How I Invest with David Weisburd

3h 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