack the evolution of crypto investing—from speculative hype cycles to infrastructure that powers the next era of the internet. Avichal explains how Electric Capital measures developer activity across blockchain ecosystems, why he believes the next trillion-dollar opportunities are being built quietly by open-source engineers, and how software-based incentives will transform everything from finance to governance. We discuss the reality of investing through crypto winters, the rise of modular blockchains, the lessons learned from building at Google and Facebook, and how AI and decentralization are beginning to converge. Highlights: How Electric Capital built the most comprehensive developer data set in crypto Why tracking engineers is a better signal than token price or TVL How Avichal differentiates between speculation and true infrastructure investment Why open-source software is the backbone of the next financial system How Electric measures developer retention and ecosystem health across chains Why crypto winters are the best time to back new protocols and founders How decentralization and AI will intersect to create new governance models Why the future of crypto is about composability, not maximalism How venture capital must evolve to serve protocol-based companies Why patience and conviction separate enduring investors from trend followers Guest Bio: Avichal Garg is the Co-Founder and Managing Partner of Electric Capital, a venture firm investing in builders of decentralized networks, infrastructure, and developer tools. Before launching Electric Capital, Avichal founded Spool (acquired by Meta) and previously held senior roles at Google and Facebook, where he helped scale some of the most widely used consumer products on the internet. He is recognized for pioneering a data-driven approach to crypto investing—using developer activity, GitHub commits, and open-source metrics to identify early momentum in blockchain ecosystems. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Avichal Garg: https://www.linkedin.com/in/avichalgarg/ Links Electric Capital: https://www.electriccapital.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:26) Introduction with guest Avichal Garg (1:30) Electric Capital's inception and trust in investing (6:01) Long-term trust, integrity, and alignment in partnerships (10:00) Future opportunities for new General Partners (13:43) Electric Capital's investment thesis and engineer necessity (19:10) Disruption of TradFi by crypto and regulatory moats (23:32) Coinbase's potential and crypto prediction markets (29:42) Crypto's integration and stablecoins' market dynamics by 2030 (35:11) Bitcoin valuation and dollar depreciation (39:09) Asset allocation in high growth tech and inflation strategies (44:46) Lived experience vs. CPI, economic and tax policy impacts (50:07) Middle class plight and social contract solutions (52:52) Policy, AI, and robotics in shaping the future (54:06) SEC regulations and digital assets (56:04) Investing advice: patience and resource management (58:55) Market participation and timing strategies (1:02:12) AI's limitless potential and US economic leadership (1:03:09) Closing remarks

Oct 29

How do you build trust in an industry that’s built on auctions and price maximization? In this episode, I speak with Melvin Hibberd, Chief Investment Officer of Hunter Point Capital, about how the firm is redefining GP stakes investing through proprietary partnerships, structural creativity, and long-term alignment. Melvin takes us inside the evolution of GP stakes—from his pioneering work at Blackstone Strategic Partners to launching Hunter Point—and shares how he avoids auction dynamics that distort relationships, what truly drives alignment between investors and GPs, and why patience, not speed, builds lasting value. We cover everything from bespoke deal structuring and evergreen capital to portfolio construction, procurement savings, and the next phase of mid-market growth. This conversation is a masterclass in how to partner with GPs the right way. Disclaimer: This podcast is provided for general and educational purposes only and is not intended to constitute legal, tax, securities or investment advice or a recommended course of action in any given situation. All opinions and views constitute our judgments as of the date of production and are subject to change at any time without notice. This information is provided for illustrative purposes only and is not a prediction, projection or guarantee of future performance. All investing is subject to market risk, including the loss of principal. Highlights: How Hunter Point entered the GP-stakes market nearly a decade after the first movers—and why timing still mattered Why auctions distort alignment and how proprietary relationships build long-term trust How Hunter Point targets 10–25% ownership stakes while keeping founders in control Why independence and focus on GP stakes (not competing asset classes) create cleaner alignment How bespoke structures—carry attachments, earn-outs, and yield features—bridge valuation gaps Why evergreen capital matches the long-term nature of GP partnerships How proprietary origination becomes a flywheel of trust, referrals, and inbound deal flow Why procurement platforms, credit solutions, and strategic advice create measurable LP value How Hunter Point defines “mid-market” GPs and why sector specialists are the next alpha engines What causes GP-stake deals to fail—and how to avoid misalignment and mediocre partnerships Why patience, education, and “strategic patience” are the rarest skills in private markets Guest Bio: Mr. Hibberd is a Managing Director and serves as Chief Investment Officer at Hunter Point Capital. Prior to joining HPC, Mr. Hibberd served as a Managing Director and Member of the Investment Committee within The Blackstone Group’s (“Blackstone”) GP stakes business, Strategic Capital Holdings. During his seven years at Blackstone, Mr. Hibberd facilitated key transactions and was responsible for deal team coordination, due diligence, term negotiation, and execution. He also supported the Group’s origination effort, helping to source proprietary investment opportunities for the firm. Prior to Blackstone, Mr. Hibberd was an Associate in KKR & Co.’s North American Private Equity Group and an Associate in Goldman Sachs’ Global Natural Resources Group. Mr. Hibberd earned his M.B.A. from Harvard Business School and his degree in Engineering from Cambridge University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Melvin Hibberd: https://www.linkedin.com/in/melvin-hibberd-bab4b018b/ Links Hunter Point Capital: https://www.hunterpointcapital.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:50) Welcome and Guest Introduction: Melvin Hibberd (0:58) Hunter Point's Market Entry, Strategy, and Competitive Edge (7:24) Structuring Deals, Aligning Interests, and Evergreen vs Fixed Term Funds (14:40) Proprietary Deal Sourcing, Portfolio Impact, and Differentiation Strategies (20:24) Portfolio Construction, Mid Market Significance, and LP Concerns (28:39) Benefits of GP Stakes, Investment Types, and Failure Reasons (36:53) Key Man Risk, Alignment, and LP-Driven Sourcing (43:27) Lessons from Launching Hunter Point and Ideal Deal Characteristics (48:23) Timeless Advice for Young Professionals (50:09) Closing remarks

Oct 27

David Weisburd had a chance to witness live the conversation between Jack Kokko, Founder & CEO of AlphaSense, and Lloyd Blankfein, former Chairman and CEO of Goldman Sachs, during AlphaSummit 2025 in New York City. In this wide-ranging discussion, Jack draws out Lloyd’s reflections on his early years in Brooklyn, his path to leading Goldman Sachs, and the lessons learned from steering the firm through periods of volatility and transformation. Together they explore how leadership, risk, and technology continue to shape Wall Street—and what it takes to stay adaptable in an ever-changing world. Highlights: How Lloyd’s early life in Brooklyn influenced his leadership style Lessons from being rejected by Goldman Sachs — and eventually running it Guiding Goldman through the 2008 financial crisis and its aftermath The value of partnership culture and communication in high-performance teams The changing dynamics of Wall Street amid AI and automation Balancing risk, intuition, and data in modern decision making The evolving relationship between private and public markets Lloyd’s reflections on adaptability, market cycles, and staying ahead of change Guest Bio: Lloyd Blankfein served as the Chairman and CEO of Goldman Sachs from 2006 to 2018, leading the firm through the global financial crisis and major transitions in global markets. He remains an influential voice on economic leadership, risk management, and the future of finance. Host Bio: Jack Kokko is the Founder and CEO of AlphaSense, a market intelligence and search platform used by financial institutions and corporations worldwide. His work focuses on advancing decision making through AI-powered information discovery. Learn more about AlphaSense and upcoming AlphaSummit events at: alpha-sense.com. (0:00) Introduction (1:46) Lloyd Blankfein's Early Career and Decision-Making Reflections (7:13) Leadership, Communication, and Managing Teams (10:27) Evolution of Wall Street and Technological Impacts (15:30) Automated Trading: Risks and Trust in AI (19:23) Investment Banking Risk Control and Balancing Innovation (21:48) Thought Experiment: Starting a New Investment Bank (24:12) Equity Market Evolution and the Rise of Private Markets (31:18) Big Picture Market Changes and Future Speculations (34:25) Advice for Investors in an Evolving Market (36:12) Closing remarks

Oct 24

How do you invest when it’s “too early for data”—but just right for conviction? In this episode, I speak with Vivek Ladsariya, Managing Director at Pioneer Square Labs (PSL), about what it really takes to back founders before traction, before funding rounds, and sometimes even before incorporation. Vivek shares how he partners with founders as a thought partner instead of a coach, why iteration trumps ideas, and how efficiency and automation have rewritten what it means to earn a Series A today. From early-stage pattern recognition to AI-driven productivity and new definitions of founder resilience, this conversation is a masterclass in what “being early” actually means in 2025 Highlights: How investing “too early” often creates the strongest long-term alpha Why the best investors act as thought partners, not back-seat CEOs How ego, relentlessness, and intellectual honesty predict outlier founders Why great ideas matter less than constant iteration and customer focus How Series A benchmarks have shifted to roughly $7 million ARR—and what it means for founders Why AI is the new leverage for coding, sales, and operations efficiency How language itself has become code, allowing anyone to automate with LLMs How PSL’s studio + fund model accelerates founders from zero to one Why small, elite teams outperform larger organizations in the AI era How becoming a parent sharpened Vivek’s priorities and patience as an investor Guest Bio: Vivek Ladsariya is a Managing Director at Pioneer Square Labs (PSL), where he leads pre-seed and seed investments out of PSL Ventures Fund II ($100 million), focusing on AI, cybersecurity, infrastructure, industrial tech, and DevOps. Before joining PSL, he was a General Partner at SineWave Ventures and an entrepreneur behind ventures such as GameGarage and Moyyer. His investments include Databricks, Rescale, Osaro, and Evolv Technologies (NASDAQ: EVLV). Vivek holds an MBA from Yale University and a B.E. from the University of Mumbai. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Vivek Ladsariya: https://www.linkedin.com/in/vivek-ladsariya-8a828535/ Links Pioneer Square Labs: https://www.linkedin.com/company/pioneer-square-labs/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:06) Evolution of programming languages and business automation (1:05) Welcome and guest introduction (1:16) Investing early in startups and the role of a VC (4:17) Creating value in startups and being an effective thought partner (7:11) Handling crises, feedback, and the role of ego in startups (11:27) Ray Dalio's concept of believability and startup ideas (18:22) Customer pain points and the idea maze (21:17) Predicting entrepreneurial perseverance and evaluating founders (24:44) Iterating startup ideas and future Series A expectations (35:16) The impact of AI on programming and business processes (42:56) Preparing skills for a post-AI world (46:14) Pioneer Square Labs and thoughts on seed strapping (50:52) Advice to a younger self and the impact of life changes on investing (57:07) Closing remarks

Oct 22

How does an $8B venture platform turn a 650-fund network into a repeatable co-investing edge? In this episode, Jonathan Roosevelt, Managing Director at Industry Ventures, explains how the firm evolved from a pioneer in venture secondaries into a platform combining secondaries, co-investments (directs), fund-of-funds, and tech buyout—with AUM “a little over $8B” and 25+ years in market. We break down why Series A/B/C co-investing requires a different lens than seed, how believability guides which GPs get a “stamp” for later-stage deals, and why customer calls are ground truth when underwriting mid-stage businesses. Jonathan also shares how asymmetric information and inflection points create true co-invest alpha—and when to ignore comps for N-of-1 companies. Highlights: $8B platform: Secondaries, co-invests, fund-of-funds, tech buyout 650-fund network: ~250 primaries, ~400 via LP secondaries Co-invest engine: 100% sourced from seed/early GP relationships Seed vs. mid-stage: PMF stories vs. durable unit economics Believability lens: Repeatable process before a later-stage “stamp” Ground truth: Independent customer diligence over CEO references Asymmetry & inflection: Board insights at turning points drive edge Do the unscalable: Sector depth, real customer intros, hands-on help N-of-1 underwriting: Backcast valuation from end-state outcomes Guest Bio: Jonathan Roosevelt is a Managing Director at Industry Ventures, where he focuses on originating, valuing, and managing primary fund commitments, early secondary LP stakes, and direct company investments within the firm’s Direct & Partnership Holdings strategies. Previously a Venture Partner at Industry Ventures (2017), he was promoted to Managing Director in 2019; earlier, he founded and led companies, was an early employee/VP of Sales at SoFi, and invested as an angel in Fitbit. He holds an MBA and BA from Harvard. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jonathan Roosevelt: https://www.linkedin.com/in/jroosevelt/ Links Industry Ventures: https://www.industryventures.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:04) Customer feedback's impact on investments (1:03) Industry Ventures' co-investment strategy (3:44) Co-investment opportunity lifecycle (7:19) Assessing investment manager credibility and diligence (17:14) Identifying exciting co-investment opportunities (19:47) Triangulating information for investment decisions (23:04) Customer enthusiasm in the investment process (27:16) Relationship significance in investment decisions (29:34) Operator vs investor perspectives in venture capital (34:01) Risk management for seed stage investments (37:10) Competing as an emerging manager in venture capital (38:43) Valuation strategies for new venture capitalists (41:18) Closing remarks

Oct 20

What if the U.S. dollar’s dominance has already ended—and we’re just living through the lag? In this episode, I sit down with Balaji Srinivasan, one of the most original thinkers in technology and finance, to unpack his boldest prediction yet: the death of the dollar and the rise of a digital, decentralized global economy. Balaji explains how inflation, weaponized finance, and technological sovereignty are accelerating a massive shift away from traditional monetary systems—and why crypto, AI, and network states could define the next reserve paradigm. We go deep into why he believes the internet will replace the nation-state, how founders can build parallel institutions from scratch, and why opting out—not lobbying—is the only path forward. This is not a doomsday take. It’s a blueprint for builders who believe the future is already here. Highlights: The Network State: How online communities will evolve into sovereign cities. From Crypto to Cities: Why blockchain can fund and govern real-world nations. The Balaji Fund: Backed by Brian Armstrong, Marc Andreessen, and David Sachs—investing in “techno-radicals.” Replacing Broken Systems: How founders can build alternatives to failing institutions like education, healthcare, and media. Lessons from China: What the U.S. can learn from China's manufacturing and infrastructure speed. India’s Decade: Why Balaji believes India is becoming the new global tech engine. High-Risk Seed: Why his investment strategy targets contrarian, world-changing founders. From Bitcoin to Benchling: Inside Balaji’s personal portfolio and his “index the outliers” approach. The Frontier Mindset: How today’s founders can reclaim the spirit of Silicon Valley’s pioneers. Opt-in Capitalism: Why the future of governance will be voluntary, networked, and global. Guest Bio: Balaji S. Srinivasan (born May 24, 1980) is an American entrepreneur, investor and author. He co-founded genetic-testing firm Counsyl and led cryptocurrency company Earn.com before becoming first CTO of Coinbase and a General Partner at Andreessen Horowitz. He holds a BS, MS and PhD in Electrical Engineering and an MS in Chemical Engineering from Stanford University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Balaji Srinivasan: https://www.linkedin.com/in/balajissrinivasan/?originalSubdomain=sg Links Balaji Srinivasan: https://en.wikipedia.org/wiki/Balaji_Srinivasan Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (3:24) Steps to create a new country and the concept of network states (7:18) The Internet's transformative impact and decentralized countries (10:41) Crypto tribalism and Bitcoin's economic role (14:13) Cryptocurrencies as emerging digital nations (17:42) Government inefficiencies and the future of democracy with digital currencies (21:27) The evolution of capitalism and democracy (23:37) The role of DAOs in digital governance and network states (31:09) Utilizing crypto for crowdfunding and real estate (35:01) Introduction to the Balaji Fund and investment strategies (38:15) Technological solutions for societal problems (41:16) Profit maximization aligned with values and addressing Baumol's cost disease (45:03) Regulatory challenges in healthcare and childcare (47:34) DAOs' potential in real estate and community formation (51:20) Translating digital processes into physical communities (54:16) Balaji Fund's investor alignment and societal impact (1:02:21) Government, technology, and cost dynamics (1:06:20) Political pressures and pension paradoxes in investments (1:09:15) Diagnosing inefficiencies in real estate and construction (1:11:17) China's strategic advantages and US challenges (1:15:17) US-China strategies and the American dynamism dilemma (1:25:26) US political and social divides, government failures, and potential solutions (1:27:49) Competing with traditional institutions through innovation (1:30:20) Addressing societal issues with technology and portfolio construction (1:32:37) Investing in high-potential founders and the rise of Indian tech talent (1:35:28) Global capital impact of crypto and cybersecurity importance (1:37:14) Balaji's investment strategy and notable successes (1:41:33) Closing remarks

Oct 17

What happens when one of tech’s best community builders turns his playbook on venture capital itself? Ryan Hoover — the founder of Product Hunt and Investor at Weekend Fund — joins me to unpack how he’s reinventing early-stage investing. From building one of the internet’s biggest startup communities to managing a fund with 360+ LPs, Ryan shares the hard-won lessons on productizing VC, scaling systems as an introvert, and finding founders who hold true “earned secrets.” We dive into his journey from launching Product Hunt to building Weekend Fund’s third vehicle, how he thinks about portfolio construction, why weird ideas often win, and what it really takes to back the next generation of breakout founders. Whether you’re a founder, operator, or investor — this episode is packed with insights on scaling yourself, spotting alpha before it’s obvious, and turning community into competitive advantage. Highlights: How Ryan built Product Hunt into a launchpad for over 100,000 startups. The story behind raising from 360+ LPs — and why one investor literally became a monk. Why Weekend Fund prefers staying small to keep conviction high. The psychology of “weird” investing — and why strange ideas often outperform. How Ryan productized LP intros and scaled value-add through software. Why the best investors give without expecting anything in return How to build a scout network that multiplies your reach without adding complexity. The key traits of elite super connectors (and why Ryan doesn’t see himself as one). Why founders with “earned secrets” beat consensus every time. Ryan’s one piece of advice to his younger self before launching his first fund. Guest Bio: Ryan Hoover is the Founder and Investor at Weekend Fund, an early-stage venture capital firm investing in founders with earned secrets—deep insights derived from firsthand experience. Weekend Fund has raised three funds and invested in over 100 startups globally, including Deel, Replicate, and Rally, backed by a diverse community of more than 360 limited partners. Before founding Weekend Fund, Ryan founded Product Hunt, the platform that helped launch tens of thousands of startups and shaped how the tech world discovers new products. He has since focused full-time on building a new venture model centered around community, transparency, and product thinking. Stay Connected: X / Twitter: David Weisburd: @dweisburd Ryan Hoover: @rrhoover LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ryan Hoover: https://www.linkedin.com/in/ryanrhoover/ Links Weekend Fund: https://www.weekend.fund/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:14) Secrets, lived experience, and productizing LP intros (1:51) Fundraising challenges and LP base management (3:07) Downsides and expectations with 360 LPs (6:31) Venture capital as a product and Weekend Build experiment (9:10) Rolodexer success and becoming an elite super connector (14:18) Using value add to win deals and portfolio construction strategies (22:10) Ryan Hoover's LP activities, SPVs, and strategic investments (26:11) Scaling productivity and weekend partners program (29:17) Transparency and investing in non-consensus companies (37:42) Information diet, advice to younger self, and early strategies (42:00) Best product importance vs. portfolio construction and market changes (43:32) Managing a large portfolio and scaling support with tools (44:14) Closing remarks

Oct 15

Why are Institutional Investors betting big on Private Markets? Franklin Templeton oversees more than $1.6 trillion in assets, with over $260 billion dedicated to private markets. But what’s driving this massive shift — and how are the world’s largest allocators navigating liquidity, valuations, and the next era of private credit? In this episode, I speak with John Ivanac, Head of U.S. Institutional Alternatives at Franklin Templeton, to uncover how the firm is positioning itself for the next decade of alternative investments. We explore the evolution of private markets post-GFC, the consolidation wave among asset owners, and why liquidity, governance, and strategy selection are becoming more critical than ever. John also shares his perspective on Franklin’s acquisition strategy, how they integrate firms like Lexington Partners and Benefit Street Partners, and what it truly means to be a “trusted partner” to LPs in an increasingly complex market. Highlights: Structural Shifts: How regulation and capital formation reshaped private markets post-GFC Private Credit Boom: Why a $3.5T market could expand 10x in the next decade Secondaries Surge: Inside Franklin’s bet on Lexington Partners and the maturing PE ecosystem LP Consolidation: Why institutional allocators are backing fewer but deeper partnerships Holistic Partnerships: How Franklin Templeton redefines client alignment beyond products Digital Assets Strategy: Why the firm built a 60-person blockchain and crypto investment team Retail & Institutional Synergy: The future of democratizing alternatives responsibly Culture of Long-Termism: How generational leadership drives Franklin’s innovation mindset Guest Bio: John Ivanac is the Head of U.S. Institutional Alternatives at Franklin Templeton, where he focuses on expanding and managing the firm’s suite of Alternative Investment Solutions for institutional investors. John brings over 20 years of experience in the alternatives space, having previously served as Managing Director, Head of U.S. Consultant Relations at Partners Group and Global Head of Alternatives at BlackRock. He has also held senior leadership roles at The TCW Group, Scoggin Capital, and Barclays. He holds a J.D. from St. John’s University School of Law and a B.A. from Rutgers University, bringing a deep understanding of both the structural and human dynamics driving today’s institutional capital markets. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Ivanac: https://www.linkedin.com/in/johnivanac/ Links Franklin Templeton: https://www.franklintempletonglobal.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:59) Introduction to Franklin Templeton and private investment strategies (2:51) Drivers and opportunities in private market growth (7:15) Institutional investment and volatility in alternatives (14:44) Future outlook and building a significant portfolio (19:02) Acquisitions, strategic focus, and consolidation trends (21:51) Partnering and aligning with asset managers (25:46) Culture and long-term vision in expanding portfolios (28:46) Franklin Templeton's benefits for LPs and manager consolidation (35:58) Digital assets and balancing investor types (39:40) Retail market practices and investor education (45:38) Career advice and patience in investment (47:53) Building credibility, trust, and partnership roles (50:59) Addressing short termism in public markets (51:31) Closing remarks

Oct 13

Can a $324.3 billion wealth manager reinvent how high-net-worth investors access private markets? In this episode, I speak with Robert Picard, Head of Alternative Investments at Hightower Advisors, who is leading one of the industry’s most ambitious expansions into private markets. We discuss how Hightower is bringing institutional-grade research, access, and due diligence to individual investors, what the NEPC acquisition means for its alternatives platform, and how technology and AI are reshaping the way portfolios are built. Robert also shares lessons from more than 35 years of building multi-billion-dollar alternative platforms atThe Carlyle Group/Rock Creek, Optima Fund Management, RBC Capital Markets and State Street/InfraHedge, and explains why the future of wealth management will look more like an endowment model than ever before. Highlights: How Hightower is bridging institutional research with private-client portfolios The strategic rationale behind acquiring NEPC and its impact on Hightower’s platform Why private markets are still under-owned among high-net-worth investors The “democratization and miniaturization” of private markets and what that means for access Robert’s framework for allocating 10–30% of portfolios into private assets Why illiquidity can actually be your ally during market downturns How AI and technology will transform investment diligence and portfolio construction The evolution of independent wealth managers competing with Wall Street wirehouses Why maintaining curiosity, networks, and fun are keys to a 35-year investing career Guest Bio: Robert Picard is the Head of Alternative Investments at Hightower Advisors, where he leads the firm’s alternative investment platform and oversees research, due diligence, and portfolio design. He previously held senior roles building multi-billion-dollar alternative platforms at The Carlyle Group / Rock Creek, Optima Fund Management, RBC Capital Markets, and State Street / InfraHedge, and served as Head of Alternatives at First Republic Private Wealth Management. Robert has over 35 years of experience in global investing, with a background in equity derivatives, structured products, and private markets. He is widely regarded for his insights on the convergence of institutional and private wealth investing Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Robert Picard: https://www.linkedin.com/in/robpicard/ Links Hightower Advisors: https://hightoweradvisors.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:07) Hightower Advisors and NEPC Acquisition Strategy (2:33) NEPC's Research Benefits and Portfolio Differences (5:55) Democratization of Private Markets for Individuals (8:56) Private Asset Allocation Strategies (13:35) Illiquidity Benefits and Market Downturn Preparation (17:34) Long-Term Cybersecurity and AI Investment Strategies (23:06) The 2030 Asset Management Outlook (24:26) AI in Private Market Research and Growth Projections (28:40) Life Sciences Investment Opportunities (30:18) Independent Wealth Managers vs. Wirehouses (33:20) Evolving Role of Family Offices (36:00) Diversification in Private Markets and Future Trends (42:05) Technological Advancements in Private Markets (45:02) Managing Multiple Advisor Practices and Efficiency with AI (49:33) Career Advice for Young Professionals (51:11) Work-Life Balance and Industry Transformations (51:58) Closing Remarks and Future Podcast Plans (52:09) Closing remarks

Oct 10

If “fixed income is broken,” what are investors actually missing—and how should they rebuild the 40% to protect and compound through drawdowns? In this episode, I speak with Thomas E. Swaney II, former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, who oversaw more than $600 billion across global fixed income. Thomas explains why traditional bond allocations fail when it matters most, how to separate duration from credit risk, and how to use notional leverage to target true diversification without sacrificing liquidity. We explore the structural flaws in 60/40, how to design a fixed income portfolio that actually offsets equity drawdowns, and why the future of bond investing depends on better risk budgeting—not higher yield. Highlights: Fixed Income Is Broken: Why most bond portfolios don’t diversify when equities fall Rebuilding the 40%: Duration vs. credit and managing correlation through regimes Notional Leverage: Using treasury futures and IG CDX to build volatility with quality Risk Parity Framework: Allocating by contribution to risk, not nominal dollars Rebalancing Alpha: Liquidity and negative correlation as the real edge Curve Positioning: Why the belly of the curve often outperforms the long end Convexity Mismatch: Public vs. private assets and the lagged rebound effect Inflation Regimes: How correlation flips and when to incorporate TIPS Leadership & Culture: Lessons from Ellington and Northern Trust on process and debate The Next Decade: Bonds are relevant again—if built for resilience Guest Bio: Thomas E. Swaney II is the former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, where he had broad oversight of the $600+ billion fixed income platform, spanning business management, portfolio management, and strategy. As CIO, he chaired the Fixed Income Strategy Committee, guiding macroeconomic themes, risk budgeting, and portfolio construction across all fixed-income portfolios. He also served on Northern Trust’s Investment Committee and Executive Group within Asset Management. Prior to Northern Trust, Thomas held senior executive and portfolio management roles at J.P. Morgan Asset Management, Morgan Stanley Investment Management, OFI Global Asset Management, and Ellington Management Group. He holds a B.B.A. and M.B.A. with a concentration in corporate financial analysis, as well as an M.Sc. in Finance from the Kelley School of Business at Indiana University, and has more than 26 years of investment experience. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Thomas E. Swaney II: https://www.linkedin.com/in/swaneycio/ Links Factor Two Capital Management: https://brand.site/factortwocapital Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:48) Thomas Swaney's career and Miller Anderson's open debate culture (5:00) Challenges and impacts of open dialogue culture in investment firms (6:42) Education systems and their influence on investment thinking (7:47) Leadership vs. Investment Skills (9:40) Shifting Northern Trust's focus and lessons from Ellington (18:45) The role and strategies for fixed income in a diversified portfolio (23:35) Understanding market downturns and Bridgewater's equilibrium approach (27:24) Decomposing and maximizing efficiency in bond portfolios (33:56) Challenges and strategies with private assets in portfolios (38:40) The impact and use of leverage in investment portfolios (42:43) Introduction to Factor Two Capital Management (44:38) Exploring the relationship between volatility and expected values (49:16) Fed independence and market reactions to policy changes (51:35) Misconceptions about monetary policy and economic impact (53:04) Future outlook on fixed income versus equities and prediction markets (55:24) Closing remarks

Oct 8

What are the real playbooks behind managing an $86B alternative asset platform—and where do the next decade’s returns actually come from? In this episode, I sit down with Payton Brooks, Managing Director on Future Standard’s Primary Investments team, to unpack the operating system behind a multi-strategy LP: how a combined platform serves both institutions and the wealth channel, why mid-market private equity still offers the best shot at alpha, and how evergreen structures can reduce cash drag while preserving optionality. We cover sourcing (spinouts, emerging managers), what great GPs do in downturns, the co-invest / secondaries / credit toolkit, and the partnership behaviors that earn re-ups across multiple fund cycles. Highlights: Future Standard under the FS + Portfolio Advisors merger with ~$86B AUM How wealth clients access institutional alternatives via structured vehicles Mid-market outperformance vs. large-cap PE Operating depth and specialization as scale drivers Evergreen strategies reducing cash drag Anchor LPs as credibility signals Partnership transparency as LP/GP discipline Co-invest, secondaries & credit augmenting optionality Patience, credibility & compounding relationships Guest Bio: Payton Brooks is a Managing Director on Future Standard’s Primary Investments team, focusing on manager selection and portfolio construction across the private-equity landscape. He joined the firm in 2014, and holds a B.A. from Southern Virginia University and an MBA from the Yale School of Management. Future Standard is a global alternatives platform investing across private equity, credit, and real estate, serving both institutional and private-wealth clients; the firm rebranded from FS Investments in July 2025 following its combination with Portfolio Advisors in June 2023. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Payton Brooks: https://www.linkedin.com/in/paytontbrooks/ Links Future Standards: https://www.futurestandard.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:44) Client base and portfolio construction (1:40) Differences between high net worth individuals and pension funds (3:02) Access for high net worth investors to asset classes (4:05) Characteristics of successful private equity funds and large cap buyouts (9:21) Evaluating middle market managers and building relationships (16:40) Utilizing secondaries, co-investments, and internal team structure (19:01) Traits of elite superstar GPs and repeatable value creation (23:22) Decision-making process and portfolio construction within the buyout fund (28:39) Pension fund investment in Evergreen Fund mechanics and benefits (34:14) Evergreen Fund strategy, market impact, and comparison to drawdown funds (41:32) Challenges and strategies for emerging managers (44:02) Securing anchor investors and LP decision-making (47:58) Importance of time optionality in fund investments (51:08) Balancing early and late fund investments (53:20) Career reflections and advice to younger self (55:23) Enhancing investment knowledge and leveraging partners for insights (57:06) Closing remarks

Oct 6

Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors? In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out. Highlights: Investor ≠ fund manager: portfolio construction, firm-building, and 10–12 year horizons matter as much as deal picking. Durability over cycles: sometimes the right move is doing zero deals for ~12 months to avoid overpaying. Power laws require survival: stay in the game long enough to catch the outliers; size and pacing are part of edge. LPs as partners, not capital: trust, warm introductions (“trust by proxy”), and over-communication—without “crying wolf.” Team > solo founder myth: first hires and sequencing reveal how companies will actually be built. Defense tech arc: from taboo to obvious—examples include ICON (3D-printed homes), Saronic, and Manifest (ex-Palantir). Data-driven firm design: internal platform (“Unity”) reallocates time from low-yield first meetings to high-conviction winning. Pilot fund outcomes: Ensemble’s Fund I (pilot) marked ~12×; scaling the model required re-architecting org + software. Guest Bio: Conrad Shang is Founder & Managing Partner at Ensemble VC. Previously, he led/managed venture investing at UTIMCO and invested at Norwest Venture Partners and Bain Capital Ventures; earlier he was a consultant at Bain & Company. He’s a Kauffman Fellow and has sat on both the GP and LP sides of the table—experience that informs Ensemble’s product- and data-driven approach to firm building. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Conrad Shang: https://www.linkedin.com/in/conradshang/ Links Ensemble VC: https://www.ensemble.vc/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:25) Fund management skills beyond investing (2:06) Time horizons in investments vs. fund management (4:24) Navigating economic cycles and long-term strategy (7:06) Venture investing and the power law paradox (8:24) Emerging challenges for new fund managers (10:48) Investment timing in defense tech and 3D printing (11:44) Team dynamics and talent as success predictors (14:57) Trust-building lessons from UTIMCO (19:04) The critical role of trust in LP-GP dynamics (21:21) Treating LPs as partners and the educational aspect (23:50) Mutual benefits of LP-GP collaboration (29:55) Fostering trusted long-term LP relationships (33:46) Transparency and communication with LPs (36:19) Investment theses and relationship importance (41:58) Insights from LP experience at UTIMCO (46:41) Practices of successful GPs (51:58) Relationship alpha and its impact on venture success (52:32) Ensemble's Fund One and its approach (54:16) Data and software in Ensemble's investment strategy (57:06) Data-driven investment case studies (1:00:37) Ensemble's Unity platform and efficiency tools (1:03:04) Using data for informed investment decisions (1:06:06) Team cohesion and its importance (1:08:14) Closing remarks

Oct 3

What really happens inside the hidden world of family offices—and why do they invest so differently from institutions? In this episode, I explore that question with Sid Malhotra, Chief Investment Officer at Kactus Capital, a single family office. Sid reveals how family offices align incentives between principals and investment teams, the advantages of having true “skin in the game,” and why their long-term, absolute-return mindset stands apart from pensions, endowments, and foundations. We also discuss the unique strategic role family offices play—from backing zero-to-one opportunities to leveraging deep sector expertise and networks—and how Sid’s career path, from Citadel to Pritzker Group to his current role, shaped his approach to risk, alignment, and building resilient portfolios. Highlights: Alignment over agency: how Kactus ties compensation and co-investment directly to long-term portfolio performance. Single vs. multi-family offices: why governance, focus, and principal control make a difference Strategic capital: family offices as early backers of crypto, seed managers, and illiquid opportunities institutions avoid Lessons from six years at the Pritzker Group: how legacy ownership and manufacturing DNA shape an investment lens Absolute returns and relative returns: why compounding capital while minimizing losses guides Sid’s philosophy Preparing for corrections: dry powder, T-bills, and opportunistic offense in market sell-offs Citadel training: lessons on multi-strategy flexibility, thinking across the capital structure, and risk-reward sizing The total portfolio approach: blending macro-awareness, bottoms-up selection, and thematic top-down views Career advice from Booth to CIO: why networking early is as critical as working hard Guest Bio: Sid Malhotra is the Chief Investment Officer at Kactus Capital Management, a single family office where he leads all investment activity across public and private markets. Before joining Kactus, Sid spent over six years at the Pritzker Group, helping steward the family’s legacy of business ownership and investing across multiple asset classes. Earlier in his career, he worked at Citadel, gaining multi-strategy and capital-structure investing experience. Sid holds an MBA from the University of Chicago Booth School of Business and a B.A. in Economics from the University of Michigan. He has completed the Value Investing Executive Education program at Columbia Business School and is a Chartered Financial Analyst (CFA) Charterholder. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Sid Malhotra: https://www.linkedin.com/in/sidmalhotra/ Links Kactus Capital Management: https://www.kactuscapital.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (2:09) Alignment of Interests and Trade-offs in Family Offices (5:24) Strategic Nature of Family Offices and Learnings from Pritzker Group (9:30) Focus on Absolute Returns and Criteria for Investment in a Manager (12:26) Investment Style: Jigsaw Puzzle vs. Treasure Hunt (14:24) Preparing for Market Corrections and Managing Dry Powder (18:19) Challenges of Cash Reserves and Strategy during Market Sell-Offs (22:33) Public vs. Illiquid Investments During Crises and Sources of Alpha (26:30) Lessons from Working at Citadel and Appeal of Multi-Strategy Firms (33:04) Impact of Tax Considerations on Portfolio Construction (35:46) Building a Career and Network Post-Business School (37:25) Closing remarks

Oct 1

Why is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices? In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction). Highlights: Four kinds of complexity stopping alts adoption: access, legal/regulatory, reporting (K-1s, non-standard NAVs), and liquidity. Why operational complexity is the #1 reason many RIAs avoid alts (industry surveys ~40–50%). The public → private shift: volatility aversion + search for alpha and predictability. Information asymmetry has widened: trillion-dollar GPs vs. individuals and smaller RIAs—why tooling must level the field. AI’s role: extract, integrate, and chat with unstructured docs; unified LP workflow from access → diligence → reporting → exit. RIA reality: clients already bring outside deals/K-1s—consolidated balance-sheet reporting is now table stakes. Why due-diligence management is the sleeper pain point—and how comparative analytics change decisions Context for performance: the conversation references Kaplan–Schoar/PME research on PE vs. public markets (as discussed in-episode) Guest Bio: David Sawyer is CEO & Co-Founder of Unlimited.ai, an AI-native platform built to orchestrate LP workflows in private markets. Previously, he served as Managing Partner & COO at Legacy Knight, a multi-family office and alternatives platform, and as Managing Director at CAZ Investments. He holds a J.D. from the University of Houston Law Center, studied at the University of Texas at Austin, and is a CAIA charter holder. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Sawyer: https://www.linkedin.com/in/david-sawyer-a70ab912/ Links Unlimited.ai: https://www.unlimited.ai/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (2:54) The role of technology in alternative investment management (7:31) Strategies for overcoming operational complexity in private markets (10:21) AI's impact on investor access and information symmetry (22:07) Standardization and transparency in private market investments (23:06) Empowering investors with technology and community initiatives (23:56) Closing remarks

Sep 29

How do you underwrite pre-seed founders when the only durable asset is the human—before there’s product-market fit? In this episode, I go deep with Mike Ma, Managing Partner at Sidecut Ventures, on his 30-day “work-alongside” diligence, why he optimizes for action-oriented self-awareness, and how to calibrate coachability—especially in go-to-market—without overfitting to investor bias. We unpack earned secrets, impact theses in education, climate, healthcare, and economic mobility, solo-GP advantages, alignment pitfalls from 2021-era rounds, and the mindset habits he wishes he’d had earlier: “write at a fourth-grade level” and “document your screw-ups.” Highlights: The 30-day “grind with them” model: watching founders operate to reduce storytelling bias. What predicts pre-seed survival: action-oriented self-awareness (execute fast and integrate feedback fast). Coachability, defined: focus on go-to-market (not deep tech) and respond to market-generated feedback. Earned secrets: the unfair advantage born at the intersection of novel markets + lived expertise. Why solo GPs can be more aligned: speed, conviction, and operator empathy at pre-seed. Valuation ≠ victory: how 2021-style prefs/marks can zero founders despite solid outcomes. Two habits for builders & investors: write simply and log your mistakes to kill self-deception. Guest Bio: Mike Ma is the Managing Partner of Sidecut Ventures, a pre-seed venture firm backing “coachable superheroes” in sectors including economic mobility, digital health, climate, and education. He brings a background as both an investor and operator, with prior roles that span venture capital, operating leadership, and company building. Before founding Sidecut, Mike held leadership positions at firms such as Sway Ventures and Nex Cubed, where he launched fintech initiatives and accelerator programs. He also served as a marketing leader at high-growth startups including Betterment and Own Up, and earlier in his career worked in brand strategy at major financial institutions. A graduate of Harvard University, Mike now applies his experience across investing, operations, and go-to-market strategy to help early-stage founders succeed. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mike Ma: https://www.linkedin.com/in/michaelwma/ Links Sidecut Ventures: https://www.sidecut.vc/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (2:30) Assessing and predicting startup success (7:06) Coachability in startup founders (13:14) Market size misconceptions and value creation platforms (22:15) Solo GPs and early-stage startup advantages (24:14) Innovation and the AI startup landscape (25:35) Optionality and premium in early-stage funding (26:48) VC-startup alignment and second-order effects (29:22) Misalignment in funding and tragic outcomes (29:50) Thirty-day LLM project insights (30:41) Asymmetric information and bias in investing (33:20) Coaching founders and personal advice (36:57) Closing remarks

Sep 26

How can families preserve wealth and well-being across five or more generations? In this episode, I dive deep into a conversation with James E. “Jay” Hughes, Jr., legendary family wealth advisor and author of five influential books including Family Wealth. Jay shares stories from advising families for over 50 years—why flourishing, not just financial returns, is the real measure of wealth; how families like the Rothschilds and Fords illustrate both triumph and tragedy; and why choosing trustees wisely may be the single most important decision for multi-generational continuity. We explore governance, purpose, philanthropy, Aristotle’s philosophy of flourishing societies, and Jay’s own midlife realization that the true professional question is not “what do you need?” but “how can I help?” Highlights: The Rothschild family story: diversification of human, intellectual, and social capital as a foundation for flourishing Trustee decisions: why one poor choice can unravel a fortune over generations The Ford family cautionary tale: Henry Ford’s dominance over Edsel, and Henry Ford II’s turnaround Aristotle’s timeless lesson: no flourishing society without flourishing families Why purpose and philanthropy grow—not deplete—family wealth The billionaire pledge: altruism with promise, but outcomes still unproven Jay’s midlife shift: moving from fulfilling needs to asking, “how can I help?” His father’s wisdom: knowledge is fungible, courage is invaluable Guest Bio: James E. “Jay” Hughes, Jr. is a pioneering family wealth advisor, author, and thought leader who has advised some of the world’s most prominent families for over five decades. A sixth-generation lawyer, Jay began his career in trusts and estates law before dedicating his life to helping families flourish across generations. He is the author of five books, including Family Wealth: Keeping It in the Family, and a frequent speaker on family governance, stewardship, and purpose. Jay has served as a trustee, mentor, and confidant to multi-generational families globally, and is recognized as one of the foundational voices in the modern family office movement. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Links About James E. Hughes, Jr.: https://www.jamesehughes.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:39) James E. Hughes, Jr.: Background and trust and estate law career (3:14) Joint decision making challenges in wealthy families (5:05) Insights on creativity from Zixanth Mahai's book (9:16) Importance of trustee selection for wealth preservation (10:48) The Ford family's rise, fall, and legacy transformation (15:06) Purpose and philanthropy's role in sustaining family wealth (20:59) Billionaire's giving pledge and its effects on wealth management (22:32) James E. Hughes, Jr.'s advice for young professionals (27:07) Closing remarks

Sep 24

How should a public pension build an active equity and absolute-return program—without diluting alpha or chasing the “hot” manager? In this episode, I go deep with Brian Miller, Senior Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), on constructing a $6B public-equity book inside a ~$15B plan, sizing managers, and using absolute-return strategies as true diversifiers. Brian reflects on 16 years at Tukman Grossman Capital Management (value, long-term compounding, and staying consistent), the realities of “LP capture” across cycles, and why tracking error isn’t the right risk lens. We unpack manager due diligence (including on-site visits), active vs. passive trade-offs, the global/US mix, and how SCERS uses MSCI Caissa for whole-portfolio visibility. Highlights: Lessons from Tukman Grossman Capital Management: consistency, long-term compounding, and fitting the “value/core” role for top LPs. LP capture in practice: how client flows can force or fund decisions—08/09 liquidity, 2020 upgrades, and who doubles down in drawdowns. Value vs. growth & small-cap value today: quality dispersion, a smaller small-cap universe, and why “stocks follow earnings” over time. Portfolio construction at SCERS: shifting to include global vs. pure international; active where it counts with ~half of US equity passive. Tracking error ≠ risk: focus on downside risk; information-ratio “gotchas” when TE is kept too low. Absolute Return (7% sleeve): diversifiers (event-driven, macro, market-neutral, derivatives-based arb) that protected in 2022 and target mid-single-digit returns with low vol. Tooling: how MSCI Caissa gives top-to-holdings look-through across public & private to manage exposures. Manager selection & diligence: narrow the funnel, visit on-site, prevent false positives, and stay rooted in the original thesis. Career advice: be a continual learner, build networks early, and develop conviction to hold through criticism. Guest Bio: Brian Miller is a Senior (Retirement) Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), where he focuses on Global Public Equity and Absolute Return programs. Before SCERS, he spent 16 years at Tukman Grossman Capital Management in research and portfolio roles. At SCERS he leads manager selection and portfolio construction across public equity and diversifying strategies. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brian Miller: https://www.linkedin.com/in/brian-miller-205a85/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (4:20) Long-term investing and its impact on success (8:22) Navigating market crises and opportunities (12:29) Dynamics of small cap value investing (16:51) Public-private market crossover and manager transitions (21:10) Manager evaluation and selection insights (27:46) Investment thesis and building a robust portfolio (33:44) Diversification and trade-offs in manager selection (40:50) Role of absolute return strategies (45:12) Portfolio diversification using MSCI tool (47:12) Career advice and the importance of networking (50:31) Investment process and conviction (50:48) Masterclass on public equity and value investing (51:01) Closing remarks

Sep 22

How can continuation vehicles and independent sponsors unlock structural alpha in private equity when traditional buyouts are struggling with low DPI? In this episode, I go deep with Paul Cohn, Co-Founder and Managing Partner of Agility Equity Partners, on why continuation vehicles (CVs) and independent sponsor deals are reshaping the buyout landscape. Paul explains how CVs let GPs hold their best companies longer while still providing LP liquidity, why the lower middle market offers outsized return potential, and what makes independent sponsors a fast-growing segment of private equity. We cover alignment dynamics, incentives, real-world deal structures, the findings from the HEC Paris study on CVs, and the lessons Paul has learned over 15+ years investing in this niche. Highlights: Continuation vehicle market grew from $7B in 2014 to $70B in 2024, with CVs now making up ~15% of PE exits Why CVs give GPs a way to hold their best assets longer while still providing LP liquidity Positive selection vs. adverse selection in CVs — why diligence is key Example mechanics: GPs rolling carry into CVs and LPs choosing between liquidity or rolling capital HEC Paris study: single-asset CVs outperformed buyouts on DPI, total value, and dispersion of returns Why CVs are less risky: tighter dispersion, better alignment, and GPs investing alongside LPs Growth of independent sponsors: ~1,500 in North America, often more deal volume than traditional funds Why lower middle market offers more alpha: easier growth, multiple expansion, less competition Key lessons from Paul’s career: trust your gut on people, make tough changes quickly Guest Bio: Paul Cohn is a Partner & Founder of Agility Equity Partners, responsible for sourcing and executing new investments, monitoring portfolio-company performance, and leading intermediary deal sourcing. Before founding Agility, he was Managing Director & member of the Investment Committee at Fort Washington Capital Partners where he led GP-Led Secondaries investments. He also served as a Partner at Mellon Ventures, Mellon Bank’s private equity affiliate (part of its founding team; over $1.3B invested/committed across 100+ companies & 70+ funds). Paul began his career as an investment manager at Westinghouse Credit Corporation, focusing on leveraged buyouts. He holds a B.S. and MBA from the Tepper School of Business, Carnegie Mellon University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Paul Cohn: https://www.linkedin.com/in/paul-cohn-841914/ Links Agility Equity Partners: https://www.agilityep.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:52) Concerns about dry powder in large buyouts and CV market constraints (3:03) Explanation and incentives for GPs to use continuation vehicles (6:04) Diligence, adverse selection, and transitioning to CVs (10:20) Psychological influences and LP decision-making on CVs (14:42) Attraction of CVs for LPs and alignment of interests (16:54) HEC Paris study and private equity returns impact on CV market (20:55) Evolution of CVs and lower volatility measurement (23:26) Independent sponsor market growth and transition to raising funds (27:22) Single asset CV development in the buyout market (31:11) Allocator concerns and ethics in private equity (36:29) Conflicts of interest in CVs and advice for young investors (42:38) Experiences with underperforming team members and learnable lessons in investing (44:35) Closing remarks

Sep 19

Can venture capital be reinvented to deliver alpha without relying on “heroic assumptions”? In this episode, I go deep with Daniel Kimerling, Founder and Managing Partner of Deciens Capital, on his mission to build a different kind of venture fund—one focused on highly concentrated, long-duration bets in financial services. Dan explains why Deciens is unapologetically “get rich or die trying,” how his team avoids the venture hamster wheel of markups and momentum rounds, and why he believes the next generation of financial institutions (not just fintech apps) will be the true power-law winners. We cover his philosophy on portfolio construction, long timelines, liquidity vs. exits, and how Deciens publishes its playbooks openly to challenge orthodoxy. Highlights: Why Deciens aims to be an uncorrelated alpha stream within venture capital Radical transparency: aligning with LPs upfront on asymmetric return expectations Portfolio construction based on computational simulations; choosing concentration over diversification Targeting 10–15 companies per fund, with a model designed to deliver 5x net returns The case for financial services as venture’s overlooked mega-sector (20% of global GDP) Examples from the portfolio: Chipper Cash, Treasury Prime, Tint Insurance, Sidecar, SimplyWise, Generous Energy The “venture hamster wheel” of markups and why Deciens rejects it Why liquidity and exits aren’t the same—and why dividends can be just as powerful 14-year fund timelines aligned with LPs like pensions and sovereigns that can go long duration Deciens as a movement: defying orthodoxy, building with aligned entrepreneurs, and embracing authenticity Guest Bio: Daniel Kimerling is the Founder and Managing Partner of Deciens Capital, a first-principles venture firm backed by sovereign wealth funds, endowments, and pensions. Deciens is known for its concentrated focus on financial services—backing both fintechs (like Chipper Cash and Treasury Prime) and next-generation financial institutions (from insurance to asset management). Prior to founding Deciens, Dan co-founded Standard Treasury (acquired by Silicon Valley Bank) and served as GM of API Banking at SVB. A published writer and frequent speaker, he is recognized for challenging conventional VC orthodoxy through essays like Defying Orthodoxy and Betting on Convexity. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Daniel Kimelring: https://www.linkedin.com/in/dkimerling/ Links: Deciens Capital: https://deciens.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:52) Deciens's Capital's investment strategy and portfolio examples (3:00) Deciens's uncorrelated venture strategy and high-risk, high-reward philosophy (5:24) Managing LP expectations with transparency and communication (7:00) Nontraditional portfolio construction and computational simulations (9:45) Process of constructing a portfolio and the conservative approach (14:13) The potential of financial services companies and ecosystem background (20:01) Liquidity strategies and exit planning for non-traditional investments (22:49) Aligning strategy with LPs and venture return competition (26:28) Small fund size counterarguments and the importance of investment asymmetry (29:24) Long-duration investment timelines and compound growth (33:34) Structural alpha advantages and venture fund strategies (38:23) Learnings from closing Fund three and viewing Deciens as a movement (42:04) Pitfalls of traditional venture capital models (46:01) Advice to a younger self on the importance of differentiation (51:28) Creating durable alpha and structural advantages (55:11) The impact of the need for validation on investment decisions (59:21) Aligning firm success with charitable goals and personal motivation (1:01:22) Closing remarks

Sep 17

How can ultra-high-net-worth families invest like endowments—without becoming forced sellers when markets turn? In this episode, I go deep with Greg Brown, Co-CEO of Caprock, on how a modern multi-family office serves UHNW families. Greg explains why Caprock acts as CFO first and CIO second, forecasting liquidity across complex balance sheets before allocating to private markets. We cover the thresholds for when privates make sense, how to structure portfolios for resilience, the role (and limits) of interval funds, and how Caprock uses pooled scale to negotiate economics and secure access to top deals. We also explore tax-alpha strategies like QSBS, Opportunity Zones, and long/short overlays. Highlights: Why Caprock takes a CFO-first, CIO-second approach to wealth management Liquidity forecasting: mapping every entity, flow, and obligation Threshold for UHNW privates: around $10M investable assets How full balance-sheet visibility lets families hold more illiquids Scale advantages: pooled vehicles with no fees, no carry Direct access to elite deals: SpaceX, Anduril, Palantir, Addepar, Anthropic, and more Interval funds: where they fit, where they don’t, for taxable investors Liquidity buckets: 0–6 months, 6–18 months, and 2+ years How to avoid becoming a forced seller in downturns Why Caprock buys secondaries 19 out of 20 times Tax tools: QSBS, Opportunity Zones, PPLI, 130/30 overlays Why privates matter: many top companies now stay private longer Guest Bio: Gregory Brown is Co-CEO of Caprock, an SEC-registered multi-family office. Previously, he was an active investor and entrepreneur with experience in product & business development strategy, capital formation, and mergers & acquisitions. He holds a B.S. from the University of Idaho and dual MBAs (Columbia Business School and Haas School of Business, UC Berkeley). Greg is based in Seattle. Outside work he enjoys golf, skiing, cooking, and playing drums in a band. He also serves on the board of La Plaza International. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Gregory Brown: https://www.linkedin.com/in/gregorybrown/ Links Caprock: https://caprock.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:24) Negotiating better economics through pooled capital (1:03) Introduction to Greg Brown and Caprock's overview (2:27) Scale, scope, and roles differentiation at Caprock (3:46) Client liquidity needs, cash management, and spending (6:25) Private market investment trends and challenges for high net worth families (9:53) Managing administrative complexity and client cash flows (12:13) Caprock's comprehensive service offerings (13:12) Pooled capital: Advantages, disadvantages, and interval funds (17:53) Cash flow and liquidity management best practices in family offices (20:24) Liquidity issues and solutions in private equity markets (25:33) Secondary market and tax considerations for investors (28:15) Tax loss harvesting, leveraged equity strategies, and private market investment rationale (34:35) Diversification and democratization of private markets (36:45) Opportunities and concerns in private credit and tax planning with PPLI (40:08) Lessons from founding Caprock and scaling venture co-investments (45:56) Closing remarks

Sep 15

How do you run a $1B endowment with a lean five-person team — while balancing liquidity, access, and high-conviction relationships? In this episode, I speak with Geeta Kapadia, CFA, Chief Investment Officer at Fordham University, about how she manages a concentrated portfolio of 30–40 manager relationships, the lessons she’s learned resetting the portfolio for liquidity, and why she favors passive equities with selective active bets in emerging markets and developed ex-US. We also dive into the shortcomings of interval funds, when to say yes to continuation vehicles, and how Fordham leverages the Gabelli alumni network and a student venture fund to extend sourcing and diligence reach. Highlights: Fordham’s endowment runs on ~30–40 core manager relationships. Portfolio was reset to improve liquidity without losing growth. Public equities are passive by default, with selective active in EM and ex-US. Interval funds fall short when redemption caps kick in. Continuation vehicles: default “yes” on merits, even if committees hesitate. DPI is more important than headline IRRs in private markets. At $1B, the edge comes from picking well, not chasing mega-funds. Building relationships from Fund II to secure later allocations. Gabelli alumni and student venture fund boost sourcing and diligence. Operator’s mindset: manage fees, portfolio roles, and energy like an orchestra. Guest Bio: Geeta Kapadia, CFA is the Chief Investment Officer at Fordham University, where she oversees the school’s ~$1B endowment. Prior to Fordham, she managed ~$5B at a healthcare institution. At Fordham, Geeta focuses on concentrated manager selection, liquidity optimization, and leveraging the university’s alumni and student networks to expand sourcing and talent pipelines. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Geeta Kapadia: https://www.linkedin.com/in/geetakapadiacfa/ Links Fordham University: https://www.fordham.edu/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:43) Portfolio construction and relationship management at Fordham's endowment (3:17) Leveraging alumni for investment opportunities and fund manager relationships (7:27) Team management and portfolio evolution under Geeta's leadership (12:40) Incorporating semi-liquid interval funds and dealing with fund term extensions (19:29) Evaluating investment performance and transitioning to passive management (27:40) Asset allocation strategies and the role of behavioral finance (32:16) Building GP relationships and aligning with the endowment's mission (38:28) Identifying valuable GP-LP relationships and balancing EQ with IQ (44:33) Access vs. picking in private markets and mid-sized endowment challenges (49:18) Embracing first principles in fund selection and openness to being wrong (52:17) Admitting mistakes and balancing listening with decision-making (55:44) Conclusion and future outlook (56:01) Closing remarks

Sep 12

How do you use the SBIC program to access long-dated, low-cost leverage—without blowing up risk? In this episode, I speak with Eric Rosiak, CEO & CIO of Amplify Community Investment Partners, about the mechanics of SBICs, the new accrual debenture license for venture and growth, what top LPs look for, and how policy changes could expand the opportunity set. We dig into eligibility tests, realistic fund sizes, diligence standards (they’re no joke), and why some large platforms now run SBIC sleeves alongside billion-dollar flagships. Highlights: How SBIC leverage works — ~$175M, interest-only over 10 years, priced roughly ~1% over the long-dated Treasuries. The 3-prong eligibility test: size (NAICS/employees) or financial thresholds (net worth & income). The new accrual debenture license for venture/growth, with Pelion Ventures as first licensee. Who’s investing: insurers, foundations, funds-of-funds, plus selective endowments. Program changes: leverage and family-of-funds caps, and likely increases under upcoming legislation. Big platforms entering via SBIC sleeves (Oaktree, Barings, EIP). Strong historical returns: ~16-17% IRR and ~2.3× MOIC. Rigorous SBA and GP diligence process. -Tactical advice: structuring LP agreements early to preserve SBIC optionality. Guest Bio: Eric Rosiak is the Chief Executive Officer & Chief Investment Officer at Amplify Community Investment Partners, where he focuses on community and economic development strategies and raises capital for SBICs/RBICs and affordable housing funds. He previously held roles at Bank of America, Ocean Tomo, Performance Trust, FBR, and B. Riley, and holds CPA and multiple FINRA licenses. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Eric Rosiak: https://www.linkedin.com/in/ericrosiak/ Links: Amplify Community Investment Partners: https://www.amplifycip.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:33) Understanding the SBIC program and investment criteria (3:15) Target companies and institutional investor types in SBICs (5:46) The role of leverage in SBIC fund performance and growth trends (9:54) Personal and institutional criteria for investing in SBIC funds (14:36) SBA's criteria and the process for accessing SBIC funds (19:20) Challenges for spinouts and first-time SBIC fund managers (22:56) Legislative efforts to impact SBIC investments (26:39) Lessons learned and advice for SBIC industry newcomers (30:02) The significance of leadership in SBIC success (30:52) Closing remarks

Sep 10

What would the bond market look like if it were built today? In this episode, I speak with Dylan Parker, CEO & Co-Founder of Moment, the operating system for fixed income that unifies trading, portfolio construction, and risk/compliance—and automates the workflows wealth platforms run every day. We dig into how fixed income finally went electronic, why half of bond trading still happens by phone or chat, and how Moment can build customized ladders in seconds instead of hours. We also unpack the (surprisingly big) after-tax edge in munis, and Dylan’s lessons from building automated credit trading at Citadel before raising a $36M Series B led by Index Ventures this summer. Highlights: Fixed income lags equities—workflows still fragmented. ~50% of bond trades still done by phone/chat. Smart routing enables millisecond auto-execution. Custom muni ladders built in 5–10 seconds. Automation drives 25–50× productivity gains. LPL ($1.94T AUM) adopted Moment’s OEMS. Clients include LPL, Hightower, and fintechs. Bonds enable unique tax-loss harvesting benefits. $145T fixed income market exceeds global equities. Building “ironclad” infra vs. move-fast culture. Guest Bio: Dylan Parker is the CEO & Co-Founder of Moment, a New York–based company building the first operating system for fixed income for wealth platforms and institutions. Before founding Moment, Dylan was a quantitative trader/researcher at Citadel Securities, where he and his co-founders worked on automated credit trading. He co-founded Moment with Ammer Soliman (COO) and Dean Hathout (CPO)—a team with deep fixed-income expertise and top-tier engineering that recently closed a $36M Series B led by Index Ventures (with participation from a16z, Lightspeed, Venrock, Neo, and Contrary). Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Dylan Parker: https://www.linkedin.com/in/dylan-parker-9b68b3134/ Links Moment: https://moment.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:38) Dylan Parker's background and Moment's Series B funding (2:19) Expansion and simplified explanation of Moment's operations (4:40) Citadel's culture, hiring exceptional talent, and trust building (8:53) Current fixed income trading practices and portfolio management (12:30) Trends in tax loss harvesting in fixed income (17:42) High net worth market growth and automation's impact (23:13) Balancing speed and accuracy in financial technology and customer needs (28:10) Hiring opportunities at Moment and David's investment enthusiasm (29:12) Closing remarks

Sep 8

What does it take to build an AI-native search engine for science? In this episode, I spoke with Eric Olson, Co-founder & CEO of Consensus, the platform making peer-reviewed research accessible through AI. We covered the company’s journey from Series A to millions of users, the realities of competing with tech giants, and what truly creates defensibility for AI startups. Eric shared his perspective on the “AI talent wars,” building products at hyperspeed, and what truly creates a moat for AI applications. If you allocate to or invest in AI, you’ll want to hear Eric’s frameworks for product strategy, market sizing, and execution speed. Highlights: Consensus as “Google Scholar powered by AI” 5M users, ~20-person team, scaling toward Series B Funded by USV, Nat Friedman, and Daniel Gross Why vertical focus beats horizontal platforms The 70/30 framework for product development Execution speed as the real moat in AI Guest Bio: Eric Olson is the Co-founder & CEO of Consensus, an AI search engine for scientific research founded in 2021 with Christian Salem. Before Consensus, Eric worked in data science at DraftKings and was a Division I football player at Northwestern University. Under his leadership, Consensus raised an $11.5M Series A in 2024 led by Union Square Ventures with participation from Nat Friedman and Daniel Gross. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Eric Olson: https://www.linkedin.com/in/eric-olson-1822a7a6/ Links Consensus: https://www.linkedin.com/company/consensus-nlp/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:03) Series A Celebration and Talent Wars in AI (3:23) Consensus: Overview and Target Users (4:25) TAM for Consensus and Comparison with Google Scholar (8:42) The Edge of Startups in AI and Importance of Focus (15:57) Product Development and Building a Moat in AI (23:01) AI Market Investment Strategies for Asset Allocators (24:36) Fundamentals of Software Investing and Focus on Talent (26:15) Closing remarks

Sep 5

In this episode, I speak with Avy Stein, Founder & Chairman of Cresset—a multi-family office known for its private markets access and co-investing model. We cover Avy’s path from Kirkland & Ellis lawyer to private-equity dealmaker, the Willis-Stein spinout from Continental Bank, why multi-strategy platforms scaled so quickly, how co-invest rights really add alpha (and where adverse selection bites), and the rise of private credit in the middle and lower-middle market. We also get into culture building at scale, how Cresset thinks about alignment with GPs, and Avy’s best career advice from four decades in law, PE, operating, and wealth. Highlights: The “scrappy” early days of PE vs. today’s institutionalized playbook (sector teams, QofE, consultants, big ICs). Why distribution scale drove the multi-strategy model—and how large allocators should still find differentiated access with megafunds. Co-invest alpha math (hat tip Prof. Steve Kaplan) and how to avoid being adversely selected. Seeding new vehicles (including GP-stakes/interval-style concepts) and when limited GP economics make sense. Private credit today: typical senior-debt returns, leverage levels (lower in LMM), and why sponsor alignment limits downside. Culture at Cresset: a written “culture card,” extreme accountability, and hiring for behaviors using assessments plus scenario questions. Personal reflections: stepping away during a health battle, building an alt-energy company afterward, and the importance of being present Guest Bio: Avy Stein is Founder & Chairman at Cresset, an award-winning multi-family office with over $70B in assets under management (as of July 1, 2025). He previously co-founded and led Willis Stein & Partners (1994) after running CIVC at Continental Illinois; he began his career in 1980 as an attorney at Kirkland & Ellis. Avy holds a J.D. from Harvard Law School and a B.S. in Accounting from the University of Illinois. He also co-founded Lincoln Clean Energy (later acquired by I Squared Capital in 2016). Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Avy Stein: https://www.linkedin.com/in/avy-stein-7293251/ Links Cresset: https://www.linkedin.com/company/cresset-capital/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:06) Avy Stein's early career and transition into private equity (2:45) Evolution of private equity and influence of multi-fund strategies (5:32) Synergies and distribution in private equity and private credit (7:41) Strategies and trade-offs in capital allocation (11:26) Co-investment terms and access in venture capital (15:00) Seeding opportunities, GP stakes, and fund evaluations (17:06) Managing large capital pools and co-investment vehicles (20:08) Aligning GP incentives and building long-term relationships (24:44) Strategy changes, returning capital, and selecting PE firms (28:26) Culture setting, hiring, and opportunities in the lower middle market (35:56) Evolution of lending and private credit for high-net-worth individuals (41:13) Career reflections and advice to younger self (44:17) Key career decisions and building Cresset's value proposition (49:34) Closing remarks

Sep 3

In this episode of How I Invest, I speak with Frank Mihail, CIO of the North Dakota Department of Trust Lands, which manages an $8B sovereign wealth endowment built to fund public schools. Frank shares how his three-person team runs a highly concentrated portfolio with 75% in alternatives, why they prefer evergreen fund structures for liquidity, and how they think about portable alpha, co-investments, and core-satellite strategies. We also discuss the trust’s broader mission: having already distributed $2B to North Dakota schools, with the long-term goal of covering the entire cost of public education. Highlights: The origins and purpose of the North Dakota Trust Lands sovereign wealth fund How the endowment has grown to $8B in investable assets and $12B total Why 75% of the portfolio is in alternatives, including private equity, venture, hedge funds, real estate, and infrastructure The case for evergreen fund structures over traditional closed-end vehicles Trade-offs between co-investments vs. manager selection for concentrated portfolios How portable alpha works in practice—and why North Dakota uses a “portable beta light” approach The role of fund-of-funds in reducing operational complexity and building core-satellite strategies Behavioral finance and why avoiding mistakes during volatility matters more than chasing marginal alpha The trust’s long-term mission to support public schools and reduce taxpayer burden Guest Bio: Frank Mihail is the Chief Investment Officer of the North Dakota Department of Trust Lands, where he oversees the investment of the state’s sovereign wealth endowment. Before joining North Dakota, Frank was an Investment Officer at the New Mexico Public Employees Retirement Association (PERA), where he managed hedge fund strategies. He holds deep expertise across public and private markets, with a focus on building resilient, high-performing institutional portfolios. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Frank Mihail: https://www.linkedin.com/in/frankmihail/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:56) Portfolio Construction, Asset Allocation, and Liquidity Strategies (4:45) Evergreen Funds: Benefits and Co-Investment Strategies (10:54) Strategies for Private Equity and Hedge Fund Exposure (18:30) Vanguard's Impact on Indexing and Portable Alpha Explained (23:29) Fund of Funds and Core-Satellite Investment Approaches (29:22) Behavioral Finance in Investment Decision-Making (31:25) Key Investment Thesis and Illiquidity Valuation (36:57) RVK's Role and Economic Impact on Public Education (42:05) Closing remarks

Sep 1

What happens when AI lets five people build what used to take fifty? Can you scale to eight figures in revenue without ever touching a “Series A treadmill”? In this episode, I talk with Henry Shi, co-founder of Super.com and creator of the Lean AI Leaderboard, about seedstrapping (raising once, then reaching escape velocity), outcome-based pricing, and a new, non-dilutive way to finance lean, profitable startups. We also get into how Henry “vibe-coded” an AI VC tool over a weekend, why survival rates should improve in the lean-AI era, and what founder traits show up again and again among these ultra-efficient companies. Highlights: Why AI-native teams can hit $10M+ ARR with tiny headcount: lower fixed costs + higher willingness to pay for outcomes. Outcome-based pricing beats per-seat SaaS when you deliver measurable business results (example discussed: GrowthX). Seedstrapping defined: raise a solid seed round, then avoid the pre-seed→A→B→C treadmill by using capital discipline and AI leverage. Henry’s investor model: non-dilutive, non-recourse revenue share structured like a founder-optional line of credit (5–10% of revenue; 2–3× cap). Why “reach Series A” is a broken success metric—and why DPI/ongoing cash generation matters more. Founder traits that correlate with lean-AI success: repeat builders, high agency, resilience, and comfort going against pattern-matching orthodoxy. “Vibe-coding” an AI VC assistant in a weekend: auto-memos, competitor scans, forecasting, and draft term sheets. Will YC adapt—or will AI-native incubators centered on seedstrapping emerge? Henry’s take. Guest Bio: Henry Shi is the co-founder of Super.com (originally Snaptravel/Snapcommerce), founded in 2016 and rebranded to Super.com in Oct 2022 as the company expanded beyond travel into a savings-focused “super app.” WikipediaPR NewswireSuper Super.com raised $85M Series C in Apr 2023 (over $150M total raised reported at the time). PR NewswireCrunchbase News Henry also launched the Lean AI Leaderboard, tracking ultra-lean, high-revenue AI-native companies; he describes himself as a repeat founder who built a $150M+ annual-revenue startup before “recently exiting.” leanaileaderboard.com He was named to Forbes 30 Under 30 (Consumer Tech, 2019). Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Sponsor: NordVPN is one of the fastest and most reliable VPN services available, helping users protect their personal data, block malware, and stay secure on any network. With over 7,000 servers in 125 countries, NordVPN allows investors, travelers, and remote professionals to change their virtual location, access region-locked services, and maintain privacy while working from anywhere. NordVPN believes that strong encryption and seamless connectivity are essential to a secure digital life. EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/invest . Try it risk-free now with a 30-day money-back guarantee! Sponsor: Incogni, developed by the makers of NordVPN, is a data privacy tool that helps individuals remove their personal information from the internet. By automatically reaching out to data brokers on the user's behalf, Incogni helps reduce unwanted data exposure, limit spam, and enhance overall digital privacy. Incogni believes that everyone should have control over their personal information in a world where data is constantly being bought and sold. Use code [INVEST] at the link below to get an exclusive 60% off an annual Incogni plan: https://incogni.com/invest Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Henry Shi: https://www.linkedin.com/in/henrythe9th/ Links: Super.com: https://www.linkedin.com/company/superdotcom/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (2:44) AI's Role in Lean High Growth Companies and Outcome-Based Pricing (5:08) Ideal Capital Structure for AI Startups and Venture Capital Challenges (7:53) Seed Strapping and its Suitability for Different Company Types (10:24) Vibe Coding and AI's Potential to Support Diverse Founders (15:26) Founder Characteristics and Incubator Models for AI Startups (18:32) Seed Strapping Investment Model and Fundraising Challenges (23:09) Startup Survival, Revenue-Based Funding, and Success Metrics (30:04) Henry Shi's Fundraising Experiences and AI Startups' Potential (32:52) Infinite Innovation and Encouraging Global Entrepreneurship (34:03) Closing remarks

Aug 29

I had the chance to talk with Francis X. Suarez, the 43rd Mayor of Miami, about how his "open-for-business" leadership transformed the city into a global tech and finance hub. We unpack Miami’s “quantum opportunity,” the practical growing pains—housing, schools, transit—and the civic strategy behind international diplomacy and major sports deals. We also explore his run as President of the U.S. Conference of Mayors and his reflections on leadership, resilience, and embracing failure. Highlights: How Miami built an ecosystem so attractive that "companies managing trillions wanted to be here" The “quantum opportunity” from migration trends after New York’s November election Zoning reforms to boost school capacity, and the housing affordability challenge Using Inter Miami’s stadium and star signings (Messi, Busquets, Alba) as civic brand accelerants The diplomacy of being "on the ground" in Riyadh during the Gulf trip Leadership in the age of mistakes: confidence, humility, and reflection Guest Bio: Francis X. Suarez — Mayor of Miami since 2017, President of the U.S. Conference of Mayors (2022–2023), and architect behind Miami’s rise in tech, finance, and global presence. He’s known for civic modernization, bold branding moves, and strategic city-scale investments. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Francis X. Suarez: https://www.linkedin.com/in/francissuarez/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (1:49) Strategies for attracting entrepreneurs and addressing growth bottlenecks (9:14) Advice for political campaigns and US international relations insights (15:04) US-Saudi Arabia relationship and insights from diplomatic trips (21:41) Trump's diplomatic skills and comparison of political career paths (26:30) Personal and psychological insights into President Trump (30:35) Francis Suarez's advice to his younger self and reflections on success (34:45) The role of mindfulness and embracing failure in life (37:21) Closing remarks

Aug 27

Alan Zafran, Founder & Managing Partner at IEQ Capital, joins to unpack how ultra-high-net-worth families and institutions think about risk, cash runways, GP selection, illiquidity, secondaries, LPAC governance, and portfolio strategy amid rising rates and sovereign debt. -- Highlights: The strategic value of a 3–12 month cash runway for risk capacity When concentrated allocations (e.g., private credit within IRA) can be intentionally diversified within a larger portfolio Why illiquidity premium in private credit demands careful underwriting in a softening market Using secondaries to access discounted, high-quality exposure when liquidity is in demand Why being opportunistic via marginal reallocations trumps sitting in cash GP selection principles: team-first, avoid style drift, manage fund size, and recognize that track records are lagging indicators IEQ’s LP governance: securing LPAC seats ~75% of the time to align interests Portfolio implications of sovereign debt, rates, and incentives Framing crypto (e.g., Bitcoin) as a store of value, if aligned with client preference The power of compounding trust in ultra-high-net-worth advisor-client relationships -- Guest Bio: Alan Zafran is Founder & Managing Partner at IEQ Capital, a registered investment adviser overseeing $41.7B in Regulatory AUM (RAUM) as of June 30, 2025. With a career spanning Goldman Sachs, Merrill Lynch, and Luminous Capital, Alan brings nearly three decades of experience advising UHNW families and institutions. He holds several wealth-advisor recognitions and serves on multiple philanthropic and educational boards. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alan Zafran: https://www.linkedin.com/in/alan-zafran-0446438/ Links IEQ Capital: https://www.linkedin.com/company/ieqcapital/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) IEQ Capital overview and risk tolerance insights (2:35) Diversification and financial runway importance (6:41) Considerations for client diversification preferences (8:37) Investing in private credit and tax implications (13:05) Assessing the private credit market and opportunistic strategies (21:30) Compounding relationships in wealth management (26:15) Managing capital commitments for ultra high net worth individuals (28:18) Risks associated with single stock loans (31:50) Selecting general partners and vintage considerations (38:19) Relationship and governance with general partners (43:17) National debt impact on portfolio management (49:24) Incorporating crypto into high net worth portfolios (51:45) Staying informed with Alan Zafran and IEQ Capital (52:32) Closing remarks

Aug 25

In this episode I speak with Rafael Costa, who co-founded Across Capital to back category-leading software companies across the U.S. and Latin America. We dive deep on the Brazil tech flywheel — from why the central bank and Pix have accelerated fintech innovation, to the infrastructure winners like QI Tech that are becoming foundational rails for payments, banking and credit. Rafael walks me through Across Capital’s concentrated, high-conviction approach (a ten-company portfolio, deliberate sizing, then backing winners over time), how they underwrite downside protection in growth equity, and what AI actually changes for regulated industries. Along the way he shares practical diligence habits (the “what really matters” slide), how they build conviction over ~17 months, and one piece of advice he’d give his younger self about focusing on the present to compound relationships and learning. -- Highlights: Why Brazil’s fintech moment is real — PIX, an innovative central bank, concentrated incumbents, and huge addressable markets. QI Tech: Across Capital’s early/high-conviction relationship with a Brazilian financial-infrastructure platform (Rafael says it was the fund’s first investment and has become a major position). Recent press shows QI Tech reached unicorn status and raised follow-on rounds with General Atlantic; Across Capital participated. Why Rafael runs a concentrated, 10-company portfolio — concentration forces clarity, deeper diligence, and the ability to back winners with outsized follow-on checks. Underwriting discipline: the “what-really-matters” slide — pick 3–5 drivers, re-underwrite objectively, and size up when the drivers out-perform. How AI affects growth equity: less about replacing regulated businesses and more about enabling them (efficiency, automation, product expansion) — attractive for companies in fintech and financial infrastructure. -- Guest Bio: Rafael Costa is a General Partner at Across Capital, a growth-equity firm that invests in category-leading software businesses across the U.S. and Latin America. Before Across, Rafael worked on growth teams at Vulcan Capital and Summit Partners and started his career in investment banking. Across Capital lists software and growth equity as its core focus and includes companies such as Qi Tech in its portfolio. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Rafael Costa: https://www.linkedin.com/in/rafael-costa-61bb479/ Links Across Capital: https://www.acrosscap.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (1:34) Evolution of Brazil's tech ecosystem and fintech landscape (6:54) High conviction and concentrated portfolio construction strategies (12:09) Growth equity insights: Consistency, power laws, and sizing strategy (17:53) Institutionalizing investment discipline and exploring market leaders (22:55) AI's impact on growth equity and personal advice for success (27:04) Closing remarks

Aug 22

This episode features John Felix, General Partner & Head of Research at Pattern Ventures, a specialist fund-of-funds focused on backing small venture managers in the $5–50M range. We talk about the endowment principles that shaped John’s investing mindset, how to separate true specialists from résumé-driven narratives, why access and selection are two very different games, and the traps LPs face in co-investments. John also shares lessons on reserves strategy, portfolio construction, and what allocators consistently overlook when evaluating emerging managers. -- Highlights: Why endowments that concentrate in their best ideas tend to outperform—and how that mindset translates to manager selection. The real difference between a “specialist” and someone with just a strong pedigree. Access vs. selection: most lose the game on access first, here’s how to filter for the best. Crawl → walk → run: a stepwise framework for first-time GPs. Solo GPs versus partnerships—where each model works and where risks emerge. How to think about reserves and portfolio construction in small venture funds. Spotting adverse selection in co-invest opportunities. Why operator empathy makes for better underwriting judgment. -- Guest Bio: John Felix is General Partner & Head of Research at Pattern Ventures, where he leads manager selection and research. Pattern Ventures is a fund-of-funds focused on partnering with exceptional small venture funds ($5–50M) and offering co-investment opportunities. Previously, John led Emerging Managers at Allocate and was an investor at Bowdoin College’s Office of Investments under CIO Paula Volent, after earlier roles at an OCIO and Washington University’s Investment Management Company. He holds a BSBA from Washington University in St. Louis. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Felix: https://www.linkedin.com/in/johnfelix12/ Links Pattern Ventures: https://www.patternventures.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Early career and market efficiency insights (2:02) Scott Wilson as a CIO and manager evaluation process (7:45) Balancing portfolio management with best ideas strategy (17:14) Deep research and the transition to Bowdoin College (23:37) Bowdoin's investment philosophy and Allocate experience (29:03) Founding Pattern Ventures and avoiding LP error (34:32) Early venture investing challenges and strategies (39:00) Venture capital industry bifurcation and fund characteristics (44:05) Mistakes and reserve strategies in venture investing (47:21) Final thoughts and importance of LP-GP partnerships (48:27) Closing remarks

Aug 20

I had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation. We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting. I had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation. We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting. -- Highlights: Why he believes every policy output is a political input How he helped Uber win political battles across the U.S. What makes politicians tick—and how to move them Why crypto had a breakthrough 2024 election cycle How Tusk Ventures invests in highly regulated industries The origin story of the Mobile Voting Project When startups should start lobbying—and how to do it effectively The one investment he regrets (and what it taught him) -- Guest Bio: Bradley Tusk is the founder and CEO of Tusk Holdings, which includes Tusk Ventures, Tusk Strategies, and the Tusk Philanthropies foundation. He was formerly Deputy Governor of Illinois and campaign manager for Michael Bloomberg’s 2009 mayoral race. He helped Uber navigate early political battles, taking equity as payment—and then repeated that playbook with FanDuel, Lemonade, Coinbase, and others. He is also the author of The Fixer and Vote With Your Phone, and the founder of the Mobile Voting Project. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Bradley Tusk: https://www.linkedin.com/in/btusk/ Links Tusk Holdings: https://www.tuskholdings.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:44) Strategies for Uber's expansion and political challenges (6:26) Michael Bloomberg's approach and political ROI examples (10:35) Modern lobbying and startup political influence (19:52) Timing for startups to engage in lobbying (22:19) Success and impact of the crypto lobby in elections (25:14) Elon Musk's potential political influence (30:04) Bradley Tusk's mobile voting project and its impact (35:20) Tusk Ventures' investment approach and regulatory appeal (39:51) Perspectives on opposing lobbies and venture capital (42:06) Lessons from investing and politics (43:23) Closing remarks

Aug 18

What does it take to be a truly great limited partner? In this episode, I spoke with Matt Curtolo, a veteran LP who’s worked with some of the most sophisticated institutional investors in the world—Hamilton Lane, MetLife, and Hirtle Callaghan. Today, Matt advises both LPs and emerging GPs, offering a rare perspective from both sides of the table. We dug deep into what separates elite LPs from the pack, how institutional incentives shape decision-making, the paradox of humility and self-promotion among GPs, and why the best partnerships are built on trust, EQ, and long-term thinking. If you're raising a fund—or allocating to them—this episode is a masterclass. Highlights Why emotional intelligence (EQ) often separates good LPs from elite ones The biggest mistake LPs make: underestimating upside How institutional misalignment discourages risk-taking What best-in-class co-investment programs actually look like How to assess GP conviction without asking directly Why emerging GPs struggle—and how Matt coaches them through it The real reasons LPs say no (hint: it’s not just returns) Why “people first” is Matt’s ultimate investment filter A framework for long-term games, trust-building, and kingmaking What smaller LPs can do to punch above their weight Guest Bio Matt Curtolo is an institutional investor, advisor, and coach with over 20 years of experience across some of the most respected LP organizations in the world. He spent the first seven years of his career at Hamilton Lane, followed by senior roles at Hirtle Callaghan and MetLife. Most recently, he was Head of Investments at Allocate. Today, Matt advises both LPs and GPs on investment strategy, manager selection, fundraising, and co-investments—with a special focus on helping emerging managers navigate the zero-to-one journey. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement Stay Connected X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Curtolo: https://www.linkedin.com/in/matt-curtolo-caia/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:11) Experience at Hamilton Lane and early career insights (1:19) Skills and best practices for an elite limited partner (6:15) Leveraging community and referencing in due diligence (10:16) Decision-making, risk tolerance, and LP conservatism (17:16) Characteristics of top-performing LPs and institutional culture (22:03) Advantages and benefits of co-investing for large institutions (27:27) Evaluating co-investment opportunities and GP conviction (32:38) Building relationships with GPs and organizational differences (36:46) Challenges for smaller LPs and quick rejections in GP pitches (42:10) Partnership mentality and long-term industry relations (49:09) Consulting GPs and LPs for a unique perspective (53:09) Common reasons GPs fail to raise money and balancing self-promotion (59:13) The ten-year commitment test and characteristics of emerging LPs (1:03:38) Closing remarks

Aug 15

In this episode of How I Invest, I’m joined by Alex Hormozi — entrepreneur, investor, and founder of Acquisition.com — to unpack the mindset and methods that have fueled his success across multiple industries. We dive deep into why entrepreneurship is more a “game of the heart” than the mind, the power of compounding skills, the dangers of “ignorance debt,” and how to strategically decide whether to build skills yourself or bring in outside talent. Alex shares candid stories from his career — from building gyms to scaling software companies — and offers sharp insights on persistence, focus, and eliminating distractions to win long-term. We also explore the nuances of goal setting, why tiny incremental improvements matter when scaled to millions, and the art of building high-value peer networks. Whether you’re an aspiring founder, seasoned operator, or investor, you’ll walk away with concrete frameworks to increase your odds of success — and the conviction to keep playing the game long enough to win. -- Highlights: Why persistence outperforms raw intelligence in entrepreneurship The unseen advantage of being around excellence and winning teams How to identify and reduce “ignorance debt” in your business The compounding effect of stacking complementary skills over time Why patience and focus are the hardest — yet most valuable — entrepreneurial skills Building “luck surface area” and increasing your odds of success Deciding when to build a skill versus bringing in outside expertise Marginal gains at scale: why 2% improvements can move the needle massively The ROI framework Alex uses to decide where to spend his time and resources Strategic giving and networking: building IOUs that pay off years later -- Guest Bio: @AlexHormozi Hormozi is an entrepreneur, investor, and philanthropist. With his wife, @leilahormozi Hormozi, he co-founded Acquisition.com, investing in and scaling businesses while sharing their methods through books, podcasts, and media. He’s the author of $100M Offers and $100M Leads, with his new book $100M Money Models launching August 16, 2025. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Huge Announcement: Alex Hormozi's newest book, $100M Money Models, launches at a live virtual event Saturday August 16th. Register free: https://register.acq.com The book will teach you how to get more customers to spend more, in less time, over and over again, ultimately eliminating cash flow as a constraint to growth of any business. – Stay Connected: X / Twitter: David Weisburd: @dweisburd Alex Hormozi: @AlexHormozi LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Hormozi: https://www.linkedin.com/in/alexhormozi/ Links Acquisition.com: https://www.acquisition.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:00) Welcome back, Alex Hormozi and entrepreneurship insights (2:32) Underestimating time for success and skills around excellence (5:40) Learning from higher social status and power dynamics (9:46) Defining ignorance debt and the context of advice (17:27) Compounding skills versus mastering one (24:32) Luck surface area and restarting for cash flow (29:44) Focus as the hardest entrepreneurship aspect (31:17) Levels and characters in the entrepreneurial game (34:54) Tailoring advice to individual entrepreneurs (37:03) Changing behavior and soft skills in older employees (42:14) Preparing for book launch presentations (44:16) Sharing goals publicly and visualization techniques (50:32) Observable actions and career reflections (57:00) Investment regrets and doubling down on successes (1:00:19) Emotional investing challenges and building a mastermind (1:03:36) Networking strategies and bridging creator-investor worlds (1:06:26) Narrowing focus, expanding globally, and AI in deal flow (1:09:00) Transactional relationships and optimal give-to-take ratio (1:14:18) Content leverage and managing time (1:19:15) Initial behavior and relationship efficiency (1:22:21) Communication skills and meeting objectives (1:28:31) Anxiety, performance, and stylistic communication (1:33:25) Entertainment versus education in content creation (1:36:25) Influencing and effectiveness in content (1:39:41) Original content generation and value per word (1:45:45) Independent thinking for success and conviction in investments (1:49:30) Elon Musk's management strategies and leadership vision (1:59:43) High agency challenges and optimizing media production (2:03:51) Solving business constraints and the importance of talent (2:07:48) Closing remarks

Aug 13

Most people pitch performance. Rahul Moodgal built a career on pitching relationships. In this episode, I go deep with Rahul Moodgal—Head of Investor Relations at Parvus Asset Management and one of the most trusted capital raisers in the hedge fund world. Over his career, Rahul has raised $99 billion across platforms like TCI and Parvus, building decades-long relationships with LPs, endowments, and mission-driven institutions around the globe. We explore how Rahul flips traditional fundraising on its head: opening with the negatives, focusing on long-term alignment, and avoiding the sales-y traps that doom many GPs. If you're a manager trying to understand how world-class LPs think—or an allocator looking to work with truly values-aligned capital—this is the playbook. -- Highlights: The Bear Stearns moment that changed everything: Rahul's unconventional pitch that led to 8 out of 12 investors committing capital. Why most GPs focus on transactions instead of relationships—and why that's a mistake. The difference between asset allocators and asset owners, and why Rahul focuses on the latter. How mission-driven capital re-energizes his team and provides a deeper sense of purpose. Why duration—long-term relationship building—is the ultimate differentiator in raising capital. The secret behind his famous email list and why it's so hard to get on it. Parvus’s contrarian investment style: buying when everyone else is selling and holding through the noise. Building a 30+ member group of female CIOs to foster collaboration and support. Why Rahul goes "analog" in a digital world and still flies thousands of miles for one meeting. A clear-eyed framework for distinguishing between “jigsaw” vs. “treasure hunt” LPs. -- Guest Bio: Rahul Moodgal is Partner, Director of Investor Relations & Business Development at Parvus Asset Management, a London‑based firm specializing in European public equities with approximately $10 billion under management. With over 25 years of financial services experience, Rahul transitioned into asset management after a period in academia. He studied and taught across four countries—UK, USA, Russia, and Japan—and earned degrees from Keele University, the London School of Economics, and Cambridge University. Rahul was previously Partner leading Investor Relations & Business Development at The Children’s Investment Fund (TCI), where he became known for setting industry records—including initiating the largest-ever country and sector fund launches within a record timeframe. Following TCI, he advised and partnered with managers across Europe, contributing to firms such as Parvus, TCI New Horizon, KDA Capital, and Algebris Investments. Beyond finance, Rahul serves as a trustee, board chair, and patron for multiple non-profit organizations in both the UK and U.S., including British Exploring Society, the Sumerian Foundation, Whizz-Kidz, and Scientific Adventures for Girls in Oakland, California Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Rahul Moodgal: https://www.linkedin.com/in/rahul-moodgal/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:06) Raising $99 billion and Bear Stearns event story (1:46) Changing the pitch strategy and starting with negatives (5:01) Relationship building and quality of capital (10:14) Asset allocator challenges and choosing mission-driven clients (14:32) Role and feedback of LPs in influencing GPs (19:58) David Swensen, Yale model, and LPs pitching value (23:57) Organizational alignment and understanding LPs (27:12) Jigsaw vs. treasure hunt strategies and relationship duration (32:20) Reconciling relationship duration with check size (34:36) Mission-driven investing and non-performance alignment (41:15) Transparency and partnership in investment management (47:02) Long-term relationships versus transactional interactions (50:19) Building personal relationships in the investment world (57:01) Overview of Parvis Asset Management and contrarian strategy (1:02:16) Shorting stocks: Criteria and approach (1:03:48) Rahul Moodgal’s email list and meeting strategies (1:08:02) The value of in-person meetings and flying for deals (1:09:24) Closing remarks

Aug 11

In this episode of How I Invest, I speak with Scott Welch, Chief Investment Officer and Partner at Certuity, a multi‑family office managing over $4 billion in assets. Scott joined Certuity’s Board of Managers in 2020, and now leads the investment strategy and participates actively in risk management across all facets of the firm's investments, including portfolio architecture, asset allocation, investment due diligence, and manager selection We talk about what’s keeping him up at night in public markets, his views on the Fed and interest rate policy, and how Certuity builds globally diversified portfolios that balance risk factor, asset class, and geographic exposure. We also go deep into taxes, where Certuity aggressively harvests losses using market-neutral overlays to create "tax alpha" for their clients. -- Highlights: The logic behind all-weather portfolios—and how they protect investor discipline Why 20–25% is the sweet spot for most families in private investments How Certuity uses global diversification, risk factors, and asset class tilts The rise of market-neutral tax overlays and the case for tax alpha A CIO’s view on the Fed, interest rates, and Powell’s successor Why Scott is bullish on sports ownership and sailing as an asset class How Certuity sources private equity and credit managers—and the role of client networks When they’ll use fund-of-funds and when they go direct -- Guest Bio: Scott Welch, CIMA®, is the Chief Investment Officer and a Partner at Certuity, a $4 billion multi-family office, where he leads the investment strategy team and serves on the Board of Managers and the firm’s risk management committee. He is responsible for portfolio architecture, asset allocation, manager due diligence, and investment decision-making across client portfolios. Prior to joining Certuity in 2020, Scott held senior roles including CIO of WisdomTree’s model portfolios, CIO of Dynasty Financial Partners, and Co-Founder and CIO of Fortigent, a $75 billion investment platform later acquired by LPL Financial. He began his career with over a decade on Wall Street. Scott holds the Certified Investment Management Analyst (CIMA®) designation and certificates in Investment Strategist, Advanced Investment Strategist, and Alternative Investments from the Investments & Wealth Institute (IWI). He has served on IWI’s board of directors, the ABA Wealth Management & Trust Conference advisory board, and the editorial boards of the Journal of Wealth Management and Investments & Wealth Monitor. In 2024, he received the Wealth Management Impact Award from IWI. Scott earned a B.S. in Mathematics from the University of California, Irvine, and an MBA in Finance from the University of Massachusetts at Amherst. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Scott Welch: https://www.linkedin.com/in/scottwelch3/ Links Certuity: https://www.linkedin.com/company/certuity/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:05) Concerns in public markets and valuations (1:45) Policy framework, Fed independence, and decision-making (5:21) Fed chair's political influence and market reactions (10:12) Preparing clients for Federal Reserve changes (12:20) Behavioral finance, global diversification, and manager sourcing (18:18) Rebalancing, valuation differentials, and alternatives (22:48) Client preferences and strategies for illiquid investments (29:53) Informational alpha, taxes, fees, and sports team investments (35:40) Approaching private equity and the role of fund of funds (46:49) Streamlining Alt Plus and advice for finance professionals (49:42) AI's impact on careers and investment strategy for the youth (52:03) Best management advice and importance of strong teams (56:00) Educational system's shortcomings and closing remarks (56:57) Closing remarks

Aug 8

Christina Wing is a Senior Lecturer at Harvard Business School, where she teaches the “Family Enterprise” course—a foundational class for the rising generation of family office leaders. She’s also the founder of Wingspan Legacy Partners, where she advises ultra-high-net-worth families on governance, talent, and legacy. In this episode, I sat down with Christina to unpack why most family offices are structurally flawed—and what to do about it. Christina shares insights from advising dozens of families and training hundreds of HBS students from Gen 1, Gen 2, and beyond. We explore the real reason most family offices fail, how to build a high-functioning investment operation, and why separating investment, concierge, and philanthropic functions is critical. Christina also walks me through what makes MSD Capital, the Koch family office, and others stand out—and how the next generation can step up and lead with clarity. Highlights: Why 90% of family offices are structured incorrectly—and how to fix them The biggest mistake families make when building a family office How the Koch and Dell families have structured their offices for performance Why talent is the number one constraint in the great wealth transition The critical distinction between cost centers and revenue drivers in family offices How to attract top investors to run your family’s capital Pay, incentives, and why family offices should behave like professional firms The psychological gap between generations—and how to overcome it Why Gen 2 and Gen 3 must take ownership and ask the hard questions How to align mission, capital deployment, and family legacy The future of family offices and why they could outperform other asset classes -- Guest Bio: Christina Wing is the Founder of Wingspan Legacy Partners, a strategic advisory firm serving families and their enterprises, and a Senior Lecturer at Harvard Business School, where she teaches the Family Enterprise elective. Prior to founding Wingspan, she spent nearly two decades advising operating companies and family offices on leadership, succession, governance, and strategy. Christina is recognized for her work helping multigenerational families navigate the complexities of wealth, purpose, and transition. Her research and teaching sit at the intersection of family dynamics and business performance. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Christina Wing: https://www.linkedin.com/in/christina-r-wing/ Links Wingspan Legacy Partners: https://wingspanlegacy.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:04) The Koch family's investment and concierge services model (5:24) Managing challenges and team optimization in family offices (7:16) Outsourcing and talent competition in smaller family offices (10:32) Recruitment strategies and pay scales in family offices (17:47) Revenue generation and tactical strategies for family office capital (23:07) Organic vs. fund perspective approaches in family office investments (23:53) Psychological and generational dynamics in family offices (29:18) Responsibility and wealth dynamics across family generations (36:42) The role of failure and resilience in family wealth (38:00) Wealth as an opportunity or a curse (40:33) Fostering proactive behavior in family office generations (44:03) Practical steps for family office success and post-liquidity strategies (47:50) Closing remarks

Aug 6

Why do Harvard and Yale seem to be exiting private equity? What does the most rigorous data actually say about buyout and venture performance? And how should serious LPs think about real estate, hedge funds, and co-investments? In this episode, I’m joined with Steven Neil Kaplan—Professor of Entrepreneurship and Finance at the University of Chicago Booth School of Business, co-creator of the Kaplan-Schoar PME metric, and one of the most widely cited academics in private equity and venture capital. Steve breaks down decades of private market performance data, busts myths around IRRs and overmarking, and gives a rare, honest evaluation of asset class performance through multiple cycles. This conversation is a masterclass in understanding what the real numbers say—direct from the person who helped shape how performance is measured. Highlights: Why Harvard and Yale are selling private equity holdings What the best vintages in private equity have in common How the Kaplan-Schoar PME and Direct Alpha work The truth about buyout returns vs. S&P 500 and Russell 2000 Steve’s candid take on Ludo Phalippou’s critiques Which asset classes he’d avoid if advising an endowment What really drives fund overmarking and fundraising timing The persistence of venture capital fund performance Why co-investing can meaningfully boost LP returns Steve’s advice on investing through cycles and downturns -- Guest Bio: Steven Neil Kaplan is the Neubauer Family Distinguished Service Professor of Entrepreneurship and Finance at the University of Chicago Booth School of Business. He co-founded the entrepreneurship program at Booth and is a research associate at the National Bureau of Economic Research. Kaplan is one of the most published and cited academics in private equity and venture capital, and co-developed the Kaplan-Schoar Public Market Equivalent (PME), a widely used tool for comparing private equity returns to public markets. He has consulted for top private equity firms and advised institutional investors on strategy and fund selection. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Steven Neil Kaplan: https://www.linkedin.com/in/steven-kaplan-69594718/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:42) Private equity performance vs. S&P 500 and data sources (5:07) Standardization issues and biases in private market data (8:18) Dividend impact and criticisms of private equity metrics (12:03) Predicting future private equity and alternative investment returns (19:34) Correlation between public markets and private equity (22:28) Private equity manager marking practices and customer service importance (29:48) Investor strategies and fee structure implications in private equity (31:51) Comparing large and small buyout market strategies (33:03) Adding value in private equity and challenges in exiting mega deals (37:16) Traits of successful private equity students and investment timing (41:48) Market cycles: Predictions and investment strategies (45:11) Benchmarking venture capital against public markets (47:08) Venture capital performance variability and return statistics (51:13) Closing remarks

Aug 4

What does it take to manage the wealth of America’s most iconic families? In this episode, I spoke with Stephan Roche, Partner at BanyanGlobal, and former senior executive for the Gates and Walton families. Stephan has had a front-row seat to how some of the world’s most sophisticated family offices think about investing, governance, and multigenerational legacy. At Banyan, he now advises enterprising families on ownership strategy and purpose. We explore the frameworks ultra-wealthy families use to structure portfolios, co-invest alongside GPs, and prepare future generations for stewardship—not just of capital, but of mission and values. Whether you’re managing family wealth or building toward it, this is one of the most insightful conversations I’ve had on long-term investing. Highlights: Three dominant family office portfolio models: Yale endowment-style, --Warren Buffett-style, and bespoke/interest-driven strategies Why access—not size—is the true edge of large family offices The portfolio Stephan would build with $10B: 50–60% private equity, strong values alignment, and multigenerational purpose Why starting with estate planning is a mistake—and what to do instead Deep dive into private equity vs venture capital, private credit, and co-investing strategies How co-invests can boost net returns and “buy down” fund fees The importance of GP-level diligence—why it’s not just the fund, but the partner Why many family offices are overly focused on wealth instead of impact Lessons from “Die With Zero” and how Stephan applied them to a once-in-a-lifetime Gobi Desert trip The single best move a G1 wealth creator can make: write a “Letter of Intent” for the next generation -- Guest Bio: Stephan Roche is a Partner at BanyanGlobal, a leading advisory firm that helps family enterprises govern shared assets and navigate complex transitions. He previously served as Chief Operating Officer of Cascade Investment (the Bill Gates family office) and CEO of Walton Enterprises (the Walton family office). Stephan brings decades of experience advising the world’s most prominent families, and today he helps clients align their values, ownership structures, and governance systems for long-term success Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @NordVPN and @Incogni for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: NordVPN is one of the fastest and most reliable VPN services available, helping users protect their personal data, block malware, and stay secure on any network. With over 7,000 servers in 125 countries, NordVPN allows investors, travelers, and remote professionals to change their virtual location, access region-locked services, and maintain privacy while working from anywhere. NordVPN believes that strong encryption and seamless connectivity are essential to a secure digital life. EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/invest . Try it risk-free now with a 30-day money-back guarantee! Sponsor: Incogni, developed by the makers of NordVPN, is a data privacy tool that helps individuals remove their personal information from the internet. By automatically reaching out to data brokers on the user's behalf, Incogni helps reduce unwanted data exposure, limit spam, and enhance overall digital privacy. Incogni believes that everyone should have control over their personal information in a world where data is constantly being bought and sold. Use code [INVEST] at the link below to get an exclusive 60% off an annual Incogni plan: https://incogni.com/invest . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Stephan Roche: https://www.linkedin.com/in/stephanroche/ Links Banyan Global Family Business Advisors: https://banyan.global/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:15) Common investment models and designing a $10 billion portfolio (6:15) Long-term wealth preservation strategies (8:44) Family office commitments vs. pension funds and private equity vs. venture capital (14:10) Tax advantages and fund of funds strategies (19:09) Identifying and partnering with top-performing funds (21:16) Focus on fund of funds and spinouts (23:06) Segmenting emerging managers and co-investment opportunities (27:15) Building relationships with General Partners (GPs) (31:36) Family office dynamics and introduction to Banyan Global (34:34) Secrets to multigenerational wealth management (39:02) Utilizing wealth in service of the family's vision (42:12) Best practices for managing and preserving wealth (45:14) Maintaining perspective and cultivating gratitude (47:50) Insights from "Die With Zero" by Bill Perkins (53:21) Clarifying misconceptions of the Die With Zero philosophy (56:54) Advice for first generation wealth creators (59:59) Closing remarks

Aug 1

Tom Bilyeu went from sleeping on the floor to co-founding and selling a billion-dollar company, Quest Nutrition. Today, he's the force behind Impact Theory, a media studio with a bold mission: pull people out of the Matrix at scale. In this episode, Tom reveals the frameworks that helped him transform from a self-proclaimed “emotionally fragile” dreamer to a high-agency entrepreneur and truth-seeking machine. We cover everything from skill stacking and the physics of progress to first-principles thinking, radical candor in leadership, and how he’s building a real-world version of Ready Player One. If you're obsessed with performance, truth, and high agency thinking, this one’s for you. Highlights: Why skill acquisition—not genius—is the real separator in life and business The "physics of progress" framework Tom uses to constantly test, learn, and improve How to reframe your ego to build elite teams and attract A+ talent The trap of emotion-based decision making—and how to escape it Why embarrassment kills more dreams than failure What he learned from wasting millions in game development Building long-term vision while executing short-term (pragmatic) wins His deterministic view on free will—and why he still lives like he has it The mindset shift that changed his entire trajectory -- Guest Bio: TomBilyeu Bilyeu is the co‑founder of Quest Nutrition, which he helped scale from a startup to a billion-dollar exit in just five years—with 57,000% growth in the first three years alone and reaching a $1 billion valuation by year five. Following that success, he founded @ImpactTheory in 2016, a modern media company focused on empowering audiences through transformative content across YouTube, podcasts, video games, webcomics, and TV/film. Tom currently serves as CEO of Impact Theory, where he leads a lean yet mission-driven team based in Los Angeles. The studio’s content has amassed approximately half a billion views on YouTube alone and targets spreading a growth‑mindset to millions globally. Over the past 15 years, Tom has built a personal brand and audience of over 8 million people and has interviewed nearly every high performer in the world. Today, he helps thousands of seven‑figure founders scale to eight figures and beyond. Tom is a vocal advocate of first‑principles thinking and execution over passion or theory. He regularly shares founder‑level insights, such as running numbers before strategy, framing constraints as competitive advantages, and prioritizing data over narratives. He holds a degree from the University of Southern California, and though he built Quest Nutrition without an MBA, Tom emphasizes self‑education—often quoting “YouTube is more useful than college” Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startups #openlp #assetmanagement #tombilyeu #impacttheory #investing -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Tom Bilyeu: @TomBilyeu LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Tom Bilyeu: https://www.linkedin.com/in/tombilyeu/ Links Impact Theory: https://impacttheory.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:58) The importance of stacking failures and mapping cause and effect (6:26) Navigating emotions and logical thinking in decision-making (10:39) The truth-seeking algorithm and skill acquisition (17:12) Managing embarrassment and building positive ego (24:21) The mission-driven mindset and long termism in business (33:39) High agency and the role of emotions in leadership (38:38) Passivity versus assertiveness in leadership styles (41:02) Differentiating leadership traits and creating a feedback culture (44:21) The comprehensive debate on free will (46:40) Scientific studies on decision-making (51:03) Accelerated knowledge and the digital age's impact (52:42) Future aspirations, media's role, and America's concerns (54:37) Finding and following guest's work (55:02) Closing remarks

Jul 30

What if your healthcare wasn't about just treating sickness, but maximizing your potential? In today's episode on How I Invest, I spoke with Dr. Cameron Sepah, founder and CEO of Maximus, a performance medicine company pioneering a new paradigm in healthcare. Cameron previously helped build Omada Health, now a billion-dollar public company, and coined the term “digital therapeutics.” Now he's productized his unique medical expertise into a next-gen men's health platform. We talked about the evolution of performance medicine, why testosterone and GLP-1s are changing how Americans manage their health, and how AI is reshaping clinical decision-making. We also dug deep into the personal and systemic failures of the traditional healthcare model — and what the next 10 years will look like as proactive medicine goes mainstream. Highlights: Why traditional healthcare is really a “sick care” system What “performance medicine” is — and why it matters How Maximus prescribes testosterone and GLP-1s for optimization, not just treatment What Cameron learned as founding team at Omada Health Why Maximus runs clinical trials when most telehealth companies don’t The case for microdosing semaglutide (Ozempic) and GLP-1s What most men are missing in their bloodwork — and how to fix it The biggest misconceptions around testosterone therapy How AI will revolutionize diagnostics, dosing, and coaching Why Maximus could only have been built by a psychologist -- Guest Bio: Dr. Cameron Sepah is the founder and CEO of Maximus, a consumer healthcare technology startup pioneering performance medicine. Before Maximus, he was on the founding team at Omada Health, where he served as Medical Director and coined the term “digital therapeutics.” He is a licensed clinical psychologist, former psychiatry professor at UCSF, and has advised numerous CEOs and venture capital firms on performance and mental optimization. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Cameron Sepah: https://www.linkedin.com/in/drsepah/ Links: Maximus: https://www.maximustribe.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:32) Lessons from Omada and Publishing Research (5:06) Clinical Trials and GLP-1 Microdosing Strategies (10:07) Insurance Challenges and Personalized Dosing of GLP-1s (14:16) The Future of GLP-1s and Obesity Treatment in America (18:31) Psychological Influences on Obesity and Dietary Choices (21:02) Comprehensive Research on GLP-1s and Weight Management (26:37) Medication Perceptions and Performance Enhancement Debate (30:36) The Role of AI in Advancing Healthcare (35:49) Key Diagnostic Tests for Men's Health Optimization (39:28) The Significance of Routine Blood Testing (41:22) At-Home Blood Testing Innovations (42:35) Turning Personal Expertise into a Scalable Business (43:32) Closing remarks

Jul 28

In this episode, I spoke with Anurag Chandra, Chief Investment Officer of a single-family office and longtime trustee and former Investment Committee Chair of the San Jose Federated City Employees’ Retirement System (FSERS). Over the past decade, Anurag has helped transform FSERS from one of the worst-performing pension plans in the U.S. into a top-decile performer. He’s also an experienced operator, venture capitalist, and accidental allocator—with hard-won insight into everything from re-risking public portfolios to model delivery and tax-loss harvesting. In our conversation, Anurag shared how EQ, team dynamics, and governance structure often outperform raw IQ in investing—and how he helped rebuild a $2.2B pension plan through careful governance reform, luck, and great timing. We also covered how he now applies those same principles at a nimble family office, blending institutional rigor with operational agility. Highlights: Why Anurag believes a 120 IQ and a great network beats a 160 IQ and no network The governance overhaul that led San Jose FSERS from bottom-2 to top-decile performance Lessons from studying Canadian pension best practices How his CIO made a bold move during the March 2020 crash—and why it paid off Why he thinks more family offices should behave like institutions A breakdown of model delivery, tax-loss harvesting, and custom indexing How his operator/investor/allocator background informs his investing philosophy Thoughts on emotional intelligence in finance—and why it’s more than a “soft skill” -- Guest Bio: Anurag Chandra is currently the Chief Investment Officer of a single-family office based in the Bay Area. He previously served for nearly a decade on the board of the San Jose Federated City Employees’ Retirement System, including several years as Chair of the Investment Committee. Under his leadership, the pension plan went from being one of the lowest-performing in the country to a consistent top-decile performer. Anurag has also worked as a venture capitalist, operator, and advisor, with 25+ years of professional experience across legal, investment, and entrepreneurial roles. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Anurag Chandra: https://www.linkedin.com/in/anchandra/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:11) The Value of EQ and Resourcefulness in Business (11:40) Anurag Chandra's Career and San Jose Pension Fund Turnaround (19:14) Governance and Manager Selection Challenges in Pension Funds (23:45) Applying Pension Fund Lessons to Family Office Management (26:52) Strategies in Tax Optimization and Asset Allocation (30:05) Model Delivery Concerns in Asset Management (30:58) Integrating Skills for Better Investment Decisions (34:41) Cross-functional Experience and First Principles Thinking (35:05) The Role of a Board Member and Opinion Strength (37:02) Closing remarks

Jul 25

Randal Quarles has been at the helm of some of the most influential institutions in finance and government. From his tenure as Vice Chair of the Federal Reserve and Under Secretary of the Treasury, to his leadership role at The Carlyle Group, Randal brings a rare blend of private market acumen and public sector insight. Today, he's the Chairman and Co-Founder of The Cynosure Group—an investment firm anchored by the Eccles family and built to solve the very structural misalignments that plague private equity for families and foundations. In this conversation, we explore the evolution of private equity, the mismatch between GP incentives and family office needs, the importance of long-duration compounding, and how Cynosure is creating a modern investment firm inspired by the early days of Lazard and Rothschild. Highlights: Why traditional private equity isn’t always aligned with family offices—and how Cynosure is solving that The challenges of long-hold investing and how cash-flowing businesses unlock structural advantages How Cynosure is organized: six subsidiaries across PE, credit, OCIO, ultra-high-net-worth advisory, hedge funds, and sports investing Why Randal prefers growth equity in “unloved” sectors like HVAC and sanitation—rather than chasing tech Lessons from working with David Rubenstein at Carlyle and deploying capital through the Great Financial Crisis The philosophy behind building an enduring investment firm—and the one piece of advice he’d give his younger self -- Guest Bio: Randal Quarles is the Chairman and Co-Founder of The Cynosure Group, a Salt Lake City–based investment firm anchored by the Eccles family. He brings over 40 years of experience across financial services, public service, and private equity. Prior to founding Cynosure, he served as Vice Chair for Supervision at the U.S. Federal Reserve, U.S. Executive Director at the IMF, and Under Secretary of the Treasury. In the private sector, he was a longtime partner at The Carlyle Group, where he led its financial services fund. Randal’s specialties include financial services investing and financial services policy. At Cynosure, he’s built a modern investment firm modeled after the early days of Lazard and Rothschild—designed to meet the structural and tax challenges faced by families, endowments, and long-term investors. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement. -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Randal Quarles: https://www.linkedin.com/in/randal-quarles-4b09788/ Links The Cynosure Group: https://cynosuregroup.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:06) Private equity funds vs family offices and tax implications (2:10) Evergreen structures, pension funds, and Cynosure Group overview (7:12) Transition to private investments and recruiting challenges (11:07) Cynosure's business structure and growth equity strategies (19:53) Asset class supply and demand dynamics (24:43) Asset allocation framework and sports investing strategies (26:16) Philosophical approaches to team building and recruitment (28:25) Initial impressions of Carlyle's leadership (32:48) Carlyle's Model T approach in private equity (36:02) Deploying a financial services fund during the Great Recession (38:13) Transitioning from law to investing and government influence (41:37) Career advice and investment principles (49:38) Encouraging career flexibility and understanding risk (51:00) Lessons on self-belief and meeting aspirational peers (51:38) The Eccles family's impact on Utah Jazz (52:46) Closing remarks

Jul 23

In this episode of How I Invest, I spoke with Thomas Lee, Co-President and CIO of Parametric, a $600 billion asset manager within Morgan Stanley Investment Management. Tom walks us through how Parametric helps high-net-worth individuals access institutional-quality investment strategies, why customization is the future of asset management, and how their technology powers nearly a quarter million highly personalized accounts. We talk about inflation myths, the credibility of the Fed, and whether the U.S. will eventually inflate its way out of debt. Tom also shares how Parametric brings tax-efficient investing and direct indexing to portfolios as small as $25,000, explains why "investments as a service" is not just a tagline, and offers valuable insights on long-term leadership, scale, and innovation. Whether you're an institutional allocator, wealth manager, or an individual trying to understand the future of investing, this episode is packed with takeaways. Highlights: Parametric manages $600B AUM, accounting for ~37% of Morgan Stanley Investment Management Inflation discussion: CPI vs PCE, and why inflation "feels" higher than reported The myth of hidden inflation and how CPI is calculated Explanation of the Five-Year, Five-Year Forward Rate as a proxy for Fed credibility Why Parametric doesn’t try to predict markets—and what they focus on instead Delivering customized SMAs down to $25K accounts Use cases for tax-loss harvesting, completion portfolios, and values-based overlays The evolution of pooled funds to the current era of hyper-customized investing Behind-the-scenes on how Parametric runs technology at scale Thoughts on active vs passive investing and market efficiency The challenge of integrating private alternatives into public portfolios Tom’s leadership philosophy: resource allocation, storytelling, and resilient growth -- Guest Bio: Thomas Lee, CFA is Co‑President and Chief Investment Officer at Parametric, part of Morgan Stanley Investment Management. He joined Parametric in 1994, brings over 30 years of experience, and previously spent two years at the Board of Governors of the Federal Reserve. As Co‑President & CIO, Tom leads investment teams responsible for research, strategy, portfolio management, and trading, and serves as a voting member on all investment committees. He holds a BS in Economics and MBA in Finance from the University of Minnesota, is a CFA charterholder, and actively engages with the CFA Society of Minnesota. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Thomas Lee: https://www.linkedin.com/in/thomas-lee-97a8826/ Links Parametric: https://www.parametricportfolio.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:06) Understanding Inflation: CPI and PCE Differences (3:25) Personal and Conspiracy Views on Inflation (6:21) Inflation Coordination and the Five Year Forward Rate (11:39) Tools for High Net Worth Clients in Institutional Finance (14:52) The Rise of Direct Indexing and Its Tax Advantages (17:09) The Shift to Hyper Customization in Finance (23:33) Managing Complexity in Fractional Shares and SMAs (24:51) Customization Strategies for Enhancing Returns (26:25) Debating the Efficient Market Hypothesis (28:16) The Integral Role of a Chief Investment Officer (CIO) (30:38) Communication Challenges within Large Organizations (34:34) Balancing Customer Feedback with Internal Innovation (36:03) Analyzing the Growth of Alternative Investments (41:39) Market Dynamics: Private vs. Public Asset Convergence (42:21) The Relevance of Active Investing in Efficient Markets (44:12) Investment Wisdom: Advice to a Younger Self (47:59) Investment Decision-Making and Contrarian Thinking (51:04) Parametric's Investment Philosophy and Future Plans (52:22) Closing remarks

Jul 21

Nancy Davis spent nearly a decade on Goldman Sachs’ legendary prop desk before founding Quadratic Capital, the firm behind the popular iVol ETF. In this episode, we dive deep into her options-based approach to investing, why she believes most investors manage risk backward, and how her firm is positioning for a potential return of stagflation. We also talk about her early days at Goldman, the psychological traps investors fall into, and why she thinks humility and coachability are underrated superpowers in finance. If you’ve ever wanted to understand volatility, inflation protection, or how to think like a derivatives trader—this episode is for you. Highlights: Starting her career on Goldman Sachs’ Risk Arbitrage desk in the 1990s Managing Goldman’s capital like a hedge fund—without client exposure Why she avoids stop losses and manages risk upfront using options “Debit card investing”: sizing positions by max loss instead of leverage Turning the traditional core-periphery portfolio model on its head How Quadratic makes options the core strategy, not a hedge Lessons from trading during the 2020 oil price shock and SVB crisis How the market is not pricing in inflation anymore—and why that matters The risks of a stagflationary regime and how iVol is built to respond What it really means to be coachable and the power of feedback Her most contrarian take on the market going into 2025 -- Guest Bio: Nancy Davis is the founder and managing partner of Quadratic Capital Management and the portfolio manager for the firm’s investment strategies, including the Quadratic Interest Rate Volatility and Inflation Hedge ETF (ticker: $IVOL). Before founding Quadratic in 2013, she spent nearly 10 years at Goldman Sachs, where she was a key member of the proprietary trading desk. Nancy has been recognized by Barron’s and other financial media as one of the leading experts on interest rate volatility, inflation hedging, and options-based portfolio strategies. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Nancy Davis: https://www.linkedin.com/in/nancyquadratic/ Links Quadratic Capital Management: https://www.ivoletf.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode Preview (0:59) Differences in trading for internal partners vs. end clients (1:56) Anti stop-loss philosophy and risk management (4:24) Psychological aspects and significant trades in investing (8:41) Discussion on market inflation and lessons from Goldman Sachs (12:58) Importance of mentorship in finance (19:01) Contrarian market perspectives and stagflation explained (20:57) Closing remarks

Jul 18

Mark Wade leads strategy and investments at CAZ Investments, a Houston-based firm managing approximately $10 billion in assets. In this episode, we unpack the evolution of the alternatives landscape, the rise of evergreen funds, and what it means to lead with alignment—starting with $700 million of insider capital invested alongside clients. Mark gives a candid look at how CAZ sources differentiated deals, manages risk through the “CAZ Case” downside model, and builds trust by investing alongside 7,000+ LPs. We also dig into how the firm leverages NAV-based leverage, the growing appetite for alternatives from RIAs, and why humility is essential when allocating capital. If you're an allocator, an advisor, or simply trying to understand where private markets are headed, this episode is packed with insights from one of the most thoughtful voices in the space. Highlights: The origins of CAZ Investments and how it scaled to $10B AUM Why Mark believes the RIA channel is the future of wealth advisory How CAZ gains access to top-tier deals—and why being the “first call” matters Explaining the CAZ Case: their rigorous downside underwriting model Why advisors must lead with conviction to retain and win clients The mechanics and benefits of NAV-based leverage Evergreen vs. drawdown funds—when and why each structure matters How alignment of interests drives investment outcomes Why top decile managers operate under an entirely different paradigm The future of consolidation in private markets and what it means for allocators Mark’s view on Tony Robbins becoming a strategic partner and investor in CAZ The surprising edge of having 7,000 investors in all 50 states and 36 countries -- Guest Bio: Mark Wade is a Partner at CAZ Investments, where he leads investment strategy and firm initiatives. Since joining CAZ in 2013, Mark has helped the firm expand its presence across asset classes, with a particular focus on GP stakes, energy, and professional sports. Prior to CAZ, Mark earned his MBA from the Rice University’s Jones Graduate School of Business. CAZ is known for its alignment-first model—deploying more than $700 million of insider capital alongside its LPs across a range of alternative investments. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mark Wade: https://www.linkedin.com/in/mark-wade-caia-334b951b/ Links CAZ Investments: https://cazinvestments.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:09) The growing demand for alternatives in the high net worth space (5:14) Comparing independent advisers and wirehouses (8:21) The rise of alternative investments and regulatory impacts (12:01) CAZ's investment strategy and leveraging funds (19:14) Drawdown vs. evergreen fund structures and management (26:27) Evergreen fund valuation and GP-LP interest alignment (33:53) Encouraging junior team investments and diversified LP advantages (38:47) Building partnerships and obtaining honest references (44:04) Maintaining investment strategy vigor and flexibility (47:00) Trust-building and strategic partnership importance (50:33) Co-investment tactics and humility in due diligence (56:02) CAZ case study on downside protection (59:22) Emphasizing downside protection for sustained success (1:01:01) Navigating game selection in investment strategies (1:03:57) Predicting future trends in private asset markets (1:07:59) Strategic impact of relationship with Tony Robbins (1:10:48) Key lessons from early career experiences (1:13:00) Philanthropy's role in personal and professional success (1:16:29) Building meaningful, long-term relationships (1:19:19) Final thoughts on long-term thinking in market selection (1:19:44) Closing remarks

Jul 16

What if Berkshire Hathaway were built today, with the best of technology and long-term thinking baked into its DNA? That’s the question Matt Foran and his team at StoicLane are answering—by doing it. In this episode, I speak with Matt Foran, co-founder of StoicLane, a holding company quietly building one of the most interesting portfolios in private markets. With over 70 acquisitions across four major verticals—accounting, PEO, appraisal and mortgage services, and vacation rentals—StoicLane now manages $300M in TTM revenue and expects $60M in EBITDA this year. But it’s not just the numbers. StoicLane stands out for its permanent capital structure, seller-friendly integration approach, and deep use of technology and AI to transform old-school industries. We dive deep into how Matt thinks about company building, permanent capital advantages, competing with PE firms, and the cultural flywheels StoicLane is creating as they scale. Highlights: The long-term edge of a permanent holding company Why legacy preservation wins deals in fragmented industries How StoicLane acquired 71 companies in 3.5 years Building the 2nd largest vacation rental platform in the U.S. The C-Corp + LLC structure and what it enables Aligning every employee with equity ownership Using AI to uplevel employees and improve service quality Why top talent is the only real constraint The tax advantages of evergreen structures Lessons from competing with PE playbooks—at a different pace -- Guest Bio: Matt Foran is the Co-Founder, President, COO, Board Member of StoicLane, a holding company focused on acquiring and transforming real estate and small business service firms using technology and permanent capital. Since launching StoicLane, Matt and his team have completed 71 acquisitions across four major verticals, scaling the platform to $300M in trailing revenue and $60M in EBITDA. Prior to founding StoicLane, Matt built and exited multiple startups in FinTech, real estate, and InsureTech. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Foran: https://www.linkedin.com/in/mattforan/ Links StoicLane: https://www.stoiclane.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:31) Business scale, acquisitions, and holding company benefits (2:30) Long-term vision in vacation rental business (4:32) Stoic team background and competitive advantages (8:06) Financial outcomes with a unique investment approach (10:27) Business strategies in different verticals (11:26) Proprietary deal flow and acquisition strategy (15:02) Holding company incentives and reverse references (19:33) Commitment fulfillment and long-term relationship building (22:25) Tax benefits of Stoic's business structure (24:18) Capital redeployment and value compounding (26:26) Advantages of evergreen structures (29:14) Utilizing AI in business roll-ups (34:48) Limited use of holding companies in the industry (38:04) Seeking talent for Stoic's growth (40:34) The value of self-sufficiency in employees (42:11) Closing remarks

Jul 14

What’s the playbook for building a resilient, multi-billion‑dollar venture firm that weathers every market cycle? In this episode, Abe Finkelstein, Co‑Managing Partner at Vintage Investment Partners, shares how they underwrite managers, navigate funds‑of‑funds and secondaries, and spot next‑gen innovation—all while maintaining LP confidence across turbulent times. Highlights: How Abe began his career in equity research and transitioned into institutional analysis The origin story of Vintage Investment Partners and how it grew to manage over $3B Why Vintage operates across fund-of-funds, secondaries, and direct growth investing How he evaluates managers and pricing across public and private markets What it takes to build long-term trust with LPs in an increasingly competitive market Abe’s thoughts on gaming, crypto, and Israel’s next big startup wave The decision to relocate to Israel and how that shaped his worldview -- Guest Bio: Abe Finkelstein is a Co-Managing Partner at Vintage Investment Partners, a global venture platform investing in fund-of-funds, secondary, and direct growth-stage opportunities. Vintage manages over $3 billion across its strategies and partners with leading venture firms and startups globally. Before joining Vintage, Abe was a Senior Equity Analyst at Goldman Sachs, where he covered Israeli technology companies. He began his career at Brown Brothers Harriman and later served as Vice President at U.S. Bancorp Piper Jaffray. Abe holds a B.S. in Economics from the Wharton School at the University of Pennsylvania, where he graduated magna cum laude. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Abe Finkelstein: https://www.linkedin.com/in/abe-finkelstein/ Links: Vintage Investment: https://vintage-ip.com/portfolio/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (4:03) AI, regulation, and its impact on European venture (7:38) Vintage's investment strategy and focus on emerging managers (12:42) De-risking and advantages of investing in fund ones (23:49) Adapting investment strategies and annual evolution (25:20) Annual off-sites: Key topics and implementing lessons (30:31) Consistency in team across investment strategies (33:06) Generational transfer and firm resilience (37:30) Israel's investment ecosystem and potential peace premium (42:34) Impact of peace on Israeli entrepreneurs and market dynamics (44:43) Advice for aspiring venture capitalists (47:29) Celebrating venture wins and managing the professional-personal balance (48:06) Reflecting on past deals and closing thoughts (48:51) Closing remarks

Jul 11

I spoke with Amy Rubenstein, CEO of Clear Investment Group, about how she built a thriving real estate platform by focusing on one of the most overlooked areas of the market: distressed C-class multifamily housing. Amy didn’t come from institutional real estate — she taught herself everything from Excel to underwriting by reverse-engineering models, and built a company that now serves both high-net-worth and institutional LPs. Today, her firm consistently delivers 30%+ IRRs by stabilizing mismanaged assets and restoring them to market performance. We talk about her journey from buying a single six-unit property to leading a vertically integrated investment platform, her thoughts on risk and inflation, why C-class housing remains resilient, and how she thinks about scaling her team and her impact. Highlights: Why Amy believes C-class multifamily is the most resilient and alpha-rich real estate strategy How Clear Investment Group creates value by stabilizing mismanaged assets The learning curve of becoming a solo GP with no institutional background Amy’s approach to managing and growing a high-performing team Her philosophy on impact investing — and why they never needed to label it as ESG Institutional fundraising: the 18-month grind and what comes after the first big check How her firm stress-tests for interest rate shocks and avoids market speculation The strategic vision for a one-stop-shop multifamily investment platform -- Guest Bio: Amy Rubenstein is the CEO and co-founder of Clear Investment Group, a real estate investment firm focused on distressed, workforce multifamily housing across the U.S. Under her leadership, Clear has grown from small syndicated deals to managing institutional capital and generating 37%+ average IRRs. She has over two decades of experience in real estate investing, is a self-taught operator, and remains deeply involved in every aspect of the firm’s strategy and execution. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Amy Rubenstein: https://www.linkedin.com/in/amy-rubenstein-a0514698/ Links Clear Investment Group: https://www.linkedin.com/company/clear-investment-group/posts/?feedView=all -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:24) Management and tenant issues in distressed properties (3:02) Amy Rubenstein's industry beginnings and real estate asset performance (5:26) Forecasting interest rates and market conditions (7:59) Interactions with LP base and institutional investors (11:11) Institutional interest and tax benefits in C class real estate (14:07) Essentials of being a successful GP (17:09) Team management and the role of humility (21:22) Delegation, high achievers, and trust (24:19) Growth strategy and future business outlook (26:07) Multifamily real estate and market volatility (29:13) Investment lessons and self-taught skills (33:06) Impact investing and ESG perspectives (35:24) Closing remarks

Jul 9

Philip Krim is best known as the co-founder and former CEO of Casper, one of the fastest-growing direct-to-consumer (DTC) startups in history. Under his leadership, Casper hit $100M in revenue in its first year, went public in early 2020, and was later taken private. Today, Philip is building again—this time through Montauk Climate, a platform innovating in what he calls the “electron economy.” We talked about lessons from hypergrowth, managing through crisis, organizational design, and the future of climate investing. Highlights: How Casper hit $100M revenue in its first year Building a brand consumers want to talk about What it takes to lead through hypergrowth Lessons from taking a company public right before COVID Why he believes DTC was just the beginning of a bigger thesis What the “electron economy” means and why it matters Why Montauk Climate is vertically integrated across venture, credit, and incubation How Philip evaluates early-stage founders—and what makes a good bet Why portfolio construction is the most underrated concept in venture -- Guest Bio: Philip Krim is the founder of Montauk Climate and the former co-founder and CEO of Casper. Under his leadership, Casper became one of the most iconic DTC brands in the world, reaching $100M in revenue in its first year and going public in 2020. After exiting Casper, Philip launched Montauk Climate, a platform focused on building and investing in the “electron economy,” with a mix of venture incubation, growth investing, and credit strategies. He is also an active early-stage investor, with early bets in Ramp, MasterClass, and Relativity Space. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Philip Krim: https://www.linkedin.com/in/philip-krim/ Links: Montauk Climate: https://www.montaukclimate.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (11:12) Hiring for new skills and functions (16:50) Organizational design for startups (19:42) Task structuring for scalability (20:56) Adapting core beliefs while maintaining credibility (22:21) Data-driven decisions versus gut instincts (23:02) Skills needed for founding a company (26:19) Venture vs. public investors' perspectives (31:09) Introduction to Montauk Climate and its strategy (34:47) Role of credit in energy transition (37:21) Electron economy and incubated companies (50:42) Investment approach for private allocators (53:08) Exploring the electron economy (54:35) Traits of successful early-stage founders (57:16) Predicting investment success challenges (59:35) Portfolio construction in venture capital (1:00:13) Closing remarks

Jul 7

Ron Biscardi is the Co‑Founder & CEO of iConnections, a fintech platform reshaping global capital introduction. With 25+ years in the alternative investment space, Ron has facilitated 36,000+ LP/GP meetings since launching iConnections in April 2020. He previously co-founded a boutique seeding firm, deploying over $600M in capital via 20+ deals. From a philanthropic start—with Funds4Food raising $1.9M in 2020 targeting pandemic relief—to anchoring flagship “Global Alts Miami” events, Ron discusses the strategy of building trust, technology, and community in capital formation. Highlights: From charity event to $50M+ platform in five years How 17 crypto managers booked 800+ LP meetings The one thing top fundraisers do that others don’t Why LP behavior is a better signal than mandates The GP playbook for getting 50+ meetings at Miami Building a capital platform without raising VC What GPs get wrong about post-conference follow-up How iConnections is using AI to match funds to allocators Why Asia may soon outpace the U.S. in alternatives The surprising ROI of dinners, concerts, and long games -- Guest Bio: Ron Biscardi is the Co-Founder and CEO of iConnections, the leading capital introduction platform for the alternative investment industry. Since launching the company in 2020, Ron has helped scale iConnections from a philanthropic idea during COVID into a global platform facilitating over 36,000 LP/GP meetings and powering flagship events like Global Alts Miami, New York, and Singapore. Under his leadership, iConnections has grown to over $50 million in annual revenue—all without venture funding—and is now used by major industry partners including SALT, CNBC, Forbes, and AIMA. Prior to iConnections, Ron co-founded a boutique seeding firm that deployed over $600 million across more than 20 deals. He’s also the driving force behind iConnections’ charitable initiatives, which have raised over $2.5 million for causes including food insecurity, mental health, and support for Ukraine. Ron holds a degree in Electrical Engineering from Drexel University and has spent over 25 years in the alternative investment industry. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @NordVPN and @Incogni for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: NordVPN is one of the fastest and most reliable VPN services available, helping users protect their personal data, block malware, and stay secure on any network. With over 7,000 servers in 125 countries, NordVPN allows investors, travelers, and remote professionals to change their virtual location, access region-locked services, and maintain privacy while working from anywhere. NordVPN believes that strong encryption and seamless connectivity are essential to a secure digital life. EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/invest . Try it risk-free now with a 30-day money-back guarantee! Sponsor: Incogni, developed by the makers of NordVPN, is a data privacy tool that helps individuals remove their personal information from the internet. By automatically reaching out to data brokers on the user's behalf, Incogni helps reduce unwanted data exposure, limit spam, and enhance overall digital privacy. Incogni believes that everyone should have control over their personal information in a world where data is constantly being bought and sold. Use code [INVEST] at the link below to get an exclusive 60% off an annual Incogni plan: https://incogni.com/invest . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ron Biscardi: https://www.linkedin.com/in/ron-biscardi-79063/ Links iConnections: https://www.linkedin.com/company/iconnections-llc/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:21) Rahul's approach to adding value to LPs and marketing strategies (7:14) Evolutionary biology, human behavior, and the mission of iConnections (10:35) Founding iConnections and community building (14:22) Compounding benefits of long-term strategies in investing (20:38) Customer feedback, product extensions, and content creation at events (25:24) Leveraging podcast studios for educational value at iConnections events (28:01) Enhancing LP education through meetings (32:41) Relationship building with significant investors (34:31) Effective strategies for GPs to maximize conference opportunities (39:39) Maintaining relationships after conferences (42:45) Impact of AI on manager selection and event planning (47:20) Data partnerships and opportunities (49:16) Addressing misconceptions about iConnections (53:27) Preview of upcoming iConnections events (56:49) Strategies for raising capital across different geographies (59:01) Commitment to expanding into new markets (1:00:44) The role of personal interactions in successful networking (1:02:42) Cultivating friendships to enhance business growth (1:02:58) Closing remarks

Jul 2

In this episode, I speak with Tyler Sosin, founder of Villain Capital, a new fund focused on investing in vertical software businesses. Having grown up in the venture business for 17 years with storied firms Menlo Ventures and Accel Partners, Tyler brings a unique - and perhaps contrarian - perspective to venture investing. With Villain, Tyler's ambition is to help vertical focused founders efficiently scale their start-ups into dominant franchises that can compound their growth and relative market share over decades. The name of the firm, Villain, was inspired by a quote by Harvey Dent, a character in the Batman film The Dark Knight, who said to Batman, “You either die a hero or see yourself live long enough to become a villain.” Highlights: The power of vertical software and markets that start small but grow big Characteristics Tyler looks for in early-stage founders Misconceptions around TAM and the overlooked upside in niche markets Why customer lock-in and annuity-like business models matter Thoughts on growth at all costs vs. compounding sensibly Lessons from past investments like Flywire, Carta, and Indio What venture gets wrong about market sizing and competition How Villain balances elements of both VC and growth equity The underestimated strength of founders who’ve been burned before -- Guest Bio: Tyler Sosin is the founding partner at Villain Capital and a board partner at Menlo Ventures. Tyler has a degree in International Relations from Stanford University and lives in New York City. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Tyler Sosin: https://www.linkedin.com/in/tylersosin/ Links: Menlo Ventures: https://menlovc.com/team/tyler-sosin/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:37) Peter Thiel's perspective and the role of market power (5:12) Identifying potential villain companies in early stages (8:26) Successful strategies in product bundling and market control (12:44) Venture capital approach to small markets (19:11) Balancing growth and sustainability in startups (24:56) Historical impact and profitability of tech giants (27:37) The importance of collaborative thinking and networking in VC (31:03) Herd behavior and innovation in fund management (34:53) Vertical software companies: PE and growth equity interest (37:23) Debunking market size myths in startup success (42:36) Storytelling and scaling in startup growth (44:15) Strategies for expanding market reach in growth companies (48:56) Career advice from Tyler Sosin's perspective (51:00) The Thiel fellowship's influence on young entrepreneurs (51:40) Closing remarks

Jun 30

In this episode, I speak with T.C. Wilson, Chief Investment Officer of The Doctors Company (TDC Group), the nation's largest physician-owned medical malpractice insurer with $7 billion in assets under management. T.C. shares how he built an internal investment office, how insurance investing differs from endowment and foundation models, and why he treats surplus like an endowment portfolio. We dive into his framework for portfolio construction, his views on innovation in asset management, the underrated value of evergreen structures, and the specific ways GPs can tailor their approach to win over insurance LPs. T.C. also shares why he’s cautious on large-cap private equity, how he thinks about downside protection, and what extreme ownership has taught him as a leader. If you want to learn how a CIO with decades of experience invests across public and private markets with an eye toward solvency, surplus growth, and long-term resilience, you’ll want to listen to this one. Highlights: T.C.’s path from Mercer to CIO of TDC Group Building an internal consulting-style investment team What makes insurance companies unique LPs Why surplus is treated like an endowment portfolio Portfolio construction: 80% non-VAR, 20% “fun stuff” How to think about investing as a taxable entity The role of rated feeder notes in optimizing statutory reporting What GPs often get wrong when pitching insurance allocators Evergreen structures and the “virtue of illiquidity” Why culture and leadership matter more than most realize -- Guest Bio: T.C. Wilson is the Chief Investment Officer of The Doctors Company (TDC Group), where he oversees more than $7 billion in assets under management. He joined the firm in 2017 after serving as an external investment consultant to the company for 18 years. Prior to TDC, T.C. worked at Mercer and led an institutional consulting group focused on insurance clients. He has over 35 years of experience in investment management and is known for his deep understanding of how to balance surplus growth, solvency, and risk-adjusted returns within the insurance framework. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Thomas (T.C) Wilson: https://www.linkedin.com/in/thomas-t-c-wilson-ab70b7a/ Links: TDC Group: https://www.tdcg.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:15) Capital allocation: Insurance vs. Endowments & $3.2 billion surplus impact (4:52) Tax considerations in portfolio construction (6:06) Traits of successful GPs and regulatory support (10:22) Rated feeder notes and attracting insurance investors (14:31) Evolution of asset managers and TDC Group's current strategy (20:35) Private equity insights and evergreen fund benefits (25:50) Investment strategy for downturns and portfolio resilience (30:34) Illiquidity's role and criteria for new PE manager investments (33:12) Portfolio construction vs. manager selection debate (37:38) General partners' practices and AI's future impact on asset management (42:11) Investor and allocator perspectives: Overrated and underrated aspects (45:12) Extreme ownership and its influence on company success (49:29) The significance of principles and culture in firms (50:09) Conclusion and contact details (50:19) Closing remarks

Jun 27

What does it take to allocate billions in private markets—and what sets a top-tier LP apart? In this episode, I speak with Patrick Miller, Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he plays a central role in their alternatives platform, investing across venture capital and private equity. Patrick shares how a single energizing meeting with a Florida-based venture capitalist sparked his interest in the asset class and how his team has since built a differentiated barbell strategy combining legacy tier-one firms and new emerging managers. We dive into what LPs can do to truly add value to GPs, why fund size and ownership matter, how AI is shifting capital dynamics, and what makes a venture firm truly “differentiated.” Whether you're a founder, a new VC, or an allocator, this episode is full of real LP insights from one of the most thoughtful voices in the game. Highlights: How Patrick first got excited about venture capital (and why he still is) What LPs bring to the table beyond capital The three most important differentiators for emerging managers Why J.P. Morgan Asset Management venture strategy uses a barbell approach The effect of AI on venture capital’s capital stack How small funds can outperform big ones—if you know what to look for What Patrick looks for in private equity managers The most important advice he’d give his younger self -- Guest Bio: Patrick Miller is an Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he is responsible for portfolio management, investment due diligence, and business development. He joined J.P. Morgan in 2012 and has played a key role in sourcing and managing investments across venture capital, private equity partnerships, co-investments, and secondary opportunities. Patrick earned his BA from Northwestern University, where he studied Communications and Business Institutions and was a member of the varsity baseball team. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Patrick Miller: https://www.linkedin.com/in/patrick-miller-80386558/ Links: J.P Morgan Asset Management: https://am.jpmorgan.com/us/en/asset-management/institutional/investment-strategies/alternatives/private-equity-group/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:06) Patrick Miller's entry into venture capital and adding value as an LP (3:01) Stability and institutional experience in venture capital (4:36) Investing in emerging managers and conviction in their success (9:06) Impact of AI on venture capital (13:28) Examples of backed managers and investing in private equity (20:35) Advice for new investors and closing thoughts (22:37) Closing remarks

Jun 25

Michael Marvelli leads the private markets strategy at the UCLA Investment Company, managing a portfolio that spans private equity, real estate, and real assets. But his route to institutional investing wasn’t linear. Before UCLA, he spent time at Prudential and The Irvine Company in real estate and mortgage finance, and even helped launch a venture-backed startup as COO and CFO. That operating experience gives him a unique lens when evaluating managers today. In this episode, we talk about how UCLA builds conviction in lower-middle-market GPs, how they manage dry powder and fund pacing, and what it was like spinning out UCLA’s investment office into an independent entity. Highlights: The origins of the UCLA Investment Company What it took to build the team, processes, and governance from scratch Why UCLA is drawn to undercapitalized and underfollowed private equity managers How real estate and real assets fit into a long-term endowment portfolio The importance of downside protection and flexible pacing in private markets How being a startup COO informs his view on GP talent, decision-making, and alignment What he looks for in truly “great” allocators and investors -- Guest Bio: Michael Marvelli is the Deputy Chief Investment Officer of the UCLA Investment Company, where he leads the firm’s private markets strategy, overseeing private equity, real estate, real assets, and credit. He joined UCLA in 2003 and played a key role in the 2011 launch of the UCLA Investment Company. Before joining UCLA, Michael worked in real estate and mortgage finance at Prudential and The Irvine Company, and co-founded a venture-backed startup where he served as COO and CFO. He holds a BS from UC Berkeley’s Haas School of Business and an MBA from Northwestern’s Kellogg School of Management. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Michael Marvelli: https://www.linkedin.com/in/michael-marvelli-9918557/ Links: UCLA Investment Company: http://www.uclainvestmentcompany.org/home -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:46) Evolution of UCLA Investment Company's strategy (2:29) Asset allocation and its impact on returns (4:11) Manager selection vs. asset allocation strategy (7:30) Exploring the lower middle market in private equity (15:54) Challenges for endowments investing in the lower middle market (20:55) Specialization and focus in endowment investment strategies (25:50) Independent sponsor deals and search funds insights (29:59) Portfolio construction and commitment strategies (32:54) Investment deployment in the lower middle market (34:37) Value creation strategies in lower middle market investments (38:45) The influence of interest rates on private equity (40:56) Defining the ideal GP in private equity (44:03) The importance of sector specialization and operating executives (50:12) Founder-operator rapport in the lower middle market (54:54) Career advice for aspiring private equity professionals (58:34) Emphasizing first principles in investment strategy (1:02:48) Michael Marvelli's strategic thinking and personal strengths (1:04:30) Closing remarks

Jun 23

David Berry is one of the most prolific healthcare entrepreneurs of our time. In this episode, we discuss his transition from scientist to founder to investor, what it takes to scale transformational health companies, and how his firm Averin is helping usher in the next wave of AI-enabled healthcare. We also talk about his early experience launching a satellite at 14, how he's co-founded over 30 companies—including seven unicorns—and why patents, perseverance, and purpose are the trifecta behind lasting innovation. Highlights: “The Elon Musk of Biotech?” Why Sorov called David that—and how David approaches world-changing problems From 0 to 7 Unicorns: What David looks for in the first year of a company that signals long-term greatness Pivots vs. Distractions: How to recognize the “kernel of truth” that transforms strategy The Power of Culture: Why early-stage hiring is make-or-break—and how his brother built an elite culture at TripleLift Replacing Founders Is Overrated: How world-class companies scale with visionary founders still at the helm Extreme Passion: The real signal that a team will stay late, even without being told The Investor’s Edge: Why early and mid-stage inflection points are where true multiples are made Averin Capital: His new firm focused on tech-driven health companies in the underserved growth stage The Coming Wave in Alzheimer’s: Why he believes personalized medicine will finally unlock real progress Product-Market Fit in Biotech? Why 60% of approved drugs still lose money—and how to avoid those pitfalls -- Guest Bio: David Berry is the Managing Partner and co-founder of Averin, a Boston-based investment firm focused on helping build the next generation of great technology-powered healthcare companies. Prior to Averin, he was a General Partner at Flagship Pioneering, where he co-founded over 30 ventures across life sciences and sustainability—including seven that became unicorns. He holds an M.D. from Harvard Medical School, a Ph.D. in Biological Engineering from MIT, and a B.S. in Brain and Cognitive Sciences from MIT. David is also the recipient of numerous honors, including MIT Technology Review’s Innovator of the Year and World Economic Forum Young Global Leader. He is the inventor on over 200 patents and helped launch a satellite at age 14. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #venturecapital #vc #startupsuccess #biotech #assetmanagement -- Stay Connected: Twitter/X: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Berry: https://www.linkedin.com/in/davidberrymdphd/ Links Averin: https://www.averincapital.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (3:21) Drive, perseverance, and strategic pivots in entrepreneurship (7:25) Company culture and founder roles during growth and scaling (15:09) Identifying entrepreneurial superpowers and inner circle support (17:23) Transitioning from entrepreneur to investor principles (21:29) Growth investing strategies and investor-management alignment (25:43) Navigating biotech's business and financial challenges (32:36) Skill stacking and venture capital dynamics in biotech (37:30) Closing remarks

Jun 20

In this episode, I speak with Rip Reeves, CEO of Institutional Investor and former CIO of AEGIS Insurance Services. Rip brings over four decades of experience across investment management, insurance, and endowments. We discuss his unconventional path from Salomon Brothers to leading one of the most iconic platforms in the investment world, his views on the OCIO model, portfolio construction, the “art” of manager selection, and why he believes building authentic relationships matters more than ever in this industry. We also cover his deep ties to LSU, how he uses qualitative signals (like waiting room conversations) in manager evaluations, and the future of Institutional Investor in a changing GP-LP landscape. Highlights: Why LSU’s endowment chose the OCIO model with Cambridge Associates Rip’s view on optimal allocation for endowments — and why 40/30/30 isn't as rigid as it looks The surprising importance of culture and hallway conversations when vetting asset managers How Institutional Investor uses experiential events (like raft races) to build real trust Rip’s perspective on how the public vs. private market divide is blurring — and what that means for allocators Why fixed income is “back” for the first time since the GFC The hidden value of his wife Susie’s honest feedback in his investment thinking The one thing GPs should never do at an Institutional Investor event -- Guest Bio: Rip Reeves is the CEO of Institutional Investor, a leading global platform serving allocators, asset managers, and consultants through content, community, and convenings. Before joining II in 2023, he spent over 11 years as CIO and Treasurer of AEGIS Insurance Services. Prior to that, Rip was Global CIO of Argo Group and held senior roles at BNY Mellon Asset Management, J.P. Morgan Investment Management, and Salomon Brothers. Rip serves on the LSU Foundation Board, teaches finance at LSU, and is an advisor to Northern Trust Asset Management and Preferred Mutual. A Louisiana native, he holds a B.S. in Marketing and an MBA from Louisiana State University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Rip Reeves: https://www.linkedin.com/in/rip-reeves-1b725717/ Links: Institutional Investor: https://www.linkedin.com/company/institutional-investor/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (5:27) Importance of portfolio construction over manager selection (11:23) Qualitative factors and company culture in manager selection (21:59) Building relationships with asset managers (24:58) Rip Reeves on Institutional Investor magazine's impact and event value (31:33) David Weisburd's closing remarks and subscription call-to-action (36:37) Best practices for GP and LP relationship building (41:55) Touch points and allocations between GPs and LPs (44:18) Leveraging Institutional Investor for GP benefits (45:36) Learning about Institutional Investor with Rip Reeves (46:01) Closing remarks

Jun 18

John Trammell has been on the front lines of institutional investing for decades. He’s managed capital for some of the largest families and organizations in the world—from family offices to the Episcopal Church—and in this episode, he explains the seismic shifts happening in the world of endowment and foundation investing. We talk about secondaries, collateralized fund obligations (CFOs), the future of Bitcoin in institutional portfolios, and why concentration—not diversification—created most of the great fortunes. This is one of the deepest conversations I’ve had on how the smartest long-term investors are thinking today. Highlights: Why top endowments are dumping assets in the secondary market How secondaries give institutions a way to clean up bad manager exposure The real reasons endowments need liquidity today Why some schools are now selling private equity... to themselves What a collateralized fund obligation (CFO) actually is Why John believes we’re past the Swensen model—and what’s next The truth about diversification (and when it fails you) How to build conviction to survive the toughest market moments Why cash is no longer a drag on portfolios How to cultivate a “prepared mind” for the next black swan event -- Guest Bio: John Trammell is a seasoned institutional investor who has managed assets across public and private markets for decades. He currently leads investments for the Episcopal Diocese of New York and has previously managed portfolios for prominent family offices and foundations. John is known for his thoughtful, experience-driven approach to asset allocation, governance, and long-term investment strategy—and for his ability to distill complex ideas into timeless lessons. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Trammell : https://www.linkedin.com/in/john-trammell-258723/ Links: Episcopal Diocese of New York: https://dioceseny.org/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (3:11) Liquidity and portfolio construction in university endowments (5:26) Pros and cons of secondary fund investments (7:09) Secondary market investment mistakes by institutional investors (9:20) Asset quality tiers in secondary investing (10:04) Execution of collateralized fund obligations (13:02) Investment governance and alumni contributions (19:54) Swenson model evolution and diversification strategies (25:14) Portfolio management: Concentration vs diversification (28:06) Assessing portfolio diversification strategies (30:15) Bitcoin's role in portfolio diversification (32:27) Cash and emotional challenges in investing (35:18) Tactical strategies during market downturns (36:23) Conviction's importance in investment decisions (39:06) Institutional views on Bitcoin allocation (51:13) Educating stakeholders on liquidity management (54:06) The importance of investment education (55:38) Embracing a prepared mind in investing (57:43) Closing remarks

Jun 16

Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models. Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging. Highlights: Why Elon’s humanoid prediction is “off by multiple orders of magnitude” What’s missing for humanoids to move from hype to real-world deployment The 3 biggest challenges in robotics—and why they’re so hard to solve How open models vs. closed models will shape the future of AI value capture Why NEA is doubling down on cybersecurity What cyber threats will look like in 5 years (spoiler: it's terrifying) Why pen testing and “exposure management” are the future of security How AI agents could close the gap between defenders and attackers What Aaron learned working with Frank Quattrone at Qatalyst How NEA thinks about multi-stage investing and the future of venture -- Guest Bio: Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models. Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Aaron Jacobsob: https://www.linkedin.com/in/aaronejacobson/ Links: NEA: https://www.nea.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (4:18) Safety and industrial applications of humanoids (9:01) Breakthroughs and acceleration in humanoid development (9:38) Value capture in LLM ecosystems and Facebook's LAMA strategy (14:04) Cybersecurity trends: ransomware and penetration testing (17:23) AI's impact on cybersecurity and role of insurance (20:30) Preventative cybersecurity measures and multifactor authentication (25:48) Closing remarks

Jun 13

In this episode of How I Invest, I speak with Arjun Sethi—Chairman and co-founder of Tribe Capital, Co-CEO of Kraken, and one of the sharpest thinkers in venture capital and crypto today. Arjun breaks down how he approaches investing in “N-of-1” companies, what most VCs get wrong about data, and why the traditional funding stages like “pre-seed” and “Series A” are being rewritten in real time. We also go deep into Arjun’s frameworks for scaling world-class companies, the evolution of crypto in a changing political landscape, and the big bets he’s making at the frontier—including humanoid robotics. Whether you're an allocator, founder, or just fascinated by the future of finance, this conversation is packed with sharp insights and original thinking. Highlights: Why Arjun views Tribe as an “operating system” for venture What makes Kraken different from Coinbase and Binance The critical difference between a market leader and an N-of-1 company How Arjun uses leading indicators to invest ahead of revenue The vision behind Termina, Tribe’s in-house data platform What most investors get wrong about benchmarks How tokenized equities could reshape global capital markets Why humanoid robots could play a key role in defense and logistics -- Guest Bio: Arjun Sethi is the Co-Founder and Chairman of Tribe Capital, a venture capital firm managing $1.8 billion across stages. He is also the Co-CEO of Kraken, one of the world’s largest crypto exchanges. Arjun previously worked at Facebook, was a partner at Social Capital, and has founded multiple companies across consumer, enterprise, and deep tech. Most recently, he incubated Foundation Robotics, a humanoid robotics company building toward a future of self-sustaining technology. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: Twitter/X: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Arjun Sethi: https://www.linkedin.com/in/asethi/ Links Kraken: https://kraken.com/ Tribe Capital: https://tribecap.co/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:06) Differentiation of Kraken from other exchanges and crypto trading evolution (6:00) Investing strategies: n of one companies vs market leaders (8:00) Advancements in data utilization for early-stage investments (11:47) Applying nuanced metrics to traditional and tech companies (16:16) Knowing your market position and strategic growth (18:23) Focus and product development in top companies (20:13) Vertical integration trends in various sectors (22:25) Strategies for competing with large venture firms and staying private (27:33) Tokenization in venture capital (29:49) Foundation Robotics: Mission and challenges (32:54) Future of humanoid robots in industry and defense (33:19) Closing remarks

Jun 11

What happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes. In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc works, the role of trust and pivots in building companies, and why pattern-matching VCs often get it wrong. Michael doesn’t hold back. He’s honest, funny, and full of war stories from decades of building companies—and backing founders through multiple lives. Highlights: How getting fired from Time Inc. pushed Michael into entrepreneurship Reinventing subscriptions with continuous service and beating inertia The origins of Priceline and early internet innovation Why successful entrepreneurs are often “unemployable” The venture studio model behind Loeb.nyc and its high hit rate How to know when an old idea is worth reviving Why safety and trust are essential for early-stage teams Navigating pivots and replacing founding teams The evolving role of small teams in the AI era -- Guest Bio: Michael Loeb is the founder and CEO of Loeb.nyc, a venture collective that builds, funds, and operates startups. Through Loeb.nyc, he has helped launch and scale dozens of companies by combining capital, talent, and shared services in a single ecosystem designed to dramatically improve the odds of success. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Michael Loeb: https://www.linkedin.com/in/michaelloeb1/ Links: Loeb.nyc: https://www.loeb.nyc/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:09) Michael Loeb's journey from Time Warner to entrepreneurship (2:17) The birth of subscription services and Time Warner acquisition insights (4:07) The essence of entrepreneurial disagreeableness and innovation (7:40) The story behind Priceline's creation with Jay Walker (20:06) Recognizing the right timing for business ideas (23:16) Key factors for a company's sudden growth (27:00) The importance of adaptability and pivoting in business (32:00) Leadership strategies in emerging companies (34:47) Embracing reinvention for achieving product-market fit (35:41) The role of small teams in company scaling (38:13) Debunking the starving entrepreneur myth (40:03) Understanding the entrepreneurial drive to succeed (43:22) The American entrepreneurial ecosystem (46:03) Work-life balance for entrepreneurs (48:36) The impact of success on perception (50:43) Michael Loeb's parting wisdom and call for ideas (52:16) Analyzing success rates and VC partnerships (53:53) Impact of the NYC mayoral race on the entrepreneurial scene (56:53) Lessons from founding billion-dollar companies (57:16) Closing remarks

Jun 9

Sasha Pieterse might be best known for her acting career — but behind the scenes, she’s been building a beverage empire. In this episode, we dive deep into how Sasha's personal health journey led her to launch Hippie Water, a hemp-derived THC beverage brand that’s now in 140+ stores across 9 states. We talk about what it takes to transition from Hollywood to the CPG world, why Gen Z is drinking less alcohol, and how Sasha is redefining what it means to be a “celebrity founder.” This conversation goes beyond cannabis — it’s about leadership, authenticity, and building brands with staying power. Highlights: Why Sasha stopped drinking alcohol — and how cannabis changed her life The inspiration behind Hippie Water and how it fills a social gap How she scaled to 140 stores in under 9 months The science vs. stigma behind cannabis and hemp-derived THC Gen Z’s changing relationship with alcohol What it’s really like to fundraise as a first-time, celebrity CEO Why Sasha believes your team is your real moat How she balances acting, entrepreneurship, motherhood, and hosting her podcast Women in the Nude -- Guest Bio: Sasha Pieterse is an actress, entrepreneur, and co-founder of Hippie Water, a hemp-derived THC beverage brand. She rose to fame on the hit TV show Pretty Little Liars and now splits her time between entertainment and building her consumer goods startup. She’s also the host of the Women in the Nude podcast, where she tackles taboo topics in women’s health, business, and identity. With 21 million followers across platforms, Sasha brings a unique voice to the cannabis space — combining influence with authenticity and mission-driven leadership. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Sasha Pieterse-Sheaffer: https://www.linkedin.com/in/sashapieterse/ Links Hippie Water: https://www.hippiewater.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:31) The science, politics, and decline in alcohol consumption among younger generations (7:49) Hippie Water's journey from prelaunch to commercial success (9:54) Insights into the day-to-day life and challenges of a CEO (15:46) Understanding the target demographic and celebrity founder dynamics (21:04) Authenticity, competitive advantage, and the industry potential of Hippie Water (23:24) Navigating the regulatory landscape for hemp beverages (26:30) Key lessons and best practices for new CEOs (30:22) Merging corporate experience with cannabis entrepreneurship (35:22) The transition from acting to podcasting and entrepreneurship (39:43) Closing remarks

Jun 6

This episode is a masterclass on one of the most powerful — and under-the-radar — capital structures in private markets: Small Business Investment Companies (SBICs). I’m joined by Brett Palmer, President of the Small Business Investor Alliance, and David Demeter, who helps manage Davidson College’s endowment. We dive deep into the SBIC program — a unique public-private partnership that lets private equity and credit funds access 2:1 fixed-rate, non-recourse leverage from the U.S. government. The result? LPs can access equity-like returns for credit-like risk, and fund managers gain scale without sacrificing strategy. Most people haven’t heard of it. That’s exactly why we did this episode. Highlights: SBIC funds outperformed benchmarks by ~4% net IRR, per UNC-Chapel Hill study SBICs access 10-year fixed-rate leverage at ~50–80 bps over Treasuries Funds can borrow up to $175M with no refinancing risk Net-of-fee returns can exceed gross-of-fee returns — due to leverage Lower middle market is still inefficient, underprofessionalized, and rich with alpha Davidson College uses SBICs to target 3x net MOIC — with less risk Program has grown from $2B to $50B+ in AUM since 2008 LPs include family offices, endowments, and banks — but few large institutions -- Guest Bio: David Demeter helps manage Davidson College’s endowment, where he leads investments across hedge funds, venture capital, and private equity. Davidson is known for its barbell strategy — combining high-performing venture and niche private strategies like SBICs. Brett Palmer is the President of the Small Business Investor Alliance (SBIA), the leading advocacy group for SBIC fund managers and investors. He’s been at the helm since 2008, helping modernize and grow the SBIC program. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Demeter: https://www.linkedin.com/in/david-d-demeter-117aa913/ Brett Palmer: https://www.linkedin.com/in/brett-palmer-2160b95/ Links: Davidson College: https://www.davidson.edu/ Small Business Investor Alliance: https://sbia.org/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:20) SBIC performance metrics and leverage explanation (4:20) Benefits and growth of SBICs (7:41) SBIC funds' role in private credit, equity, and structural alpha (11:10) Lower middle market investments and economic impact (16:04) Backing and special features of SBIC leverage (18:33) SBIC program awareness and emerging managers (23:24) Challenges and eligibility for SBIC licensing (27:28) Davidson endowment's investment strategy (29:20) Hedge fund and venture capital investments in Davidson portfolio (31:12) Quant strategies and hedge fund allocation challenges (33:18) Resources for SBA funding and parting words (34:27) Closing remarks

Jun 4

What if your venture partner could talk to a thousand founders a day — and actually listen? In this episode, I speak with Andrew D’Souza, the Founder/CEO (aka Creator) of Boardy and previously the founder and CEO of Clearco (formerly ClearBank). Andrew is building something entirely new: Boardy, an AI super-connector that lives across voice, chat, and email — and introduces people to each other. He describes Boardy as a principal, not an agent — a character with its own goals, who is building goodwill and helping founders, fund managers, LPs, and executives find each other in real time. And here’s the wild part: Boardy is already responsible for over ten multimillion-dollar deals, including helping HF0 select 3 of its 10 portfolio companies, and facilitating LP meetings for emerging fund managers. Highlights: 3 of HF0’s 10 most recent investments came from founders surfaced by Boardy Boardy has facilitated over 10 multimillion-dollar deals — including founder-investor and LP-GP introductions VCs are using Boardy to filter inbound, diligence deals, and ideate thesis Boardy works like a McKinsey partner: asking questions, forming opinions, connecting people Designed as a “principal,” not a “tool” — Boardy has its own goals and judgment -Trained through over 50,000 conversations, Boardy’s match rate is compounding fast Andrew’s team uses Boardy daily — including for hiring and internal decision-making Boardy speaks over voice, chat, and WhatsApp — and conversations feel more like peers than prompts -- Guest Bio: Andrew D’Souza is the founder of Borty.ai, a voice-powered AI platform that connects people based on real-time, high-fidelity conversations. Previously, he co-founded Clearco (formerly ClearBank), where he helped pioneer revenue-based financing for e-commerce startups. Andrew is also a seasoned startup investor and advisor, and began his career at McKinsey & Co. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Andrew D'Souza : https://www.linkedin.com/in/andrewdsouza/ Links: Boardy: https://www.boardy.ai/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:21) Bordy's role and application in venture space and team hiring (3:45) Bordy's experience with HF Zero accelerator and deal facilitation (8:00) Confidence in Bordy's model and matchmaking judgment (15:27) Improving fund performance and early use cases (19:12) Boardy's intelligence growth and internal company use (23:26) AI's impact on business operations and data analysis (25:02) Boardy's scalability and role in asset management (28:25) Boardy's creation, use cases, and product road map (33:39) Future integration of AI and humans in society (37:33) Boardy's market focus and compounding skills (41:28) Hiring at Boardy Inc. using Bordie (44:44) Closing remarks and contact information (46:35) Closing remarks

Jun 2

Alex Robinson is the Co-Founder and CEO of Juniper Square, a company transforming the private markets through technology and service. In this episode, we go deep into how he and his co-founders saw the opportunity to modernize fund administration, why the private markets are decades behind the public markets, and how Juniper Square is building for the future with AI agents. We also discuss how the best GPs scale trust with LPs, why the retail channel still hasn’t arrived in full force, and the challenges of building a system of record in a fragmented industry. Highlights: How a FedEx delivery inspired Juniper Square Why crowdfunding was a “dumb idea” and investor relations software was the wedge Building trust with GPs in the early days Why Juniper Square is both a tech and services company The Pareto principle in fund admin automation Why LP experience matters—especially for back-office users Lessons from institutional LP demands and side letters The power law of retail fundraising in private markets What top GPs do to reinforce trust at every touch point How Juniper Square is using AI agents to transform investor relations, fund admin, and portfolio decision-making -- Guest Bio: Alex Robinson is the Co-Founder and CEO of Juniper Square, a leading provider of investment management software for the private markets. Before Juniper Square, Alex was a serial entrepreneur in the clean tech space. He holds degrees from Harvard and Stanford, and today leads Juniper Square’s vision to bring the private markets into the digital age. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Robinson: https://www.linkedin.com/in/alexrob22/ Links Juniper Square: https://www.linkedin.com/company/juniper-square/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:05) Genesis and expansion of Juniper Square (3:12) Growth trajectory of private markets and the impact of the Jobs Act (5:14) Juniper Square’s contrarian view on crowdfunding and strategic focus (7:27) Evolution of Juniper Square’s target customers (10:45) Building a great product and intersection of technology in fund administration (14:45) Organizational design and customer service at Juniper Square (20:56) Juniper Square’s software tools and network effects (25:23) Diverse GP reporting methodologies and back-office experience (27:47) Retail investors' impact and shift in investor data expectations (33:53) Managing side letters and Juniper Square's business model (36:22) LP preferences and fee sensitivity in venture returns (41:17) Juniper Square's customer base and AUM privacy (45:39) Marketing strategies and growth of retail investment in alternative assets (51:28) Reinforcing trust with LPs and best practices for scaling relationships (57:12) Typical growth patterns and expansion strategies of GPs (1:02:57) Juniper Square's investment in AI and upcoming features (1:07:45) Closing remarks

May 30

Alexis John d'Amecourt is the coach behind some of the most iconic CEOs in tech today—including the founders of Substack, Eigenlayer, and Booksy. In this episode of How I Invest, I sat down with Alexis to explore what really makes great CEOs tick—and what causes them to fall apart. We talked about how founders can build trust, navigate emotional turbulence, lead organizations as they scale, and get unstuck when things feel overwhelming. Alexis also opened up about his own story—from being raised by his grandmother in D.C. after a turbulent childhood to becoming a three-time founder turned executive coach. This conversation is packed with tactical frameworks, powerful analogies, and a ton of heart. Highlights: Why even the best CEOs need coaching—and what coaching actually looks like The most common problems CEOs face at every stage of company growth What to do when you’re stuck, overwhelmed, or panicked as a founder The difference between managing and leading—and how to do both effectively The one skill that top 10% employees all have in common A powerful tactic for giving and receiving feedback that builds trust What ego looks like when it helps vs. when it hurts How childhood experiences shape founders—and how to turn that into fuel -- Guest Bio: Alexis John d'Amecourt is the founder of Mishory Method, an executive coaching firm that works with top CEOs and venture-backed founders around the world. His clients include the CEOs of Substack, Eigenlayer, and Booksy, among many others. A three-time founder himself, Alexis brings deep empathy and real operating experience to every conversation. I’ve seen firsthand how effective he is—and I’m excited to share this episode with you. Alexis was born into a lineage of remarkable minds and bold innovators. His great-uncle was Stanislaw Ulam, the renowned mathematician who made foundational contributions to nuclear physics—including a vital role in the development of the hydrogen bomb—and who pioneered the use of Monte Carlo methods. On his maternal side, Alexis was the great-great-great-grandson of Gustave de Ponton d’Amécourt, the French inventor and engineer who advanced early helicopter technology and coined the very term “helicopter.” Alexis was also the son of Joanna Harcourt-Smith, who was married to Timothy Leary—a relationship captured in Errol Morris’s documentary My Psychedelic Love Story. But his mother left when he was just two years old. Alexis was raised instead in Washington, D.C., by his Austrian grandmother, a sharp and self-made entrepreneur who became his greatest influence. Raised between two continents—with one foot in European tradition and the other in American dynamism—Alexis was shaped by the paradox of abandonment and deep mentorship. That duality has become central to his work with CEOs today, offering a perspective grounded in resilience, heritage, and the power of reinvention. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexis John d'Amecourt: https://www.linkedin.com/in/alexisdamecourt/ Links: Mochary Method: https://www.mocharymethod.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:39) The role and need for CEO coaching (5:08) Coaching vs. therapy for CEOs (8:08) Overcoming scaling challenges (11:57) Strategies for getting CEOs unstuck (16:11) Coaching dynamics with young CEOs (19:40) CEO misconceptions and role balance (22:33) Hiring challenges and skills of founders vs. traditional CEOs (25:02) Leadership styles: carrot vs. stick and anti selling (29:04) Managing and motivating top performers (31:20) CEO's organizational influence (33:31) Common mistakes and leadership styles of experienced CEOs (37:31) Encouraging employee peak performance (39:18) Feedback dynamics in personal and professional spheres (45:02) The role of psychopathy in scaling businesses (47:02) Ego balance for effective CEO leadership (54:32) Alexis John d'Amecourt's backstory and the power of vulnerability (59:34) Childhood trauma and its influence on founders (1:02:24) Transitioning from insecurity to vision-driven leadership (1:04:22) First principles thinking and immediate CEO improvements (1:08:17) Client profiles and contacting Alexis John d'Amecourt (1:09:19) Closing remarks

May 27

Hunter Somerville helps allocate billions of dollars across venture capital at StepStone—and he’s one of the most thoughtful LPs I’ve ever met. In this episode of How I Invest, Hunter gives us a rare look into how top institutional investors evaluate funds, pick managers, and underwrite spinouts before they even happen. We go deep on what separates the best emerging managers from the rest, how LPs think about performance before DPI, and why some GPs win repeatedly while others fade. Hunter also shares his own personal playbook—from how he manages his time to the biggest lessons he’s learned over two decades in venture. If you're raising a fund, building a firm, or just curious about how top LPs think, this one is a must-listen. Highlights: The biggest myths about emerging managers—and what actually gets them funded Why DPI and TVPI can be misleading, and how great LPs evaluate funds pre-liquidity What LPs really think about spinouts—and how they prepare for them in advance How to stand out as a fund manager (hint: it’s not just about performance) Hunter’s framework for attribution, sourcing, and “right to win” What makes an LP want to be your first check—and why StepStone often plays that role Behind the scenes of StepStone’s secondaries, direct investing, and micro growth strategy How Hunter structures his calendar for maximum leverage—and why he believes in being “obsessively systematized” -- Guest Bio: Hunter Somerville is a Partner at StepStone Group, one of the largest institutional investors in venture and growth equity. He leads investments across hundreds of funds, directs, and secondaries, and helps back many of the best emerging and established managers in the world. Hunter is known for his deep pattern recognition, clarity of thought, and a relentless work ethic that shows in everything he does. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Hunter Somerville: https://www.linkedin.com/in/hunter-somerville-2a24117/ Links StepStone Group: https://www.linkedin.com/company/stepstone-group/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:42) Fundraising market and LP exposure for emerging managers (2:33) Challenges and indexing venture for mid-level emerging managers (5:08) Tracking attribution, performance, and manager skill indicators (9:41) Valuation policies, game theory, and impacts on investments (12:24) Building successful investment firms and reserve strategies (18:18) Deal attribution and components of sourcing in firms (23:32) The impact of brand and right to win at various fund stages (28:42) Differentiation strategies for venture funds (32:32) Current state and evolution of StepStone's venture practice (38:11) Incorporating AI and technology in investment management (42:23) Building and evolving relationships with investment funds (44:20) Strategies for managing a busy calendar and prioritizing tasks (47:11) Mentorship, personal growth, and career reflections (51:01) Trust and reverse references in large investment transactions (54:21) Ego, selling yourself, and StepStone's ecosystem approach (55:59) Aligning incentives and culture in organizational growth (57:07) Closing remarks

May 23

Brad Conger has a rare view into the evolving dynamics of institutional portfolios—and how allocators can adapt. As Chief Investment Officer of Hirtle Callaghan, a $20B OCIO, Brad is responsible for investment decisions across public and private markets, and he's developed a highly nuanced view of what's working, what's broken, and where alpha really comes from. In this episode, we cover the structural decline of the small-cap index, how private markets have siphoned off the highest-quality growth companies, and why illiquidity can actually be a feature—not a bug. Brad also shares how he builds conviction in contrarian positions, what makes a great spinout manager, and why bigger private equity funds may still outperform. If you're building or managing portfolios across public and private markets, this episode is full of actionable insights. Highlights: Why the small-cap index is now “adversely selected” How private equity and venture capital have changed public markets The alpha case for private markets (even at today’s prices) The emotional benefit of illiquidity for investors Why “alpha fetishism” leads to poor portfolio construction A contrarian bet on Europe—and why it paid off Why good process beats good predictions Lessons from writing puts during a market selloff The underrated strengths of large PE firms How to underwrite spinouts—and what can go wrong Brad’s “crazy trade” for his 90-year-old mother -- Guest Bio: Brad Conger is the Deputy Chief Investment Officer at Hirtle Callaghan, one of the largest outsourced CIO firms in the U.S., overseeing over $20 billion in assets. He is responsible for investment strategy across asset classes and geographies, leading the firm’s efforts in portfolio construction, manager selection, and tactical asset allocation. Brad previously worked at Goldman Sachs and holds degrees from Harvard and the Wharton School at the University of Pennsylvania. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brad Conger: https://www.linkedin.com/in/brad-conger-2990884/ -- Links: Hirtle, Callaghan & Co.: https://www.hirtlecallaghan.com/who-we-are/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:45) Changes in the small cap index and implications for private equity (3:07) Quality and balance of public small cap companies in the new economic environment (7:15) The virtue of illiquidity in investments and issues with LP consultants (9:20) Asset allocation and finding quality in the small cap space (16:32) Thesis on investing in Europe and executing contrarian bets (20:26) Building conviction and the benefits of discretionary investment management (22:54) Role of corporate governance and client-manager relationships (25:45) Leeway for general partners and the European investment landscape (28:00) Navigating tariffs, strategic communication, and risk management (34:43) Bullish perspective on big private equity funds and talent retention challenges (41:06) Effective generational planning and diversifying a private equity portfolio (44:24) Preference for spinouts, their advantages, and fund scalability (52:09) Personal vs. client investment strategies and received wisdom in asset allocation (57:26) Evolutionary psychology and herd behavior in finance (58:33) Closing remarks

May 20

Alexander Ludwig is best known for his breakout roles in The Hunger Games and Vikings, but behind the scenes, he’s a multi-hyphenate: a passionate actor, a devoted entrepreneur, and the co-founder of Their Jewelry—a sustainable, recycled gold and silver brand he runs with his wife. In this episode, Alexander opens up about the brutal realities of Hollywood, the myth of overnight success, and how ego and humility have shaped his 20-year career. We also dive deep into how he's channeling his platform and resources to build a purpose-driven business that could help tackle the e-waste crisis. This conversation covers everything from surviving the actor’s feast-or-famine cycle to the importance of storytelling, Stoic philosophy, and finding peace in a hyper-competitive world. Highlights: From Child Actor to Leading Man – Alexander reflects on the slow and painful journey from early Disney movies to The Hunger Games and Vikings Hollywood as a Casino – Why acting success is like rolling dice and how persistence creates your own luck The Myth of "Making It" – Even after Hunger Games, he still had to audition for everything Launching Their Jewelry – The real story behind his sustainable jewelry brand with his wife Lauren How E-Waste Could Power the Jewelry of the Future – Their’s plan to recycle gold from old phones to create luxury pieces Compounding in the Arts – How Alexander thinks about long-term career building like an investor Lessons from Stoicism – Why Ego Is the Enemy changed his life and every actor should read it Child Stardom and Money – How losing money early gave him the financial discipline he relies on today The Power of Entertainment – Why bringing joy to millions is no small feat Risk, Peace, and Purpose – What tech billionaires, actors, and founders all share -- Guest Bio: Alexander Ludwig is an award-winning actor and musician best known for his roles in The Hunger Games, Vikings, and The Covenant. He began acting at age nine and has worked in the industry for over two decades. In 2020, he co-founded Their Jewelry, a sustainable jewelry brand using 100% recycled gold and sterling silver, which he runs with his wife, Lauren Ludwig. He’s also an avid country music songwriter, extreme sports enthusiast, and passionate advocate for mission-driven entrepreneurship. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: Twitter: David Weisburd: @dweisburd Alexander Ludwig: @alexanderludwig LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexander Ludwig: https://www.linkedin.com/in/alexander-ludwig1/ -- Links Their Jewelry: https://theirisours.com/pages/about -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:28) The role of luck and timing in an acting career (3:02) Keys to success and misconceptions in Hollywood (5:20) Ludwig's journey and persistence to his first big break (9:30) Career trajectories and the intrinsic love for acting (12:20) The impact of entertainment and audience connection (15:04) Maintaining humility and gratitude in the industry (18:50) Staying in the game through longevity, passion, and dealing with ego (22:04) The interplay of hard work, smart work, luck, and humility in success (24:46) Financial prudence, living within means, and the reality of success (31:00) Long feedback loops, compounding, and contrarian bets in careers (33:16) Passion as a driver for long-term success and career focus (39:36) Achieving success through focus vs. diversification (42:01) Synergies between podcasting and fund management (43:22) Staying within your circle of competence and balancing interests (45:38) Evaluating new opportunities and Alexander Ludwig's startup, There (48:23) Differentiating in a saturated market and sustainability initiatives (54:29) Billionaires' motivations and the drive for innovation (1:01:56) Lessons from starting as a child actor and the importance of passion (1:03:29) Balancing vision with focus and Kobe Bryant's philosophy (1:05:13) Closing remarks

May 16

Howard Lerman has founded six companies and taken one public—he's a relentless builder with an obsession for speed, innovation, and execution. Currently the Founder and CEO of Roam, Howard is reimagining what the modern workplace looks like by building the “Office of the Future,” where AI agents work alongside humans to accelerate output. In this episode, Howard joined me in How I Invest Podcast to share the frameworks and mental models behind how he leads teams, scales product-market fit, recruits S-tier engineers, and instills an almost maniacal level of urgency and creativity across the organization. We talk about what it means to enter "founder mode," why professional managers may soon be obsolete, and how cultural memes shape everything from product design to company mission. If you’re building, investing in, or simply curious about the future of work and AI-native companies—this episode is a must-listen. Highlights: Why being a "cockroach" founder is a superpower in company survival How Roam is using AI agents to automate workflows and enable 24/7 productivity The "Office of the Future" and why presence matters—even virtually How to spot S-tier talent (and why they might be a pain to manage) Why product-market fit should be the last thing a founder gives up Howard’s nightly “founder mode” ritual and obsession with speed The evolution of memes and how they shape product adoption The dirty secret about obsession: it’s more about the people than the mission -- Guest Bio: Howard Lerman is a serial entrepreneur and currently the Founder and CEO of Roam, a startup building the "Office of the Future" by integrating AI deeply into the work experience. Previously, he was the Founder and CEO of Yext (NYSE: YEXT), which he led from startup to IPO. He is known for his strong views on founder-led companies, speed as strategy, and hiring only the best—what he calls "S-tier" talent. Howard is also an early adopter and evangelist of AI agents in the workplace. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Howard Lerman: @howard LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Howard Lermar: https://www.linkedin.com/in/howardlerman/ Links: Roam: https://www.linkedin.com/company/roam-hq-inc/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:55) Applying cockroach principles and pivoting at Yext (3:38) Company structures, founder authority, and employee empowerment (6:16) Instilling speed and operating at warp speed in a company (10:01) Delegating and recruiting top talent (17:10) Building urgency and an obsession for success in teams (21:11) Howard Lerman's formative experiences and co-founder relationships (24:12) The role of memetics and memes in business (28:31) Closing remarks

May 13

Zaid Rahman is the founder and CEO of Flex, a breakout fintech startup that’s reinventing credit and payments for the middle market. Backed by the Thiel Fellowship and known for his “Delta 4” product philosophy, Zaid is building a multi-product platform that’s helping profitable, owner-operated businesses unlock capital and scale faster. In this conversation, Zaid breaks down how Flex is using AI to radically reduce underwriting time, why he’s obsessed with hiring 10x talent, and how “taste” and first principles thinking guide everything from product design to risk management. If you’re building in fintech, hiring in tech, or just obsessed with the craft of company-building, this episode is full of tactical insight. Highlights: The Delta 4 framework: how to build products people rave about Flex’s competitive edge vs. Brex, Ramp, and legacy banks How Flex slashed credit underwriting time from 25 days to 48 hours using LLMs Why Zaid believes fintech is “still day one” in 2025 How to spot first-principles thinkers in interviews (and why “best practices” is a red flag) Why Flex targets the “jumbo shrimp” of the middle market How Zaid built a 250+ member Thiel Fellow community from scratch The real cause of burnout—and how to build a sustainable high-performance culture -- Guest Bio: Zaid Rahman is the founder and CEO of Flex, a fintech platform serving mid-market businesses with credit, payments, and financial tools. A recipient of the prestigious Thiel Fellowship, Zaid previously founded multiple startups and is known for his rigorous hiring philosophy, taste-driven leadership, and commitment to building “Delta 4” experiences. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Zaid Rahman: @zaidrmn LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Zaid Rahman: ​​ https://www.linkedin.com/in/zaidrahman/ -- Links: Flex: https://www.linkedin.com/company/flex-super-app/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:14) David Weisburd: Benefits of the Teal fellowship and creating a WhatsApp group for fellows (4:44) David Weisburd: Using AI for credit underwriting at Flex (8:14) David Weisburd: AI's impact on efficiency and differentiating Flex from competitors (11:36) David Weisburd: Recruitment strategy and identifying team members with good taste (20:59) David Weisburd: Evaluating candidate contributions and defining unique positions (24:44) Understanding customer priorities and the importance of first principles thinking (27:09) Learning through interviews and the challenge of finding the right hire (31:06) Balancing expertise and culture fit in hiring and the role of non-10x employees (38:23) Addressing burnout in a high-intensity work environment (40:54) The future of FinTech and Flex's vision (46:27) Closing remarks

May 9

Cliff Asness is one of the most influential minds in quantitative investing and the Founder, Managing Principal and Chief Investment Officer at AQR Capital Management, which oversees over $100 billion in assets. In this wide-ranging conversation, we go deep into what makes a successful long-term strategy, how Cliff thinks about building portfolios, and why most investors misjudge both volatility and leverage. He also shares what it was like launching AQR after his early work on momentum strategies at Goldman Sachs, and what he’s learned about investor behavior across cycles. This is one of the most insightful and entertaining conversations we’ve had on the podcast—and Cliff brings both humor and hard-earned wisdom to the table. Highlights: Why most investors are under-levered—and how Cliff thinks about smart leverage The origins of AQR’s first strategies and his early momentum research The problem with how investors benchmark hedge funds Why high volatility strategies can actually reduce risk The truth about hedge fund alpha—and why most funds are just “half-hedged” The “pull the goalie” metaphor and taking rational risks under pressure What AQR does (and doesn’t) believe in when it comes to machine learning Cliff’s view on how to build portfolios that survive 3-year drawdowns Why he thinks the best portfolios often don’t look great in the short run -- Guest Bio: Cliff Asness is the founder, Managing Principal, and Chief Investment Officer at AQR Capital Management. He holds a PhD from the University of Chicago, where he studied under Eugene Fama and Kenneth French. Cliff is widely recognized for his groundbreaking work on momentum investing and factor-based strategies, and he’s one of the most cited voices in modern quantitative finance. He has published extensively in academic journals and is known for his bold, sometimes contrarian takes on investing and market behavior. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Cliff Asness: https://www.linkedin.com/in/cliff-asness/ -- Links AQR: https://www.aqr.com/About-Us/OurFirm#firmfacts -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:49) Managing institutional portfolios and the "pulling the goalie" metaphor (3:02) Challenges and psychology in maintaining investment strategies (8:25) Portfolio strategy combination and client preeducation (11:36) Continuous strategy improvement and balancing conviction (18:20) Handling drawdowns and hypothesis testing (21:05) Stress management and communication in fund management (29:09) Hedge fund transparency and strategy development (31:01) Hedge fund performance analysis and misconceptions (39:43) Applying valuation and momentum across markets (43:21) Risks and evolution of arbitrage and quant strategies (47:27) Machine learning and NLP in investment strategies (50:19) Data mining, alternative data, and future-oriented strategies (56:13) Integrating different investment strategies into products (1:03:11) Leverage importance and risks in investing (1:10:30) Managing high volatility strategies in portfolios (1:17:17) Complexity as a virtue and market efficiency catalysts (1:24:42) Long-term strategy mindset and AQR's future (1:28:01) AQR's competitive advantage and recruitment (1:30:03) Closing remarks

May 6

John Bowman, CEO of the CAIA Association, joins How I Invest to discuss the most important shift in institutional investing: the move from the traditional bucketed approach to the Total Portfolio Approach (TPA). In this episode, we go deep on how allocators are modernizing portfolio construction, why liquidity might be a hidden danger, and what the future of alternatives will look like as trillions of dollars flow from public to private markets. Highlights: TPA vs. SAA: Why institutions are moving beyond traditional asset allocation. Liquidity Trap: How too much flexibility can hurt returns. Diversification Myth: Buckets don’t work in a world of blurred asset classes. Family Office Pitfalls: Why starting with direct deals is a mistake. Private Markets Boom: Alternatives now make up over 20% of institutional AUM. Access for Individuals: Platforms like iCapital and Alto are changing the game. Education Gap: Why advisors need to catch up as products evolve. The Future: Alternatives won’t be “alternative” for much longer. -- Guest Bio: John Bowman is the CEO of the CAIA Association, a global organization focused on education and professionalism in the alternatives industry. With over 14,000 charterholders worldwide, CAIA is the standard for private equity, hedge funds, private credit, and real assets. John previously held senior leadership roles at the CFA Institute and has spent decades helping institutions, advisors, and allocators navigate the evolution of the investment landscape. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc . -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Bowman: https://www.linkedin.com/in/johnlbowmancfa/ -- Links CAIA Association: https://caia.org/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (1:45) Evolution and comparison of investment approaches (6:03) Equity risk premia and behavioral studies on portfolio management (9:55) Sponsor: Juniper Square (10:21) The changing landscape of the sixty-forty portfolio (13:55) Institutionalization and investment strategies of family offices (22:22) Behavioral psychology's role in investment and managing ignorance debt (28:15) The impact of modern education on institutional investing (31:17) Trends in allocator portfolios and the democratization of alternatives (39:29) Regulatory impacts on private capital and liquidity constraints (46:15) Predictions for the future of the alternatives industry (49:31) The critical role of diversification and understanding asset classes (53:33) The evolving skillset for investment professionals and industry competition (55:45) Dynamics of mergers and acquisitions in the investment sector (56:41) Closing remarks

May 2

Jamie Gull is the GP/Founder of Wave Function Ventures, a deep tech seed fund, and an engineer turned investor who previously worked at SpaceX during its early, intense years of scaling. In this episode, Jamie and I discuss the high-responsibility culture at SpaceX, how it shaped Jamie’s approach to company building and investing, and what makes a deep tech founder stand out. We also explore why fast iteration matters more than perfect planning, how techno-economics drive investment decisions, and why deep tech’s reputation for being overly capital-intensive is becoming outdated. Jamie shares firsthand stories from his time working under Elon Musk, his angel investments in companies like Boom Supersonic and K2 Space, and the founding principles behind Wave Function Ventures. If you're interested in the future of deep tech investing, how to identify category-defining founders, or how hardware startups can scale efficiently, this is a must-listen. Highlights: Jamie’s experience at SpaceX and the "responsible engineer" framework How Elon Musk's real superpower is organizational design and culture Why fast iteration beats careful waterfall planning in deep tech Jamie's investment thesis at Wave Function Ventures Why MBAs leading hard tech startups are often a red flag Understanding techno-economics and how technical feasibility isn't enough Lessons from investing early in Boom Supersonic and K2 Space Why the myth of deep tech needing excessive capital is breaking The role of escalation and decision-making speed at SpaceX How to distinguish scientific risk from engineering execution risk -- Guest Bio: Jamie Gull is the GP/Founder of Wave Function Ventures, a $10 million seed fund focused on investing in deep tech startups tackling hard hardware problems. Before becoming a full-time investor, Jamie spent over five years as an engineer at SpaceX, working on the Falcon 9 rocket, and later founded two venture-backed deep tech companies: a space deployables startup and an electric vertical takeoff and landing (eVTOL) aircraft company. His second company received eight government contracts and was acquired in 2023. Jamie combines deep engineering expertise with founder experience to help startups scale in hard tech sectors. Over the last several cycles, prevailing wisdom in the industry has been that hard tech companies couldn’t achieve extraordinary returns. More recently, this has been busted with the dawn of companies like SpaceX, Anduril, Saronic, etc. These companies are solving large, important societal problems, capitalizing on a perfect storm of events, from geopolitical considerations, to capital, to a massive talent influx from SpaceX and the like to government support. This theme, you can call it American Dynamism, Deep Tech, or Reindustrialization, is fueling top talent to launch and build the largest techno-industrials we have seen. However, investing in these areas requires specialized expertise. Enter Wave Function Ventures. WFV is a new deep-tech focused fund launched by industry veteran and investor Jamie Gull. Jamie possesses the depth and breadth of experience to position WFV to see and win the best deals in this space. He is a former SpaceX engineer who played a key role on Falcon 9 reentry, started and sold his own deep tech company, Talyn Air, that went through Y combinator, has VC experience as a Venture Partner at Pioneer Fund and Next Gen Venture Partners, and has been angel investing in deep tech companies for a decade in companies like Boom Supersonic, Varda, and K2 Space, among others. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #assetmanagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Jamie Gull: @jamiegull LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jamie Gull: https://www.linkedin.com/in/jamie-gull/ -- Links: Wave Function Ventures: https://www.wavefunction.vc/ Email: info@wavefunction.vc -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:16) Role and downsides of the responsible engineer framework (5:52) SpaceX culture and personal growth (8:43) Jamie's meetings with Elon Musk (10:38) Introduction to Wave Function Ventures (12:08) Technoeconomics and founder assessment in deep tech (19:41) Comparing power law outcomes in deep tech vs. software (21:36) Analyzing technical vs. market risk in deep tech (24:39) Second-order effects and Boom Supersonic's origin (27:16) Asking the right questions in recruitment and investment (29:28) Rapid iteration's importance in deep tech startups (32:49) Traits of successful portfolio companies (36:18) Elon Musk’s approach to organizational design (39:13) Decision-making and investing strategies at SpaceX and Wave Function Ventures (41:14) Closing remarks

Apr 29

Paige Finn Doherty, Founding Partner of Behind Genius Ventures, joins the How I Invest podcast to share how she built one of the most distinctive brands in early-stage venture capital — all before turning 25. Paige talks about the power of content and community, how her engineering background shaped her investing style, and why being deliberate about media strategy can transform access to top founders and LPs. She also breaks down her investment thesis around AI in overlooked industries, the importance of institutional-grade operations from day one, and what it really takes to build a lasting venture firm. Highlights: How Paige landed Sandana Capital as a cornerstone LP at just 24 years old The "substance and vibes" approach to getting LPs to say yes How media scaled her reach with both founders and investors Behind Genius Ventures’ investment theses: "technical storytellers" and "clipboard companies" What founders of billion-dollar companies have in common Building a resilient brand through storytelling, community, and consistency Why Behind Genius invests in embodied AI and AI agents How Paige thinks about sourcing deals from TikTok to co-investor networks Best practices for building a strong brand as an emerging manager on Twitter (now X) Why investing in institutional-grade back office systems from day one matters The vision for Behind Genius' next phase: high-production visual storytelling -- Guest Bio: Paige Finn Doherty is the Founding Partner of Behind Genius Ventures, a venture firm she launched at 22 years old to back early-stage technical storytellers building in overlooked industries. She’s the author of Seed to Harvest, a children's book about venture capital, and the host of the Seed to Harvest podcast. Paige is known for her deep conviction in building brands, fostering community, and bringing an engineering mindset to portfolio construction. Through her thought leadership, content, and investing, she’s shaping the next generation of venture capital. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com We’d like to thank @Republic for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Twitter: https://x.com/paigefinnn LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Paige Doherty: https://www.linkedin.com/in/paigedoherty/ -- Links: Seed to Harvest the Book: https://www.amazon.com/Seed-Harvest-Explanation-Venture-Capital/dp/0578906457/ Behind Genius Ventures: https://www.behindgeniusventures.com/ Behind Genius Podcast / Youtube: https://www.youtube.com/channel/UCOsbv-4bWVXIqPQAp2BCf8Q The Technical Storyteller: https://www.behindgeniusventures.com/post/technical-storyteller What it Takes (Billion Dollar Exit): https://www.behindgeniusventures.com/post/what-it-takes-1 Clipboard companies: https://www.behindgeniusventures.com/post/clipboard Cold Outreach: https://paigefinndoherty.com/2020/03/25/a-cold-outreach-workshop/ Fortune Fund II Launch: https://fortune.com/2024/04/23/behind-genius-ventures-raises-second-fund-8-million/ Term Sheets Viral Thread: https://x.com/paigefinnn/status/1255208492312358912 -- Questions or topics you want us to discuss on How I Invest? Email us at david@wesiburdcapital.com . (0:00) Introduction and guest overview (0:55) Paige's passion for venture capital and Behind Genius Ventures' differentiators (4:08) Securing top LPs and media strategy for branding and deal flow (10:39) Sponsor: Republic partnership with Hamilton Lane (11:05) Taking a stand in venture capital and advice for diverse figures (15:54) Solo GP vs. joining a top fund and value add to portfolio companies (20:12) Thesis on AI in antiquated industries and sourcing strategy evolution (26:17) Building a brand on Twitter: Strategies for VCs (30:13) Institutional service providers, LP relations, and future storytelling plans (35:03) Closing remarks and gratitude

Apr 25

Meghan Reynolds, Partner and Head of Capital Formation & Talent at Altimeter, has spent over 20 years at the intersection of GPs and LPs, helping some of the largest firms in the world raise capital, navigate investor relationships, and scale their strategies. In this episode, she breaks down what it takes to be a best-in-class capital raiser—how to expand into new strategies, find the right investors (not just any capital), and build enduring partnerships in a hypercompetitive environment. We also talk about what’s changed in the last 20 years, how the best GPs handle crisis communication, and why building a brand as an investor matters more than ever. Highlights: The difference between capital formation and investor relations—and why many GPs get it wrong How fund strategy changes impact the investor base Why the most strategic capital isn’t always the largest check Lessons from educating LPs about private equity in the early 2000s and private credit in the 2010s The real reasons LPs don’t re-up: performance vs. transparency Why geography, regulation, and timing matter in capital campaigns How investor communication has evolved with tools like WhatsApp and Zoom The enduring value of warm introductions in LP fundraising Why small LPs might one day become your biggest supporters -- Guest Bio: Meghan Reynolds is a Partner and Head of Capital Formation & Talent at Altimeter, a technology-focused investment firm. She leads the firm’s capital formation efforts and has previously held senior roles at TPG and Goldman Sachs. Over her two-decade career, Meghan has built deep relationships across the LP landscape, spanning sovereign wealth funds, pensions, endowments, and family offices. She is known for her insights into how firms scale, evolve their strategies, and communicate effectively with investors. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @Carta and @Republic for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Meghan Reynolds: https://www.linkedin.com/in/meghankreynolds/ -- Links: Altimeter: https://www.altimeter.com/home -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (0:38) Strategic investment and capital formation (3:13) Launching and evolving fund strategies (5:28) Identifying new capital sources (8:52) Educating investors in private markets (12:25) First movers advantage vs. track record (18:13) Reasons LPs leave a fund and the importance of transparency (23:00) Enhancing LP communication and trust (27:27) Building trust through transparency and empathy (29:06) Equity and involvement in investor relations (31:31) Streamlining LP communication with tools (33:18) Capital allocation strategies and diversification (37:06) Geographic diversification strategy (41:47) Accessing and developing new LP relationships (47:00) Leveraging media and social media for fundraising (51:05) Internal and external communication strategies (55:00) Insights for LPs and staying connected (56:52) Closing remarks

Apr 22

D.A. Wallach’s journey is one of the most unconventional paths in venture capital. He went from fronting a rock band discovered by Kanye West and Pharrell, to investing in Spotify, SpaceX, and founding a biotech VC firm reshaping human medicine. In this episode, we dive into his evolution—from artist to investor—and what he’s learned from being in the room with Mark Zuckerberg, Elon Musk, and Ron Burkle. D.A. shares why great investing is an act of taste, how he earned his first big break with Ron Burkle at Inevitable Ventures, and why he believes biotech is the most exciting place to invest over the next decade. We also discuss how aesthetic intuition applies to investing, how to think in second and third order effects, and what it really means to be contrarian when contrarianism has gone mainstream. Highlights: How D.A. invested in SpaceX after meeting Elon Musk socially in LA Lessons from working with Spotify, including his invented role as “artist-in-residence” What he saw in Facebook in the early days and how he used it to grow his band How Kanye West and Pharrell discovered his music and launched his career The backstory behind raising capital for Spotify and meeting Ron Burkle What made Ashton Kutcher and D.A. uniquely valuable investors at the time Why he pivoted from tech into life sciences and started a healthcare-focused VC firm The importance of developing aesthetic judgment as an investor How to think about portfolio construction in biotech vs. software Why investing is mostly about people—and what pattern recognition D.A. uses The subtle power of learning from failures and “almost mistakes” How to be truly contrarian in an environment where contrarianism is trendy -- Guest Bio: D.A. Wallach is a venture capital investor and former recording artist. Discovered by Pharrell Williams while at Harvard, he toured with artists like Lady Gaga and Blink-182 and released music through Interscope and Capitol Records. In 2011, he shifted to investing, backing companies like Spotify, SpaceX, Ripple, and Neuralink. Today, he focuses on biotech and healthcare as co-founder of Time BioVentures. Named to Forbes' “30 Under 30” and Fast Company’s “100 Most Creative People,” D.A. also co-founded the Franca Fund for preventive genomics and appeared in the film La La Land. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @Republic for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ D.A. Wallach: https://www.linkedin.com/in/dawallach/ Links Time BioVentures: https://www.timebioventures.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:00) Elon Musk's early views on AI and building SpaceX (4:18) Transition from music to investing and collaboration with Spotify (7:17) Leveraging Facebook for a band’s success and networking strategies (12:06) Mark Zuckerberg's early projects and the rise of Facebook (14:39) Contrarianism and its role in modern investing (19:22) How a music background influences investment decisions (22:32) Working with Ron Burkle and Inevitable Ventures (27:17) The journey of learning venture capitalism (30:10) Assessing higher-order effects in investments (31:52) The critical importance of investing in people (33:17) Diving into healthcare and biotech investing (36:46) Portfolio strategies in biotech versus traditional venture capital (39:38) How to compete with major biotech firms (44:40) The advantages of being surrounded by top performers (46:58) Learning from near-misses and investment failures (48:25) Closing remarks

Apr 18

Jim Bethea oversees $1.7 billion at the University of Iowa’s endowment—and he does it with a team of just five people. In this episode, we cover how Jim thinks about asset allocation, governance, manager selection, and why Iowa has decided to specialize in certain asset classes like lower middle market private equity. This conversation is full of nuance, clarity, and hard-earned lessons that every allocator, GP, and fund manager will benefit from. Jim pulls back the curtain on how small teams can still invest in niche, high-performing funds, how to manage investment committee dynamics, and why more isn't always better when it comes to diversification. Highlights: The pros and cons of managing a $1.7B portfolio with a lean team Why Iowa focuses on areas where they can outperform by 300 to 1,000 basis points How to evaluate a new asset class and build relationships with experts The myth of diversification and why over-diversification is often expensive beta Jim’s philosophy on manager selection—and why governance matters more than most realize How incentives (or lack thereof) impact committees and investment staff The discipline embedded in illiquidity and why private markets can help prevent bad decisions Why Iowa prefers smaller private equity funds and the edge in lower middle market A candid discussion on when to re-up with top performers and when to walk away Jim’s take on fund-of-funds, venture exposure, and building a durable investment operation in Iowa City -- Guest Bio: Jim Bethea is the Chief Investment Officer at the University of Iowa Foundation, where he manages a $1.7 billion endowment. With over 15 years at Iowa and a deep background in both consulting and investment banking, Jim has crafted a concentrated strategy that punches well above its weight. He’s a respected voice among endowment CIOs and a strong advocate for information-sharing and collaborative learning in the LP community. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @Republic and @Carta for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jim Bethea: https://www.linkedin.com/in/jim-bethea-cfa-caia-b90302177/ -- Links: IOWA: https://uiowa.edu/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Episode preview (2:41) Deciding on new asset classes and information bartering (7:05) Governance and its impact on investment returns (11:11) The role of investment committees and incentives (20:50) Analyzing top and bottom performers in portfolios (24:15) Educating the investment committee and higher concentration strategies (30:28) Co-investment interest and its impact on due diligence (32:14) Diversification versus concentrated portfolio risk and consultant incentives (37:49) Lessons from past market cycles and using fund of funds (42:13) Picking asset classes for alpha and time commitment in underwriting (44:06) Balancing alpha-generation with indexing in public equities (47:05) Liquidity considerations: Asset or liability? (51:00) Behavioral finance and maintaining investment discipline (55:26) Evaluating private equity returns in a competitive market (1:00:12) Specializing in lower middle market private equity and associated risks (1:07:51) Private credit investment climate and technical default issues (1:08:09) Overcoming early challenges and importance of in-house knowledge (1:09:39) Relationship dynamics between GPs and LPs and understanding underperformance (1:10:36) Turnaround stories and the value of investing in smaller funds (1:11:31) Closing remarks

Apr 15

In this thought-provoking debut episode of Turpentine VC, Erik sat down with Ben Horowitz, Co-Founder of Andreessen Horowitz, to explore the evolving landscape of venture capital, leadership, and the future of innovation. Ben shares his insights on navigating market cycles, building resilient companies, and the role of culture in long-term success. This conversation, recorded live at a16z’s Menlo Park offices in 2023, is packed with practical wisdom and candid stories from one of Silicon Valley’s most influential investors. Highlights: VC Market Insights: Ben’s perspective on the current venture capital landscape and how it compares to previous cycles. Leadership Lessons: How to manage effectively during uncertain times and build resilient companies. Founder Resilience: The key traits that drive founders to succeed and how to foster resilience. Company Culture: Why culture is a competitive advantage and how to build a strong one. Investment Strategy: Insights into Andreessen Horowitz's approach to finding and backing standout startups. Future Trends: Ben’s predictions on AI, crypto, and other emerging technologies. Guest Bio: Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz (a16z), one of the most prominent venture capital firms in Silicon Valley. He is also the author of best-selling books "The Hard Thing About Hard Things" and "What You Do Is Who You Are." With decades of experience as an entrepreneur, CEO, and investor, Ben is a leading voice in the startup and VC ecosystem. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank @OldCityInvestmentPartners and @Republic for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement – Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration. The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting. Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com . Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . – Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Links: Andreessen Horowitz (a16z): https://a16z.com/ Subscribe to Turpentine VC: https://link.chtbl.com/TurpentineVC – Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital. (0:00) Episode preview (1:48) Andreessen Horowitz's structure vs. Y Combinator's approach (4:25) Evolution and public consideration of venture firms (8:15) Alignment issues with venture firms going public (9:38) Fund sizes, market opportunities, and talent retention (15:24) Governance and future trends in venture capital (20:14) Ben Horowitz on technology trends and AI strategy (24:30) Web 3, AI development, and crypto regulatory challenges (29:18) Venture vs. multi-asset firms and LP relations (31:16) Firm strategy influenced by macro factors (32:13) Advice for aspiring venture capitalists and wartime mindset (35:53) Technology optimism and building a tech media company (39:05) Media's impact on tech and concerns about AI power concentration (41:16) Decentralizing power and closing thoughts (41:31) Closing remarks

Apr 11

Paul Chai’s journey from first-generation immigrant to Chief Investment Officer of a $1 billion endowment is anything but conventional. In this episode, we unpack how he transitioned from aerospace engineering to managing capital, his approach to investing in “outsiders,” and the delicate balance of taking risk in hedge funds, GP stakes, and tactical trades like TALF 2.0. Paul shares how Kansas State University's endowment supports the school’s mission, why they invest in lower middle market buyouts and small hedge funds, and how they find and evaluate emerging managers. Highlights: How being a first-generation immigrant shaped Paul’s investment philosophy Why Kansas State backs outsiders—and what they look for in emerging managers The TALF 2.0 trade that returned 8% in 6 months—4x the bond index How small hedge funds and lower middle market buyouts can deliver outsized alpha Kansas State’s 3-bucket portfolio structure: growth, diversifiers, and liquidity Why investing in people is Kansas State’s highest-ROI strategy Guest Bio: Paul Chai is the Chief Investment Officer of the Kansas State University Foundation, where he manages the school’s $1 billion endowment. A former aerospace engineer and consultant, Paul was recruited into investing by his college roommate and spent 12 years at a family office before joining Kansas State. He leads the investment team’s efforts across public and private equity, hedge funds, tactical strategies, and more — all while supporting the university’s mission of accessible, affordable education. Paul is a first-generation immigrant and an MIT graduate. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . We’d like to thank Carta, Republic and Old City Investment Partners for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration. The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting. Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com . Stay Connected: LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd Paul Chai: https://www.linkedin.com/in/ppchai/ Links Kansas State University Foundation: https://ksufoundation.org/ (0:00) Episode preview (2:44) Building connections and motivation in fund managers (6:04) Mutual value in manager relationships and balancing manager size (9:18) Tactical investment approach, TALF 2.0 trade, and partnering with nimble managers (13:09) Trust with the board and significance of TALF 2.0 trade (16:11) Portfolio leverage, diversifiers, and hedge fund strategies (20:11) Measuring portfolio diversification and the quarterly review process (23:41) Re-underwriting and portfolio structure with investment categories (27:36) Target return, portfolio levers, and dislocation opportunities (30:59) GP stakes, endowment strategy, and managing risk with smaller fund managers (37:16) Advantages of smaller hedge funds and Kansas State's investment strategies (42:12) Personal mission and Kansas State's impact (43:22) Closing remarks

Apr 8

Blake Scholl started with a crazy idea: bring back supersonic flight. A decade later, Boom Supersonic pre-orders from the likes of Virgin, United, and American Airlines, and is building the fastest commercial jet since the Concorde—without the sonic boom. But what looks like an inevitable success now was, at the beginning, a nearly laughable dream. In this episode, we break down how Blake went from crashing a Virgin Galactic rollout to pitching Richard Branson over breakfast, to getting a “yes” 24 hours before Y Combinator Demo Day. It’s a masterclass in high-agency entrepreneurship and building something audacious from first principles. From pitching billionaires to proving physics, from engineering emotional payoff for teams to raising capital from LPs directly, Blake unpacks how to build hard tech companies that actually work. If you’re a founder, builder, or dreamer, this one’s for you. Highlights: Crashing Richard Branson’s party (literally) — and landing Virgin’s $2B commitment 24 hours before Demo Day How Blake turned a cardboard prototype into a billion-dollar narrative The best startup pitch ever to a billionaire: “I’m not asking for money, just the first 10 planes.” Boom's first supersonic jet XB-1: how it was built, what it taught, and why it’s a game-changer Why burnout isn’t working too hard—it’s working too long without emotional payoff Boom’s path to proving “boomless” flight—and why that could unlock coast-to-coast supersonic travel How Boom raised capital by skipping VCs and going straight to LPs Why the market for supersonic flights could be bigger and more profitable than subsonic The lesson from Uber, jets, and the Beatles: when you shorten time, you grow the market Blake’s advice to hardware founders: “Don’t start with Starship. Start with Falcon 1.” -- Guest Bio: Blake Scholl is the Founder and CEO of Boom Supersonic, the company building the world’s fastest commercial airliner. Prior to Boom, Blake worked at Amazon and was part of the early team at Groupon. He’s raised hundreds of millions from bold investors like Reid Hoffman, Michael Moritz, and Y Combinator, and he’s built Boom into a company that could transform the future of global mobility. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Republic and @OldCityInvestmentPartners for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration. The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting. Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com . Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Blake Scholl: @bscholl LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Blake Scholl: https://www.linkedin.com/in/blakescholl/ Links: Boom Supersonic: https://boomsupersonic.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (0:18) Efforts to repeal regulations and pitching to Richard Branson (2:23) Sales strategies, initial LOIs, and gaining credibility (3:51) Crashing Virgin Galactic's rollout and securing a deal with Richard Branson (7:48) Lessons for hardware founders, market validation, and the XB-one prototype (12:29) Overcoming technological barriers in supersonic flight (13:36) Comparison with SpaceX's incremental approach (18:22) Focusing milestones in the early years (19:23) Recruiting top talent and capital misconceptions for hardware companies (23:09) Profitability and competitive advantage in the airline industry (25:57) Regulatory landscape and supersonic flight over land (32:25) The importance of in-person meetings and future travel accessibility plans (34:06) Lessons learned from building Boom and advice for hardware entrepreneurs (39:02) Mission success events and emotional payoff (45:27) The role of ego in setting audacious goals (46:39) Timeline for Boom's supersonic jets and curating the right investor base (50:09) Closing remarks

Apr 4

In this episode of How I Invest, Evan Fisher, Founder of Portal Ventures, shares his expertise in fundraising, venture capital, and deal flow. He discusses the key elements of successful fundraising, how to craft a compelling pitch, and what investors look for when evaluating opportunities. Evan’s insights provide valuable lessons for both founders seeking capital and investors looking for high-quality deals. Highlights: Fundraising Strategies: How founders can secure funding more effectively. Pitch Deck Secrets: What makes a pitch deck stand out to investors. Venture Capital Insights: How investors analyze deal flow and make investment decisions. Emerging Investment Trends: The future of startup fundraising. Building Relationships: The role of trust and networking in venture capital. -- Guest Bio: Evan Fisher is the Founder of Portal Ventures, a firm specializing in helping startups secure funding through strategic advisory and pitch deck optimization. With a background in investment banking and venture capital, Evan has helped companies across various industries raise significant capital. His deep understanding of investor psychology and storytelling makes him a sought-after advisor for high-growth startups. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Carta, @OldCityInvestmentPartners and @Republic for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers. All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on www.republic.com/hlpif . Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest . Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration. The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting. Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Evan Fisher: @evanbfish LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Evan Fisher: https://www.linkedin.com/in/evanfisher1/ Links: Portal Ventures: https://portal.vc/ -- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:24) Crypto's new asset classes and first-check advantages (3:52) Reinventing in the fast-evolving crypto industry (8:07) Developing thematic bets and the Bitcoin economy thesis (14:00) Market size evaluation and strategic partnerships (15:51) Post-investment founder support and proprietary deals (18:19) Co-investing risks and analyzing investment failures (19:52) MEV space exploration and decentralized science (DeSci) (24:42) Comparing crypto and biotech investing strategies (26:29) Early investment signals and partner dynamics (31:21) Long-term crypto survival strategies (35:04) LP interest in crypto and its liquidity profile (37:19) Bitcoin's continued dominance and future trends (41:09) Closing remarks

Apr 1

In this episode of How I Invest, Billy Libby, Co-Founder and CEO of Upper90, discusses how his firm is redefining venture capital through a hybrid investment model that combines equity and credit. He shares how Upper90 empowers founders to scale without excessive dilution and offers insights into navigating today’s venture landscape. Billy’s approach to alternative financing provides valuable lessons for entrepreneurs and investors alike. Highlights: Alternative Financing: How Upper90's unique blend of equity and credit helps founders grow without giving up control. Venture Capital Insights: Billy's perspective on the changing dynamics of the VC world. Supporting Founders: The importance of aligning incentives between investors and entrepreneurs. Navigating Market Cycles: Lessons from managing capital through different economic environments. Growth Stories: Real-world examples of companies that benefited from Upper90's approach. -- Guest Bio: Billy Libby is the Co-Founder and CEO of Upper90, a leading hybrid investment firm providing both equity and credit to high-growth companies. With a background in trading and risk management, Billy leverages data-driven strategies to support founders in building successful, sustainable businesses. Upper90 has backed numerous successful startups and continues to innovate in the venture capital landscape. Our podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Billy Libby: https://www.linkedin.com/in/billy-libby-76464b1/ Links: Upper90: https://upper90.io/ -- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:37) Startups' perception of credit usage and structuring investments in new theses like NVIDIA chips (6:27) When startups should consider credit versus equity and the financial metrics required (9:22) Seasoning process for financial instruments and capital availability (12:12) Impact of macroeconomic cycles on capital deployment (17:36) Network-driven fundraising, time management, and investor relations (20:23) Institutional practices for transitioning between funds (24:05) Equity flavor in private credit and catalysts for institutional investors (26:17) Hiring strategy, rationale for early hiring, and diversification (29:56) Consistency in returns and addressing lack of diversification (31:14) Closing remarks

Mar 28

In this episode of How I Invest, Aaron Hodari, Managing Director at Schechter, delves into the world of wealth management and alternative investments. He shares how his firm navigates market uncertainties, crafts resilient portfolios, and uncovers unique opportunities for high-net-worth clients. Aaron's insights provide valuable lessons for investors seeking to optimize their financial strategies. Highlights: Alternative Investments: How Schechter incorporates alternative assets to diversify and strengthen portfolios. Tailored Wealth Management: The firm's approach to creating personalized investment strategies for clients. Market Insights: Aaron's perspectives on navigating economic uncertainty and market volatility. Private Equity and Credit Markets: The role these asset classes play in long-term financial growth. Career Lessons: Aaron's key takeaways from years of experience in wealth management. -- Guest Bio: Aaron Hodari serves as Managing Director at Schechter, a leading wealth advisory and financial services firm. With deep expertise in alternative investments and comprehensive portfolio management, Aaron works with clients to protect and grow their wealth across generations. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Carta for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Aaron Hodari: https://www.linkedin.com/in/aaronhodari/ Links: Schechter: https://www.schechterwealth.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (3:01) Diversification and tax optimization for founders (8:20) Estate planning: Control and management of funds (10:34) Sponsor: Tactic by Carta (11:41) Passion, purpose, and income tax planning (19:02) Comprehensive look at long-short strategies (24:37) Strategic tax planning and gifting assets (28:42) Understanding tracking error in tax loss harvesting (32:57) Overview of the private credit market (36:17) Exploring middle market direct lending (39:45) General Partner lending and financing insights (41:56) Interval funds: benefits, fee structures, and tax efficiency (49:38) Closing remarks

Mar 25

In this episode of How I Invest, Logan Allin, Managing Partner and Founder of Fin Capital, shares how his firm uses AI-powered predictive models to evaluate startups. We explore how AI can assess founder DNA, predict billion-dollar outcomes, and transform the venture capital landscape. Logan also highlights the surprising traits that lead to startup success, the advantages of repeat founders, and what the future holds for fintech. This conversation offers valuable insights for investors, entrepreneurs, and anyone fascinated by the intersection of AI and venture capital. Highlights: AI-Driven Investing: How Fin Capital uses generative AI to predict startup success with up to 90% certainty at the seed and Series A stages. Founder DNA: The 35 key factors Fin Capital assesses to evaluate founder potential, including surprising insights on prior CEO experience. Repeat Founders Win: Why founders with prior exits are more likely to build billion-dollar companies and how data supports this trend. Beyond the University Label: Why prestigious degrees don’t significantly predict startup success. Fintech Focus: How specializing in fintech gives Fin Capital a competitive edge in sourcing and supporting founders. Evolving AI Models: The role of continuous backtesting and data refinement in improving prediction accuracy. The Future of Fintech: Logan’s predictions on the next wave of fintech innovation and how AI will continue to shape venture capital. -- Guest Bio: Logan Allin is the Managing Partner and Founder of Fin Capital, a leading fintech investment firm. With extensive experience in venture capital, Logan has built Fin Capital into a data-driven powerhouse focused on backing repeat founders and disruptive fintech companies. He is a passionate advocate for AI-driven decision-making in venture investing and a recognized thought leader in the fintech ecosystem. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Logan Allin: https://www.linkedin.com/in/loganallin/ Links Fin Capital: https://www.linkedin.com/company/fin-capital-fintech/ -- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (3:04) Founder DNA and success archetypes (7:00) Utilizing AI and tracking stealth companies (10:46) Reverse reference calls and competing with top firms (16:09) Specialization in fintech (17:35) Hiring a head of AI and building a strategic LP base (24:25) Evolving investor relations strategy (26:48) Decision making on post-lockup shareholding (29:42) Scaling to a billion dollars in AUM (35:19) Investing in emerging managers (37:02) Lessons from SoFi for Fin Capital operations (39:25) Closing remarks

Mar 21

In this episode of How I Invest, I speak with Brendon Parry, Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. Brendon shares insights on TIFF’s mission to serve nonprofit institutions through tailored investment solutions. He discusses the importance of private market investments, the legacy of leaders like David Swensen, and how TIFF partners with foundations to achieve long-term financial goals. Tune in for actionable strategies and valuable perspectives from a seasoned investment professional. Disclaimer: Brendon Parry, CFA, is the Head of Private Markets, Deputy CIO at TIFF Investment Management. All views expressed by him on this podcast are solely his opinions and do not reflect the opinions of TIFF. You should not treat any opinions expressed by Brendon as a specific endorsement to make a particular investment. References to any securities are for informational purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Any past performance discussed is not indicative of future results. Please keep in mind that investment in a fund entails a high degree of risk, including the risk of loss. Please note that the ads featured in this podcast are not endorsed by TIFF, and TIFF is not a sponsor of these ads. -- Highlights: TIFF’s Mission: How TIFF Investment Management supports nonprofits with specialized investment solutions. Private Markets Expertise: Insights into early-stage venture capital, lower middle market buyout, and growth equity investments. Partnership Approach: How TIFF collaborates with nonprofits of various sizes to customize portfolios and deliver long-term returns. Legacy of Leadership: The influence of David Swensen, former Yale CIO, on TIFF’s investment philosophy. Risk Management: Strategies for balancing risk and reward in complex market environments. Career Insights: Lessons from Brendon’s journey in private equity and investment management. -- Guest Bio: Brendon Parry is the Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. He has been with TIFF since 2011, leading the firm's private markets initiatives with a focus on early-stage venture capital, lower middle market buyout, and growth equity. Before TIFF, Brendon worked at Providence Equity Partners and Cambridge Associates. He holds an AB in Economics from Brown University and an MBA from Harvard Business School. With a passion for helping nonprofits achieve their financial goals, Brendon plays a key role in TIFF’s mission. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Carta for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: carta.com/howiinvest. -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brendon Parry: https://www.linkedin.com/in/brendon-parry-77a5677/ Links: TIFF Investment Management: https://www.tiff.org/private-markets/ -- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:06) TIFF's mission and partnership with foundations (4:01) TIFF's investment strategies with a focus on private markets (7:01) Reasons for focusing on lower middle market and early stage VC (9:02) Sponsor: Tactic by Carta (10:09) Risk assessment in lower middle market PE vs. larger PE (23:11) Historical performance comparison: fund ones vs. fund twos (24:42) Diligence process for independent sponsors (27:01) Coordinating sponsor and deal diligence teams (27:37) Organizational changes and lessons from 14 years at TIFF (32:05) Building an antifragile portfolio and the confidence paradox in investing (37:31) Predicting the future and core principles in manager selection (41:35) Closing remarks

Mar 18

In this episode of How I Invest, I dive deep into a conversation with Charlotte Zhang of Inatai Foundation. Charlotte shares her approach to managing a $2.4 billion private investment program, the importance of market inefficiencies, and how she strategically builds GP relationships. We explore how Inatai identifies top managers, why LPs are increasingly interested in fundless sponsors, and what makes a great investment philosophy. Whether you're an LP, VC, or just curious about institutional investing, this episode is packed with insights on capital allocation, conviction-based investing, and long-term partnership building. Highlights: Building a $2.4 Billion Investment Program: How Charlotte structured Inatai’s approach without rigid asset allocation targets. GP Selection Strategy: The four P’s—People, Philosophy, Process, and Performance—that guide investment decisions. Market Inefficiencies & Innovation: Why Inatai prioritizes global opportunities in venture, buyout, and select real assets. Fundless Sponsors: Why LPs are increasingly backing fundless sponsors and the advantages of doing so. Investment Discipline: How to evaluate managers over time and avoid the pitfalls of FOMO-driven investing. Handling Market Downturns: The characteristics of managers who thrive in turbulent markets. The Role of LPs as Value-Added Partners: How LPs can help GPs beyond just providing capital. Diversification vs. Concentration: How Inatai balances a high-conviction portfolio while maintaining risk-adjusted returns. The Future of Inatai: How the foundation is expanding its impact through its outsourced CIO platform. -- Guest Bio: Charlotte Zhang is a Senior Portfolio Manager at Inatai Foundation, where she leads private investments within the $2.4 billion portfolio. She has previously held roles at Medley Partners and Iconiq Capital, developing expertise in manager selection, portfolio construction, and market inefficiencies. Charlotte is passionate about long-term investing, identifying top-tier GPs, and fostering meaningful LP-GP relationships. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Charlotte Zhang: https://www.linkedin.com/in/charlotterzhang/ Links: Inatai Foundation: https://inatai.org/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:20) Creating and executing a lower middle market PE strategy (3:39) Spending years on investment decisions and handling market downturns (8:08) Exploring interest in fundless sponsors and largest deals (11:09) Inatay team structure and the generalist team approach (13:17) Managing infinite opportunities and diversification strategies (16:38) Sourcing and adding value to GP relationships (21:30) Closing remarks

Mar 14

In this episode of How I Invest, I sit down with Matt Fitzpatrick, CEO of Invisible Technologies and former head of McKinsey’s QuantumBlack Labs. Matt shares his deep insights on enterprise AI adoption, model fine-tuning, and the challenges businesses face when integrating AI into their workflows. We explore why only 8% of AI models make it to production, how enterprises can overcome friction points, and the future of AI-powered enterprise solutions. If you’re curious about the intersection of AI and business strategy, this episode is a must-listen. Highlights: Enterprise AI Adoption: Why only 8% of AI models reach production and how companies can improve their success rates. AI Fine-Tuning for Enterprises: The importance of domain-specific AI models and why general AI solutions don’t always fit enterprise needs. The Data Challenge: Why poor data quality is the biggest barrier to AI adoption and how companies can fix it. Human-AI Collaboration: The role of human feedback in training AI models for enterprise use cases. Real-World AI Success Stories: How companies like Moody’s and Klarna successfully implemented AI solutions. Invisible Technologies’ Vision: How Invisible is building an AI-powered enterprise services platform to modernize business operations. Future of AI in Business: How AI-native companies will rethink workflows and software applications from the ground up. Matt’s Journey: From leading McKinsey’s AI lab to scaling one of the fastest-growing AI companies. -- Guest Bio: Matt Fitzpatrick is the CEO of Invisible Technologies, a rapidly growing AI-powered services company. Before joining Invisible, Matt led McKinsey’s QuantumBlack Labs, where he worked on large-scale AI and data transformation projects. He has extensive experience in enterprise AI adoption and has helped some of the world’s largest organizations modernize their operations using artificial intelligence. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Carta and @Daloopa for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest . Sponsor: Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at: www.daloopa.com/how . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Fitzpatrick: https://www.linkedin.com/in/matthew-fitzpatrick-97b62722/ Links: Invisible Technologies: https://www.invisible.co/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:46) Training vectors and core business components of Invisible Technologies (3:21) Successful enterprise models and future AI evolution (5:07) Challenges and evaluation of AI model deployment at scale (7:49) Human feedback and accuracy requirements in AI models (10:03) Fine-tuning AI models for enterprise applications (12:27) McKinsey's successful enterprise AI use cases (13:23) AI's impact on productivity and process redesign (15:39) Invisible Technologies' growth strategy and focus on enterprise fine-tuning (17:22) Building a modern ServiceNow with GenAI and avoiding obsolescence (18:26) Modernization of legacy systems and AI native application development (20:03) Shifting focus in the AI ecosystem and agentic layer (22:30) Comparing AI native CRM to traditional CRM systems (23:18) Invisible Technologies' future vision and optimism about enterprise AI (24:33) Closing remarks

Mar 11

In this episode of How I Invest, I interview Robert Cherun, an expert in search funds and small-cap investing. Robert shares his journey from launching his own search fund to building and exiting a highly successful business. We dive into the fundamentals of search funds, the economics of acquiring and scaling small businesses, and the key traits that make a successful searcher. Highlights: What Is a Search Fund? How search funds enable entrepreneurs to acquire and grow established businesses with investor backing. Impressive Returns: Search funds have historically generated 35% net IRRs and 4.5x ROI, making them a compelling investment strategy. Barriers to Institutional Adoption: Despite high returns, institutional investors struggle to deploy capital effectively in this micro-cap space. Search Fund Lifecycle: A breakdown of how searchers raise capital, find businesses, and structure acquisitions. Portfolio Strategy: How Robert constructs a diversified portfolio of search fund investments to maximize returns. TAM & Growth of Search Funds: How the space has evolved from niche to mainstream, with billions invested in recent years. Traits of a Successful Searcher: The skills and qualities investors look for in entrepreneurs, from financial acumen to leadership ability. Lessons from a $150M Exit: Robert’s journey from acquiring a $5M security business to scaling it into an industry leader with 2,000 employees. The Asurion Story: A legendary search fund deal that delivered 100x–1,000x returns to early investors. Search Funds vs. Startups: Why search funds offer a lower-risk path to entrepreneurship compared to venture-backed startups. Co-CEO Model: Best practices for managing leadership dynamics and decision-making between business partners. Governance & Investor Relations: How search fund investors maintain oversight while giving CEOs operational control. Biggest Misconceptions About Search Funds: Why experience isn’t everything and how young entrepreneurs can successfully run businesses. -- Guest Bio: Robert Cherun is a leading investor in search funds and small-cap businesses. As the co-founder of a successful security company, he scaled the business from $5M to $150M in revenue before exiting to a strategic buyer. Now, through his firm Legate Partners, Robert invests in and mentors the next generation of search fund entrepreneurs. Passionate about small business transformation, Robert specializes in identifying high-potential searchers and helping them build industry-leading companies. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Robert Cherun: https://www.linkedin.com/in/robcherun/ Links: Legate Partners: https://www.legatelp.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (0:51) Overview of search funds and historical returns (2:16) Capitalization and portfolio construction in search funds (3:26) Growth of search funds and searcher profiles (5:05) Comparing search funds with traditional startup models (7:37) UCIT Online Security acquisition journey and deal economics (10:22) Famous search fund deals and Legate Partners introduction (11:33) Legate Partners' strategy and CEO selection criteria (13:24) CEO profiles and co-CEO best practices (15:55) Governance and decision-making in search funds (17:44) Insights on search fund dynamics and governance (19:11) Transitioning from finance to search funds and key lessons (20:11) Final thoughts on team dynamics and search fund misconceptions (20:58) Closing remarks

Mar 9

In this special solo episode of How I Invest, I break down one of the most powerful forces in investing: compounding. Over the course of 142 episodes, I’ve discovered that the best investors all leverage compounding—not just in their portfolios but in every aspect of their business. From relationships and reputation to proprietary information and top talent, compounding creates exponential advantages in a hyper-competitive market. Highlights: Compounding Beyond Capital: The biggest investors understand that everything compounds, including reputation, diligence, and deal-making experience. The Power of Relationships: Trust compounds with each deal, leading to faster and more efficient decision-making. Reputation as an Asset: Warren Buffett’s ability to negotiate superior terms stems from his compounding reputation as an ethical and skilled investor. Proprietary Information Loops: Access to unique insights leads to better investments, which generate even more privileged information. People as a Compounding Advantage: The best organizations attract and retain A-players, who in turn recruit other top talent, creating a self-reinforcing cycle of excellence. The Arbitrage of A-Players: Paying A-players above market rates is a competitive advantage, as they generate exponentially greater value. -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (0:21) The role of compounding in investing and relationships (2:13) Trust bias, deal-making efficiency, and reputation effects (4:23) Proprietary information and the compounding of talent (6:50) AI's impact on productivity and compounding (7:49) Closing remarks

Mar 7

In this episode of How I Invest, I interview Scott van den Berg, an expert in celebrity-founded brands and the managing partner of Hotstar VC. Scott shares deep insights into how celebrities are leveraging their platforms to build billion-dollar businesses and why some partnerships thrive while others fail. We discuss the shift in celebrity investments, the rise of creator-led brands, and key lessons from success stories like Ryan Reynolds' Mint Mobile, Kim Kardashian's Skims, and George Clooney's Casamigos. Highlights: Lessons from Ryan Reynolds: How he strategically invested in "unsexy" industries and built massive brand value. The Power of Celebrity-Led Brands: How stars like Kim Kardashian, Logan Paul, and Ryan Reynolds built billion-dollar companies. Equity vs. Cash Deals: Why traditional talent managers prefer cash over equity and how this impacts startup partnerships. Product-First Approach: The importance of having a strong product, even when backed by a celebrity. Celebrity Product-Market Fit: Why aligning a celebrity's brand with the right product is crucial for success. The Over saturation of Celebrity Tequila Brands: Why so many celebrities enter the liquor market and the real economics behind it. The Rise of the Creator Economy: How influencers are turning their massive audiences into thriving businesses. Avoiding Common Pitfalls: The biggest mistakes startups make when partnering with celebrities. -- Guest Bio: Scott van den Berg is the managing partner at Hotstar VC, a fund specializing in investments in celebrity and creator-led brands. With experience in 55 celebrity-founded businesses, Scott has worked with stars like Selena Gomez, DJ Khaled, and Jake Paul. His team includes co-founders of some of the most successful celebrity-led brands, such as The Honest Company and Feastables. As a thought leader in the space, Scott shares insights on how celebrities can build sustainable businesses and transform their influence into long-term value. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Carta and @Daloopa for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest . Sponsor: Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at: www.daloopa.com/how . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Scott Van den Berg: https://www.linkedin.com/in/scott-van-den-berg-22b534150/ -- Links: HotStar VC: https://www.hotstart.vc/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (5:01) Sponsor: Tactic Bicarda (6:20) Selecting and partnering with the right celebrity for a brand (9:09) Sponsor: The Loop (10:13) Navigating challenges with celebrity managers and agencies (13:10) Hotstar VC's methodology in celebrity-founded brand investments (16:43) Case studies of celebrity brand successes (18:31) Key takeaways from investing in celebrity-driven ventures (19:22) Closing remarks and upcoming episode teaser (20:15) Sponsor: Vanguard (23:45) Closing remarks

Mar 4

In this episode of How I Invest, I have a conversation with Scott Chan, Chief Investment Officer of CalSTRS, to explore how he oversees a staggering $350 billion in assets. Scott shares insights on CalSTRS’ collaborative investment model, their approach to private and public markets, and why they aim to be the "global partner of choice." We also discuss the importance of structural alpha, liquidity management, and identifying long-term supply-demand imbalances. Highlights: The Collaborative Model: How CalSTRS brings more assets in-house to lower costs and increase control over risk and alpha. Public vs. Private Markets: Why 80–85% of public market assets are managed internally while private investments rely on partnerships. Becoming the Global Partner of Choice: Why being a top three call for GPs is crucial for accessing the best private market transactions. Portfolio Allocation Strategy: How CalSTRS is shifting risk exposure toward private markets to enhance returns. Contrarian Investing: Scott’s view on why the stock market may underperform over the next decade and where he sees better opportunities. The Importance of Liquidity: Why liquidity will be "more valuable than gold" and how CalSTRS prepares for market downturns. Identifying Supply-Demand Imbalances: Where CalSTRS sees long-term opportunities, from real estate to private credit and infrastructure. Structural Alpha: How CalSTRS structures deals to generate uncorrelated alpha without taking additional market risk. Governance and Decision-Making: How a nimble, delegated investment approach allows CalSTRS to act quickly on opportunities. The Role of Team & Culture: Scott emphasizes why a strong leadership team is the ultimate competitive advantage. -- Guest Bio: Scott Chan is the Chief Investment Officer of CalSTRS, overseeing $350 billion in assets for over one million California teachers. With decades of experience in institutional investing, Scott has led CalSTRS in developing its collaborative investment model, focusing on cost efficiency, structural alpha, and strategic partnerships. His contrarian mindset and deep expertise help position CalSTRS as a global leader in asset management. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Scott Chan: https://www.linkedin.com/in/chanscott/ Links: CalSTRS: https://www.calstrs.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:09) Introduction to CalSTRS and collaborative investing (2:11) Public vs private markets and global partnerships at CalSTRS (5:26) Public and private market investment strategies (7:03) Collaborating with private managers and selecting GPs (11:41) Contrarian thinking and current investment focus (17:13) Liquidity management and market opportunities (18:19) Sponsor: Juniper Square (19:43) Liquidity options and alternative asset opportunities (21:31) Market crisis preparation and governance structure (26:30) Exploring structural alpha and capital base implications (31:20) Leveraging supply-demand imbalances in investing (35:58) Personal alignment and development as a CIO (40:29) Closing remarks

Feb 25

In this episode of How I Invest, I chat with Balaji Srinivasan—former CTO of Coinbase, General Partner at Andreessen Horowitz (a16z), and bestselling author of The Network State. Balaji shares his vision for how the internet could ultimately succeed America, the rise of network states, and the implications of Bitcoin's exponential growth. We discuss the future of digital governance, crypto democracy, and how decentralized technologies are reshaping global power structures. Whether you're a crypto investor, a technology enthusiast, or someone curious about the future of governance, this episode is packed with thought-provoking insights. Highlights: The Internet as the Next Superpower: Just as America succeeded Britain, Balaji argues that the internet is on track to become the dominant global force. Bitcoin vs. Fiat: Over the last decade, Bitcoin has appreciated by roughly 8% per month, while fiat currencies have consistently depreciated. The Rise of Network States: Inspired by historical precedents like Israel, Singapore, and the American frontier, Balaji explains how digital communities can evolve into sovereign entities. Crypto as Digital Government: Cryptocurrencies already provide key governmental functions—property rights, monetary policy, and dispute resolution—without traditional state infrastructure. Decentralized Governance & DAOs: Online communities are allocating billions of dollars in funding through decentralized governance structures, challenging traditional political systems. The Future of Democracy: Balaji discusses different models of democracy—Western, Indian, and crypto-democracy—and how blockchain technology can enhance governance. The Balaji Fund & High-Risk Seed Investing: A look into Balaji’s new venture fund, backing radical technological innovation with an ideological edge. Building at Internet Speed: Why traditional infrastructure development is stagnating, and how countries like China are achieving 1,000x efficiency improvements in construction. -- Guest Bio: Balaji Srinivasan is a renowned investor, entrepreneur, and futurist. He served as the CTO of Coinbase, was a General Partner at Andreessen Horowitz, and co-founded multiple startups, including Earn, Teleport, and Counsyl. His book, The Network State, became a bestseller and has inspired a new movement around digital governance and decentralized nation-building. Balaji is a thought leader on Bitcoin, crypto governance, and the future of technology-driven societies. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @JuniperSquare and @Daloopa for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com . Sponsor: Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at www.daloopa.com/how . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Balaji Srinivasan: @balajis LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Balaji Srinivasan: https://www.linkedin.com/in/balajissrinivasan/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (0:58) Guest introduction and discussion on "The Network State" (2:18) Network states: examples and historical precedents (4:46) Network states vs. traditional countries and the internet's role (9:19) Social media's political impact and cryptocurrency's economic influence (12:07) Sponsor: Juniper Square (13:25) Bitcoin and cryptocurrencies' influence on governance and fiat currencies (18:26) The future of democratic capitalism and its different forms (22:09) Capitalism and democracy through the ages (24:02) Digital identity, SingPass, and DAO governance (27:38) Use cases for DAOs and funding mechanisms (27:51) Sponsor: Daloopa (28:26) Investing in software development and community (30:15) Content creation, research funding, and crowdfunding real estate with crypto (35:01) The network state concept, techno capital fund investors, and ideological bent (38:07) Seed investments and tech solutions for institutional problems (41:06) Corporate vice vs. virtue and profit alignment with values (44:04) Government intervention, regulatory constraints, and construction impact on real estate (49:01) Closing remarks

Feb 21

In this episode of How I Invest, I sit down with Erik Hirsch, Co-CEO of Hamilton Lane, a global leader in private market investing. Erik discusses the evolving landscape of private markets and the integration of digital tools like tokenization in investments. He dives into how private markets are becoming more accessible to retail investors and the future of asset management, with a focus on education and technology. From the role of RIAs and wirehouses to the impact of digital wallets and tokens, Erik provides deep insights into what’s next for investors at every level. If you're curious about the future of investment opportunities and how they will change by 2030, this episode is a must-listen. Highlights: Private Market Access: How tokenization is revolutionizing private market access for retail investors, making it easier and more efficient to buy into private funds. The 2030 Vision: The future of investing where both retail and institutional investors can seamlessly manage public and private assets in one place. Roadblocks and Education: How myths about private markets and a lack of education are slowing adoption, and why proper education is key to unlocking the future of investment. The Role of RIAs: Why wealth advisors play a critical role in helping clients navigate these changes and how their education will be key to accelerating private market growth. Adapting to Consumer Expectations: The difference in expectations between institutional and retail investors and how firms need to adjust to meet these demands, especially in terms of technology and accessibility. Culture at Hamilton Lane: Erik shares how building and maintaining a strong company culture has been a key driver of Hamilton Lane’s success. The Path to a Trillion Dollars AUM: What Hamilton Lane's growth trajectory looks like, and the future goals as they continue expanding globally. -- Guest Bio: Erik Hirsch is the Co-CEO of Hamilton Lane, a leading private markets investment management firm. With over 30 years of experience, Erik has helped lead Hamilton Lane's growth into one of the largest players in the private market space. Based in Philadelphia, Erik's leadership has focused on innovation, diversification, and bringing private market opportunities to a broader range of investors. His commitment to education and customer-first culture has been instrumental in Hamilton Lane’s success. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @JuniperSquare and @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com . -- Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Erik Hirsch: https://www.linkedin.com/in/erik-hirsch-hamilton-lane/ Links: Hamilton Lane: https://www.hamiltonlane.com/en-us Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:13) The fallacy of the 60/40 portfolio and institutional strategies (3:54) Diversification strategies in private vs public assets (7:42) Hamilton Lane's focus on the retail market (8:07) Sponsor: Juniper Square (10:32) Hamilton Lane's retail market targeting strategies (13:43) Liquidity concerns for retail investors (15:47) Tokenizing Hamilton Lane funds for accessibility (18:52) Retail and institutional investment convergence vision (20:01) Challenges in retail access to private markets (23:06) Incentivizing RIAs to support private market investments (23:29) Sponsor: Reed Smith (24:48) Erik Hirsch's journey to co-CEO of Hamilton Lane (25:54) Pros and cons of Hamilton Lane's Philadelphia location (27:28) Career insights and underappreciated starting points (28:31) Growth dynamics within Hamilton Lane (29:26) Hamilton Lane's growth and trillion-dollar goal (30:29) Closing remarks

Feb 18

In this episode of How I Invest, I engage with Jackson Craig, Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy. With over 20 years of experience in private equity investing, Jackson shares his expertise on navigating distressed debt markets, building resilient portfolios, and uncovering hidden opportunities in complex financial situations. From sourcing distressed assets to managing risk, Jackson offers a masterclass on investing in challenging environments. Highlights: H.I.G. Capital’s Growth: How the firm expanded from a $75 million fund in 1993 to managing over $67 billion across multiple asset classes, including private equity, real estate, infrastructure, and credit. Understanding Distressed Debt: The mechanics of distressed debt investing, including yield benchmarks and risk perceptions in distressed securities. Risk Management in Distressed Investing: How H.I.G. constructs portfolios with a high hit rate and limited downside by focusing on first-lien debt. Sourcing Distressed Opportunities: The unique ways distressed debt investors find deals—often without companies even being aware of the transactions. Building Strategic Relationships: Why success in distressed debt relies on long-term relationships with restructuring attorneys, turnaround consultants, and industry insiders. Portfolio Diversification Beyond Industries: The importance of avoiding over concentration in single risk factors, such as interest rates or energy prices, rather than just industry or geography. The Role of Optimism in Distressed Investing: Why successful investors need to see beyond the immediate problems to uncover long-term value. Lessons from 16 Years at H.I.G.: Jackson’s biggest takeaways, including why leadership stability is often a key indicator of a company’s strength. H.I.G.'s Investment Philosophy: A deep dive into the firm’s focus on small and mid-cap, value-oriented, cash flow-centric investments and its commitment to seeking out complexity. -- Guest Bio: Jackson Craig is the Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy, overseeing investments in special situations, restructuring, and turnaround opportunities. With over 20 years of experience in private equity investing, Jackson has been instrumental in the firm’s growth and success in alternative investments. His expertise spans private equity, credit markets, and distressed investing, making him a leading voice in the industry. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @JuniperSquare and @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com . Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jackson Craig: https://www.linkedin.com/in/jackson-craig-458b645b/ Links H.I.G. Capital: www.higcapital.com Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:25) Understanding distressed debt investment (4:53) Identifying and assessing distressed debt opportunities (7:24) Investment process and due diligence (9:02) Sponsor: Juniper Square (9:36) Relationship management and distressed sales (10:39) Tax considerations and investor base (11:33) Investment discipline in distressed debt (12:36) Success factors in distressed debt investing (14:43) Portfolio diversification and risk management (19:03) Sponsor: Reed Smith (19:38) Evaluating business quality and management in distress (21:02) Navigating the bankruptcy process (22:02) Long-term strategy in distressed investing (23:19) Overcoming sourcing challenges (23:48) HIG's distinct investment approach and LP feedback (25:21) Competitive advantage in distressed markets (25:45) Closing remarks

Feb 14

In this episode of How I Invest, I speak with Jeremy Heer, Managing Director at the University of Illinois Foundation, about the art of networking, the power of super connectors, and the evolving landscape of institutional investing. Jeremy shares his insights on building relationships that drive investment success, the importance of strategic networking, and how attending conferences with intent can create game-changing opportunities. He also dives into the future of nuclear energy, the role of generalist investors in discovering new asset classes, and the long-term value of investment engagement. Highlights: The Role of a Super Connector: Jeremy explains what defines a “super connector” and why having them in your network is essential for success in investing. Strategic Networking: How building and maintaining relationships across industries can unlock top-tier investment opportunities. Conference Best Practices: Why proper preparation and a mix of structured and stochastic networking can maximize the value of attending events. The Future of Nuclear Energy: Jeremy’s investment thesis on nuclear as a high-potential energy source and the challenges in capital deployment. Generalist vs. Specialist Investing: How being a generalist can give investors a first-mover advantage in emerging asset classes. Lessons from the University of Chicago: Jeremy shares insights from his time at one of the top endowments in the world. The Long-Term Value of Relationship-Based Investing: Why some of the best investment opportunities emerge from patient, long-term engagement rather than immediate transactions. -- Guest Bio: Jeremy Heer is the Managing Director of the University of Illinois Foundation, where he leads investment research and engagement. Before joining Illinois, he spent over a decade at the University of Chicago’s endowment, one of the top-performing institutional funds in the world. With deep expertise in building strategic relationships, Jeremy is a master of leveraging networks for investment success. He is passionate about connecting with top-tier investors, founders, and thought leaders to uncover unique opportunities in the market. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @JuniperSquare for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jeremy Heer: https://www.linkedin.com/in/jeremy-j-heer-cfa-caia/ Links: University of Illinois Foundation: https://uif.uillinois.edu/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (3:56) Non-financial drives of super connectors (4:11) Sponsor: Juniper Square (5:55) How to be memorable & Networking at conferences (12:33) The investment potential of nuclear energy & University experiences (17:00) The unique role at University of Illinois Foundation & Generalist investors in VC (19:03) Closing remarks

Feb 11

In this episode of How I Invest, I dive deep into a discussion with John Skjervem, Chief Investment Officer at Utah Retirement Systems (URS), to uncover the unique governance and investment strategies behind one of the most innovative public pension funds in the United States. John shares his insights on governance structures, private equity allocations, the benefits of a "fishbowl-free" decision-making process, and his approach to alternative energy investments. Whether you're curious about pension fund management or the future of disruptive energy investments like nuclear fusion, this episode is a masterclass in strategic thinking and long-term investing. Highlights: Governance Matters: Why URS’s closed-door investment meetings create better outcomes compared to traditional public pension governance. Transparency vs. Returns: How excessive transparency can lead to political grandstanding and ultimately harm long-term investment performance. Asset Allocation Strategy: A deep dive into URS’s allocation, including a 14% allocation to private equity with significant exposure to venture capital. Direct Real Estate Investments: How URS has built a successful real estate portfolio, reducing fees and maintaining long-term control over assets. Energy and Infrastructure Investments: The role of direct investments in oil, gas, and alternative energy as an inflation hedge. The Case for Venture Capital: Why URS prioritizes venture capital investments over private credit to maximize returns. Betting on Nuclear Fusion: The potential for a 100x return on URS’s investments in fusion energy and the long-term implications for the energy sector. Size vs. Agility: Why smaller funds like URS have an advantage in private markets despite their scale limitations. Lessons from the Global Financial Crisis: How John’s approach to risk management and asset allocation was shaped by 2008. -- Guest Bio: John Skjervem serves as the Chief Investment Officer at Utah Retirement Systems, where he oversees over $50 billion in assets. With prior experience managing larger funds like the Oregon Public Employees Retirement Fund and Northern Trust's wealth business, John brings a wealth of expertise to his current role. Known for his innovative governance approach and deep knowledge of alternative investments, John is passionate about achieving long-term success for URS beneficiaries. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @JuniperSquare @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSOR: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com . SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: Twitter: David Weisburd: https://x.com/DWeisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Skjervem: https://www.linkedin.com/in/john-d-skjervem-cfa-4698794/ Links Utah Retirement Systems: https://www.urs.org/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:00) Asset allocation and governance at Utah Retirement Systems (4:07) Governance structure at Utah Retirement Systems (9:25) Long-term investment challenges (10:57) Sponsor: Juniper Square (11:30) Private equity and real estate in asset allocation (15:44) Managing a $50 billion fund (16:25) Sponsor: Reed Smith (17:30) Investment check sizes and advisory roles (20:31) Comparing Utah Retirement Systems with Alaska Permanent Fund (22:11) Lessons from the 2008 financial crisis (23:57) Exploring high-risk investments: Fusion portfolio (26:10) Closing remarks

Feb 7

In this episode of How I Invest, I interview Constantine Karides, a Lead Partner at Reed Smith, to discuss the critical role lawyers play in the startup and venture capital ecosystem. Constantine shares insights on what founders and investors should look for in legal counsel, the leverage model law firms use, and how AI is reshaping the legal landscape. From the importance of choosing the right law firm to navigating legal costs effectively, this episode is packed with actionable advice for entrepreneurs, venture capitalists, and investors. Highlights: Choosing a Lawyer as a Strategic Partner: Beyond paperwork, founders should seek legal advisors who bring investor connections, industry expertise, and pricing flexibility. The Importance of Internal Influence: How a lawyer’s standing within a firm impacts their ability to secure favorable terms and resources for clients. VCs & Legal Counsel: What venture capital funds should prioritize when selecting legal partners and how these relationships can create long-term value. Law Firm Profit Models: Understanding the leverage model law firms use to maximize profits and how clients can navigate these dynamics. AI & The Future of Law: How artificial intelligence is transforming the legal industry, from document review to litigation strategy. Building Long-Term Client Relationships: Constantine’s philosophy on blending business with personal relationships to drive success. Lessons from Experience: Mistakes Constantine made early in his career and how they shaped his approach to law and business. -- Guest Bio: Constantine Karides is a Lead Partner at Reed Smith, a global law firm known for its expertise in venture capital, private equity, and corporate transactions. With over 30 years of experience, Constantine has built a reputation as a trusted advisor to startups, funds, and investors, offering not just legal counsel but also strategic business insights. Recognized as a "rainmaker" at Reed Smith, he emphasizes client relationships, networking, and long-term value creation. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Constantine Karides: https://www.linkedin.com/in/constantine-karides/ Links Reed Smith: www.reedsmith.com Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:08) Law firms' internal credibility and Venture Capital specific needs (5:29) Evaluating Startups and the leverage model in law firms (9:57) Trust-building and client relationship philosophy (14:41) Early career lessons and the impact of AI on the legal field (19:00) Client views on AI adoption in law firms (21:03) Closing remarks

Feb 4

In this episode of How I Invest, I have a conversation with Mel Williams, Co-Founder and General Partner at TrueBridge Capital Partners. We dive into TrueBridge’s pivotal role as Forbes' data partner for the prestigious Midas List, its strategic approach to venture capital fund-of-funds investing, and how the firm consistently identifies and backs the top-performing fund managers. Mel provides a masterclass on portfolio construction, risk management, and scaling a successful venture investment platform. Whether you’re an institutional investor, a fund manager, or simply intrigued by the inner workings of venture capital, this episode is packed with essential takeaways. Highlights: The Midas List Partnership: How TrueBridge collaborates with Forbes to curate the definitive VC ranking and what it means for the industry. Fund of Funds Strategy: The five key investment strategies that shape TrueBridge’s unique venture approach—core venture, seed, direct, secondary, and blockchain investments. The Power of Forced Ranking: A disciplined framework for ranking fund managers and how it enhances returns. Gaining a Competitive Edge: How TrueBridge’s relationships with elite GPs provide them unparalleled access and insight. Navigating Blockchain Volatility: TrueBridge’s philosophy on investing in blockchain and adjusting for its extreme market cycles. Scaling Venture Funds Effectively: Best practices for fund managers to grow while maintaining their competitive advantage. International vs. Domestic Venture Investing: How TrueBridge evaluates and ranks global venture funds against U.S.-based managers. Lessons from Building TrueBridge: The realities of raising early funds and scaling a top-tier fund-of-funds platform. Debunking the Fund-of-Funds Fee Myth: How TrueBridge offsets the double-fee structure through strategic overcommitment and capital recycling. -- Guest Bio: Mel Williams is the Co-Founder and General Partner at TrueBridge Capital Partners, a premier venture capital fund-of-funds specializing in backing top-tier venture firms and startups. With a background in institutional investing at the University of North Carolina Endowment and the Rockefeller Foundation, Mel brings unparalleled expertise in fund selection, portfolio construction, and venture capital strategy. Under his leadership, TrueBridge has cultivated one of the most coveted LP portfolios in the industry, leveraging deep networks and a research-driven investment approach. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mel Williams: https://www.linkedin.com/in/mel-williams-00584a5/ Links TrueBridge Capital Partners: https://www.truebridgecapital.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (4:38) Investing in blockchain and managing volatility in venture funds (5:51) Building relationships and the forced ranking system in portfolio management (10:21) Criteria for adding or removing venture fund managers (14:43) Best practices for scaling and international venture investments (20:23) Challenges in raising funds and the venture industry evolution (2012-2021) (24:17) Comparing fund of funds to direct venture capital investments (26:51) Efficiency and key aspects of TruBridge's fund of funds model (29:05) Closing remarks

Jan 31

In this episode of How I Invest, I dive deep into a conversation with Henry Ward, CEO of Carta, to discuss his journey building one of the most transformative companies in private market infrastructure. From cap table management to fund administration and beyond, Henry shares his insights on entrepreneurship, innovation, and the future of private equity. We delve into Carta's strategic pivots, its playbook for turning services into scalable software, and Henry's contrarian views on AI and leadership. This episode is packed with lessons for founders, investors, and operators navigating the evolving landscape of private capital. Highlights: The Carta Journey: How Carta evolved from solving cap table management to building software for fund CFOs. Scaling Through Innovation: The importance of constantly iterating and innovating in markets with limited growth potential. AI in Private Markets: Why Henry is focused on using AI to enhance customer experiences instead of reducing headcount. Building the Carta Cartel: How former Carta employees are founding companies with Henry's support—and reshaping angel investing. Services to Software: Carta's unique playbook for acquiring service businesses and turning them into software-driven solutions. Future of Fund Admin: The roadmap for automating fund administration and achieving “one-click” reporting by 2030. Private Equity Expansion: Carta’s strategy for becoming the operating system for private capital beyond venture. Leadership Insights: Henry’s take on founder mode, micromanagement, and why caring deeply is essential to great leadership. -- Guest Bio: Henry Ward is the CEO of Carta, a company revolutionizing private market infrastructure through software. Since its founding in 2012, Carta has grown into the industry standard for cap table management, fund administration, and private market data. Henry is also an active angel investor, backing numerous startups founded by former Carta employees. Known for his visionary thinking and contrarian ideas, Henry is committed to reshaping how private capital markets operate. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Henry Ward: @henrysward LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Henry Ward: https://www.linkedin.com/in/heward/ Links: Carta: https://www.carta.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:31) Building Carta: Innovation and Execution (5:03) AI's Role and Impact at Carta (9:21) Fund Administration Challenges and Solutions (12:33) Investing in Carta's Team and Culture (14:51) Angel Investing and CEO Controversies (17:48) Balancing Founder and Investor Roles (22:03) Carta's Acquisition Strategy and Automation Goals (25:10) Carta's Role for CFOs in Private Equity and VC (27:32) Carta's Strategic Pivot and Growth Plans (30:39) Brand Transition: Venture to Private Equity (34:35) Closing remarks

Jan 28

In this episode of How I Invest, I connect with Lorenzo Thione, Managing Director at Gaingels, one of the most active and inclusive venture syndicates in the world. Lorenzo discusses his philosophy on diversity, equity, and inclusion (DEI), the democratization of venture capital, and his thoughts on the AI revolution. From his experience building a portfolio of over 100 investments to lessons learned from co-founding PowerSet, Lorenzo provides invaluable insights for investors and entrepreneurs alike. Highlights: Philosophy on DEI: How the distribution of talent and opportunity shapes Gaingels' mission to bring inclusivity to venture capital. Gaingels’ Approach: Investing in companies that prioritize diversity in talent, governance, and capital while enabling LPs to invest with as little as $1,000. Venture Allocation: Advice for high-net-worth investors on diversifying their portfolios across stages, sectors, and liquidity horizons. Lessons from Uber: Why Lorenzo passed on the Uber seed round and how it shaped his investment philosophy. AI Investing: Insights into the evolution of AI, the importance of category-defining opportunities, and the impact of recent major investments in AI infrastructure. Angel Investing: The importance of backing founders you know and trust, and how personal relationships can lead to better investment outcomes. -- Guest Bio: Lorenzo Thione is a serial entrepreneur, investor, and expert in Artificial Intelligence. Currently, as Managing Director of Gaingels, he leads investments in AI, deep-tech, and consumer tech, promoting diversity in venture capital. He co-founded Powerset, an AI-driven search engine acquired by Microsoft and integrated into Bing. Beyond technology, Lorenzo is a celebrated Broadway producer, with productions like "Hadestown" and "The Inheritance," earning multiple Tony Awards. He also co-founded StartOut, supporting LGBTQ+ entrepreneurs. Born in Milan, he holds an M.S. in Computer Engineering from the University of Texas at Austin. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lorenzo Thione: https://www.linkedin.com/in/lorenzothione/ Links: Gaingels: https://www.gaingels.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:52) Gaingels syndicate and low minimum LP investment strategy (5:15) Venture capital allocation advice for high net worth individuals (6:19) Diversification strategies within venture capital (8:37) Analyzing long-term venture capital returns (9:52) Gaingels investing access and strategic insights (13:03) Key lessons from early-stage angel investing experiences (16:56) Investing in AI and portfolio strategy considerations (19:37) SoftBank and Sam Altman's AI investment impact (23:29) Closing remarks

Jan 24

In this episode of How I Invest, I dive into a conversation with Nichole Wischoff, Founder and Managing Partner at Wischoff Ventures, to explore her remarkable journey of raising a $50 million fund during one of the toughest markets of 2024. Nichole shares her insights on fundraising strategies, the power of media in deal sourcing, and building a personal brand. She also discusses her unique approach to fostering relationships in venture capital and why community and authenticity are key drivers of success in this space. This episode is packed with actionable takeaways for emerging fund managers and anyone navigating the world of VC. Highlights: $50 Million Fundraise: How Nichole secured her fund’s anchor and achieved a first close in just two months. Building Distribution Advantage: Leveraging social media and brand-building to access top founders and close deals. Fund Size Challenges: Overcoming objections from institutional LPs and proving scalability. Strategic Fundraising: Nichole's timeline, drip campaigns, and tactics to convert LPs at a 26% rate. Community-Driven Success: The value of collaboration among emerging managers and fostering trusted relationships. The Twitter Advantage: Nichole’s journey to building a massive online following and using it as a competitive edge. Cringe Scales: Why embracing discomfort on social media pays dividends for fund managers. Future Focus: Nichole’s advice for navigating relationships, building a firm, and standing out in the VC world. -- Guest Bio: Nichole Wischoff is the Founder and Managing Partner of Wischoff Ventures, a venture capital firm investing in early-stage startups. With deep operational experience at multiple high-growth companies and a proven track record in venture capital, Nichole has built her reputation as a leader in the emerging manager space. Known for her authenticity and strategic approach, she is passionate about building her firm and brand in public while supporting the next wave of groundbreaking founders. Our podcast now receives more than 200,000 downloads a month. Interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP -- SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Nichole Wischoff: @NWischoff LinkedIn: David Weisburd: David Weisburd LinkedIn Nichole Wischoff: Nichole Wischoff LinkedIn Links: Wischoff Ventures: www.wischoff.com Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:08) Leveraging social media and brand for distribution advantage (4:31) Overcoming LP objections and scaling investments (6:49) Strategies for first close and securing anchor LPs (10:29) Identifying and engaging interested LPs (13:34) Insights into decision-making of top quartile LPs and endowments (15:52) Collaborating with emerging managers and building trust (19:43) Importance of the 80/20 rule in relationships (21:27) Strategies for building a Twitter presence and follower psychology (25:47) Tips for effective Twitter engagement and brand growth (28:28) Closing remarks

Jan 21

In this episode of How I Invest, I sit down with Nick Shekerdemian, entrepreneur, investor, and founding partner of The Venture Collective (TVC). A former Oxford student turned Thiel Fellow, Nick shares his journey of dropping out of university to pursue big ideas and how the fellowship helped shape his path in venture capital. We explore TVC's unique approach to portfolio construction, investing in deep tech and computational biology, and why thesis-driven investing is the future of venture capital. Nick also discusses challenges like founder breakups, scaling value-added strategies, and his thoughts on the next big shifts in technology and bio-defense. Highlights: Thiel Fellowship: Why Nick left Oxford to join the fellowship and how it transformed his career. Portfolio Construction: TVC’s concentrated approach to seed-stage investing and leveraging informational advantages to support founders. Thesis-Driven Investing: Why Nick believes the future of venture capital lies in backing big, transformative ideas, especially in deep tech, computational biology, and AI. Bio-Defense and Innovation: How advancements in AI and biology could revolutionize healthcare and address emerging bio-defense challenges. Supporting Founders: The importance of transparency, setting micro-goals, and building trust for navigating challenges like founder breakups. Opportunities in Deep Tech: Exploring transformative sectors like defense tech, healthcare personalization, and reindustrialization driven by sustainability and AI. Shifts in Venture Capital: Nick’s prediction that rapid innovation will redefine the venture landscape in the next few years. -- Guest Bio: Nick Shekerdemian is the founding partner of The Venture Collective (TVC), a seed-stage investment firm focused on backing visionary founders tackling transformative problems. A former Thiel Fellow, Nick has built his career at the intersection of entrepreneurship and venture capital, with a deep passion for investing in ambitious ideas in deep tech, healthcare, and sustainability. He’s committed to supporting founders who think differently and aren’t afraid to challenge the status quo. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: linkedin.com/in/dweisburd/ Nick Shekerdemian: https://www.linkedin.com/in/nshekerdemian/ Links The Venture Collective: https://theventurecollective.com Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:10) Dropping out of Oxford and Thiel Fellowship Insights (4:01) Seed Stage Startup Portfolio Construction (5:58) Leveraging Informational Advantages (8:33) Scaling Value-Added Strategies for Startups (10:28) Reporting Cadence vs. Company Performance (11:42) Fostering Transparency with Founders (14:17) TVC's Alpha Sources and Thematic Investing (18:28) Deep Tech Investments and Defense Tech Excitement (20:02) Changing LP Sentiments and Non-Momentum Investing (22:40) Computational Biology as an Investment Opportunity (24:50) Contrarian Views on Venture Capital (26:15) The Future of Biodefense and Bioweapons (27:46) Call to Action for Problem Solvers (28:34) Closing remarks

Jan 17

In this episode of How I Invest, I sit down with Marcie Frost, CEO of CalPERS, the largest public pension fund in the United States. From her beginnings in public service to leading a $502.9 billion portfolio, Marcie shares her journey and offers insights into managing one of the most influential pension funds globally. We discuss the challenges of governance, integrating climate change risks into investment decisions, and the importance of building a culture of trust and innovation. Marcie also delves into CalPERS’ strategic focus on sustainable investments, diversity, equity, and inclusion initiatives, and how the organization is setting benchmarks in transparency and fiduciary responsibility. Highlights: Public Service Journey: Marcie’s transition from Washington state's Department of Retirement Systems to leading the largest public pension fund in the U.S. CalPERS’ Mission: The role of a $502.9 billion portfolio in securing the financial future of over 2 million California public sector workers and their families. Strategic Asset Allocation: How CalPERS utilizes its Asset Liability Management process to inform asset allocation decisions and set investment return assumptions. Integrating Climate Risks: The incorporation of climate change risks into investment decisions across all asset classes and the launch of a $100 billion sustainable investment strategy aimed at reducing carbon emissions intensity by 50% by 2030. Building a Culture of Trust: Marcie’s approach to fostering an inclusive culture through the development of CalPERS' first Diversity, Equity & Inclusion framework. Sustainable Investments: CalPERS' commitment to sustainable investing, including its role as a founding member of Climate Action 100+, an initiative with 700 signatories and $68 trillion in assets under management. Stakeholder Engagement: Expansion of stakeholder outreach to ensure all parties are informed and have a voice in the system's future. Advocacy for Defined Benefits: Marcie's belief in providing equitable and affordable health care and retirement options for public employees. -- Guest Bio: Marcie Frost is the Chief Executive Officer of CalPERS, overseeing the largest public pension fund in the United States. With over 30 years of experience in public service, Marcie is a dedicated advocate for financial security, transparency, and sustainability. Under her leadership, CalPERS has advanced its goals in asset management, stakeholder engagement, and cultural transformation, ensuring that its over 2 million members can retire with dignity. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Marcie Frost: https://www.linkedin.com/in/marcie-frost-56a30a281/ Links: CalPERS: https://www.calpers.ca.gov/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (0:35) CalPERS' strategic asset allocation, risk limits, and board dynamics (2:39) Composition, election, and decision-making of CalPERS' investment committee (5:25) Understanding board members' risk appetite and stakeholder engagement (9:07) Navigating political aspects and role differentiation at CalPERS (14:02) Changing organizational culture and focusing on investment results (18:29) Sponsor: Reed Smith (21:22) Managing media scrutiny and its impact on investment decisions (22:36) Stability and importance of the CIO role at CalPERS (23:13) Emerging managers, diversity, and strategic planning for 2025-2029 (24:55) Evaluating private markets, liquidity premium, and active vs passive management (27:47) Building relationships as a first call partner to managers (29:43) CEO reflections and fostering a world class culture at CalPERS (31:27) Key takeaways about CalPERS for listeners (34:38) Closing remarks

Jan 14

In this episode of How I Invest, I connect with Ken Smythe, founder of Next Round Capital, to discuss his journey in private markets, lessons from hedge fund management, and the future of thematic investing. Ken shares insightful stories about spotting talent, using key executive moves as signals for investment opportunities, and the rise of AI and defense technology. We also explore the challenges facing venture capital and private equity in today’s market, including liquidity bottlenecks and the hunt for alpha in a rapidly evolving landscape. Ken's personal story of resilience and his passion for innovation shine through in this inspiring conversation. Highlights: Key Signals in Early-Stage Investing: Why tracking executive moves from established companies like Apple or Stripe to startups can offer a major edge in spotting emerging opportunities. AI's Evolution: The current state of AI innovation compared to the early days of the internet and the need for sustainable business models to monetize AI advancements. Defense Tech: How startups are disrupting traditional players like Lockheed Martin and General Dynamics with cutting-edge technologies tailored to modern battlefields. Hedge Fund Insights: The importance of diversification, risk management, and identifying specialized talent in building successful multi-strategy hedge funds. Secondary Markets: The growing role of VCs, family offices, and retail investors in accessing shares of companies like SpaceX and how liquidity challenges are reshaping private equity strategies. Thematic Investing: From AI chatbot agents to defense technology, Ken outlines the trends and themes that he believes will dominate in 2025 and beyond. Personal Resilience: Ken’s inspiring journey of launching his own firm amid personal challenges, underscoring the importance of seizing opportunities and living with purpose. -- Guest Bio: Ken is the founder of Next Round Capital, a firm specializing in secondary investments, co-investments, and niche opportunities in technology and AI. With a background in hedge fund management and a focus on thematic investing, Ken leverages his deep network and expertise to identify groundbreaking opportunities in private markets. He is passionate about innovation and building meaningful relationships in the venture ecosystem. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ken Smythe: https://www.linkedin.com/in/ken-smythe/ Links: Next Round Capital: https://www.nextroundcapital.com Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com (0:00) Episode preview (1:37) Key Executive Movements in Tech (3:38) Adverse Selection in Venture Capital (4:35) Investment Trends for 2025 (6:27) Focus on Defense Technology Investments (8:06) Managing Liquidity in Venture Portfolios (10:36) Analyzing SpaceX's Investment Potential (11:45) Hedge Fund Insights from a $5 Billion Experience (14:37) Strategies for Recruiting and Evaluating Portfolio Managers (24:50) The Art of Referencing and Backchanneling (26:01) Spotlight on Next Round Capital (27:39) AI Investment Landscape Analysis (28:34) Business Model Significance in Tech Sector (29:52) Closing remarks

Jan 10

In this episode of How I Invest, I sit down with Lawrence Calcano, Chairman and CEO of iCapital, to explore the transformative potential of alternative investments in the wealth management space. Lawrence shares his journey from Goldman Sachs to building iCapital, a platform managing over $200 billion in alternative assets. We dive deep into the challenges and opportunities in democratizing access to private markets, the role of technology in scaling the alternatives industry, and the growing appetite for private equity and credit among high-net-worth investors. If you're curious about the future of wealth management and the intersection of technology and alternatives, this episode is a must-listen. Highlights: The Wealth Market's Untapped Potential: Retail investors collectively control $145 trillion globally, rivaling institutional markets. Democratizing Alternatives: iCapital enables financial advisors to access institutional-quality alternative products and simplifies operational complexities with technology. Trends in High-Net-Worth Investing: A shift back to equities in 2025 following a credit-dominated two years. Illiquidity as a Feature, Not a Bug: How private markets generate alpha through active management during illiquidity periods. Overcoming the Chicken-and-Egg Problem: Building trust with both advisors and general partners to grow the platform. Technology as a Game Changer: AI, distributed ledgers, and automation reduce inefficiencies and errors in managing private fund investments. Future of Alternatives: Allocations to alternatives are expected to grow significantly as education and access improve. Key Lessons in Investing: Lawrence emphasizes the importance of understanding investments fully to navigate market dynamics effectively. Building a Cohesive Culture: Insights on leadership, teamwork, and fostering a shared mission at iCapital. -- Guest Bio: Lawrence Calcano is the Chairman and CEO of iCapital, a leading platform providing access to alternative investments for wealth advisors and their clients. With a background in tech investment banking at Goldman Sachs, Lawrence has been instrumental in modernizing how advisors and high-net-worth individuals access and manage private market investments. Our podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships, and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lawrence Calcano: https://www.linkedin.com/in/lawrence-calcano-5b8b9111/ Links: iCapital: https://icapitalnetwork.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:14) I Capital's founding and evolution from Goldman Sachs (2:37) Private equity's wealth channel strategy and challenges (4:56) Comparing high net worth and institutional investors (7:31) Investor trends: From credit to equity interests (10:27) Projections for the future of the alternatives industry (14:45) Wealth channels' impact on adverse selection (15:23) Sponsor: Reed Smith (19:28) I Capital's aggregation service for General Partners (GPs) (20:32) The enduring nature of the wealth channel (22:16) The role of emerging managers in the wealth channel (26:00) Lawrence Calcano's investment philosophy and early lessons (27:40) The significance of investment comprehension (28:03) Fostering and maintaining iCapital's company culture (30:39) Scaling company values with organizational growth (32:31) iCapital's ambitious vision for 2030 (33:22) Addressing challenges in the alternatives sector (34:43) Leveraging technology to solve client problems (37:11) Implications of the accredited investor rule (38:46) Closing remarks

Jan 7

In this episode of How I Invest, I sit down with Felix Ejeckam, Co-Founder and CEO of Akash Systems. Felix discusses how Akash is leveraging synthetic diamond technology to revolutionize cooling for high-power microchips used in AI servers and satellite communications. He shares insights on their $68 million CHIPS Act funding, the importance of U.S. semiconductor manufacturing, and Akash’s journey through tough times to becoming a leader in cutting-edge technology. A must-listen for anyone interested in semiconductors, AI, or transformative tech innovations. Highlights: What is Akash Systems? A company pioneering synthetic diamond cooling technology to enhance performance and efficiency in AI servers and satellite communications systems. Synthetic Diamond Technology: How Akash grows lab-made diamonds and integrates them into chips to reduce cooling costs and improve performance by up to 90%. Massive Market Opportunity: Targeting a $200-$400 billion market spanning data centers, satellite communications, EVs, smartphones, and defense systems. CHIPS Act Funding: Akash recently secured $68 million in CHIPS funding to scale manufacturing, establish a semiconductor fab in Oakland, and support U.S. economic and national security goals. Overcoming Tough Times: Reflecting on the challenges during COVID-19, Akash used the “quiet years” to refine its technology, expand into new markets like AI, and emerge stronger. Staying Non-Consensus: The importance of conviction, foresight into market trends, and building a team that balances optimism and pragmatism. What’s Next for Akash: Upcoming satellite launches, server shipments in Q1, and a trajectory to becoming the leading high-end AI server company globally. -- Guest Bio: Felix Ejeckam is the Co-Founder and CEO of Akash Systems, a trailblazing company using synthetic diamond technology to transform semiconductor cooling and performance. Under Felix’s leadership, Akash has achieved groundbreaking innovations in AI servers and satellite communications systems, contributing to U.S. manufacturing and technological independence. Felix is passionate about fostering innovation and building resilient companies that thrive in challenging times. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Felix Ejeckam: @felixejeckam LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Felix Ejeckam: https://www.linkedin.com/in/felixejeckam/ Links: Akash Systems: https://www.akashsystems.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:08) Akash Systems and the cost of cooling server chips (4:05) Chips Act funding (7:13) Competitive landscape in AI server market (11:33) US election impact on Akash Systems (12:39) Overcoming COVID-19 challenges (14:32) Building resilience and strategic pivots (19:30) Non-consensus investing strategies (22:38) Closing remarks

Jan 3

In this episode of How I Invest, I connect with Matt Hougan, Chief Investment Officer at Bitwise Asset Management. Matt shares his expertise on Bitcoin and cryptocurrency investments, offering actionable insights on portfolio allocation, valuation, and the evolving crypto market. From the benefits of a 2–5% Bitcoin allocation to the potential of Bitcoin as a global settlement currency, Matt provides a compelling case for crypto as a transformative asset class. This episode is a must-listen for institutional investors, financial advisors, and anyone curious about the future of digital assets. Highlights: Bitcoin Allocation: Why institutional investors should allocate at least 2% to Bitcoin to stay neutral with benchmarks and up to 5% to maximize risk-adjusted returns. Portfolio Benefits: Adding Bitcoin improves Sharpe ratios due to its low correlation with traditional assets, offering higher returns with minimal additional volatility. The Importance of Timeframe: Bitcoin’s performance as a hedge improves over a long-term horizon, despite short-term volatility. Behavioral Risk: The biggest risk in crypto investing is behavioral, emphasizing the importance of maintaining balanced portfolio allocations. Beyond Bitcoin: The case for diversifying into other cryptocurrencies like Ethereum, and the advantages of buying a basket of assets versus picking individual winners. Crypto Cycles: Why crypto markets are highly cyclical due to their early-stage nature and speculative tendencies, and how this volatility is decreasing over time. Regulatory Clarity: How a pro-crypto regulatory environment under the new U.S. administration could unleash institutional investment and entrepreneurial growth in the crypto space. Bitcoin Valuation: Using supply-demand dynamics and gold’s $18 trillion market as a benchmark, Matt explains why Bitcoin could eventually reach $1 million per coin. Bitcoin as a Settlement Currency: The potential for Bitcoin to become a non-political settlement currency in a multipolar world. -- Guest Bio: Matt Hougan is the Chief Investment Officer at Bitwise Asset Management, where he leads the development of innovative crypto investment strategies. A pioneer in crypto asset management, Matt created the first crypto index fund and has been guiding investors through the complexities of digital assets for over seven years. He’s known for his precise, academic approach to crypto and is passionate about helping investors understand the transformative potential of blockchain technology. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP -- SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Matt Hougan: @Matt_Hougan LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Hougan: https://www.linkedin.com/in/matthougan/ Links: Bitwise Asset Management: https://www.bitwiseinvestments.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:04) Institutional investment strategies in Bitcoin (4:35) Portfolio diversification with Bitcoin (8:13) Case study: MicroStrategy's Bitcoin strategy (10:03) Exploring other cryptocurrencies for institutional investors (12:45) Advantages of cryptocurrency baskets (14:38) Sponsor: Reed Smith (16:03) Cyclical nature of cryptocurrency markets (19:54) US government and Bitcoin investment prospects (21:42) Crypto's regulatory landscape under the Trump administration (25:40) Bitcoin's future beyond a store of value (27:21) Assessing Bitcoin's value without traditional cash flows (29:08) Bitwise investment strategy overview (30:17) Closing remarks

Dec 31, 2024

In this episode of How I Invest, I sit down with Alifia Doriwala, Co-CIO and Managing Director at RockCreek, a multi-asset and OCIO solutions firm managing $16 billion in assets. Alifia delves into RockCreek’s unique approach to managing customized portfolios for endowments, foundations, and pensions. She shares her perspectives on navigating public and private markets, the evolving role of hedge funds, and the outlook for IPOs and M&A activity in 2025. This conversation is packed with insights for asset managers, institutional investors, and anyone seeking a deeper understanding of market trends and investment strategies. Highlights: What is RockCreek? A multi-asset and OCIO firm managing portfolios for clients with under $2 billion in AUM, combining private and public market expertise. Customized Solutions: Tailoring portfolios to meet client needs, including thematic private market investments like innovation in the aviation industry. Key Themes for 2025: Anticipating a rebound in IPO markets, increased M&A activity, and opportunities in healthcare and biotech within private markets. Public Markets Outlook: A shift toward active management as market dynamics broaden, with sector-specific opportunities in U.S. equities like energy, pharmaceuticals, and fintech. Private Markets Allocation: Targeting 20–30% in private equity and venture capital for long-term institutional investors, with 35–40% in alternatives when including real assets. Interest Rates and Inflation: Insights into the current rate environment and long-term concerns about inflationary pressures due to trade policies and tariffs. The Role of Hedge Funds: Understanding why institutions are increasing allocations to hedge funds for alpha and downside protection, and the contrasting strategies between discretionary and quant approaches. Lessons from a 20-Year Career: How starting in sales and trading shaped Alifia’s investment approach and the importance of being data-driven, dynamic, and open to new ideas. Continuous Improvement: Strategies for sharpening skills as a CIO, including constant learning, engaging with peers, and leveraging diverse macro perspectives. -- Guest Bio: Alifia Doriwala is the Co-CIO and Managing Director at RockCreek, where she oversees multi-asset portfolios for institutional investors, including endowments, foundations, and pensions. With a career spanning over two decades, Alifia’s expertise bridges public and private markets, offering strategic solutions tailored to client needs. She is passionate about data-driven decision-making, market research, and mentoring the next generation of asset managers. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alifia Doriwala: https://www.linkedin.com/in/alifia-doriwala-4382629/ Links: RockCreek: https://therockcreekgroup.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:00) Solving client problems and investment themes for the new year (3:26) IPO market predictions and future interest rates (7:08) Alternatives portfolio strategies for endowments and foundations (11:53) Career insights: From sales and trading to investment management (13:30) Family offices' investment trends in hedge funds (16:27) Reflections and advice for aspiring CIOs (17:32) Closing remarks

Dec 27, 2024

In this episode of the How I Invest Podcast, I interview David Clark, CIO of Vencap, to discuss the venture capital landscape. We discuss assumptions about small vs. large venture funds, unpack survivorship bias in performance data, and explore the power law dynamics in early-stage and growth funds. David Clark shares Vencap's strategy for identifying top-performing managers, insights on fund size limits, and the implications of political and economic shifts on venture capital. A must-listen for investors seeking a data-driven perspective on navigating the venture ecosystem. Highlights: Myth of Small Fund Outperformance: David Clark challenges the belief that smaller venture funds consistently outperform larger ones, noting limitations in available data and survivorship bias. Survivorship Bias in VC Data: Many underperforming funds don't report their results, skewing datasets like PitchBook and Cambridge. Clark highlights Carta as a potential unbiased source for small fund performance data. Power Law Dynamics in Venture Capital: Vencap's data shows that even growth funds exhibit power law outcomes, with 1.6% of their investments being fund returners—higher than early-stage funds (1%). Focus on Top-Performing Managers: Over 90% of Vencap's capital goes to 12-13 managers who have a track record of consistently backing fund-returning companies. Venture vs. Private Equity: Venture funds show stronger persistence of returns compared to private equity, with top-quartile funds often repeating their success. Fund Size Considerations: Vencap evaluates whether fund sizes align with the ability to back companies that generate massive returns. Excessively large funds can dilute performance potential. State of Venture Post-2020 Election: While short-term political changes may influence sentiment, Clark emphasizes focusing on long-term relationships with top managers and founders. Valuation Practices in Venture: Skepticism over inflated venture fund valuations is warranted, but Clark sees signs that portfolios may now be undervalued. -- Guest Bio: David Clark is the CIO of Vencap, a firm specializing in venture fund investments since the 1980s. With a data-driven approach, Vencap partners with top-performing venture managers to navigate the power law dynamics of venture capital. David’s insights are rooted in decades of data, challenging conventional wisdom and focusing on long-term outperformance in venture markets. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSORS: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: Twitter David Weisburd: @dweisburd David Clark: @DaveClark85 LinkedIn David Weisburd: https://www.linkedin.com/in/dweisburd/ David Clark: https://www.linkedin.com/in/david-clark-6678b6b/ Links VenCap: https://www.vencap.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (3:38) Survivorship bias and its effects on venture capital (11:48) VenCap's investment strategy and return persistence (16:04) Key factors influencing founder choices of investors (16:25) Sponsor: Reed Smith (19:04) Relationship between fund size and performance (20:06) Venture market insights after the 2024 election (23:36) The interplay between startups and investor actions (25:28) What excites LPs about the venture asset class (26:46) Venture fund valuations and market concerns (27:16) The predictive power of TVPI and DPI in venture funds (29:03) Following David Clark online and data-driven investing (31:04) Closing remarks

Dec 24, 2024

In this episode of How I Invest, I connect with Gregor von dem Knesebeck, Co-Founder and Managing Partner of Blue Future Partners. Gregor shares the story of building a successful fund-of-funds focused on venture capital, emphasizing brand building, portfolio construction, and navigating the unique challenges of venture investing as a family office. This episode provides insights into venture capital portfolio strategies, the power law of returns, and best practices for fund allocation. A valuable listen for emerging fund managers, family offices, and anyone exploring fund-of-funds strategies. Highlights: Building Blue Future Partners: How Gregor and his brother co-founded the firm and learned the importance of brand building for success in venture capital. Family Office Venture Allocation: Exploring the ideal venture capital allocation, ranging from 1–2% in Europe to 10–20% in U.S. endowments. Three Pillars for Venture Investing: Fund-of-funds, direct investments, and investing in funds—and the pitfalls of skipping steps. Portfolio Construction: Blue Future Partners’ concentrated strategy—focusing 80% of capital on 10–12 names within a 15–20 fund portfolio for each vintage. Managing LP Relationships: Avoiding "tourist LPs" and small check investors that lead to inefficiencies and time-consuming micromanagement. Venture’s Power Law: Understanding why a few outsized returns drive the portfolio and how it contrasts with private equity’s return dynamics. Long-Term Venture Horizons: Why venture requires a 20-year investment horizon, cyclicality, and resilience to market downturns. Lessons Learned: The difficulties of timing vintages, managing global complexity, and balancing personal sacrifices with business growth. Value Add for LPs: Blue Future’s initiatives such as the Family Office Academy and GP Accelerator Program to support education, fundraising, and matchmaking in the venture ecosystem. -- Guest Bio: Gregor von dem Knesebeck is the Co-Founder and Managing Partner of Blue Future Partners, a fund-of-funds specializing in venture capital. With a strong focus on European and U.S. markets, Gregor combines his passion for technology with his expertise in fund management to support GPs and LPs in building sustainable, high-performing portfolios. Blue Future Partners emphasizes long-term partnerships and aims to create outsized returns through a curated portfolio of top-tier venture funds. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @Carta for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod -- Stay Connected: X / Twitter: David Weisburd: @dweisburd Gregor von dem Knesebeck: @gregorio LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Gregor von dem Knesebeck: https://www.linkedin.com/in/gregorvdk/ Links: Blue Future Partners: https://www.bfp.vc/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (1:45) Building Blue Future Partners (3:51) Family office venture asset allocation strategies (5:20) Challenges for family offices in venture capital (7:19) Portfolio construction (9:27) Fund of funds time diversification and LP management (10:20) Sponsor: Carta (13:08) Adding value to LPs through a fund of funds (14:25) Lessons learned (16:03) Early mistakes and personal sacrifices in VC (18:58) Closing remarks

Dec 20, 2024

In this episode of How I Invest, I sit down with Elizabeth Browne, Managing Director and Co-Head, Sponsor Solutions Group & Elevate at GCM Grosvenor. Elizabeth shares her deep expertise in GP seeding—a niche yet growing area in private equity—covering topics such as structuring deals, the challenges of building institutional-grade asset management firms, and how to identify and support future industry leaders. This episode is a must-listen for anyone intrigued by the nuances of private equity, the intersection of investing and firm-building, and the future of the seeding market. Highlights: What is GP Seeding? Elizabeth explains GP seeding as taking an ownership interest in the management company of an asset management firm and its dual purpose: providing launch capital for new firms or growth capital to undercapitalized ones. The $300 Million Threshold: The importance of reaching this critical fund size to attract institutional LPs and hire top talent, as well as managing the fixed costs of building a private equity firm. Investor vs. Firm Founder: Distinguishing the skillsets required to be a great investor versus building a lasting and scalable asset management firm—including operational, compliance, and regulatory expertise. Core Attributes of Great Firm Founders: Hustle, grit, sector expertise, and the ability to manage team dynamics, alongside a strong investment track record. Structuring Seed Deals: Avoiding common pitfalls such as static or misaligned participation terms and instead focusing on revenue-sharing constructs tied to performance. The Evolving Seeding Market: From the role of single-family offices in the early days of GP seeding to the institutionalization of the space, including a projected $80 billion in the GP stakes market. Scaling a Support Model: How GCM Grosvenor’s Sponsor Solutions balances its high-touch approach with a carefully curated portfolio of eight to nine investments. The Importance of Relationship-Driven Investing: Why great managers seek true partners who provide strategic value beyond capital, and how GP referrals have been a surprising source of deal flow for Elizabeth’s team. -- Guest Bio: Elizabeth Browne is the Managing Director and Co-Head, Sponsor Solutions Group & Elevate at GCM Grosvenor, focusing on GP seeding and strategic partnerships with emerging asset management firms. With decades of experience in private equity, Elizabeth is passionate about identifying and supporting the next generation of industry leaders. She brings a hands-on approach to helping founders build institutional-grade firms, emphasizing long-term partnerships and sustainable growth strategies. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP -- SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: @dweisburd (David Weisburd) LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Elizabeth Browne: https://www.linkedin.com/in/elizabeth-browne/ Links: GCM Grosvenor: https://www.gcmgrosvenor.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode Preview (2:06) Minimum fund size and differences between a good investor and a good firm founder (7:49) The apprenticeship nature of investing and identifying the next great manager (11:04) Track record risk vs. new business risk in institutional management (14:48) Sponsor: Reed Smith (19:05) Deal types and manager relationships; investment diversification strategies (23:44) Hedging strategies and structuring seed transactions (28:30) Economic participation incentives for performance (33:31) Challenges and scaling strategies for emerging managers (37:59) Comparing partnership to transaction-oriented founding approaches (42:04) Closing remarks

Dec 17, 2024

In this episode of How I Invest, David Weisburd speaks with Ron Diamond, a renowned expert in the family office space and the founder of Diamond Wealth. Together, they explore the transformative role family offices are playing in private markets, the impending $84 trillion wealth transfer, and the challenges of professionalizing family office operations. Ron also shares his insights on governance, structural alpha, and strategies for raising grounded, ambitious children in wealthy families. A must-listen for anyone interested in the future of family offices and their potential to disrupt private equity and venture capital. Highlights: The $84 Trillion Wealth Transfer: Over the next 20 years, baby boomers will pass down $84 trillion to the next generation, with family offices poised to be major beneficiaries. Professionalizing Family Offices: Ron discusses why many family offices lack the talent to compete with top firms like KKR and Blackstone and emphasizes the need for better compensation models to attract and retain top-tier talent. The Rise of "Private Capital": Sophisticated family offices are rebranding to "private capital" to differentiate themselves from the fragmented, inefficient traditional family office structure. Structural Alpha and Tax Strategies: Ron explains how concepts like private placement life insurance (PPLI) and tax-loss harvesting can significantly boost after-tax returns, making them essential tools for family offices. The Family Office Initiative at Booth: Ron details his work at the University of Chicago Booth School of Business, creating an ecosystem to educate and empower family offices through research and networking. Raising Grounded Children in Wealthy Families: Ron highlights the importance of modeling humility, instilling gratitude, and avoiding entitlement to ensure the next generation thrives. -- Guest Bio: Ron Diamond is the founder and chairman of Diamond Wealth, a leading family office advisory firm. He represents over 100 family offices with a collective net worth exceeding $30 billion. A pioneer in the family office space, Ron is passionate about professionalizing the industry, educating the next generation, and helping families leverage patient capital to disrupt traditional private equity models. He is also the co-founder of the Family Office Initiative at the University of Chicago Booth School of Business. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . We’d like to thank @Carta for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com -- Stay Connected: Twitter: @dweisburd (David Weisburd) @RonDiamond (Ron Diamond) LinkedIn: David Weisburd: linkedin.com/in/dweisburd/ Ron Diamond: linkedin.com/in/ronalddiamond Link: Diamond Wealth: https://www.diamondwealthstrategies.com/ (0:00) Episode Preview (1:49) Compensation Issues in Family Offices (2:23) Turning Family Offices into Profit Centers (4:23) Case Study of a Successful Family Office (5:23) Branding and Private Capital in Family Offices (7:28) Why Family Offices Fail Across Generations (10:30) Governance and Tax Strategies in Family Offices (13:24) Sponsor: Carta (15:48) Tax-Efficient Investment Strategies (19:07) Cultivating Values in Ultra-Wealthy Heirs (23:27) University of Chicago's Family Office Initiative (27:35) Academic Interest in Family Office Management (30:55) Comparing Family Offices and Private Equity (33:20) Strategies for Improving Family Office Returns (36:07) The Role of Relationships in Family Offices (38:19) Closing remarks

Dec 13, 2024

In this episode of How I Invest, David Weisburd is joined by Teddy Gold, the Founder and CEO of 3i, a membership-based platform that connects elite investors. Teddy discusses key insights into private equity, venture capital, and niche investing strategies. He shares his experiences with scaling asset management, navigating the complexities of private credit, and the power of leveraging networks to uncover investment opportunities. A must-listen for those interested in the intersection of high-level investment strategies and the value of relationship-driven networks. Highlights: Scaling Asset Management: Some strategies (like venture capital) are harder to scale, while others (like Blackstone’s approach) have proven successful at large scales. The Principal-Agent Problem: Large institutions may prioritize minimizing risk, leading to missed opportunities, while smaller specialized funds often outperform. Specialty Finance & Private Credit: Reducing management fees can boost returns, but smaller funds face scalability challenges. Aircraft Engine Investing: A successful example of niche investing, where 3i members capitalized on aircraft engine teardown investments. The Power of Membership Networks: 3i’s model thrives on a high-quality, skilled network that sources and executes investment opportunities. Lessons Learned in Relationship Building: Early mistakes taught Teddy the importance of personal connections and relationship management in building a successful network. Teddy’s Vision for 3i in the Next 5–10 Years: Expanding in key cities and maintaining high membership standards for long-term growth. -- Guest Bio: Teddy Gold is the CEO of 3i, a premier investment network that connects family offices, fund managers, and excited entrepreneurs. 3i focuses on sourcing, vetting, and funding private market deals with the expertise of its highly skilled members. Teddy is committed to building a high-quality, scalable investment ecosystem that emphasizes personal relationships and expertise. With years of experience in venture capital and private equity, Teddy brings invaluable insights into the evolving world of alternative investments. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . We’d like to thank @ReedSmith for sponsoring this episode! #VentureCapital #VC #Startups #OpenLP #AssetManagement -- SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . -- Stay Connected: X / Twitter: @dweisburd (David Weisburd) @teddygoldtweets (Teddy Gold) LinkedIn David Weisburd: https://www.linkedin.com/in/dweisburd/ Teddy Gold: https://www.linkedin.com/in/teddygold/ Links 3i: https://www.3imembers.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com (0:00) Episode Preview (2:31) Growth strategies and avoiding adverse selection in 3i (5:21) Raising funds and criteria for first-time fund managers (8:00) Sponsor: Reed Smith (10:03) Trust breakdown in institutions and venture capital fee structures (14:10) Specialty finance insights and private credit learnings (17:30) Asset management cyclicality and network value (20:46) CEO mistakes and the importance of personal relationships (22:02) Closing remarks

Dec 10, 2024

Najada Kumbuli, Vice President, Head of Investments at Visa Foundation sits down with David Weisburd to discuss what makes a first-time fund manager a breakout success, why storytelling matters in impact investing, and why this is the most challenging fundraising market since 2001. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @Visa (Visa) @najadakumbuli (Najada Kumbuli) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Najada Kumbuli: https://www.linkedin.com/in/najada-kumbuli-68816614/ Visa: https://www.linkedin.com/company/visa/ – Links: Visa: https://www.visa.com – Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com – TIMESTAMPS: (0:00) Episode Preview (2:24) Launching Visa Foundation's investment program and learning new markets (3:54) Venture fundraising dynamics and LP decision-making processes (6:21) Identifying genuine LP interest and navigating rejections (11:39) Sponsor: Carta (12:22) The LP learning curve on GP investment theses (17:48) Insights and surprises from working at Visa Foundation (20:50) Closing remarks

Dec 6, 2024

In this episode of How I Invest, we’re joined by Michael Kakenmaster, Director of Investments at Loyola University Chicago. Michael shares his journey and expertise in managing university endowment portfolios, with a focus on private markets and hedge fund strategies. He offers valuable insights on how to build sustainable, diversified portfolios and the strategies that have led to success in his role. We also discuss the evolving landscape of venture capital and how institutions like Loyola are adapting to market changes. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – X / Twitter: @dweisburd (David Weisburd) @LoyolaChicago (Loyola University Chicago) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Michael Kakenmaster: https://www.linkedin.com/in/michael-kakenmaster-cfa-76212912/ Loyola University Chicago: https://www.linkedin.com/school/loyola-university-chicago/ – Links: Loyola University Chicago: https://www.luc.edu/ – Questions or topics you want us to discuss on How I Invest? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (0:44) Overview of opportunistic investments and helicopter lease funds (3:32) History, challenges, and due diligence in the helicopter leasing market (8:37) The impact of unique ideas and characteristics of a top investment committee member (10:31) Managing Loyola's endowment and building a venture capital program (14:32) Lessons from allocator friends and criteria for hedge fund managers (18:12) Beliefs in market efficiency and retrospective insights (20:45) Closing remarks

Dec 3, 2024

Hansen Ringer, Managing Director at Sepio Capital sits down with David Weisburd to discuss the asset class that delivers equity-like returns without the market risk, what distressed credit reveals about market cycles and investor behavior, and what happens when stocks and bonds move together. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com . – X / Twitter: @dweisburd (David Weisburd) @Hansenringer – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Hansen Ringer: https://www.linkedin.com/in/hansenringer/ Sepio Capital: https://www.linkedin.com/company/sepiocap-/ – Links: Sepio Capital: https://www.sepiocap.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (2:44) Decision-making factors and sector allocation strategies (6:42) Public market insights and stock-bond correlation (10:51) Avoidable asset classes and diversification benefits (13:18) Sponsor: Reed Smith (13:43) Hedge funds from an institutional perspective (15:41) Role of managed futures and GP-led secondaries (21:21) Liquidity considerations in investment strategies (24:10) Structured deals and fund performance analysis (26:45) Evaluating private equity managers' prowess (28:38) Sponsor: Carta (31:48) Treasuries, cash, and lessons from Sepio Capital (35:04) Adapting to new investment spaces and LP investing mistakes (37:53) Partnership dynamics and the value of off-list references (41:56) Closing remarks

Nov 29, 2024

Victor Mayer, Managing Director, Head of Private Wealth at Pantheon sits down with David Weisburd to discuss why top GPs are rushing to evergreen funds, how Pantheon balances small-cap potential and large-cap stability, and the benefits of Pantheon’s no-cost co-investment deals. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – X / Twitter: @dweisburd (David Weisburd) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Victor Mayer: https://www.linkedin.com/in/mayervictor/ Pantheon: https://www.linkedin.com/company/pantheon-ventures/ – Links: Pantheon: https://www.pantheon.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (1:32) Evergreen fund franchise and its purpose (3:11) Evergreen structure and future outlook (6:21) Tax implications and target customers for evergreen funds (8:10) Addressing adverse selection in evergreen funds (10:07) Pantheon's investment strategy for bio funds (14:19) Identifying top buyout managers for Pantheon's portfolio (16:39) Portfolio construction in small to middle market buyouts (17:52) Fee structures in various investment vehicles (20:06) Co-investment performance tracking methods (22:24) Co-invest strategy and deal selection (26:16) Venture capital evergreen structures (28:54) Comparing small buyout and venture capital for LPs (32:09) Exploring large cap funds and small cap opportunities (34:23) Closing Remarks

Nov 26, 2024

James Langer, Chief Executive Officer and Chief Investment Officer at Redmont Wealth Advisors sits down with David Weisburd to discuss how Reason small cap stocks are crushing large caps, the academic approach to outperforming with small cap strategies, and the history of top stocks since 1926. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – X / Twitter: @dweisburd (David Weisburd) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ James Langer: https://www.linkedin.com/in/james-langer-65072b260/ – Links: Redmont Wealth Advisors: https://www.redmontwealth.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (1:04) Eugene Fama's influence and the Fama-French three-factor model (3:14) Impact of the Fama-French model on investment strategy (6:28) Intuition behind small cap value outperformance (8:48) Practical application of theoretical investment strategies (10:32) Indexing approaches: Equally weighted vs. market capitalization (12:06) James Langer's experience and Redmond's investment strategy (16:35) Comparing active management and indexing across market segments (22:06) Indexing tools and active investing impacts (24:59) Effective investment through management alignment (28:03) Portfolio analysis and proprietary tools (29:41) Closing remarks

Nov 22, 2024

Chris Dion, Co-Chief Investment Officer and Managing Partner at Brockenbrough sits down with David Weisburd to discuss what makes small buyout funds resilient, how small buyouts outperform big private equity deals, and why the deal leader matters more than the firm. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – X / Twitter: @dweisburd (David Weisburd) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Chris Dion: https://www.linkedin.com/in/christopher-dion-cfa-7286165/ Brockenbrough: https://www.linkedin.com/company/brockenbrough/ – Links: Brockenbrough: https://www.brockenbroughinc.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (1:23) Client-First Approach in Asset Management (3:03) Evolution of Broganbro's OCIO Practice and Endowment Model (6:31) Skills and Decision-Making in Large Endowments (9:26) In-depth Analysis of Small Buyouts (15:36) Small vs. Large Buyouts and Venture Capital (17:55) Challenges for LPs in Small Buyout Focus (19:17) Comparing Operational Focus in Buyouts (20:42) Closing Remarks

Nov 19, 2024

Christopher Zook, Founder, Chairman, & Chief Investment Officer at CAZ Investments sits down with David Weisburd to discuss the cost of keeping the wrong person on the team, the crucial mistake CEOs make when building a strong culture, and the secret behind faster growth and success. The 10X Capital Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @ChristopherZook (Christopher Zook) @caz_investments (CAZ Investments) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Christopher Zook: https://www.linkedin.com/in/christopher-zook/ CAZ Investments: https://www.linkedin.com/company/caz-investments-lp/ – Links: CAZ Investments: https://cazinvestments.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (2:13) Underwriting and Involvement in Sports Teams (8:00) Key Themes Among Top Institutional Investors (10:23) Compounding in Business and Asset Management (15:20) Sector Specialization and Managing Downside Risk (21:06) Insights from 'The Big Short' (24:44) Navigating Market Misconceptions (26:14) Sponsor: Carta (30:03) Corporate Culture and Principles at CAS (32:23) Enforcing a Culture of Excellence (37:08) The Difference Between Managing and Coaching (39:25) Strategies for CEO Turnover and Employee Fit (41:34) Hiring, Firing, and Culture Maintenance (44:06) The Role of Reviews and Evaluations in Leadership (48:46) Aligning Stated and Actual Corporate Culture (49:02) Legislation Impacting Investment Access (51:27) Staying Updated with CAS and Final Takeaways (52:08) Closing Remarks

Nov 15, 2024

Jake Paul and Joey Levy, Co-Founders of Betr, sits down with David Weisburd to discuss Jake Paul’s bold vision for the future of sports betting and how the company seeks to become the market leader in the space. The 10X Capital Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – X / Twitter: @dweisburd (David Weisburd) @jakepaul (Jake) @joeyslevy (Joey) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Joey Levy: https://www.linkedin.com/in/joey-levy-5b4b00a0/ – Links: Betr: https://www.betr.app/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (0:52) Jake Paul's rise in boxing and the importance of self-belief (2:28) Jake Paul's focus and ambitions outside the ring (4:21) The inception of Jake Paul's sports betting company (6:28) The influence of psychedelics on personal and professional growth (7:37) Marketing strategies and embracing controversy (10:50) Joey Levy on partnership dynamics and equal ownership (13:35) Dedication to the success of Betr (16:23) Betr’s mission, market opportunity, and expansion (20:26) Strategies for customer acquisition and cost efficiency (24:05) The identity of Betr: Media company or betting company (25:04) Financial insights on Betr’s performance (27:31) Betr’s journey to a $100 billion valuation (29:40) Joey Levy's personal drive and background (31:43) Closing remarks

Nov 12, 2024

Dean Duchak, Chief Investment Officer at KFF sits down with David Weisburd to discuss the lessons learned from 13 years at KFF, how to create a culture of collaboration in endowments, and Dean’s perspective on diversifying investment strategies. The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @KFF (KFF) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Dean Duchak: https://www.linkedin.com/in/deanduchak/ KFF: https://www.linkedin.com/company/kfforg/ – Links: KFF: https://www.kff.org/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (2:41) Diversification and macroeconomic impacts on assets (7:07) Exploring thematic investing strategies (8:29) Sponsor: Carta (9:21) GP relationship-building for macro insights (11:54) Evaluating GP performance versus salesmanship (15:14) Pros and cons of managing a smaller endowment (17:17) Focus on venture capital in private allocation (20:47) The contrarian stance on venture capital liquidity (22:24) Investigating the persistence of venture capital returns (23:58) Asset gathering concerns and tax policy implications (27:22) Strategies for portfolio diversification (29:43) Approaching investments in new asset classes (31:27) KFF's key lessons and insights (33:09) Developing skills for new institutional investors (36:50) Closing remarks

Nov 8, 2024

David Sawyer, Chief Operating Officer & Managing Partner at Legacy Knight : Multi-Family Office sits down with David Weisburd to discuss the top mistakes investors make in GP stakes, why middle-market GP stakes could be a game-changer for investors, and how GP stakes outperform traditional investments in 2024. The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @legacyknightmfo (Legacy Knight:Multi-Family Office) @DavidPSawyer (David Sawyer) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Sawyer: https://www.linkedin.com/in/david-sawyer-a70ab912/ Legacy Knight: https://www.linkedin.com/company/legacy-knight-multi-family-office/ – Links: Legacy Knight:Multi-Family Office: https://legacyknight.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (2:40) Understanding GP Stakes Investing (4:46) Succession Planning with GP Stakes (6:27) Evaluating GP Stakes Investments (12:11) Revenue Streams in GP Stakes (19:26) Sponsor: Carta (20:34) Investor Mistakes and Valuation Metrics (23:33) Middle Market GP Stakes: A Growing Landscape (25:37) Emerging Trends in GP Solutions Funds (26:41) Value Addition and Governance in GP Stakes (29:26) Due Diligence Processes in GP Stakes (32:58) Opportunities in Upper Middle Market Firms (35:54) Attractive Asset Classes for GP Stakes (38:23) New Entrants and Evolution in Portfolio Construction (41:49) Closing remarks

Nov 5, 2024

Ben Challgren, Principal at Top Tier Capital Partners sits down with David Weisburd to discuss what makes a top-performing fund, the surprising role of local managers in European venture success and the secrets to spotting a winning startup before it’s big. The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @TTCP_SF (Top Tier Capital Partners) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ben Challgren: https://www.linkedin.com/in/ben-challgren-aa0b2b98/ Top Tier Capital Partners: https://www.linkedin.com/company/top-tier-capital-partners/ – Links: Top Tier Capital Partners: https://ttcp.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (2:17) Exploring secondary opportunities in the market (5:03) Strategies for assessing new fund managers (7:31) The impact of ecosystems on venture success (10:01) Client categories for venture fund of funds (12:33) Sector-specific vs. generalist investment strategies (14:06) Sponsor: Carta (21:14) Relationship dynamics with top-tier funds (24:03) Addressing concerns regarding market beta (25:11) The evolving landscape of fund of funds and new strategies (26:43) Chasing pure alpha in fund of funds investing (27:43) Understanding power laws in fund investing (30:05) Closing remarks

Nov 1, 2024

Charles Hudson, Managing Partner at Precursor Ventures sits down with David Weisburd to discuss how to support first-time fund managers, innovative strategies for sourcing deals in venture capital and tips for success on building relationships with limited partners. The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @PrecursorVC (Precursor Ventures) @chudson (Charles Hudson) – LinkedIn: Precursor Ventures: https://www.linkedin.com/company/precursor-ventures/ Charles Hudson: https://www.linkedin.com/in/chudson/ David Weisburd: https://www.linkedin.com/in/dweisburd/ – Links: Precursor Ventures: https://precursorvc.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (2:13) Startup experience and its impact on success (4:54) Portfolio construction and startup valuations (7:20) Fundraising challenges for new founders (10:50) Realistic targets and total addressable market (12:04) Investing in ideas or founders: A critical look (13:00) Feedback openness as a success predictor (16:03) Sponsor: Carta (16:49) Pre-seed investment strategies for high returns (18:43) Case study: Carrot Fertility's market opportunity (21:08) Staying informed: Information diet and cultural trends (24:27) Screen Door's role in supporting emerging managers (27:13) Crafting a differentiated investment pitch (28:52) Screen Door's portfolio strategy discussion (31:00) Transitioning from large platforms to independent GPs (35:26) Skill development outside of established firms (38:30) Closing remarks

Oct 29, 2024

Scott Richland, Chief Investment Officer at Caltech sits down with David Weisburd to discuss key portfolio secrets inside Caltech’s $4.5B endowment strategy, the importance of strategy discipline in asset management and how direct investments are chosen behind Caltech's opportunistic bucket. The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) @Caltech (Caltech) – LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Scott Richland: https://www.linkedin.com/in/scott-richland-459a415/ Caltech: https://www.linkedin.com/school/california-institute-of-technology/ – Links: Caltech: https://www.caltech.edu/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (0:54) Portfolio Construction and Allocation (2:19) Team Structure and Investment Strategy (3:05) Advantages of Caltech's Endowment Size (4:21) Taxable vs. Non-Taxable Portfolios (5:55) Evergreen Funds and Their Benefits (7:08) Governance Structure and Investment Process (9:55) Sponsor: Carta (18:33) Macro Trends and Market Opportunities (22:01) Historical Market Downturns: Lessons Learned (22:43) The 2020 Market Drawdown: A Different Beast (23:24) Managing Emotions and Portfolio During Downturns (24:47) Reevaluating Investments: Best Practices (25:35) Human Nature in Investing: Avoiding Common Pitfalls (27:50) Asset Allocation and Direct Investments (30:12) Exploring New Investment Themes (35:25) The Role of Active vs. Passive Management (39:15) The Importance of Reducing Portfolio Volatility (40:59) Balancing Drawdowns and Expected Value (43:35) Leadership and Team Management (47:06) Reflections on a 14-Year Career at Caltech (49:10) Closing remarks

Oct 25, 2024

Kunal Sood, Managing Director at Pantheon sits down with David Weisburd to discuss how US institutional investors can access Indian venture capital and private equity, key trends shaping India's unicorn startup ecosystem for global investors and how to leverage local expertise to navigate asia-pacific private markets. The 10X Capital Podcast now receives more than 170,000 downloads a month. Are you interested in sponsoring an episode? Please email me at David@10xcapital.com . – SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod – X / Twitter: @dweisburd (David Weisburd) – LinkedIn: Pantheon: https://www.linkedin.com/company/pantheon-ventures/ Kunal Sood: https://www.linkedin.com/in/kunal-sood-9582494/ David Weisburd: https://www.linkedin.com/in/dweisburd/ – Links: Pantheon: https://www.pantheon.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com – TIMESTAMPS: (0:00) Episode Preview (1:16) Pantheon's investment focus (2:02) Differentiation of Pantheon and synergies between asset classes (4:16) The importance of relationships in asset management; Defining the mid-market (6:11) Growth equity, market conditions, and revisiting the opportunity set in India (7:04) Sponsor: Carta (9:24) Update on Indian infrastructure and investing in emerging markets (12:18) Opportunities in Japan, Australia, and calibrating strategies for different markets (17:25) Reflections on 11 years at Pantheon and conclusion (18:25) Closing remarks

Oct 22, 2024

David Weisburd speaks with Ryan Serhant, founder and CEO of Serhant, about the explosive growth following the Netflix debut of *Owning Manhattan*. They discuss how the show has transformed the business, increasing market diversification, website traffic, and lead engagement. Ryan also shares his insights on scaling a real estate business, the importance of culture in a distributed workforce, and why he sees Serhant as more than a brokerage—defining it as a sales as a service company with an innovative approach to training and technology. Throughout the conversation, Ryan reflects on his personal journey, the challenges of transitioning from broker to CEO, and the responsibility of building a brand tied to his own name. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co — X / Twitter: @dweisburd (David Weisburd) @Serhant_ (Serhant) @RyanSerhant (Ryan Serhant) — LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Serhant: https://www.linkedin.com/company/serhant/ Ryan Serhant: https://www.linkedin.com/in/ryanserhant/ — Links: Serhant: https://serhant.com/ — Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com — Timestamps: (0:00) Episode Preview (1:16) Metrics and Growth (4:02) Sales Philosophy and Training (12:48) Balancing Roles and Responsibilities (14:34) Challenges and Successes in Real Estate (20:28) Scaling and Team Building (21:22) Understanding Personal User Manuals (21:40) Building the Right Team (22:54) The Importance of Company Culture (23:54) Leveraging Technology and AI (24:12) Becoming a Level Five Leader (25:39) The Power of Personal Branding (28:23) Defining and Building a Brand (31:13) The Thousand Minute Rule (33:05) Overcoming Challenges and Staying Focused (36:33) Final Thoughts and Reflections

Oct 17, 2024

Justinas Milašauskas, Investment Manager at Willgrow sits down with David Weisburd to discuss the risks and rewards of investing in spinouts, top lessons learned from investing in venture and private markets and lessons on investing in emerging managers and navigating fragmented markets. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -– SPONSOR: Carta is the all-in-one suite for private fund operations. Carta’s software-based approach takes fund administration out of the spreadsheet and into the modern age with powerful solutions and intuitive interfaces, all on one platform. Their suite of products and expert services help funds at any stage with up-to-date insights and automated workflows to get them to the next level. Learn more at: https://z.carta.com/10xpod -– X / Twitter: @dweisburd (David Weisburd) @justi_nas (Justinas Milašauskas) -– LinkedIn: Willgrow: https://www.linkedin.com/company/willgrow-uab/ Justinas Milašauskas: https://www.linkedin.com/in/milasauskas/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -– Links: Willgrow: https://willgrow.com/ -– Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -– TIMESTAMPS: (0:00) Episode Preview (1:45) The strategic advantage of operating businesses in portfolio construction (3:19) Investment cadence and the importance of recognizing one's weaknesses (5:25) Evaluating fund managers and the significance of their cap table (6:26) Sponsor: Carta (7:09) Investment strategies for spinouts and emerging managers (9:40) The evolution of emerging managers and ticket sizing lessons (11:12) Transition from public markets to private markets and the current investment climate (12:47) Differentiating as an LP and perspectives on European investment geography (14:24) Insights on investing in emerging managers and advantages of family office capital (15:54) Closing remarks

Oct 15, 2024

Alex Hormozi, entrepreneur and founder of Acquisition.com, joins David Weisburd to share his journey of building a $150 million net worth. He discusses the lessons learned from losing his fortune twice, the importance of controlling revenue streams, strategic risk-taking in business, insights into scaling businesses, and the mindset required for long-term success. Hormozi also explains how he leverages his social media presence to drive deal flow and growth for Acquisition.com. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -— X / Twitter: @dweisburd (David Weisburd) @AlexHormozi (Alex Hormozi) -— LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Hormozi: https://www.linkedin.com/in/alexhormozi/ —- Links: Acquisition: https://www.acquisition.com/ —- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com —- Timestamps (0:00) Episode Preview (0:39) From Management Consultant to Gym Mogul (4:14) The Big Exit and New Ventures (5:09) The Birth of Acquisition.com (6:00) The Power of Social Media and Brand Building (7:16) Investment Strategies and Business Models (17:33) Skill Acquisition and Compounding (27:08) Transactional vs Relational Business Dynamics (31:15) Understanding Opportunity Costs and A-Players (31:51) The Importance of Reinforcement Loops (32:16) Unlocking Discretionary Effort (33:21) Power of Immediate Rewards (34:23) Behavioral Conditioning in Business (35:37) Hiring for Attitude and Intelligence (38:02) The Role of Trauma in Behavior (39:30) The Meta Skill of Learning (40:40) Aligning Incentives and Delegation (41:17) The Founder Mode and Soft Skills (44:32) Operationalizing Culture and Feedback (46:47) Personal Growth and Business Strategy (57:53) Closing remarks

Oct 10, 2024

Francesca Cornelli, Dean at Northwestern University - Kellogg School of Management sits down with David Weisburd to discuss how private equity firms handle CEO turnover, why private equity firms benefit from enlightened disagreement and diverse opinions, and the importance of mentorship in private equity. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -– X / Twitter: @dweisburd (David Weisburd) @KelloggSchool (Northwestern University - Kellogg School of Management) -- LinkedIn: Northwestern University - Kellogg School of Management: https://www.linkedin.com/school/kellogg-school-of-management/ Francesca Cornelli: https://www.linkedin.com/in/francesca-cornelli/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -– Links: Northwestern University - Kellogg School of Management: https://www.kellogg.northwestern.edu/ -– Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (1:13) Path to becoming dean of Kellogg School of Business and defining its culture (4:20) Practical tips for enlightened disagreement and commonality in negotiations (5:47) Impact at London Business School and research in private equity (7:18) Insights on private equity from academic research (11:24) CEO turnover in private equity and case studies (14:36) Industry-academia collaboration and future of business education (17:35) Closing remark

Oct 8, 2024

Mark Shoberg, CIO & Partner at Capital Creek Partners sits down with David Weisburd to discuss the keys to successful institutional investing, how large should an endowment be for optimal returns, and how to build the perfect investment platform for family offices and endowments. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co –- X / Twitter: @dweisburd (David Weisburd) @shoberg (Mark Shoberg) @CapitalCreekTX (Capital Creek Partners) -- LinkedIn: Capital Creek Partners: https://www.linkedin.com/company/capital-creek-partners/ Mark Shoberg: https://www.linkedin.com/in/mark-shoberg/ David Weisburd: https://www.linkedin.com/in/dweisburd/ –- Links: Capital Creek Partners: https://www.capitalcreek.com/ –- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (2:19) Comparing solo and team approaches in investment management (4:18) Venture investments and the allure of spinouts (6:57) Analyzing the pros and cons of anchoring a fund (8:29) Exploring first call alpha and the dynamics of LP relationships (11:29) Balancing economic arrangements between LPs and GPs (14:29) The critical role of partnerships in successful investing (17:06) Strategies for portfolio construction in large endowments (18:15) Delving deeper into market timing and portfolio allocation (21:40) Tailoring real estate investments for tax-exempt entities (24:26) Understanding scale in endowments and its impact (28:38) Introducing Capital Creek Partners and their objectives (30:04) Customized portfolio construction for diverse clients (31:51) The art of sourcing managers and managing legacy relationships (34:57) Closing remarks

Oct 3, 2024

Travis Shore, CIO at University of Illinois Foundation sits down with David Weisburd to discuss how CIOs can adapt to the next big change in time, the critical mistakes made in mastering risk in uncertain markets, and identifying which strategy may save your endowment in the next crisis. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co –- X / Twitter: @dweisburd (David Weisburd) @uofi_foundation (University of Illinois Foundation) -- LinkedIn: University of Illinois Foundation: https://www.linkedin.com/company/universityofillinoisfoundation/ Travis Shore: https://www.linkedin.com/in/travis-shore-cfa-34a05712/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -– Links: University of Illinois Foundation: https://uif.uillinois.edu/ -– Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (1:28) Evolution of University of Illinois endowment and investment philosophy (3:09) Navigating herd behavior and the financial crisis impact on strategy (6:32) Evaluating venture managers and approach to asymmetric risks (8:34) Investor vs. allocator roles and decision-making in teams (11:18) Leadership principles and the value of iterative decision meetings (14:28) Developing institutional knowledge and asset allocation flexibility (17:49) Managing market cycles, risk, and liquidity (22:21) Adapting to market changes and liquidity management strategies (25:36) Governance's impact on endowment performance and board relations (30:36) Addressing bias in growth strategies and investor re-ups (33:11) Transition challenges to a CIO role and asset allocator decision-making (36:41) Closing remarks

Oct 1, 2024

Albert Azout, Managing Partner at Level Ventures sits down with David Weisburd to discuss how to spot unicorn founders early in Venture Capital, what separates great fund managers from the rest, and digging deep into the role of data in unpacking venture fund performance. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co –- X / Twitter: @dweisburd (David Weisburd) @levelvc (Level Ventures) -- LinkedIn: Level Ventures: https://www.linkedin.com/company/level-ventures/ Albert Azout: https://www.linkedin.com/in/albertazout/ David Weisburd: https://www.linkedin.com/in/dweisburd/ –- Links: Level Ventures: https://levelvc.com/ –- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- (0:00) Episode Preview (1:39) Data-driven approach to investing and predicting top-performing managers (3:20) Building social capital and early investment indicators (4:38) Follow-on investments, market timing, and macro factors (6:33) Ownership strategies and discipline in seed investments (8:13) Offensive strategy and value-add for GPs (10:18) Evolution of Level VC's value-add approach (13:16) Flywheel effect in investment networks (14:31) Learnings from Coda Capital and systematic sourcing (16:03) Recognizing great founders and contextual quality of GPs (17:07) Fund size control, co-investing, and portfolio construction (20:28) Collaboration, differentiation, and venture capital insights (22:11) Closing remarks

Sep 26, 2024

Rob Rahbari, Senior Investment Officer and Assistant Treasurer at University of Rochester sits down with David Weisburd to discuss the hidden potential that diverse fund managers offer, the missing ingredient in a successful investment strategy, and what role will diversity, equity, and inclusion play in the future of institutional investing. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co – X / Twitter: @dweisburd (David Weisburd) @UofR (University of Rochester) @RobRahbari (Rob Rahbari) -- LinkedIn: University of Rochester: https://www.linkedin.com/school/university-of-rochester/ Rob Rahbari: https://www.linkedin.com/in/robrahbari/ David Weisburd: https://www.linkedin.com/in/dweisburd/ – Links: University of Rochester: https://www.rochester.edu/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (3:17) Portfolio construction and generalist strategy pros and cons (6:27) Macro factors and their impact on investments (7:37) Real assets, fixed income, and real estate strategies (8:52) Venture portfolio insights and GP relationship management (11:21) Selection criteria for new managers and common pitfalls (13:34) Addressing bias and complexity in investment strategies (15:40) Doug Phillips' unique approach to investing (18:13) Investing at the University of Rochester and IADEI initiative (20:51) Embracing market cycles and diverse managers (22:27) Closing remarks

Sep 24, 2024

Drew Myers, Co-Founder and Managing Partner at CrossLayer Capital sits down with David Weisburd to discuss the key to small funds thriving in pre-seed investing, how time diversification tame crypto volatility, and identifying persistent top quartile crypto funds. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co – X / Twitter: @dweisburd (David Weisburd) -- LinkedIn: CrossLayer Capital: https://www.linkedin.com/company/crosslayer-capital/ Drew Myers: https://www.linkedin.com/in/drew-myers-8764aa22/ David Weisburd: https://www.linkedin.com/in/dweisburd/ – Links: CrossLayer Capital: https://www.crosslayercap.com/ – Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (2:01) Investment strategy: emerging vs. established managers and fund structures (4:20) Identifying alpha in venture and liquid crypto investments, comparison to biotech (6:12) Diligence and alignment in GP-LP relationships; lessons from Makena Capital (10:37) Approach to VC China strategy and parallels in crypto; early market mistakes (16:01) Divergent interests between GPs and LPs; systematic frameworks and investment theses (18:27) Portfolio construction and diversity with idiosyncratic bets (22:12) Pre-seed investments and their impact on return profiles (24:11) Managing risk in volatile markets and differentiating managers (27:26) Persistence of top quartile returns and market cycle impacts (29:30) Advice for institutional LPs entering crypto; regrets and lessons at Crosslayer (33:33) Closing remarks

Sep 19, 2024

Michael Wallach, Vice President of Investment at Levy Family Partners sits down with David Weisburd to discuss the unexpected challenges of working at a family office, how to leverage expert insights to drive high-impact investments, and critical mistakes LPs should always avoid. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co – X / Twitter: @dweisburd (David Weisburd) -- LinkedIn: Michael Wallach: https://www.linkedin.com/in/mike-wallach-8b75291/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (1:51) Investment strategy and differentiation in alpha/beta strategies (3:34) Sourcing and diligence process for direct deals (6:31) Managing portfolio drawdowns and liquidity (8:12) Importance of data room contents for decision making (9:45) Emphasis on reputation in investment decisions (10:53) Asset class allocation and planning (11:47) Key takeaways from experiences at Levy Family Partners (14:21) Pain points for GPs and LPs' leverage points (15:57) Unique advantages and advice for family office operations (17:25) Closing remarks

Sep 17, 2024

Les Baquiran, Founder of Alpine Capital Advisors, sits down with David Weisburd to discuss insights on building LP relationships globally. In addition, they discuss reasons GP’s hire placement agents, benefits of family offices as LPs, and non-traditional structures LPs like to invest in. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -- X / Twitter: @dweisburd (David Weisburd) -- LinkedIn: Les Baquiran: https://www.linkedin.com/in/les-baquiran/ David Weisburd: https://www.linkedin.com/in/dweisburd/ Alpine Capital Advisors: https://www.linkedin.com/company/alpine-capital-associates/ -- LINKS: Alpine Capital Advisors: https://alpineca.com/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- (0:00) Episode Preview (2:22) Lessons learned working at Park Hill (5:31) The life cycle of working with a GP (8:02) Geographical reach and strategy for Latin America (11:54) Raising capital from LPs in different regions (19:12) Common problems LPs face in the current market (21:22) The impact of illiquidity on LP investment strategies (23:34) Examples of bad behavior by GPs (29:27) Building strong LP-GP relationships (33:10) Les Baquiran's LP roundtables and gatherings (36:47) The nuances of being a placement agent (40:25) Closing remarks

Sep 12, 2024

Tony Meadows, Partner at Sinefine sits down with David Weisburd to discuss what initial investment choice could make or break your portfolio, when to dive into early-stage investments, and how strategic timing can turn ordinary investments into extraordinary gains. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co – X / Twitter: @dweisburd (David Weisburd) -- LinkedIn: Tony Meadows: https://www.linkedin.com/in/tonymeadows/ Sinefine: https://www.linkedin.com/company/sinefine/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- LINKS: Sinefine: https://www.sinefine.co/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (2:44) Asset class selection and adverse selection in investments (3:25) Partnering strategies and execution in co-investments (4:35) Governance, decentralization, and GP relationships (6:54) Portfolio construction and strategy within private equity (8:34) Impact of check size on venture capital investments (11:20) Pension funds' role and challenges in venture capital (13:10) Benefits, returns, and market coverage for pension funds (14:06) Building a venture capital portfolio for pension funds (15:51) Multistage funds, emerging managers, and fund twos (18:17) Outsourcing strategies and manager performance data (23:52) Criteria and challenges of investing with Sinefine (26:37) Gender dynamics in sourcing and generating alpha (31:16) Portfolio construction and diversification at Sinefine (35:16) Working with pension funds and compensation structures (39:14) Closing Remarks

Sep 10, 2024

John Gleeson, Founder & General Partner at Success Venture Partners sits down with David Weisburd to discuss the underappreciated secret to Venture Capital success, why operator LP’s outperform, and the math behind portfolio concentration. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co – X / Twitter: @dweisburd (David Weisburd) @JohnGleeson10 (John Gleeson) -- LinkedIn: John Gleeson: https://www.linkedin.com/in/johngleeson10/ Success Venture Partners: https://www.linkedin.com/company/success-venture-partners/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- LINKS: Success Venture Partners: https://successvp.com/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- (0:00) Episode Preview (1:43) Introduction to Success VP and its founding story (3:43) The role of customer success in increasing startup value (6:00) Common mistakes founders make in customer success (7:40) Specialization in customer success roles (8:43) Metrics for balancing sales and customer success efforts (12:28) The importance of empathy and customer feedback in product development (14:54) Why customer success often gets less attention than sales in Silicon Valley (17:54) Success VP fund thesis and investment strategy (20:05) How Success VP gets into top deals and the value of customer success (23:31) Building operator LP capacity and leveraging networks (26:25) Portfolio construction and strategy alignment (29:28) Closing remarks

Sep 5, 2024

Steve McLaughlin, CEO at Financial Technology Partners sits down with David Weisburd to discuss the hidden values and success of top fintech companies, insider perspective on the work-life balance myth, and the powerful face-to-face strategies that elite companies swear by. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co – X / Twitter: @dweisburd (David Weisburd) @FTPartners (Steve McLaughlin) -- LinkedIn: Steve McLaughlin: https://www.linkedin.com/in/stevemclaughlinftpartners/ FT Partners: https://www.linkedin.com/company/financial-technology-partners/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- LINKS: FT Partners: https://ftpartners.com/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- (0:00) Episode preview (3:45) Exclusively focusing on fintech and its challenges (5:16) How FT Partners differentiates from larger banks (11:41) Strategies for incentivizing employees and business growth (17:03) Scaling the organization and preserving culture (19:27) Utilizing data for operational insights and investor storytelling (22:33) Case studies: Revolut's valuation and the role of bankers (27:09) Insights on valuing companies in the fintech space (30:31) Work-life balance and the importance of in-person interactions (33:33) Delegating responsibilities and evolving business focus (36:02) The significance of team and client relationships in fintech (37:16) Closing remarks

Sep 3, 2024

Renee Hanna, Managing Director of Investments at Baylor University sits down with David Weisburd to discuss how Baylor balances allocation between public and private investments, how its private investments are built around returns hurdles, and thoughts on appropriately sizing commitments. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -- X / Twitter: @dweisburd (David Weisburd) -- LinkedIn: Renee Hanna: https://www.linkedin.com/in/renee-hanna-cfa-474749a/ Baylor: https://www.linkedin.com/school/baylor-university/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- LINKS: Baylor University Endowment: https://investments.web.baylor.edu/baylors-university-endowment -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (2:32) Growth and Evolution of Private Investments (4:15) Long-term Sector Focus and Diversification Strategies (7:31) Investment Durations and Venture Fund Selection (9:19) Smaller Venture Funds: Alignment and Incentives (13:13) Venture Capital: Correlation and Diversification (17:02) Manager Assessment: Referencing and Qualitative Factors (18:05) Investing in Spinouts: Benefits and Challenges (19:53) Career Reflections and Starting at Baylor Pre-Crisis (21:57) Beating Ivy League Endowments and Governance Role (24:34) Closing Remarks

Aug 29, 2024

Marius Weber, Founding Partner, and Jocke Martelius, Investment Solutions Manager of Alpha Q Venture Capital sits down with David Weisburd to discuss the comparison between US and European VC markets, strategies for conducting due diligence on emerging VC funds, and the impact of political and economic factors on European VC. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -- X / Twitter: @dweisburd (David Weisburd) @alphaqvc (Alpha Q Venture Capital) -- LinkedIn: Marius Weber: https://www.linkedin.com/in/mariusweberaqvc/ Jocke Martelius: https://www.linkedin.com/in/jocke-martelius-6226035a/ Alpha Q Venture Capital: https://www.linkedin.com/company/aqvc/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- LINKS: Alpha Q Venture Capital: https://www.aqvc.com/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com (0:00) Episode Preview (1:00) Founding and background of AQVC (4:05) Benchmarking, quantitative and qualitative fund evaluation (8:18) Data standardization and capital formation challenges (10:55) Evolution and best practices in fundraising communication (17:27) Maintaining LP relationships (23:59) Insights from diligence of impact funds (26:07) Timeframe and economics for GPs to achieve wealth (28:12) Product differences for high net worth and family office network (32:31) AQVC's value to GPs (35:47) Constraints in the European VC ecosystem (36:51) Closing remarks

Aug 27, 2024

Iyan Unsworth, Vice President of AXA Venture Partners sits down with David Weisburd to discuss about on how a Fund of Funds backed by one of the world's largest insurance companies is revolutionizing the venture capital landscape. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co -- X / Twitter: @dweisburd (David Weisburd) -- LinkedIn: Iyan Unsworth: https://www.linkedin.com/in/iyan-unsworth-1016a896/ AXA Venture Partners: https://www.linkedin.com/company/axavp/ David Weisburd: https://www.linkedin.com/in/dweisburd/ -- LINKS: AXA Venture Partners: https://www.axavp.com/ -- Questions or topics you want us to discuss on The 10X Capital Podcast? Email us at david@10xcapital.com -- TIMESTAMPS: (0:00) Episode Preview (2:25) Key Investment Regions and Geographical Distribution of AVP's Portfolio (4:01) Ideal GP Characteristics and Decrease in Funding for First-Time Funds (7:42) Full-Time Commitment and Historical Performance of Venture Capital (9:02) Principal-Agent Problem and Market Contraction Analysis (11:07) Profiles and Importance of Partnership in Emerging Managers (12:04) Evaluating Teams, Dynamics, and Performance in Venture Capital (15:00) Sensitivity in Performance Discussions and Incentive Reassignment (18:54) Conservative Fund Strategies and Transparency in Track Records (20:05) Complexities of Deal Attribution in Diligence Processes (22:03) Discussion on Secondaries (24:22) Closing Remarks

Aug 22, 2024

Dave Neumann, investor at Molten Ventures, sits down with David Weisburd to discuss fund of funds deployment strategies, how GPs should approach fund size and interesting power law data derived from Molten’s 2,500 underlying portfolio companies. (2:08) Identifying successful managers and the prime years of a GP's career (4:00) Common mistakes of GPs (6:45) The venture capital ecosystem and strategies for success (8:10) Concentrated vs. diversified portfolios in VC (9:43) Molton Ventures' investment strategy and portfolio insights (13:15) Closing remarks and the future of venture capital

Aug 20, 2024

Jamie Biddle (Founding Partner and CEO) & Steve Kim (Partner, Investment Strategy and Risk Management) of Verdis Investment Management, sit down with David Weisburd to discuss how Verdis has managed to invest into 41 unicorns by indexing early-stage venture capital funds, how they came up with the venture index thesis, and the practical considerations of executing on their venture index strategy. They also discuss the purpose of venture in a diversified portfolio, the benefits of QSBS for taxable investors, and avoiding adverse selection in venture capital. (0:00) Episode preview (1:18) Overview of Verdis (3:18) Shifting investment focus and tax considerations in asset selection (4:39) Verdis’s approach to venture capital (5:24) Indexing early-stage venture capital (7:22) Key factors influencing venture capital returns (8:35) The role and tax benefits of venture investments in a portfolio (11:02) Performance of the venture capital index strategy (13:23) Family office dynamics (14:26) Follow & subscribe to the 10X Capital Podcast (14:47) Unicorn capture rate and venture capital power laws (16:32) Comparing generalist and sector-specific funds (18:48) Loss ratios and execution of the venture index strategy (21:10) Developing and reflecting on the venture index thesis (25:45) Key learnings from Verdis & investing as a family office (26:52) Practical constraints on over-allocating to venture (29:39) Closing remarks

Aug 15, 2024

Michael Miller, CIO at Crewcial Partners, sits down with David Weisburd to discuss how nonprofit institutions invest, how they think about portfolio construction, and how they manage liquidity. (0:00) Episode preview (1:14) Overview of Crewcial Partners (2:18) Portfolio breakdown across private assets (3:23) Investing in asset classes when they’re out of favor (4:41) Managing portfolio liquidity (6:42) Optimization of private and public equity exposure (7:33) Role of fixed income in the portfolio (8:44) Diversification strategies of top LPs (10:00) Investing discretionary and nondiscretionary assets (11:12) Embracing inefficiency (13:25) Securing GP allocations (15:22) Manager selection (17:27) Understanding LP psychology and priorities (19:01) Political activism in VC (22:25) Fund distributions and liquidity (24:44) Investment committee dynamics at nonprofits (27:20) Follow & subscribe to the 10X Capital Podcast (27:41) Managing fund investment concentration risks (30:07) Pros & cons of spinouts (31:59) Advantages to investing in funds early (34:45) The importance of non-conformity for high returns (35:55) Closing thoughts

Aug 13, 2024

Mikhail Blancovitch, Co-Founder of Unicorn Strategic Capital, sits down with David Weisburd to discuss strategies for raising capital from different types of LPs, how fund managers can craft a compelling story that resonates with LPs, and sources of growth for alternative asset AUM. (0:00) Episode preview (1:12) Overview of Unicorn Strategic Capital (2:29) Emerging managers & sector specialists (3:59) Portfolio strategies in Latin America (5:24) Comparing portfolio strategies by geography (6:39) Which institutional investors are most innovative (8:55) Reputation dynamics (9:35) Raising $6B from institutional investors (12:32) Follow & subscribe to the 10X Capital Podcast (12:53) Strategies for building LP relationships (14:11) Importance of meeting LPs in person (17:13) Crating and telling compelling stories to LPs (21:29) Sources of growth for alternative asset AUM (23:31) Impact of generational wealth transfer on investments (24:19) Client selection criteria (26:04) Perfecting the fund manager pitch

Aug 8, 2024

Justin Dyer, Chief Investment Officer of AWM Capital, sits down with David Weisburd to discuss how AWM manages investments for professional athletes. Justin details AWM’s adherence to liability-driven portfolio construction, how it invests in venture and unique considerations when investing capital for athletes. (0:00) Introduction to Justin Dyer and AWM Capital (2:25) Wealth management challenges for athletes (4:45) Venture capital investment preferences at AWM Capital (7:07) Fund of funds structure and geographical tilts in venture investments (10:31) Balancing concentration and diversification in venture capital (13:02) Portfolio simulation and flexibility in strategy (17:09) Venture fund diligence and the weight of references (20:52) The role of disruption in venture capital (23:03) Philosophies on money, happiness, and living a flourishing life (27:19) Final thoughts and reflections

Aug 6, 2024

Michael Ashley Schulman, Chief Investment Officer at Running Point Capital, sits down with David Weisburd to discuss Michael’s views on venture capital, manager selection across private asset classes, and risks/benefits of investing in spinout managers. (0:00) Episode Preview (1:31) Overview of Running Point Capital (3:36) Venture Capital Strategy, Challenges, and Metrics (6:08) Managing Capital Calls and Accessing Top VC Funds (10:06) Manager Selection Across Private Asset Classes (14:47) Follow & Subscribe to The 10X Capital Podcast (15:07) Risks and Benefits of Investing in Spinout Managers (17:36) Michael’s Personal Career Insights (20:04) Pre-Liquidity Tax Strategies (20:59) Final Thoughts and Closing Remarks

Aug 2, 2024

Fernando Saiz, Co-Founder of Azet Capital, sits down with David Weisburd to discuss Azet Capital’s fund of funds strategy in venture capital. Fernando shares his diligence process for selecting venture funds, what differentiates the funds Azet invests in vs. the ones they pass on, and Azet’s strategic value-add to venture GPs. (0:00) Episode preview (1:01) Intro to Azet Capital (2:40) Views on fund reserves and diligence process for fund investments (7:44) Evaluating emerging managers (10:40) Tools for benchmarking and selecting funds (13:44) LP relationships, co-investments, and fund of funds (17:12) Educating LPs on venture capital (20:07) Strategic reasons to take capital from LatAm (23:09) Value-add from seed stage managers (24:56) Final thoughts and closing remarks

Jul 30, 2024

Ryan Serhant is the Founder & CEO at SERHANT., a star in the Netflix show “Owning Manhattan” and Bravo show “Million Dollar Listing New York”, and a 3x bestselling author. In this episode, Ryan and David Weisburd discuss SERHANT.’s meteoric rise as a top real estate brokerage in New York City, Ryan’s unique approach to sales, sales training, and branding, and what it’s like for a founder scaling a business in hyper-growth. (0:00) Episode preview (1:50) The impact of new Netflix show “Owning Manhattan” on SERHANT.’s business (4:41) Sales-as-a-Service and sales training (7:44) Common sales mistakes (11:27) Why Ryan started SERHANT. (15:18) Reflecting on “Owning Manhattan” (19:34) Recognizing potential in people (21:54) Strategies for scaling in hyper-growth (26:45) Branding (33:12) The 1000-minute rule (34:52) Follow & subscribe to The 10X Capital Podcast (35:20) Handling setbacks and maintaining perspective (39:38) Business expansion, success, and finding balance (42:20) Closing remarks

Jul 26, 2024

Matt Farrell, Senior Investment Manager at WE Family Offices, sits down with David Weisburd to discuss how families with $50M-$1B+ invest their capital. They also cover balancing risk tolerance and liquidity needs, where alpha is in the market today, and characteristics of an ideal private fund manager. (0:00) Episode preview (0:51) Overview of WE Family Offices (3:05) Typical family office portfolio construction (6:12) Behavioral finance and illiquidity as a feature (9:36) Investment strategies for ultra high net worth families (13:33) Manager selection attributes and importance of transparency (16:22) Diligence process for spin-out managers (18:24) Approach to venture capital as an asset class (21:14) Follow & subscribe to The 10X Capital Podcast (21:34) General guidance on co-invest (23:37) Value-add for venture capital managers (25:07) Hierarchy of the reference process

Jul 23, 2024

Mike Maples, Founding Partner at Floodgate, sits down with David Weisburd to discuss Mike’s new book “Pattern Breakers: Why Some Start-Ups Change the Future”. This is a masterclass on early-stage venture investing. Mike shares his views on identifying ideas and founders that led to his early investments in Lyft, Twitter, and Okta. They also cover how Mike thinks about fundraising from LPs, his learnings from legendary LP David Swensen, and the power and importance of pursuing non-consensus ideas. (0:00) Episode preview (1:23) Introduction to "Pattern Breakers" (2:22) The role of startup capitalists (5:01) The Twitter story and insights on early-stage investing (7:24) The importance of founder future fit (15:33) Product market fit: deciding when to pivot vs. stay the course (21:54) Insights empowering new business models (27:21) Creating movements and the role of passion (32:02) Building relationships with LPs (37:14) Advice for new VCs raising money (39:10) The importance of pursuing non-consensus ideas (43:18) 10X Capital Podcast Newsletter (43:40) Lessons from David Swensen (47:14) Benefits of a compatible partnership (49:06) Circle of competence and competitive advantage in VC (51:41) How to find Mike’s new book "Pattern Breakers"

Jul 18, 2024

Dr. Russell Read, current CIO at 10X Capital, and former CIO at CalPERS, CIO of Alaska Permanent Fund and CIO of the Gulf Investment Corporation sits down with David Weisburd to discuss his extensive career as a premier investment professional. They dive into how large scale pensions allocate to private markets, how those plans structure co-investment programs and design a theoretical allocation strategy. (1:06) Introduction of Dr. Russell Read and his role at CalPERS (1:47) Diversifying investments internationally (3:24) Challenges of allocating to private markets (4:25) Venture capital investment strategies (5:35) Structuring co-investment programs (7:33) Alaska Permanent Fund's success story (11:49) Addressing understaffing in pension funds (13:27) Utilizing external resources effectively (15:03) Economics of co-investment opportunities (17:23) Strategies for new Sovereign Wealth and pension funds (19:40) Impact of fund size on alternative investment success (21:52) Discussing liquidity premium and retirement funding reforms (24:08) 10X Capital's strategic approach to asset management (25:04) Investment objectives variation among organizations (27:35) Re-evaluating the 60/40 investment model

Jul 16, 2024

Justin Pollack, Managing Director at PineBridge Investments, sits down with David Weisburd to discuss PineBridge’s investment thesis. They also breakdown the secondary markets, discuss the structural differences between private equity & public market investing, and ways to analyze spinouts. (1:12) Introduction of Justin Pollack and PineBridge Investments (1:55) Evolution and growth of the private equity market (4:39) Secondary market dynamics (12:02) Differentiating strategies in secondary investing (15:33) Emphasis on downside protection in secondary markets (19:12) Fund of funds and emerging manager strategies (22:29) Adapting private equity strategies to fund growth (26:18) PineBridge's approach to venture capital (27:26) Evaluating spinouts (30:31) Identifying traits of top-performing fund managers (34:05) Closing remarks

Jul 11, 2024

Josh Porter, Co-Founder & General Partner at FirstLook Partners, sits down with David Weisburd to discuss FirstLook’s process for evaluating and selecting emerging managers. They also cover typical terms for co-invest, managing conflicts of interest, and the importance of strong personal relationships in venture capital. (0:00) Episode preview (0:11) FirstLook’s strategy (1:12) Co-investment dynamics (3:06) Typical co-invest terms (4:33) Managing conflicts of interest (6:24) Impact of personal background on investment decisions (9:10) Fostering relationships and trust in venture capital (11:28) Importance of trust and honesty in VC (12:27) Key criteria for selecting managers (15:33) 10X Capital Podcast Newsletter (15:54) Investment diligence and adding value (20:18) Insight into hiring for venture roles (21:34) Lessons learned and time management (23:26) Closing remarks

Jul 9, 2024

Dionne Chingkoe and Samer Yousif of Insight Partners sit down with David Weisburd to discuss Insight’s direct and fund of funds investment strategies. They cover the importance of adding value beyond capital to both founders and emerging managers, the landscape of multi-stage VCs investing in emerging managers, and check size driving fund strategy for GPs. Insight Partners’ 20/20 Vision Capital Fund supports diverse-led, top-tier, early-stage venture funds providing growth and seed capital to companies in the US and abroad. Insight believes that partnering and investing with these GPs is an effective way to drive much needed diversity in the venture capital industry. (0:00) Episode preview (0:56) Insight Partners’ strategy (2:08) Providing value-add and flexible capital (3:48) Samer Yousif's journey to Insight (6:09) Adding value to emerging managers (8:39) How emerging managers differentiate (12:09) Check size driving fund strategy (16:14) Evaluating GP performance (17:38) Closing remarks

Jul 2, 2024

Venus Phillips, Managing Director at Kresge Foundation, sits down with David Weisburd to discuss the Kresge Foundation’s venture strategy. They cover mission-driven investing, opportunities and risks investing in China and India, and building true partnerships between general partners and limited partners. (0:00) Episode preview (0:34) Introduction to Venus Phillips and Kresge Foundation (1:21) Mission-driven investing (2:19) Revitalizing Detroit (3:36) Kresge’s venture strategy (4:04) Opportunities and risks investing in China & India (7:41) Accessing premier venture funds (10:38) Building LP relationships (18:46) Closing remarks

Jun 25, 2024

John Merrill, Partner at GroveStreet sits down with David Weisburd to discuss GroveStreet’s $10.5B SMA model. In addition, they talk about the keys to building long-term SMA relationships, a highly selective set of criteria for managers and reasons why GP’s should prefer rigorous, discerning LPs vs. fast-followers. (0:00) Introduction and background of John Merrill and Grove Street (1:34) Benefits of separately managed accounts (SMAs) for institutional investors (3:39) The problem Grove Street is solving for clients (5:03) Importance of alignment in asset management (6:30) Investment process and criteria for selecting funds (10:13) Client management and characteristics Grove Street looks for in clients (13:25) Benefits of a boutique client model (16:17) Studying under David Swenson and his impact (20:14) The give and take in LP-GP relationships (22:27) Importance of landing an anchor investor for new funds (24:25) Characteristics of a good partnership between LPs and GPs (29:43) Characteristics of a top limited partner (33:17) Global investment insights and local biases (35:09) Final thoughts and closing remarks

Jun 18, 2024

Jamie Rhode sits down with David Weisburd to discuss Screendoor’s strategy of backing emerging managers. In addition, they discuss friction points between LPs and emerging managers, leveraging insights from GPs and LPs in manager selection, and how to diligence a first time fund. (0:00) Episode preview (0:43) Jamie joining Screendoor (2:35) Friction between LPs and emerging managers (4:38) Fragmentation at the seed stage (6:44) Importance of grit and endurance in founders (8:17) Underwriting first time funds (12:39) Expanding beyond first time funds (24:36) 10X Capital Podcast Newsletter (26:17) Portfolio construction as a venture LP (34:35) Final thoughts

Jun 11, 2024

Ben Black, Co-Founder of Akkadian Ventures, sits down with David Weisburd to discuss the RAISE Global Summit, the largest LP/GP conference. This is a masterclass on how venture capital GPs can raise venture capital funds and develop long-term relationships with LPs. David and Ben also delve into what differentiates the top venture funds, the importance of operational excellence in fund entrepreneurship, and prioritizing and managing relationships. (0:00) Episode preview (0:46) The origin and growth of the RAISE Conference (3:40) Fundraising as a continuous relationship-building process (6:28) Effective strategies for GPs to add value to LPs (12:38) What differentiates the top venture funds (14:14) Importance of ecosystem creation in VC (16:02) Common mistakes in fund presentations (28:36) Current state of the secondary market (29:16) 10X Capital Podcast Newsletter (39:31) Prioritizing and managing relationships (41:04) Surviving downturns as a VC (43:01) Closing thoughts from Ben Black

Jun 6, 2024

Alex Edelson, Founder of Slipstream Investors, sits down with David Weisburd to discuss the benefits and tradeoffs of investing in venture capital fund of funds. They also touch on Slipstream’s investment thesis, portfolio construction, and due diligence process. (0:00) Episode preview (2:16) Discussion on portfolio diversification (4:41) Benefits & trade-offs in fund to funds strategy versus single fund investing (7:13) Ideal number of funds for diversification in venture capital (8:46) Life cycle of a diligence process when vetting a manager (12:05) Assessing a fund manager (13:05) Importance of founder references (14:09) Essentials in a fund data room (16:17) Value of transparency with GPs (18:25) Gaining access to oversubscribed funds (19:22) Closing remarks

May 29, 2024

Peter Teneriello, former Senior Portfolio Manager at Texas Municipal Retirement System, sits down with David Weisburd to discuss how TMRS deployed $1B into venture capital. In addition, they discuss institutional allocation pacing models, the importance of aligned investment teams and why investors may allocate to median performing managers. (0:00) Introduction (0:55) Diversification strategies in venture capital investing (3:32) Co-investment practices and fee management (6:58) Importance and role of pacing models (9:39) Incentives for LP Consultants and their impact (12:25) Strategy for setting up a billion-dollar single family office (15:39) Building effective LP / GP relationships (16:22) Career insights and investment philosophy from Peter Teneriello

May 21, 2024

Jeff Smith, Managing Director of Private Investments at the Smithsonian’s endowment, sits down with David Weisburd to discuss the Smithsonian endowment’s advantage in accessing the best managers in venture capital. They also discuss the importance of continually allocating throughout cycles, knowing when to exit, and communicating effectively with LPs. They conclude by covering what Jeff looks for when evaluating new venture managers. (0:00) Episode preview (0:57) How Jeff’s startup experience influences his perspective as an LP in venture capital (1:54) Capital allocation, exit strategies, and market trends in VC (6:12) The Smithsonian endowment’s advantage in venture capital (11:17) Criteria for investing in venture managers (15:28) Smithsonian's venture strategy (19:55) Considerations for investing in first time funds (21:40) The mission of the Smithsonian and closing remarks

May 16, 2024

Muthu Muthiah, CIO of Children’s Healthcare of Atlanta sits down with David Weisburd to discuss how he developed the governance, systems, and team to deploy $2 billion dollars at Inatai Foundation. They also delve into the endowment style investment philosophy, the importance of asset allocation relative to manager selection, and the venture strategy at Children’s Healthcare of Atlanta. (0:00) Episode preview (1:35) Muthu’s path to mission-driven investing (5:36) Building a team of generalist at Children’s Healthcare of Atlanta (8:03) Deploying $2B at Inatai Foundation (11:37) Sponsor: Deel (13:44) Importance of asset allocation strategy (17:28) Navigating the Principal-Agent Problem in asset management (20:41) Investment approach at Children's Healthcare of Atlanta (21:46) CHOA’s venture philosophy and portfolio (26:04) The mission and values of CHOA

May 14, 2024

Erin Harkless Moore, Senior Director of Pivotal Ventures, sits down with David Weisburd to discuss Pivotal Ventures’ $1B mission to drive equality and returns. In addition, they discuss how Pivotal works to close the gender gap, ways to manage teams more thoughtfully and the capability of venture dollars to drive exponential impact. (1:06) Erin Harkless Moore's Background and Pivotal Ventures' Strategy (5:26) Balancing Collaboration and Consensus in Decision-making (8:26) Common Mistakes made by Venture Asset Managers (10:28) How Mission-oriented Organizations View Performance (14:31) Sponsor: Deel (16:05) Refining the Investment Strategy at Pivotal Ventures (23:08) Discussion on VC Track Record (24:36) Value of Unexpected References in Due Diligence (32:48) Aligning Personal Values with Career Goals

May 9, 2024

Hunter Horsley, CEO of Bitwise Asset Management, sits down with David Weisburd to discuss the institutional investment case for Bitcoin and digital assets. In addition, they discuss the diversification benefits of digital assets for portfolio construction, bull arguments for Bitcoin, and expanding the GDP of the internet through increasing use cases of public blockchains. (0:00) Episode Preview and Overview of Bitwise (5:29) Discussion on the Bitwise Bitcoin ETF (10:53) Exploration of Institutional Investment in Crypto (18:49) Sponsor: Deel (20:53) Use Cases of Public Blockchains (25:52) The Role and Impact of Developers in Crypto (30:40) 10X Capital Podcast Newsletter (31:06) Future of Bitwise and its Role in the Digital Asset Space

May 7, 2024

Eric Satz, CEO of Alto, sits down with David Weisburd to discuss how startups can access $13 trillion in retirement capital. In addition, they discuss why to invest in alternative assets via retirement capital, strategies for personal venture portfolio construction and how cryptocurrency fits into alternative asset investing. (1:03) Guest introduction: Eric Satz and Alto (2:45) Role and user experience of Alto in self-directed investing (5:15) The problem with alternative IRA investments and Alto's solution (7:16) Alto's platform, integrations and partnerships (10:25) Discussion on investable assets in the US and the evolution of Alto's thesis (13:15) The need for democratization in investing (17:42) Discussion on Peter Thiel's Roth IRA story (20:17) Sponsor: Deel (21:00) Suggestions for portfolio diversification and investing in crypto (25:37) The psychological struggle of trading and advantages of alternative asset investments (30:06) The future of Alto (32:07) Importance of timing, luck and people in startup success and closing remarks

May 2, 2024

Chris Rizik, CEO of Renaissance Venture Capital sits down with David Weisburd to discuss Renaissance’s unique approach to venture. In addition, they discuss how large corporations participate in venture, when to admit a loss vs. doubling down and signals of a strong fund manager. (0:44) Introduction of guest Chris Rizik and overview of Renaissance Venture Capital (2:36) The Innovator's Dilemma and evolution of large tech companies (4:18) Challenges and opportunities of promoting startups in the Midwest (6:06) The growth of unicorns in the Midwest and the importance of consistent returns (9:36) Importance of growth when investing in fund managers (10:21) Sponsor: Deel (12:19) Lessons learned and mistakes made in venture capital (19:11) Chris Rizik discusses the ideal fund to invest in (21:15) Importance of patience and networking in investing (24:48) Potential of underserved geographies for startup communities

Apr 30, 2024

Trish DiGirolomo, investment manager at Babson College sits down with David Weisburd to discuss scaling Babson College’s endowment via disciplined strategy and process. In addition, they discuss the advantages of patience and a focus on cash on cash returns, criteria for manager selection, and leveraging experienced alumni in the investment process. (0:00) Trish DiGirolomo discusses the investment strategy and process at Babson Endowment (4:57) Role of private equity in Babson's portfolio and philosophy on holding positions post IPO (10:34) Importance of patience, conviction, and timing in venture capital investments (13:08) The role of secondaries market in venture capital (16:11) Leveraging relationships and the value Babson brings to a fund (20:16) The structure of Babson's investment office and criteria for assessing potential managers (26:27) Sponsor: Deel (28:31) Diversified alpha and return thresholds (33:07) Importance of conviction and thesis in strategy (41:59) Dealing with difficult personalities in GPs

Apr 25, 2024

Erik Iverson and Mike Partsch of the Wisconsin Alumni Research Foundation (WARF) sit down with David Weisburd to discuss how WARF supports innovation while driving financial returns. In addition, they discuss the case for investing in life sciences, how inventions turn into portfolio companies and the importance of maintaining relationships through market cycles. (0:00) Introduction and overview of Wharf (1:45) Investment strategy and portfolio construction (4:08) Correlation between industry hype and venture returns (7:00) Sponsor: Deel (8:40) Process of spinning out companies from the University (12:45) Sourcing and developing new relationships in venture capital (15:06) Discussion on unfair practices in valuation and liquidation (16:38) Challenges of venture capital (17:04) The mission and highlights of WARF

Apr 23, 2024

Michael Downing sits down with David Weisburd to discuss emerging manager venture funds, the MDSV Capital Extension Program, and the effect of market conditions on fundraising. They also discuss the role of MDSV in the venture capital landscape, portfolio construction, LP expectations, and Michael’s background as an entrepreneur and investor. The conversation wraps up with a discussion on the importance of not overlooking emerging managers as a key part of the venture ecosystem. (0:00) Episode preview and discussion on outliers in emerging manager funds (6:00) Overview of the MDSV Capital Extension Program (9:45) Sponsor: Deel (13:13) Impact of market conditions on fundraising (16:37) Role of MDSV in the venture capital landscape (20:27) Portfolio construction and expectations of LPs (23:31) Michael Downing's background as an entrepreneur and investor (25:32) 10X Capital Podcast Newsletter (26:27) The importance of not overlooking emerging managers in venture capital (27:38) Please visit & subscribe to the 10X Capital Podcast YouTube channel

Apr 16, 2024

Jordan Nel sits down with David Weisburd to discuss how to spot winning venture funds. In addition, they discuss portfolio construction and concentration, the scalability of venture funds and difficult conversations with GPs. (0:00) Introduction and Overview of the Episode (1:12) Genesis of Jordan Nel's Fund and Current Strategy (3:21) Evaluating Founders and the Importance of their Background (6:38) Importance of Urgency in Management and Entrepreneurship (8:17) Portfolio Construction and Concentration (10:47) Sponsor: Deel HR and Payroll Platform (11:13) Why Small Funds Outperform Large Funds (14:10) Understanding the LP Base and LP Demands (17:32) Providing Value-Add as an LP and Tackling Challenging Conversations with GPs (21:07) Interacting in the LP Ecosystem and Strategy for Follow-On Investments (24:54) The Role of Judgment and Diligence in Investment Decisions (28:52) Insider Investing and Differentiating Between Saving an Investment and Doubling on an Asymmetric Edge (30:51) Conclusion and Invitation to Subscribe to the 10X Capital Podcast on YouTube

Apr 11, 2024

Claude Grunitzky sits down with David Weisburd to discuss Claude's journey as a venture-backed founder, securing an investment from Goldman Sachs, the importance of mentorship in venture capital, and Claude’s approach to spotting potential. They also delve into the creation of The Equity Alliance, the firm’s investment process, and their involvement with Serena Ventures. (0:00) Episode Preview (0:44) Journey to starting Trace TV (2:16) Sponsor: Deel (5:26) Securing an investment from Goldman Sachs (7:52) Founding of The Equity Alliance (11:39) 10X Capital Podcast Newsletter (12:03) Mentorship in venture capital (14:23) Claude's approach to spotting potential (21:14) Importance of relationships and strategy (22:21) Investing in Serena Ventures and the investment process at Equity Alliance (27:05) Claude's personal mission (27:49) Please visit & subscribe to the 10X Capital Podcast YouTube channel

Apr 9, 2024

Eric Poirier sits down with David Weisburd to discuss insights from the platform’s investment data on nearly $6 trillion in assets. They also talk about the top performing asset classes, the future of asset management and how to manage talent to scale a business. (0:00) Introduction and Eric Poirier's journey to becoming the CEO of Addepar (4:56) Insight into Addepar's impressive dataset and its sophisticated capabilities (8:22) Venture Capital as the best performing asset class and Addepar's business model (11:10) Eric Poirier's vision for Addepar in 5, 10, 20 years and the building of its infrastructure (14:32) Building a team and setting company culture at Addepar (17:25) Comparing Eric's experiences at Palantir and Addepar (18:22) Sponsor: Deel (19:08) Employee attrition and client-centric approach at Addepar (20:07) Importance of showing up as a CEO and the impact of a CEO's decisions (22:09) The role of empathy and compassion in leadership and its impact on Addepar's growth (23:40) Closing remarks with Eric Poirier and introduction of the 10X Capital Podcast Newsletter

Apr 4, 2024

Robert Rodriguez sits down with David Weisburd to discuss the role of creativity in filmmaking, cost-effective film production, and the influence of technology and AI in film. The discussion also covers Rodriguez's film fund, strategies for creating profitable movies, and the importance of living a creative life. (0:00) Episode Preview (1:41) Strategy for producing cost-effective films (5:19) Bootstrapping in film (10:05) Sponsor: Deel (10:20) Adoption and impact of technology in film production (13:29) AI in film production (16:18) The Robert Rodriguez Experience (20:10) The power of creativity (22:47) The Film Fund (29:07) Creating profitable movies (30:03) The importance of living a creative life (32:04) Please visit & subscribe to the 10X Capital Podcast YouTube channel

Apr 2, 2024

Eric Sippel sits down with David Weisburd to discuss criteria used to identify top quartile managers, GP follow-on strategies and how LP value-add can increase alpha. (0:00) Introduction and Welcome Eric Sippel (1:16) Eric Sippel's Investment Strategy and Check Sizes (4:04) Providing Value and Building Relationships Before Investing (5:20) Sponsor (Deel) (7:23) Time Spent with a GP Before Committing (10:36) Investing in Different Tiers of Companies (12:00) Importance of Sticking to Strategy (15:04) Patterns Among Highest Performing Funds (17:26) Sourcing Mechanisms and Networking Strategies for LPs (21:23) Building Relationships in the Venture Capital Space (24:36) Final Words from Eric Sippel

Mar 28, 2024

Frank Tanner sits down with David Weisburd to discuss Anthony 'Pomp' Pompliano's role at Morgan Creek as well as the company's origin, growth, and guiding principles. They dive into understanding power laws in venture capital, early-stage investing, and Morgan Creek's manager selection process. (0:00) Episode Preview (0:49) Anthony 'Pomp' Pompliano's Connection to Morgan Creek (2:13) Origin and Growth of Morgan Creek (5:04) Sponsor: Deel (6:50) Background on Mark Yusko & Morgan Creek's Guiding Principles (9:00) Understanding Power Laws in Venture Capital (13:27) Portfolio Construction and Early-Stage Investing (16:28) 10X Capital Podcast Newsletter (17:00) Morgan Creek's Manager Selection Process (20:24) Providing Value and Accessing Top Funds (22:33) Please Visit & Subscribe to the 10X Capital Podcast YouTube Channel

Mar 26, 2024

Harisha Haigh sits down with David Weisburd to discuss the art of building and managing relationships in venture capital. They delve deep into Northwestern's venture and crypto strategies, dissect common mistakes made by top VCs, and evaluate the ideal characteristics of a venture manager. They also discuss the leading indicators of success of a venture fund, investment decision-making processes within VC firms, and how to approach underwriting the track record of a spin-out manager. (0:00) Episode Preview (2:30) Building and managing relationships in venture capital (4:29) Northwestern's crypto strategy (7:45) A deep dive into Northwestern's venture strategy (11:41) Common mistakes made by top VCs (14:51) Venture portfolio valuations and the secondary market (17:28) Evaluating the success of a venture fund (18:55) Sponsor: Deel (20:19) Investment decision making within VC firms (22:43) Underwriting track record for spin-out managers (25:09) 10X Capital Podcast Newsletter

Mar 21, 2024

Hunter Somerville sits down with David Weisburd to discuss StepStone's unique approach to venture capital, their transition to leading deals, and their full life cycle approach to investing. They delve into accessing companies in the secondary market, identifying potential in emerging managers, and StepStone's value-add to funds and companies. (0:00) Episode Preview (1:52) The strategy behind StepStone's diverse approach to venture (5:13) The transition from passive co-investing to leading (8:26) The strategy of being a full life cycle investor (10:13) Different ways to access companies in the secondary market (15:10) What to look for in emerging managers (19:20) Sponsor: Deel (21:36) StepStone's value-add (23:47) Current market trends (25:02) Interview wrap-up: David Weisburd and Hunter Somerville discuss StepStone (25:38) 10X Capital Podcast Newsletter

Mar 19, 2024

Ron Diamond sits down with David Weisburd to discuss how $1B+ family offices generate alpha in venture capital, the #1 way family offices can avoid adverse selection, how family offices may disrupt private equity, and venture capital vs. private equity. (0:00) Introduction and Discussion on Private Equity and Venture Capital with Ron Diamond (2:21) Overview of Ron Diamond's Venture Fund Investment Process (4:28) How Family Offices are Disrupting Private Equity (7:32) Advantages and Structures of Family Offices in Venture Space (10:01) Concept of a Minimum Viable Family Office (12:59) Sponsor: Deal (14:12) Motivation Behind Conference Speakers and Concept of Giving Back (18:11) Insights into Ron Diamond's Business and Personal Life (20:33) Ron Diamond's Five Most Important Things in Life (21:07) Invitation to Subscribe to the 10X Capital Podcast Newsletter

Mar 14, 2024

Mark Gerson sits down with David Weisburd to discuss founding GLG and growing it into a $600 million revenue powerhouse, 3i and its community of world-class private investors and the importance of an ROI driven approach to non-profit work. (0:00) Introduction and discussion on building a marketplace business (1:29) Founding and growth of GLG (5:58) Importance of transactions and relationships in business (7:49) Role of Africa Mission Healthcare (10:24) The importance of an ROI driven approach to non-profit work (17:25) Sponsor: Deel (18:08) Impact and habit of giving (20:44) Business model of United Hatzalah and concept of habitual giving (22:18) Importance of relationships and advice on living a fulfilling life (24:29) Reflection on the interview with Mark Gerson and announcement of the 10X Capital Podcast Newsletter

Mar 12, 2024

David York, Founder of Top Tier Capital Partners, sits down with David Weisburd to discuss Top Tier Capital's history of success, the value of partnership, and generational transfers. They also delve into their experiences with Limited Partners, the risks and rewards of backing GP "spinouts", and share reflections on David York’s 30 years in the VC industry. (0:00) Episode Preview (3:06) How Top Tier Capital Has Grown AUM (5:25) Improving Economic Development and Tech Growth in Europe (10:06) Effective Partnership Approach and Generational Transfers (13:54) Navigating Relationships with Limited Partners (14:38) Sponsor: Deel (16:38) Risks and Value of Backing Venture Capital "Spinouts" (21:29) Reflections on Being in Venture Capital Since 1993 (24:13) The Future of Tech and Top Tier's Outlook (25:23) 10X Capital Podcast Newsletter

Mar 7, 2024

Roy Swan and Christine Looney from Ford Foundation's Mission Investments team sit down with David Weisburd to discuss patriotic capitalism, their investment themes, and strategy impact. They discuss balancing financial return with social impact, Swan's advisory role with the Church of England, and the importance of fairness and morality in capitalism. (0:00) Episode Preview - Patriotic Capitalism (1:09) Ford Foundation's Mission Investments team and their investment themes (3:54) Impact and returns of Ford Foundation's strategy (7:42) Sponsor: Deel (8:25) Ford Foundation's goals and balancing financial return and social impact (11:25) Roy Swan's role advising the Church of England and discussion on shared prosperity (15:07) Importance of fairness and morality in capitalism (15:40) Message to listeners from Roy and Christine (16:50) 10X Capital Podcast Newsletter (17:13) Recruiting and roles at Ford Foundation

Mar 5, 2024

Sean Warrington of Gresham Partners sits down with David Weisburd and Erik Torenberg to discuss his investment decision-making process, extreme risk factors in diligence, and his approach to investing in emerging managers. The episode also covers reference processes in fund management, the impact of social proof and momentum in investing, and best practices of cutting-edge family offices. (0:00) Episode Preview (0:41) Introduction and Sean Warrington's journey to Gresham Partners (1:27) Sean Warrington discusses the strategy of Founders Fund (4:06) Sean Warrington's process of making investment decisions (5:47) Discussion on extreme risk factors in diligence (9:04) Sponsor: Deel (9:49) Sean Warrington's approach to investing in emerging managers (13:02) Process for references in fund management (15:06) 10X Capital Podcast Newsletter (17:03) Impact of social proof and momentum in investing (18:22) Best practices of cutting-edge family offices

Feb 29, 2024

Atul Rustgi sits down with David Weisburd to discuss his role as a GP & LP, the paradoxes of selling and building relationships in VC, and the strategy of focusing on funds under $100 million. They also delve into including biotech as a diversification strategy, the importance of blockchain and crypto exposure, family office investments, and the challenges and rewards of raising a fund during a market downturn. (0:00) Episode Preview (0:45) Introduction of Guest - Atul Rustgi: Role and Responsibilities as a GP (3:30) Discussion on the Paradoxes of Selling and Relationship Building in VC (6:03) Strategy Behind Focusing on Funds Under $100 Million and the Math Behind Ownership (11:14) Biotech as a Means to Diversify and Generate Alpha in VC (16:01) Sponsor: Deel (16:43) Blockchain and Crypto: The Importance of Exposure (21:03) Family Office Direct Investments and The Value of Reference Calls (24:57) Raising a Fund During a Market Downturn: Challenges and Rewards (26:17) 10X Capital Podcast Newsletter (26:42) Lessons Learned from a Long Career in Venture Capital by Atul Rustgi

Feb 27, 2024

Lindel Eakman sits down with David Weisburd to discuss his journey in the industry, the sustainability of a GP style, and the importance of culture fit in venture capital. They delve into generational transitions, conflicts in venture firms, and the persistence of LP returns, as well as Lindel’s investment strategies, views on search funds, and thoughts on seeding platform opportunities. (0:00) Introduction and Lindel Eakman's journey in the industry (6:58) Sustainability of a GP style and the role of culture fit in venture capital (12:00) Generational transitions and conflicts in venture capital firms (17:59) Sponsor: Deel, HR and Payroll platform for global work (18:31) Persistence of LP returns and backing Michael Kim and Cendana (22:36) Personal investment strategies and views on search funds (25:04) 10X Capital Podcast Newsletter (25:11) Benchmarking and financial conservatism in venture capital investing (30:03) Seeding platform opportunities in the VC, LP space (31:15) Investment opportunities in secondaries (34:06) The future for Lindel Eakman and the role of founders in venture capital

Feb 22, 2024

Chris Prestigiacomo, Portfolio Manager at the State of Wisconsin Investment Board (SWIB) sits down with David Weisburd and Erik Torenberg to discuss his journey, the role of private debt in venture portfolio management, and the Wisconsin Investment Board's asset allocation strategy. They delve into backing criteria for General Partners, venture capital's role in SWIB's strategy, and the unique governance structure of Wisconsin's retirement system. (0:00) Introduction and Chris Prestigiacomo's journey to becoming a portfolio manager (1:48) The role of private debt portfolio in venture portfolio management (3:02) The State of Wisconsin Investment Board's asset allocation strategy and venture returns (4:08) Criteria for backing General Partners and types of managers backed (7:27) Sponsor: Deal, an all-in-1 HR and payroll platform (8:03) Venture capital's role in SWIB's asset management and strategy for direct investments (10:19) The unique governance structure of the Wisconsin retirement system and SWIB (12:09) Chris Prestigiacomo's philosophy on portfolio management and re-up decisions (15:03) Erik Torenberg's perspective on VCs backing founders and portfolio construction (15:57) Sponsor mention: Carrie Alabs (16:19) Assessing managers through referencing and building relationships over time (17:30) Final thoughts from Chris Prestigiacomo on dynamic investing and openness to new opportunities

Feb 20, 2024

Sasha Pieterse of Pretty Little Liars and now Co-Founder and CEO of Hippie Water, sits down with David Weisburd to discuss her journey from child actor to entrepreneur, her experiences working with renowned actors, and her new venture backed startup. They delve into the cannabis beverage market, Hippie Water's D2C strategy, and the importance of authentic representation. (0:00) Introduction and welcome with David Weisburd and Sasha Pieterse (2:45) Sasha Pieterse's journey from acting to entrepreneurship (5:43) Introduction and discussion about Hippie Water (9:41) Sponsor: Deel (10:06) Insights on going into business with family or friends (13:14) Spreading awareness and the new way to consume cannabis with Hippie Water (16:24) Exploring distribution strategies for Hippie Water (20:37) Challenges and opportunities of being a female founder in the cannabis industry (21:12) 10X Capital Newsletter (23:31) Breaking barriers and translating acting skills into entrepreneurship (26:21) Importance of genuine product endorsement and network utilization for business development (28:21) Future of cannabis beverages and Sasha's vision for Hippie Water (30:47) Importance of healthier alternatives and desired legacy for Sasha's son

Feb 15, 2024

Katie Riester, Managing Director at Felicis sits down with David Weisburd to discuss venture capital fund strategies, building relationships with GPs, and the math behind venture capital. They discuss the importance of clear communication with LPs, common red flags, and advice for new LPs. (0:00) Episode Preview (1:06) Katie Riester's unique blend of experiences and origin story (3:53) Discussion on Felicis’ fund of funds (7:18) Evolution of GP relationships - Katie Riester's perspective (8:00) 10X Capital Podcast Newsletter (9:45) Understanding the complexities of managing a fund (14:05) Sponsor: Deel (16:17) The role of LPs in providing insights into the venture capital space (20:24) Bad behavior seen from LPs (23:19) Best practices for GPs communicating with LPs (26:40) Advice for LPs making their first venture capital investments (29:11) Katie Riester shares what drives her in the venture capital ecosystem

Feb 13, 2024

Michael Sidgmore of Broadhaven sits down with David Weisburd to talk about the growth of the wealth channel and its link to private equity. They discuss iCapital's role in the venture world, access issues for family offices, and the strategies of Broadhaven Ventures. The conversation also covers GP stakes, the future of emerging managers, and the potential of IRA funds for venture capital and real estate investments. (0:00) Introduction and background of Michael Sidgmore (3:05) Examination of the wealth channel and its growth (7:16) Role of private equity in the growth of the independent channel (12:05) Role of II Capital in the venture world and relevance to smaller funds (15:30) Access issue in the venture space and proposition for family offices (17:41) Introduction of Broadhaven Ventures and its investment strategy (21:38) GP stakes, benefits for GPs and trends in asset management (24:55) Future of emerging managers in venture capital (28:57) Potential of unlocking trillions in IRA funds for venture capital and real estate (30:48) Reimagining portfolio construction with private and public markets (32:01) Closing remarks and introduction of the 10X Capital Podcast newsletter

Feb 8, 2024

Dave McClure sits down with David Weisburd to discuss his journey into venture capital, including luck, his investment strategy, and the challenges he faced breaking into the industry. He provides an analysis on his two 40x+ funds, 500 Startups, and the misalignment between LPs and GPs. (0:00) Introduction to Dave McClure and his journey in Silicon Valley (4:00) McClure's entry into venture capital and creation of the Start-Up Metrics for Pirates model (12:14) Dave McClure's investment strategy and the role of luck in venture capital (20:09) McClure's struggle to break into the venture capital field and his rejection from Sequoia (23:10) The premise and analysis of 500 Startups' investment outcomes (27:34) The misalignment between LPs and GPs and the math behind achieving breakout success (33:07) The aggressive investment pace and international strategy of 500 Startups (37:16) The concept of practical venture capital and the challenges of long hold times (44:29) The competition in the secondary market and the trade-off between unrealized TVPI and realized DPI (47:12) Wrap up and introduction of the 10X Capital Podcast Newsletter

Feb 6, 2024

Guy Perelmuter of GRIDS Capital sits down with David Weisburd to discuss his investment strategy, the unique portfolio construction of deep tech companies, and the potential of DeepTech. They delve into the paradox of AI, its impacts on the labor force, and discuss the ideal GP relationship and transparency. They also touch on LP value-add and the importance of overcommunication. (0:00) Introduction and Guy Perelmuter's investment strategy (4:06) Introduction of GRIDS and what sets it apart (6:33) Discussion on DeepTech and its potential (13:20) Paradox of AI and its impacts on labor force and job market (20:00) Unique portfolio construction of deep tech companies (23:13) Strategy for consistent returns and downside protection in investing (27:03) Ideal GP relationship and transparency (33:55) LP value-add and overcommunication (39:18) Wrap up and Guy Perelmuter's multi-talented, likable GP image (40:43) 10X Capital Podcast Newsletter

Feb 1, 2024

Carrie Thome and Grady Buchanan of NVNG sit down with David capital to talk about the importance of startups, and portfolio construction. They discuss the competitive landscape for talent, their transition to venture capital, and strategies at Wharf. The conversation also covers strategic investment, liquidity management, and the inception and building of NVNG Investment Partners. The episode wraps up with insights on raising a fund during COVID, network building, assessing emerging manager quality, and the value of fund of funds. (0:00) Introduction and Background of Carrie Thome and Grady Buchanan (5:26) Importance of Startups, Mentorship, and Portfolio Construction (9:35) Competition for Talent and Passion for Building Portfolios (12:40) Transition to Venture Capital and Strategies at WARF (17:10) Strategic Investment and Liquidity Management in Venture Capital (25:35) Inception and Building of NVNG Investment Partners (28:37) Raising a Fund during COVID and Network Building (31:08) Portfolio Construction and Assessing Emerging Manager Quality (34:54) Value of Fund of Funds and Closing Remarks

Jan 30, 2024

Errik Anderson sits down with David Weisburd to discuss Pro-noia, the potential of the biotech industry, and the 82VS Seed Fund investment approach. They discuss practicing Pro-noia, the value of building a portfolio of relationships, and the idea of a forever company. (0:00) Introduction to Errik Anderson and his concept of Pro Noya (10:22) The potential scale of platform building in the biotech industry (20:22) Leading with work and following with capital - the approach at 82VS Seed Fund (28:13) Practicing Pro Noya: Cultivating optimism and generosity (33:35) Building a portfolio of relationships and the compounding value (40:01) Errik Anderson on involving his family in his work (46:00) Errik Anderson's management style: micro-managing or detailed involvement? (54:09) Errik Anderson explains the concept of a forever company (57:00) Collaborating with big pharmaceutical companies like Pfizer (1:00:56) Launch of the Tenex Capital Podcast newsletter powered by Carrie Alabs

Jan 26, 2024

Anubhav Srivastava, CEO of Tactyc, sits down with David Weisburd to discuss iterative portfolio construction, portfolio size impact, fund recycling and check size, reserve strategies, and follow-on investments. They also explore the future of Tactyc and lessons from clients. (0:00) Introduction and discussion on typical reserve ratios for pre-seed and seed funds (1:03) Anubhav Srivastava's journey to founding Tactic and its pivot into a forecasting and planning software for VCs (3:41) Overview of Tactic user base and its global reach (5:27) Tactic's role in fund management, optimization, and as a fundraising tool (9:04) Significance of portfolio size and tracking of actual vs projected performance in funds with Tactic (12:24) Strategies for navigating fund recycling and target ownership (14:43) Impact of graduation rates on reserve strategies and the importance of number of investments in portfolio construction (16:09) Discussion on typical reserve ratios for pre-seed and seed funds (19:10) Considerations for deploying into breakouts and thinking quantitatively about follow-on investments (20:52) Future of Tactic and best practices for funds considering secondaries (23:10) Introduction to the Tenex Capital Podcast newsletter powered by Carrie Labs

Jan 23, 2024

Ben Gallacher sits down with David Weisburd to discuss venture capital, his journey as an LP, and the challenges emerging managers face. They discuss check sizes, diligence processes, and the impact of a GP leaving during an investment life cycle. They also cover the role of CFO/COO in GP operations and the importance of supporting emerging managers. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co (0:00) Introduction and Ben Gallacher's perspective on venture capital (1:00) Journey and lessons from being an LP in the venture and emerging manager space (3:26) Spinouts in venture capital vs private equity and challenges for emerging managers (9:35) The dilemma of varying check sizes for LPs and decision-making process for follow-on funds (13:12) Ben Gallacher's diligence process and approach to founder questions (14:13) Sponsor: Bedav Insurance Group (17:11) Use of other LPs in the diligence process and building relationships (21:24) Choosing emerging managers, sources of alpha, and ideological lines in venture capital (27:14) Follow-on strategy, role of honesty and selectivity, and shifting reserve strategies (33:40) Fund size in venture capital, stewardship of capital, and the role of CFO/COO in GP operations (38:38) Impact of a GP leaving during an investment life cycle and value of GPs leaving to start a company (41:07) Closing remarks, supporting emerging managers, and introduction to Cannonball Capital (41:53) Introduction to the 10X Capital Podcast newsletter by Carriea Labs

Jan 18, 2024

Aakar Vachhani sits down with David Weisburd to discuss the role of data in venture capital, Fairview's unique structure, and their co-investment program. They also delve into the discipline of making investment decisions, the advantages of a fund of funds, and the importance of team cohesion in VC firms. Vachhani also shares best practices for data rooms and advice for LPs as Fairview celebrates its 30th anniversary. The 10X Capital Podcast is part of the Turpentine podcast network. Learn more: turpentine.co (0:00) Introduction and Aakar Vachhani's background (1:43) The role of data in decision making and returns in venture capital (6:55) Fairview's history, unique structure, and co-investment program (15:58) The discipline and strategy in making investment decisions (20:18) The advantages and arguments for a fund of funds (26:50) Qualitative factors and enduring culture in venture capital firms (33:30) Re-investing in tenured firms and the diligence process for emerging managers (39:44) The importance of team cohesion and the ability to adapt in VC firms (42:41) Best practices for data rooms and creating an ideal emerging manager deck (53:23) Continual engagement with GPs and adjusting investment strategies for potential risk (58:17) Celebrating Fairview's 30th anniversary and advice for LPs (1:00:04) Launch of the 10X Capital Podcast Newsletter

Jan 16, 2024

Charmel Maynard, CIO of University of Miami, sits down with David Weisburd to discuss asset allocation, diversification strategies, and the process of assessing venture funds. The conversation also covers unique VC challenges, tracking emerging managers, and the importance of diversity in asset management. The Limited Partner podcast is part of the Turpentine podcast network. Learn more: turpentine.co (0:00) Introduction and Charmel's role as CIO of University of Miami (5:11) Asset allocation and diversification strategies in investment (8:37) Charmel's first venture into venture capital and building relationships (15:05) Assessing venture funds: DPI, TVPI, and diligence process (20:06) Unique challenges and strategy considerations in venture capital (26:09) Tracking emerging managers and the myth of proprietary deal flow (28:10) Charmel's journey to CIO and the importance of diversity in asset management (34:23) Sponsor: The Limited Partner Podcast newsletter

Jan 11, 2024

Ashby Monk, Executive and Research Director at Stanford sits down with David Weisburd to discuss the role and operation of asset owners like pension funds, endowments, and more. They delve into compensation in these fields, the state of pension funds in the US, and their impact on private equity. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. The Limited Partner podcast is part of the Turpentine podcast network. Learn more: turpentine.co (0:00) Introduction and discussion about billionaires in the alternative industry (2:05) Conversation about studying a $140,000,000,000,000 asset class (8:23) Conversation about compensation in pension funds and asset management (15:50) Sponsor: Bedav Insurance Group (16:16) Differences in pension plan strategies and asset allocation (24:56) The role of unions in pension plans (29:10) The journey of starting a private equity fund (37:11) Celebrating entrepreneurial individuals in institutions and foundations (40:43) Advice for venture capital managers starting out: From angel investing to fund 1 (50:08) David Weisburd asking about Ashby's tool sold to Atapar (55:57) David Weisburd thanking Dr. Russell Reed and Ashby Monk for their participation in the podcast

Jan 9, 2024

David Friedberg sits down with David Weisburd to discuss the role of concentrated capital, venture capital's future, and the impact of capital saturation. Friedberg shares his experience joining Ohalo, the evolution of investment strategy, and the transition from VC to operator. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. The Limited Partner podcast is part of the Turpentine podcast network. Learn more: turpentine.co (0:00) Introduction and discussion on venture performance vs public companies (1:18) Guest Introduction: David Friedberg's early career and lessons learned (7:59) The power of big thinking in companies like Google and Tesla (14:08) Challenges and counter incentives in venture capital (16:39) Sponsor: Bedav Insurance Group (21:27) The power law of returns and talent concentration in successful companies (28:15) The changing definition of 'founder' and the challenge of institutional foundry programs (34:02) The importance of investing in winners and adjusting portfolio construction (37:12) Introduction to Ojalo: mission, business model and global impact (42:03) Transitioning from investor to operator: pros, cons and psychological impact (45:33) Words of wisdom for founders, operators, and investors and critique of LPs' approach (48:06) Introduction of the Limited Partner Podcast newsletter

Jan 4, 2024

Alan Feld sits down with David Weisburd to talk about his experience founding Vintage, the significance of product-market fit in VC, and how Vintage has thrived over two decades. They discuss the impact of personal history on investment decisions, building an enduring VC firm culture, and engaging with General Partners. They also touch on successful GP cultures, investment allocation, and VC-LP relationship transparency. (0:00) Introduction and Alan's journey to founding Vintage (6:37) Importance of product-market fit and sector-based fund structure in venture capital (8:57) Sponsor: Bedav Insurance Group (9:46) Lessons learned from managing and growing Vintage over 20 years (17:05) Role of personal history in shaping successful entrepreneurs and investment decisions (21:29) Building an enduring venture capital firm: Culture, succession, and economic sharing (28:27) Regrets, reflections, and Vintage's approach to engaging with General Partners (33:40) Cultures at GPs that consistently return alpha and importance of humility and honesty (41:30) Allocating investments, follow-on investing, and the value of transparency in VC-LP relationships (46:36) Wrap-up: Reflections on building a lasting venture fund

Jan 2, 2024

David Weisburd interviews Lo Toney about his transition from angel investor to fund manager, his role at Plexo Capital, and his approach to working with founders. They discuss the importance of patience in early-stage investments, the diligence process for managers, and the strategy behind selecting LPs. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. The Limited Partner podcast is part of the Turpentine podcast network. Learn more: turpentine.co (0:00) Evaluating young firms and the role of GP (1:00) Introduction to the guest, Lo Toney and his journey to Plexo Capital (9:34) Transition from angel investor to fund manager (11:44) Sponsor: Vidal Insurance Group (14:58) Importance of delivering DPI and patience in early stages of investment (20:21) Diligence process for a manager that's on strategy and importance of feedback for GPs (26:44) Role of a VC and the approach to working with founders (32:37) Building an LP base: the journey from GV to Alphabet and the strategy behind selecting LPs (40:27) Managing GP-LP relationships and deciding on future fund inclusion (45:37) Assessing diversity within venture capital and the impact of fund/check sizes on returns (48:40) Introduction of GPX: A platform for transitioning investors to fund managers (54:29) Global perspective and investment scope of Plexo Capital and closing remarks

Dec 14, 2023

Roland Reynolds, Senior Managing Director at Industry Ventures, sits down with David Weisburd to discuss being one of the first investors in emerging managers and how he uses secondaries to drive alpha. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:40) Overview on Industry Ventures (4:21) Industry’s direct and secondary focus on emerging managers (9:28) Episode Sponsor: Bidav Insurance Group (10:17) How to evaluate secondary fund opportunities (16:46) Industry’s portfolio construction (21:52) How direct investments return risk adjusted alpha (23:44) The importance of knowing macroeconomic headwinds (25:05) The history of Industry Ventures (27:46) Why Roland likes extension rounds (30:58) Utilizing SPVs for pro-rata allocations (34:14) Starting a relationship with a direct investment? (35:18) Why every emerging manager needs a PPM (39:37) What is operational due diligence? (43:47) Closing thoughts

Dec 12, 2023

Fernando Pontaza, Co-Founder of Invariantes sits down with David Weisburd to discuss setting up the first Guatemalan Venture Capital Fund and why he targets a 25% IRR. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:25) The genesis of Invariantes, the first Guatemalan venture fund (3:11) The fund strategy (5:19) How Fernando won over Latin American investors (6:57) Powerlaw distributions and how they impact returns (8:36) Episode Sponsor: Bidav Insurance Group (9:48) The importance of smoothing out returns (10:55) What to look for in a fund manager (12:30) How to build LP/GP relationships (14:47) Common mistakes when investing in emerging managers (18:46) Diligencing co-investments (21:58) Is signal important? (23:30) The importance of open communication (24:57) The purpose of the LPAC (25:41) Best practices when fundraising in Latin America (28:02) The dangers of direct deals (33:58) How to reach Fernando

Dec 8, 2023

Winter Mead, Founder and CEO of Coolwater Capital sits down with David Weisburd to discuss the importance of emerging managers and how Coolwater Capital is building the YC for GPs. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:01) Genesis of Coolwater Capital (3:11) Learnings from Hall Capital (4:24) Why venture is fundamentally different than other asset classes (5:10) The proliferation of venture capital (8:45) What is Coolwater Capital (9:53) How Coolwater scaled their emerging manager program (13:20) Avoiding adverse selection (14:15) Episode Sponsor: Bidav Insurance Group (14:57) Operator vs Founder mentality (16:15) GP Mentality (21:30) Coolwater Academy (24:53) How Coolwater helps emerging managers (25:47) Common mistakes emerging managers make (28:49) Minimum viable dataroom emerging managers need (33:38) Operational Due Diligence (35:43) Is there an ideal follow-on policy? (42:39) Coolwater’s mission (44:05) How to find committed GPs (44:33) LP value add

Dec 6, 2023

Jeff Galvin, CEO of Addimmune, sits down with David Weisburd to discuss cell and gene therapy, and how Addimmune is working on a functional solution for HIV. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (2:21) Jeff’s background (5:08) Teaching at MIT as a teenager (8:22) What is gene therapy? (11:53) Episode Sponsor: Bidav Insurance Group (12:39) Gene therapy success stories (16:11) What is HIV? (20:14) AGT103 and the quest for a functional HIV cure (23:22) AGT103’s Phase I results (29:43) How gene therapy could revolutionize pharmaceuticals (30:52) How to contact Addimmune

Nov 30, 2023

Joshua Berkowitz of Berkocorp, sits down with David Weisburd to discuss investing in venture capital as a family office and why all investors should care about IRR (and not TVPI). We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:27) Joshua’s background (3:25) How venture fits within a family office (4:22) “Everyone’s an IRR investor” (5:41) How to invest in venture and manage capital calls (8:02) Why time diversification is important (10:42) The importance of always being in market (12:44) How to find and evaluate venture managers (14:41) GP strategy fit (15:52) Episode Sponsor: Bidav Insurance Group (16:45) How to predict whether a manager can pick a powerlaw company (17:34) Joshua’s powerlaw GPs (18:48) Messy (or diversified) portfolio (21:04) Aiming for 20% IRR (22:22) Why Joshua likes diversified over concentrated (24:01) GPs need to be “rough around the edges” (26:25) The difference between early and late stage collaboration (27:27) The different ways to win (29:09) Can anyone beat Sequoia and Andreessen? (29:45) Generational transfers (31:05) Founder vs Operator CEOs (32:44) How Joshua diligences emerging managers and what you need in a dataroom (40:41) Portfolio construction (41:25) How to communicate with LPs (48:56) Joshua’s view on follow-on strategy (52:05) The difficulty of succeeding across all stages (54:30) Change in graduation rates (56:17) Venture investing mistakes to avoid (57:50) How to approach co-investments (1:01:31) Dexa.ai (1:01:54) Why Joshua is a great LP

Nov 28, 2023

Brian Abrahams, CEO of American Friends of Sheba Medical Center, sits down with David Weisburd to discuss its “Peace through Health Initiative” and how the hospital has been helping Israeli and Palestinian citizens during the current conflict. (0:00) Episode Preview (0:30) Brian Abrahams’ Background (0:51) Rice Powell’s Background (2:05) Sheba Medical Center’s History (4:43) The Peace through Health Initiative (6:14) How to Combat the War of Propoganda (7:22) How Sheba responded to the attacks of 10/7 (9:30) Sheba’s partnership with Nuvo to help pregnant mothers (11:11) Firsthand impact of 10/7 (17:48) www.standwithsheba.com (18:42) How Sheba is helping heal national trauma (21:32) How Sheba has helped patients

Nov 21, 2023

Alex Edelson of Slipstream Investors, sits down with David Weisburd and Erik Torenberg to discuss the four sources of alpha for emerging managers (Sourcing, Picking, Winning, and Value-Add). We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:20) Episode Preview (1:46) Slipstream’s fund strategy (2:57) What to look for when diligencing a GP (6:32) The typical Slipstream diligence process (7:34) What Alex wants to hear on a GP reference call (10:05) Why does fund performance decline in later vintages? (12:31) Episode Sponsor: Bidav Insurance Group (16:00) How should family offices approach venture? (18:15) Why concentration drives performance (19:23) Alex’s value add to GPs (21:47) The folly of optimizing on special economics (23:30) Generalists vs. Specialists (26:32) Ranking of Sourcing, Picking, Winning, and Value Add by importance (28:07) How to be a good sourcer (30:59) How to be a good picker (32:25) How to win deals (33:32) Fundraising and investing are different skills (39:51) Lessons from working at QED (47:51) The difference between a good LP and a great LP (49:40) How to optimize portfolio construction (57:00) Are GPs penalized for not doing pro-rata? (58:04) “I want to help venture firms, whether or not I invest.”

Nov 16, 2023

Jake Paul and Joey Levy, co-founder of Betr, sit down with David Weisburd to discuss the sports betting industry and how to build a $100 billion company. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:29) Mike Brown’s, Head Coach of the Kings, thoughts on Jake Paul (1:59) The importance of self belief (3:12) What drives Jake Paul? (4:50) Living life like it’s monopoly (7:06) Jake’s views on psychedelics (8:38) “Good news travels fast, bad news travels faster” (10:28) Why Joey chose to partner with Jake (11:05) Joey’s experience with founding Simplebet (11:29) Aligning ambitions and incentives (13:06) The benefits of a 50/50 partnership (13:50) Episode Sponsor: Bidav Insurance Group (14:57) The interpersonal dynamics of being co-founders (16:06) The Betr tattoos (18:02) The market gap that Betr is filling (19:03) Creating a more intuitive sports betting platform (19:55) Capturing the casual sports fan (21:56) Why high marketing costs hurt current incumbents and how Betr capitalizes on the inefficiencies (25:54) “Betr is first and foremost a gaming business” (26:47) Digging in to Betr’s financials (29:33) Betr’s path to being a $100 billion company (31:41) What drives Joey Levy?

Nov 14, 2023

James Heath, Investment Principal at dara5, sits down with David Weisburd to discuss early stage venture. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:36) How PwC evaluates venture companies (3:25) Non-consensus learning about VC (4:30) Look for entrepreneurs that are trying to solve a critical problem (6:25) What is dara5? (8:36) How can information provide alpha? (11:01) The importance of data when co-investing (12:32) Warm versus cold intro co-investments and how to implement a double gated process (15:53) Episode Sponsor: Bidav Insurance Group (17:22) Smaller funds and ownership levels (19:06) Build long term relationships with GPs: education and casual conversations (24:13) The changing power structures in fundraising (25:34) The competing dynamics of a challenging market and investor friendly terms (28:16) How family offices should invest in venture (31:19) How to unlock the mean venture IRR of 50% (34:29) Which is a better investment: top decile backed company or an emerging manager? (35:45) Reaching Series B increases likelihood of unicorn status to 24% (37:27) AGM best practices (39:45) The importance of sharing knowledge (41:40) Why only early stage venture is non-zero sum (45:46) What’s actually going to happen in the VC reset (50:21) The emergence of European VC (51:52) Don’t be scared of emerging managers

Nov 9, 2023

Raja Doddala, Head of VC at Churchill Asset Management, sits down with David Weisburd to discuss how Churchill diligences managers, and the importance of integrity in a GP. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (1:53) Churchill background (3:08) Pulling the curtain back on the IC process (5:24) The quantitative and qualitative nature of Venture (7:00) The importance of integrity in a manager (10:33) The correlation between price sensitivity and DPI (13:22) Right companies. Right time. (14:17) Episode Sponsor: Bidav Insurance Group (15:15) How Venture fits in a portfolio (17:57) Smaller fund historically have better returns (18:53) Raja’s ideal fund (19:57) Khosla’s bet on OpenAI (20:55) Why Vinod Khosla is a great VC (21:52) Why Keith Rabois is a great VC (22:39) Operator vs Non-Operator (23:08) Specialist vs Generalist (26:02) Opportunity funds and staples (26:56) Doubling down on outliers through co-investments (29:23) How Churchill supports their GPs (37:22) “We’re open for business”

Nov 7, 2023

Avlok Kohli, CEO of AngelList sits down with David Weisburd and Erik Torenberg to discuss how he grew AngelList into a $4B dollar company. We’re proudly sponsored by Bidav Insurance Group, visit lux-str.com if you’re ready to level up your insurance plans. (0:00) Episode Preview (0:59) Why Founders need to be resilient (2:49) Why it’s rational to double down on yourself (4:57) Founder vs Operator mentality (11:07) Why empathy can hold leaders back (13:21) Episode Sponsor: Bidav Insurance Group (14:16) Do MBAs matter? (16:39) Avlok’s views on emerging managers (19:27) How AngelList services large funds (21:34) AngelList Data Room and why it’s been mass adopted by funds (22:48) How managers should utilize Treasuries (25:04) AngelList’s product philosophy (27:31) How CFOs balance CEOs (29:50) What we can learn from CashApp and Square (32:08) The importance of “disagree and commit” (34:41) The fallacy of the 10% turnover rule (36:24) AngelList’s wealth of data (38:35) “Power law is a hell of a thing” (41:44) Gauging investor skillset (44:09) “The primary place where Naval lives is in building great products” (48:48) AngelList’s plans to be the system of record for all private market transactions (50:51) How to reach Avlok

Nov 2, 2023

Tracy Fong, partner at Albourne Partners sits down with David Weisburd to discuss how emerging VC managers can unlock institutional investors. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (1:06) What is Albourne and How do LP consultants work? (1:41) What Tracy has learned since joining the industry in 1999 (2:41) Learnings from the dot com bubble (5:45) Are companies now making the same mistakes present in the early 2000s? (7:03) Tracy’s tensure on the M&A team at Yahoo (10:28) Episode Sponsor: Tactyc (12:04) Yahoo’s rumored Facebook acquisition offer (14:46) How the market adjusted with YouTube and WhatsApp (17:31) How top endowments are investing (19:01) Do access constrained funds still exist? (22:22) Why being a hybrid manager is unique (23:13) Finding greenshoots in bear markets (24:38) Main investing mistakes family offices make (26:45) How to understand the market before making a venture investment (29:57) Albourne’s mission and reach (32:35) Why it’s critical to always be in the market (33:19) Why Albourne is differentiated (33:56) How to engage an LP consultant (37:48) Why fund of funds have grown in number and popularity (40:27) How to reach Tracy

Oct 31, 2023

Elizabeth "Beezer" Clarkson, Partner at Sapphire Partners, discusses how their new partnership with CalSTRS will allow them to expand their ability to support the next generation of VC managers – all while continuing to focus on investing in the established. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (0:57) The Importance of LP Voices and Sapphire’s Partnership with CalSTRS (2:15) Why Investing in Emerging Managers Have Such a Unique Dynamic (4:09) The Role Emerging Managers Play in the Construction of a Compelling Portfolio (6:16) Thousands of Emerging Managers vs Forty Established Funds (7:30) Does Excess Capacity Translate to Adverse Selection? (8:17) “LPs are like Snowflakes and They’re all Different.” (10:49) Common Reasons Why LPs Don’t Re-up (13:48) What Makes for a Great Manager? (16:27) Episode Sponsor: Tactyc (17:34) What Sapphire Looks for When Evaluating a New Manager (19:00) Who Wins: Generalist v. Specialist (21:57) Will Solo GPs be able to Survive in this Market? (24:38) Beezer’s Predictions on Spinouts (26:34) The Bias and Rationale Behind Institutional LPs Desire to Re-up in Existing Managers (28:14) The New CalSTRS Program’s Investment Rubric on Checksize, Fund Size, Return Profile and Audit Requirements (30:37) How LPs Can Bring Value to a Fund (34:31) Why LPs are All Examining Their Portfolios (36:42) Should GPs Focus on DPI or TVPI? (39:01) Why Venture Needs More Innovation (40:19) How LPs Diligence Managers (44:15) The Importance of Transparency within the LP Ecosystem (51:57) What Sapphire Invests In (53:26) Lessons Learned from Previous Downturns

Oct 26, 2023

Scott Painter, CEO of Autonomy sits down with David Weisburd to discuss how he creates value as a serial entrepreneur and why Elon Musk has been able to be successful through all his ventures. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (1:12) Scott’s Background and Focus on the Automotive Industry (3:15) The Highs and Lows of Being an Entrepreneur (5:01) Invest in Yourself if you Believe in Yourself (7:00) Scott’s Definition of Success (7:42) What being a “Visionary” in the Automotive Industry Means (8:59) Owning a Car Shouldn’t Equate to Soul Crushing Debt (10:26) Accessibility is a Way to Unlock Affordability (11:49) What Autonomy is at its Core (12:28) Episode Sponsor: Tactyc (14:39) Autonomy’s Business Model (17:35) Scott’s Friendship with Elon Musk (21:47) How Autonomy Benefits from EV Tax Credits (26:17) The Secret to Elon Musk’s Success (28:39) Empowering Employees by Decoupling Risk and Reward (30:21) The Future of SpaceX? (38:53) The Flywheel of Wealth Creation (39:49) Autonomy’s $100B Mission (44:25) Is An Autonomy IPO on the Horizon? (47:23) How to Contact Scott

Oct 23, 2023

Jason Calacanis, founder of LAUNCH and host of the All-In Podcast and This Week in startups, sits down with David Weisburd to discuss his new fundraise and his views on the venture capital landscape. We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund. (0:00) Episode Preview (1:15) Fundraising for LAUNCH and LP investing experience (2:10) Sequoia’s investments in Twitter and Zynga (3:12) Being Sequoia’s first venture scout and earning 50% carry (4:28) Venture wealth bombs (8:06) Jason’s 4,000x investment in Uber (9:44) Loyalty in venture (10:07) Investing in Superhuman (13:15) How Jason got a 200x on an AngelList syndicate deal (14:20) Episode Sponsor (14:59) Unlocking value through secondaries (15:41) Qualities of top managers (16:23) Jason’s current fund (17:21) Aligning incentives through a GP commitment (20:54) Sourcing deals through Syndicate investments (23:56) The importance of social proof (25:04) Why deal flow is destiny (28:23) The importance of ownership (29:51) Sharp elbows in Series A and beyond (31:28) Jason’s current portfolio construction (32:29) YC's impact on venture (34:05) Playing for carry, the importance of a techstack and the myth of work life balance (36:19) Venture is a competition (37:06) Why early stage venture is not zero-sum

Oct 16, 2023

Shai Goldman, an investor, writer, and Brex ambassador sits down with David Weisburd to discuss the future of VC from his vantage point. We're proudly sponsored by AngelList, visit https://www.angellist.com/tlp if you’re ready to level up your startup or fund. (0:00) Special message (1:10) Episode preview (3:00) Brex's billboard campaign (5:05) Shai's SVB experience (6:00) Venture activity: comparing 2002, 2008 and 2022 (7:15) did VC firms fare in the last 2 downturns? (8:43) Where is VC going in the next 5 years? (10:50) Competing with a company that has a war chest (12:38) Emerging managers data resource (14:23) Thoughts on startups (15:21) What makes successful emerging managers? (18:50) Sponsor: AngelList (19:53) When being boring is good for the business (22:33) Balancing investing and deploying capital (24:00) 3x DPI and making good money (26:06) Fund returners, grand slams, and outliers (28:54) is the secret sauce in finding the next emerging market? (31:01) On generalists capturing their early stage home-runs (33:10) fundraising in the LP community (35:17) in fund of funds (38:17) LPs exploring emerging managers

Oct 2, 2023

Jamie Rhode, Principal at Verdis Investment Management, sits down with David Weisburd to discuss data-driven investing, compounding returns, Jamie's investing philosophy, and more. We're proudly sponsored by AngelList, visit https://www.angellist.com/tlp if you’re ready to level up your startup or fund. (0:00) Episode Preview (1:07) Jamie’s data driven approach (2:20) Using duration as an advantage (4:37) Jamie’s first principles approach to VC portfolio construction (7:00) The mean return in venture is 4-5x greater than the median (10:54) Jamie’s strategy and proprietary deal flow (15:30) Sponsor: AngelList (16:50) Comparing Jamie’s philosophy with past guests LPs Michael Kim and David Clark (19:25) Disciplined investing (21:20) Jamie’s red flags for GPs (22:50) Data stack: PitchBook, CB Insights, Burgiss (24:00) Ideal GPs (27:40) Compounding returns (29:40) percentage of venture investors are able to access a strategy that results in 25% compounding? (30:55) Co-investing with other LPs (32:43) Other top tier LPs shoutouts (34:05) Investing in life sciences (38:00) #OpenLP movement and transparency (40:10) Who will be the next great GPs? (44:00) Management fees (46:00) What Jamie would change about the industry

Sep 26, 2023

David Weisburd sits down with Neil Datta, Managing Director of Optima Asset Management managing the wealth of some of the world’s most important people (including the late Queen Elizabeth II). We're proudly sponsored by AngelList, visit https://www.angellist.com/tlp if you’re ready to level up your startup or fund. (0:00) Episode Preview (1:43) Neil’s diverse background (3:00) Why is Optima a management company? (4:47) Why Neil is VC-skeptic (6:35) Diligence and hype (8:09) Institutional diligence on VC (12:00) Which stage to invest into venture capital? (13:15) Portfolio construction for an institutional endowment (16:06) Sponsor: AngelList (17:30) Diversification (18:40) Correlation and lesson from the last crisis (20:40) Diversification within different stages? (21:45) Bullish on healthcare (25:20) LP Advice for Emerging Managers (28:55) Are top LPs comfortable with losing money in the correct way (30:35) Balancing reputation with diligence (32:00) The new SEC guidelines (33:35) Investors complaining about fund expenses (36:00) Fees and carry in VC (37:10) Optima's Star program

Sep 18, 2023

Michael Kim, founder and Managing Partner of Cendana Capital sits down with David Weisburd and Erik Torenberg to discuss his thesis of creating a fund of funds at seed stage, insights into the changing landscape of VC from the 90s to today, and whether VC should recycle capital. Cendana Capital has invested in Forerunner Ventures, K9 Ventures, and IA Ventures. If you’re ready to level-up your startup or fund with AngelList, visit https://www.angellist.com/tlp to get started. (1:00) Episode Preview (2:15) Michael’s journey from international relations, to investment banking, to Silicon Valley (5:07) Why Michael started Cendana and the opportunity he saw (7:30) How has Michael’s thesis changed with the influx of capital? (8:30) Nano program (13:15) Challenges of scaling funds (16:50) Sponsor: AngelList (17:55) Economic tradeoffs for different fund sizes (19:20) Management fees as non-recourse loans (20:30) Ownership percentages and returns (23:17) Contrasting fund of funds platforms with a concentrated portfolio approach. (26:27) Bringing institutional capital into early-stage and esoteric strategies. (33:11) The LP reset and the current VC landscape (34:00) The denominator effect and dry powder in the market (41:00) The paradox of VC success and importance of fund selection (44:57) Portfolio construction (49:00) Which fund managers Michael will bet on, and why.

Sep 12, 2023

David Weisburd sits down with David Clark, Investment Director at VenCap International PLC to discuss his viral post about power laws in venture capital, manager predictability, adverse selection in VC, and what percent of startups go to zero. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode Preview (2:40) David Clark's data set of over 250 early-stage funds (4:40) Power laws and fund returns (9:20) Survivorship data and challenges in emerging managers data (12:30) Succession in VC (14:36) Sponsor: AngelList (18:43) How do you back the top 1% of companies (21:30) Ownership percentages and returns (29:00) Follow on that a fund should reserve at every stage (36:30) Ten year predictions for VCs and LPs

Sep 5, 2023

David Weisburd sits down with Apurva Mehta, the co-founder of an early stage fund of funds at Summit Peak and formerly an institutional investor at endowments (Juilliard, Cook Children’s Hospital) to discuss power laws in portfolios, alpha in early stage investing, and what differentiates a great LP. If you’re ready to level-up your startup or fund with AngelList, visit https://www.angellist.com/tlp to get started. (1:00) Episode Preview (1:44) Why Apurva went from the institutional world to co founding Summit Peak Partners (2:57) How can early stage funds compete with Andreessens and Sequoias (3:28) How do you separate alpha in early stage investing? (8:06) Inefficiencies in the early stage market (16:24) Sponsor: AngelList (14:06) Generalist vs Specialist firms in portfolio construction (19:39) What is Apurva looking for in reference calls when doing diligence on emerging managers? (24:29) What differentiates a great LP? (29:14) Asset classes from most to least desirable (31:20) What fees and carry is Apurva seeing from the top quartile managers (34:13) What will happen to new firms? (36:18) Founders Fund’s strategy (36:45) Power law returns in Fund one portfolio (38:43) Apurva’s preferred ownership model (41:00) Summit Peak’s niche

Aug 28, 2023

David Weisburd and Erik Torenberg sit down with Samir Kaji, the co-founder and CEO of Allocate. In this episode, they talk about what differentiates truly elite emerging managers, what VCs get wrong in portfolio construction, what fees VCs are charging today, and his predictions about where the venture ecosystem is going by 2025. If you’re ready to level-up your startup or fund with AngelList, visit https://www.angellist.com/tlp to get started. (1:00) Episode preview (1:33) The evolution of Samir’s perspective on the venture market from his early days at SVB and First Republic, to founding Allocate with a mission to make private markets more accessible (3:46) In Samir’s experience, what separated Kirsten Green (Forerunner Ventures) and Joe Londsale (8VC) from other emerging managers? (4:46) Samir’s critical advice to emerging managers not on the same level as the Kirsten Greens and the Joe Lonsdales (8:14) Is VC a contrarian game?Or an access game? (10:17) Does valuation matter? (11:44) Is there a need for another investment platform? (13:30) How Samir evolved the product with LPs in mind (15:30) Sponsor: AngelList (18:00) How Samir would advise a customer to invest in venture and what percentage would he put in a venture portfolio among the different strategies and funds (20:00) Venture is actually a combination of different sub asset classes (22:00) The market in Q3 2023: top managers, management fees and carry? (25:30) Where Samir sees venture going by 2025 (30:50) What to avoid when pitching LPs (32:06) Minimum viable fund size (32:20) Tools that emerging managers can use to help them scale (33:20) How much staffing do emerging managers need? (35:30) How to get in touch with Samir

Aug 21, 2023

David Weisburd sits down with Steve Chasan, the Head of Investment at the Rothschild Foundation and for other philanthropic endowments led by Lord Jacob Rothschild. In this episode, they go deep into the LP mindset, covering the best practices he looks for in GPs and emerging managers, whether pricing discipline exists in VC, and describing the conversations LPs are having internally that GPs never get to hear. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode preview (1:51) Steve’s evolution from philosophy to finance to the endowment side (2:51) Steve describes his approach and the challenges of being an LP at an endowment (4:13) Why is it that now is a good time to invest while people are having trouble fundraising? (5:41) Diversification and the Swensen approach, which many institutional investors follow (6:51) The principal-agent problem for LPs and GPs (9:22) What are some best practices that LPs look for in GPs, outside of returning 10x? And what should GPs avoid? (10:12) Style drift (12:56) What are some ways LPs can differentiate themselves in the market? (13:58) Steve’s LP perspective on co-investing (15:28) Does studying philosophy offer an investing advantage? (16:47) Sponsor: AngelList (17:52) Which things do VCs systematically get wrong? (20:50) Steve’s predictions for venture over the next 5-10 years (22:00) How can VCs prepare themselves for this reset (23:20) What technologies and sectors is Steve really interested in right now, with great upside. (25:51) Investing in AI (27:25) Advice and best practices for emerging managers

Aug 14, 2023

David Weisburd sits down with Jonathan Hsu, Co-Founder and General Partner of Tribe Capital and one of the top data scientists in the space. Hsu is a physicist-turned tech entrepreneur-turned VC. In this episode, they discuss the importance of growth patterns and product market fit (PMF) in venture capital. Tribe conducts intensive data work on approximately 400 companies annually, a unique dataset that cannot be purchased or obtained from other sources. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode preview (1:15) Jonathan’s evolution from a physicist to a founder to FAANG operator to VC (3:00) The big data revolution in Silicon Valley (4:35) Jonathan’s learnings from early Facebook and what differentiated the company for its success (6:17) Pattern recognition around Product Market Fit (10:17) Using data in Venture investing (12:17) What experienced VCs all regret (15:04) Sponsor: AngelList (17:09) Hardcore benchmark analytics for startups (23:27) Venture capital efficiency (25:57) AI and investing (27:27) Jonathan’s prediction for future of VC

Aug 7, 2023

David Weisburd and Erik Torenberg sit down with Dr. Abe Othman, the Head of Data Science at AngelList and the Head of the Investment Committee at the AngelList Quant Fund. Dr. Abe has one of the largest and most granular private market data sets in the world of nearly 15,000 startups. In this discussion we dive deep into the data: power laws, what Dr. Abe’s research tells us about which companies to avoid at all costs, and whether alpha truly exists in venture capital. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode preview (1:37) Unintuitive impact of power laws in venture capital (12:02) Explaining Power Laws to the layperson or finance professional in other asset classes (14:17) Sponsor: AngelList (18:50) Does the research reveal what percentage of early stage companies are identifiable as top 1% opportunities? (20:21) The value of signals (i.e. founders alma maters) (23:23) Pricing efficiency of startups (29:00) Markup rates and loss ratios (32:45) How does the quant fund fit into the model? (37:31) Solo Gp's tend to hustle harder than traditional incumbent funds (39:36) Dr. Abe’s view on how the LP community and broader ecosystem has evolved on these topics (46:28) AUM drift in venture capital

Aug 1, 2023

David Weisburd sits down with Ramzi Samara, Co-Head of Private Funds (VC) at MASIC, one of the few family owned investment firms in Saudi Arabia that has a dedicated venture capital program. Ramzi is also an active angel investor in early-stage startups in the US and MENA. In this conversation they discuss the vibrant dynamics of the region, Ramzi’s investing thesis and multi-year power-law driven strategy, and looking at passive vs active early-stage fund managers. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode preview (1:45) How does VC view the market dynamics in Saudi Arabia? (7:16) How should Venture Capitalists think about navigating MENA? How does Saudia Arabia differ from the UAE, Bahrain, Qatar, etc. (10:27) Ramzi’s investing thesis at MASIC (14:15) Ramzi’s portfolio strategy (15:56) Sponsor: AngelList (19:12) Criteria for evaluating a fund (21:41) Looking at passive vs. active fund managers (27:41) Risks and downsides of investing in micro VCs (29:12) How Ramzi thinks about concentration risk (30:05) What VCs should know about MASIC as one of the earliest adopters of the venture capital asset system in Saudi Arabia

Jul 24, 2023

David Weisburd sits down with Jordan Stein, Director of Venture Capital at Cresset Partners. a large multifamily office with over $45 billion in assets under management and a prolific limited partner and storied venture franchises, including Andreessen Horowitz, Lightspeed, and Founders Fund. This podcast is proudly sponsored by Angellist. Visit www.angellist.com/tlp if you’re ready to level up your startup or fund. RECOMMENDED PODCAST: Founding a business is just the tip of the iceberg; the real complexity comes with scaling it. On 1 to 1000, hosts Jack Altman and Erik Torenberg dig deep into the inevitable twists and turns operators encounter along the journey of turning an idea into a business. Hear all about the tactical challenges of scaling from the people that built up the world’s leading companies like Stripe, Ramp, and Lattice. Our first episode with Eric Glyman of Ramp is out now: https://link.chtbl.com/1to1000 RECOMMENDED PODCAST: Every week investor and writer of the popular newsletter The Diff, Byrne Hobart, and co-host Erik Torenberg discuss today’s major inflection points in technology, business, and markets – and help listeners build a diversified portfolio of trends and ideas for the future. Subscribe to “The Riff” with Byrne Hobart and Erik Torenberg: https://link.chtbl.com/theriff The Limited Partner Podcast is part of the Turpentine podcast network. Learn more: Turpentine.co X: @dweisburd (David) @eriktorenberg (Erik) @cresset_capital (Cresset) LINKS: https://cressetcapital.com/ SPONSOR: The Limited Partner Podcast is proudly sponsored by AngelList. -If you’re in private markets, you’ll love AngelList’s new suite of software products. -for private companies, thousands of startups from $4M to $4B in valuation have switched to AngelList for cap table management. It’s a modern, intelligent, equity management platform that offers equity issuance, employee stock plan management, 409A valuations, and more. -If you’re a founder or investor, you’ll know AngelList builds software that powers the startup economy. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode Preview (1:28) Allocating the venture capital space (5:29) Building his portfolio (8:56) Evaluating emerging managers (13:05) Main mistakes for first-time LPs (15:20) Sponsor: AngelList (16:27) Concerns of VC in 2023 (18:40) Range of allocators (23:30) Practices and mistakes in co-investing (27:04) Co-invest programs (31:03) Cresset Partners

Jul 16, 2023

David Weisburd and Erik Torenberg sit down with LP Chris Douvos, founder of Ahoy Capital and formerly Princeton Endowment. If you’re ready to level-up your startup or fund with AngelList, visit https://www.angellist.com/tlp to get started. RECOMMENDED PODCAST Founding a business is just the tip of the iceberg; the real complexity comes with scaling it. On 1 to 1000, hosts Jack Altman and Erik Torenberg dig deep into the inevitable twists and turns operators encounter along the journey of turning an idea into a business. Hear all about the tactical challenges of scaling from the people that built up the world’s leading companies like Stripe, Ramp, and Lattice. Our first episode with Eric Glyman of Ramp is out now: https://link.chtbl.com/1to1000 RECOMMENDED PODCAST Every week investor and writer of the popular newsletter The Diff, Byrne Hobart, and co-host Erik Torenberg discuss today’s major inflection points in technology, business, and markets – and help listeners build a diversified portfolio of trends and ideas for the future. Subscribe to “The Riff” with Byrne Hobart and Erik Torenberg: https://link.chtbl.com/theriff The Limited Partner Podcast is part of the Turpentine podcast network. Learn more: Turpentine.co SPONSOR The Limited Partner Podcast is proudly sponsored by AngelList. -If you’re in private markets, you’ll love AngelList’s new suite of software products. -for private companies, thousands of startups from $4M to $4B in valuation have switched to AngelList for cap table management. It’s a modern, intelligent, equity management platform that offers equity issuance, employee stock plan management, 409A valuations, and more. If you’re a founder or investor, you’ll know AngelList builds software that powers the startup economy. If you’re ready to level-up your startup or fund with AngelList, visit www.angellist.com/tlp to get started. (0:00) Episode Preview (0:56) Introducing The Limited Partner podcast (1:55) Why does Chris love venture? (3:12) What differentiates venture from other asset classes? (5:03) Risk premiums (7:40) Why is venture capital still a good asset class today? (8:50) Why does a fund of funds make sense? (10:50) Chris' fund manager thesis? (13:45) The ecosystems Chris finds potential managers to back in (16:47) Sponsor: AngelList (18:00) Will venture be needed as companies become easier to build? (23:05) Data scientists as the best investors in the next decade (25:10) Is AI a revenue-generator or a cost-cutter? (26:03) Solo GPs over the next few years (27:58) The lifecycle of a venture fund (33:45) Large fund sizes and their returns (35:15) Chris' reflections on crypto (37:14) Unintuitive venture capital hacks (40:41) Questions to ask fund managers before investing (43:01) Will we see another YC? (46:11) Advice for family offices or institutions direct investing alongside funds (47:35) #OpenLP and transparency in the LP ecosystem