How I Invest with David Weisburd

What if the biggest opportunity in venture today isn’t finding the next unicorn—but solving the liquidity problem created by companies staying private twice as long as they used to? In this episode, I sit down with Ravi Viswanathan, Founder and CEO of NewView Capital, to discuss how the venture ecosystem is evolving beyond the traditional fund model. Ravi explains why he left NEA to build a firm focused on liquidity solutions, how company-led secondaries are becoming a critical tool for founders and employees, and why the future of venture may depend on balancing long-term ownership with thoughtful liquidity. We also explore the DPI drought, continuation vehicles, cap table management, and why relationships remain the ultimate source of edge in venture capital. Highlights: Why companies staying private longer created a structural liquidity gap The rise of company-led secondaries and founder-controlled liquidity How employee liquidity can improve retention and long-term alignment Why the venture industry can no longer ignore DPI The tension between FOMO investing and long-term conviction How continuation vehicles may reshape venture portfolios Why capital often masks product-market fit during boom cycles The relationship-driven lesson Ravi wishes he learned earlier in his career Guest Bio: Ravi Viswanathan is the Founder and CEO of NewView Capital, a growth-stage investment firm managing more than $3 billion and focused on primary, secondary, and hybrid investments in leading technology companies. Prior to founding NewView in 2018, Ravi spent 15 years as a General Partner at NEA, where he backed category-defining companies including MuleSoft, Braintree, Acquia, Cyence, and GlobalLogic. Over more than two decades in venture capital, Ravi has built a reputation for partnering with exceptional founders, identifying enduring technology businesses, and helping shape the evolution of liquidity and capital formation in private markets. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ravi Viswanathan: LinkedIn:https://www.linkedin.com/in/raviswanathan/ Questions or topics you want us to discuss on How I Invest? Email us at [email protected]. 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) Why He Left NEA to Launch a $1.3 Billion Venture Fund (1:02) Are the Best Venture Companies Already Obvious by Series B? (3:33) The New Secondary Market Trend Reshaping Venture Capital (5:02) Why Employees Need Liquidity Long Before an IPO (7:03) The Hidden Benefits of Letting Employees Sell Shares (11:38) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Crisis? (13:17) Why Venture Capital May Never Return to Historical DPI Levels (20:18) Are Continuation Vehicles the Next Big Venture Trend? (24:35) The One Thing That Compounded Most Over 25 Years in Venture (28:20) How Easy Money Created an Entire Generation of Zombie Startups

What if the biggest inefficiency in investing today isn’t asset selection—but the fact that most investors still optimize for pre-tax returns instead of after-tax outcomes? In this episode, I sit down with Jeff Bramel, Partner at a16z Perennial, to discuss why real assets remain one of the most misunderstood areas of institutional investing. Jeff explains how structural diversification works beyond traditional portfolio theory, why private real estate behaves differently from public markets, and how tax efficiency can dramatically reshape long-term returns for taxable investors. We also explore opportunistic investing, portfolio construction, risk management, and why real estate may offer one of the largest remaining pockets of structural alpha. Highlights: Why after-tax returns matter more than headline returns The hidden inefficiencies inside private real estate markets How depreciation transforms the economics of taxable investing Why structural diversification matters more than historical correlations The problem with overly rigid institutional asset allocation models How opportunistic investing can add hundreds of basis points annually Why higher-return assets often become safer over long time horizons The overlooked relationship between taxes, compounding, and alpha Guest Bio: Jeff Bramel is a Partner at a16z Perennial, where he focuses on real assets and institutional portfolio construction. He has more than 25 years of experience managing large and complex investment portfolios across public and private markets, with expertise spanning real estate, infrastructure, energy, agriculture, asset-backed investments, and alternative strategies. Jeff is known for applying first-principles thinking to portfolio management, combining deep quantitative analysis with a focus on structural diversification, cash-flowing assets, and after-tax optimization for long-term investors. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn:

What if the greatest threat to generational wealth isn’t bad investing—but the inability to think beyond the next liquidity event? In this episode, I sit down with Eric Becker, Founder and Chairman of Cresset, to discuss why he built a modern multi-family office after decades as an entrepreneur and investor. Eric explains the structural conflicts inside traditional wealth management, why most ultra-high-net-worth families lack true family office infrastructure, and how long-term thinking changes the way businesses, portfolios, and families compound over generations. We also explore governance, tax-aware investing, succession planning, and lessons from companies that have endured for centuries. Highlights: Why most wealth management firms fail entrepreneurs after liquidity events The hidden conflicts embedded inside traditional wirehouses Why family governance matters as much as investment performance The concept of “asset protection as compartments in a submarine” Why the next generation is often the greatest risk to family wealth How enduring companies survive across centuries and multiple crises Why building a business for the long term paradoxically accelerates growth The overlooked importance of stewardship in investing and leadership Guest Bio: Eric Becker is the Founder and Chairman of Cresset, a multi-family office and wealth management platform overseeing more than $250 billion in assets under management and advisement. Prior to founding Cresset, Eric built and invested in multiple businesses as an entrepreneur, beginning with a healthcare technology company he launched while attending the University of Chicago. He is also the author of The Long Game, a book exploring the lessons behind companies and families that have endured for generations, drawing on interviews with some of the world’s longest-lasting organizations and business leaders. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/

What if the biggest problem in asset management today isn’t investment performance—but misalignment between managers and the investors they serve? In this episode, I sit down with Luke Sarsfield, Chairman and CEO of Ridgepost Capital, to discuss how incentive structures shape long-term outcomes in private markets. Luke explains why Ridgepost leaves most carried interest with underlying managers, how alignment creates better LP relationships, and why middle market specialists can offer diversification that many large-cap private portfolios lack. We also explore long-term thinking, public versus private market pressures, culture, mentorship, and why compounding relationships may be the most valuable asset in investing. Highlights: Why alignment matters more than asset gathering in private markets The hidden correlation risk inside large private equity portfolios Why Ridgepost focuses on management fee ownership over carry How long-term incentives improve investment decision-making The tension between public market short-termism and private market compounding Why culture and mentorship compound harder than capital The importance of building teams without creating groupthink Why relationships become the ultimate competitive advantage over time Guest Bio: Luke Sarsfield is Chairman, Director, and Chief Executive Officer of Ridgepost Capital, an investment platform focused on partnering with specialized alternative asset managers. Prior to Ridgepost, he spent more than two decades at Goldman Sachs, where he served in several senior leadership roles including Global Co-Head of Goldman Sachs Asset Management and Chief Commercial Officer of Asset and Wealth Management. Across his career, Luke has focused on building enduring investment businesses, aligning incentives between managers and LPs, and helping scale world-class investment platforms with a long-term orientation. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://ww

What if the biggest opportunity in private equity today isn’t buying companies—but buying liquidity from investors who are forced to sell great assets for reasons unrelated to performance? In this episode, I sit down with Ryan Levitt, Co-Head of LP Secondaries at ICG, to discuss why secondaries have evolved into one of the most attractive areas in private markets. Ryan explains how LP secondaries can outperform traditional buyouts with lower downside risk, why DPI pressures are reshaping institutional portfolios, and how rules-based allocators create structural inefficiencies. We also explore return dispersion, continuation vehicles, GP relationships, and why access and information matter more than sourcing in modern secondaries investing. Highlights: Why secondaries have historically outperformed most buyout funds The growing return dispersion inside private equity How DPI pressures are fueling record secondary market activity Why LPs often sell their best assets instead of their worst The hidden inefficiencies created by rules-based allocators Why access and information matter more than sourcing in secondaries How continuation vehicles are changing private markets liquidity Why culture and mentorship compound harder than compensation early in a career Guest Bio: Ryan Levitt is Co-Head of LP Secondaries at ICG, a global alternative asset manager with more than $126 billion in assets under management across private equity, credit, structured capital, and real assets. At ICG, Ryan focuses on originating and leading LP secondary transactions, co-investments, and primary fund commitments globally. Prior to joining ICG, he was a Partner and Portfolio Manager at Pomona Capital, where he helped build the firm’s private wealth interval fund platform, and earlier in his career he invested across direct equity and debt transactions at GE Capital. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisbur

What if the biggest venture returns are already gone by the time a category has a name? In this episode, I sit down with Niko Bonatsos, Founder and Managing Partner of Verdict, to discuss why the best venture opportunities emerge before consensus exists. Niko explains why “50% of the profits are made before a vertical even has a name,” how he identifies “freak” founders with extreme rates of learning, and why most VCs are structurally incentivized to follow momentum instead of creating conviction. We also explore why consumer and gaming are deeply undervalued today, how AI is changing company formation, and why relationship-building compounds harder than capital in venture investing. Highlights: Why the biggest venture profits are captured before categories are named The definition of a “freak” founder and why rate of learning matters most Why most VCs optimize for markups instead of outcomes How AI is compressing company-building timelines dramatically Why consumer, gaming, and crypto are deeply underappreciated today The hidden advantage of immigrant and neurodivergent founders Why “small thinking” competes with breakthrough ideas How relationship-building became General Catalyst’s long-term edge Guest Bio: Niko Bonatsos is the Founder and Managing Partner of Verdict, an early-stage venture firm focused on backing unconventional founders building entirely new categories. Prior to launching Verdict, he spent 15 years at General Catalyst, where he helped expand the firm from an emerging venture platform into one of the world’s leading investment franchises. Niko is known for investing early in overlooked markets, partnering with highly technical founders, and developing a reputation for identifying “freak” entrepreneurs with exceptional rates of learning and conviction. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: h

What if the biggest opportunity in venture today isn’t funding new companies—but solving the liquidity crisis created by companies staying private for 20 years? In this episode, I sit down with Jared Carmel, Founder and Managing Partner of Manhattan Venture Partners, to discuss how venture secondaries evolved from a gray market into critical infrastructure for private capital markets. Jared explains why nearly $3 trillion is now trapped in aging venture funds, how DPI became the defining metric for LPs, and why secondary liquidity is now essential for founders, employees, and venture firms alike. We also explore continuation vehicles, cap table management, institutionalization of the secondary market, and why trust compounds faster than capital in private investing. Highlights: Why companies staying private for 20+ years changed venture forever The $3T liquidity problem sitting inside venture capital Why DPI matters more than IRR for LPs today How secondaries became institutionalized after years as a “gray market” Why trust compounds faster than capital in private markets The hidden risks inside retail SPVs and secondary hype cycles How continuation vehicles are reshaping venture fund liquidity Why “land and expand” became MVP’s core investment strategy Guest Bio: Jared Carmel is the Founder and Managing Partner of Manhattan Venture Partners, a leading venture secondary investment firm managing billions across primary and secondary private market investments. He has spent more than a decade helping institutionalize venture secondaries, building liquidity solutions for founders, employees, and investors in many of the world’s most valuable private technology companies. Through MVP’s “Land and Expand” strategy, Jared has invested across category-defining businesses including SpaceX, Anthropic, Databricks, xAI, and Coinbase, while helping shape the modern private liquidity ecosystem. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: <a href="https://www.linkedin.com/in/dwei

What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself? In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax alpha has become one of the fastest-growing themes in wealth management. Brent explains how long-short tax-loss harvesting strategies evolved from niche institutional products into mainstream planning tools, why tracking error is often misunderstood, and how sophisticated investors think about balancing risk, leverage, and after-tax returns. We also explore trader funds, operational risk, and why tax management may matter more than active management for many investors. Highlights: Why tax alpha can matter more than active management returns How long-short portfolios create recurring tax-loss harvesting opportunities The hidden risks behind aggressive tax-loss harvesting strategies Why tracking error is often a feature, not a flaw The operational complexity most investors underestimate How trader funds generate ordinary losses Why the best tax strategies are tied to assets investors already want to own The difference between tax planning and “the tax tail wagging the dog” Guest Bio: Brent Sullivan is an independent tax analyst, software developer, and writer focused on tax-aware investing and portfolio construction. He publishes widely followed research on tax alpha, long-short investing, and advanced wealth management strategies through his platform Tax Alpha Insider. Brent specializes in analyzing the mechanics, risks, and implementation details behind sophisticated tax planning strategies used by advisors, family offices, and institutional investors. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapita

What if the key to outperforming isn’t taking more risk—but building a portfolio strong enough to survive volatility without breaking? In this episode, I sit down with Doug Hanly, CIO of the Louisiana State Police Retirement System, to discuss why liquidity, simplicity, and process are the foundations of durable investing. Doug explains why he views short-term government credit as the “supply depots” of a portfolio, how preparation during calm periods creates opportunities during crises, and why avoiding mistakes matters more than chasing complexity. We also explore governance, manager selection, portfolio construction, and how small incremental improvements compound into long-term outperformance. Disclaimer: The thoughts and opinions expressed in this material and oral presentation are the author's and not necessarily those of the Louisiana State Police Retirement System, the Board of Trustees of the Louisiana State Police Retirement System, or the State of Louisiana. The statements and conclusions in this material and oral presentation are not binding on the State of Louisiana and its agencies, officers, and employees and do not alter the law of the State of Louisiana or policies of the Louisiana State Police Retirement System. In the event of a conflict between the material contained in this document and the applicable law, regulation, or policy, then the law, regulation, or policy is controlling. Highlights: Why liquidity creates optionality during market dislocations The hidden risk of fragile portfolios during crises Why simplicity often outperforms complexity in investing How governance shapes long-term investment outcomes The importance of “killing weak ideas early” Why smaller specialist managers often outperform larger funds How incremental improvements compound into durable alpha The role of preparation and psychology during drawdowns Guest Bio: Doug Hanly, CFA, CAIA, is the Chief Investment Officer of the Louisiana State Police Retirement System, where he oversees total portfolio strategy across public and private markets for the $1.5 billion pension fund. He previously held investment roles at Atala Financial, Windrose Advisors, Mass General Brigham, and the Washington University Investment Management Company. Doug also teaches hedge funds at LSU, founded the Next CIO Institute, and is known for his disciplined approach to governance, risk management, and institutional portfolio construction. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decis

What if the best investment opportunities are the ones most investors avoid because they’re too hard, too small, or too inefficient to pursue? In this episode, I sit down with Raphael, Deputy CIO and Co-Leader of HighVista Strategies, to discuss the concept of “beautifully inefficient” markets and why durable alpha often exists where few investors are willing to spend time. Raphi explains how governance structures shape investment outcomes, why lower middle market private equity and biotech remain compelling, and how long-duration capital creates structural advantages in venture investing. We also explore continuation vehicles, portfolio concentration, and why the best allocators balance diversification with conviction. Highlights: What makes a market “beautifully inefficient” Why alpha often lives in small, overlooked markets The hidden role governance plays in investment performance Why continuation vehicles could reshape private markets How lower middle market private equity creates durable alpha Why biotech may be one of today’s most misunderstood sectors The difference between diversification and diworsification Why long-duration venture capital remains structurally attractive Guest Bio: Raphael is the the Deputy CIO and Co-Leader of HighVista Strategies, a $14 billion investment firm focused on alternative assets and differentiated sources of alpha. He has extensive experience across portfolio management, securities analysis, and risk management, investing across equities, private markets, biotechnology, commodities, fixed income, and exotic risks. At HighVista, Raphi helps lead the firm’s investment strategy across venture capital, private equity, private credit, and public markets with a focus on identifying scalable inefficiencies and long-term opportunities. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisb

What if the best venture investments come from ignoring consensus and trusting your own taste before the market catches up? In this episode, I sit down with Maya Bakhai, Founding Partner of Spice Capital, to discuss how cultural intuition, narrative cycles, and conviction shape venture investing. Maya explains how working with Kevin Durant at 35 Ventures gave her access to top-tier deal flow while teaching her to think independently, why “narrative premiums” distort venture markets, and how the best founders build with unconditional conviction long before a category becomes popular. We also explore cultural arbitrage, creator economy investing, and why early-stage venture is ultimately a game of taste, not consensus. Highlights: Why “tier one” signaling can become a trap for investors The concept of “narrative premium” in venture capital How cultural arbitrage led Maya to her Crocs investment thesis Why the best founders build with or without investor support The difference between sales-driven and taste-driven investing How creator economy startups survived after falling out of favor Why bottoms-up investing beats market-map investing The hidden downside of relying too much on consensus opinions Guest Bio: Maya Bakhai is the Founding Partner of Spice Capital, an early-stage venture firm focused on consumer, fintech, and internet culture. Before launching Spice Capital, she worked at 35 Ventures alongside Kevin Durant and Rich Kleiman, helping build one of the most active celebrity-backed investment platforms in technology. Maya has invested in companies across creator economy, commerce, and emerging consumer behavior trends, and also writes the newsletter Hot Sauce, where she shares insights on venture capital, startups, and culture. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

What if the biggest winners in AI won’t come from having the best model—but from building the strongest feedback loops around users? In this episode, I sit down with Hans Tung, Managing Partner at Notable Capital and longtime Midas List investor, to discuss how decades of investing across consumer internet and global technology shaped his thesis around AI. Hans explains why Anthropic stood out early through its developer ecosystem, how network effects emerge inside AI systems, and why the most enduring companies are built around positive feedback loops. We also explore physical AI, prosumer behavior, immigrant founders, and the psychological traits required to build category-defining companies. Highlights: Why Hans chose Anthropic over OpenAI early on How AI models can develop network effects through developers The “Intel Inside” analogy for AI infrastructure companies Why positive feedback loops create enduring moats The hidden advantage immigrant founders have in Silicon Valley Why category-defining founders often feel “different” from everyone else How physical AI could reshape global industries outside the U.S. Why prosumers are the best signal for future consumer behavior Guest Bio: Hans Tung is Managing Partner at Notable Capital and one of the most respected global venture investors of the past two decades, consistently recognized on the Forbes Midas List. He has invested in category-defining companies including Airbnb, Coinbase, Peloton, Slack, TikTok parent ByteDance, and Anthropic, spanning the U.S., Asia, and Latin America. Prior to Notable Capital, Hans was a Managing Partner at Qiming Venture Partners and earlier worked at Bessemer Venture Partners, building a career around identifying major shifts in consumer technology, marketplaces, fintech, and AI. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https:

What if the biggest source of alpha today isn’t stock picking—but structuring portfolios more intelligently after taxes? In this episode, I sit down with Shang to discuss why tax alpha is becoming one of the most important themes in wealth and asset management. Shang breaks down how long-short tax-aware strategies work, why manager selection matters more than most investors realize, and how investors should think about tracking error, leverage, and operational risk. We also explore portable alpha, hedge fund tax structures, and why the explosion of tax-focused products may create as many risks as opportunities. Highlights: Why after-tax returns matter more than pre-tax performance The hidden importance of manager selection in tax-loss harvesting How tracking error creates both opportunity and risk Why volatility can improve tax-loss harvesting outcomes The difference between economic substance and “tax-only” strategies How portable alpha changes portfolio construction Why institutional borrowing rates are now accessible to individuals The risk of “tax tail wagging the dog” in investment decisions Guest Bio: Shang is a fintech and investment executive with deep experience across wealth management, ETFs, and institutional portfolio solutions. He previously held senior roles at Goldman Sachs, PIMCO, and J.P. Morgan, and helped scale some of the fastest-growing ETF platforms in the industry, including Simplify Asset Management and Tema ETFs. Shang focuses on developing innovative investment solutions for advisors, family offices, and individual investors, with expertise spanning tax-aware investing, derivatives, and portfolio construction. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Shang Chou: LinkedIn:<a href="https://www.linkedin.com/in/shangc

What if the best opportunities in venture today aren’t in new deals—but in existing companies right before an inflection point? In this episode, I sit down with Ryan Moore, Founder of Revenant VC and longtime venture investor, to discuss why he made the shift from primary venture investing to secondaries after more than two decades in the industry. Ryan explains how longer liquidity timelines are reshaping venture capital, why secondary investing is less about discounts and more about information asymmetry, and how founder relationships and insider alignment create the best opportunities. We also explore organizational metabolism, LP evolution, and why small, focused funds may outperform in a world dominated by mega-platforms. Highlights: Why secondaries are becoming one of the most attractive areas in venture The hidden value of buying before an inflection point Why insiders—not secondary firms—are the real competition How organizational metabolism predicts startup success Why founder relationships compound over decades The problem with groupthink in venture capital Why small funds often outperform oversized platforms How co-invest structures are reshaping the LP-GP relationship Guest Bio: Ryan Moore is the Founder of Revenant VC, a venture firm focused on secondary investments in high-growth private technology companies. Prior to founding Revenant, he spent more than two decades as a leading venture capitalist and co-founded Accomplice VC, where he was an early investor in companies including DraftKings, AngelList, PillPack, and Skillz. Ryan has built a reputation for identifying exceptional founders early and brings deep expertise across venture investing, liquidity markets, and company building. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. 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 Mo

The biggest edge in private equity is finding deals by going where others won't. In this episode, I sit down with Oscar Fahlgren, Chief Investment Officer of Mubadala Capital, to discuss how embracing complexity and scale creates asymmetric opportunities in global private markets. Oscar explains why large, complex deals often have less competition, how Mubadala Capital uses its balance sheet to anchor and syndicate multi-billion dollar investments, and why partnership—not control—is central to their strategy. We also explore the fallacy of short-term DPI, the rise of GP partnerships, and how long-term capital and alignment drive better outcomes across cycles. Highlights: Why complexity reduces competition in large-scale deals How Mubadala writes multi-billion dollar checks with limited competition The hidden flaw in the industry’s obsession with DPI Why long-term compounding beats constant capital turnover How GP partnerships scale without becoming asset gatherers Why competitive processes often produce the worst partnerships The advantage of permanent capital in structuring deals How alignment—not control—drives better investment outcomes Guest Bio: Oscar Fahlgren is the Chief Investment Officer and Global Head of Private Equity at Mubadala Capital, where he leads global investment strategy across a diversified portfolio. He has been with Mubadala since 2010, helping build its private equity platform into a global investment business with significant scale and reach. Prior to Mubadala, he worked at Terra Firma Capital Partners and began his career in law and leveraged finance, bringing a cross-disciplinary approach to investing and complex transactions. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Oscar Fahlgren: LinkedIn:<a href="https://www.link

What if the highest-return investments are the ones that reshape the future—not just the ones that fit today’s market? In this episode, I sit down with L.R. Fox, Managing Director of NEXT Global Capital, to discuss why he rejected the traditional path of “build wealth first, give later” and instead built a strategy around impact from day one. Fox explains why capital is a vote for the future, how the best investments often sit outside crowded sectors, and why frontier technologies with real-world impact can outperform conventional venture. We also explore his “buy, build, invest” framework, how he creates entirely new markets, and why resilience—not IQ—is the strongest predictor of success. Highlights: Why every dollar is a vote for the future you want to create The hidden alpha in impact investing most investors ignore Why the best opportunities exist outside crowded sectors How Fox’s “buy, build, invest” framework creates new industries Why resilience is more predictive than intelligence The difference between optimizing for returns vs inevitability How family offices can outperform by breaking traditional models Why solving hard, real-world problems drives the biggest outcomes Guest Bio: L.R. Fox is a serial entrepreneur, investor, and philanthropist, and the Managing Director of NEXT Global Capital, a family office focused on building and funding companies shaping the future. A Forbes 30 Under 30 honoree, he began his journey in the foster care system and went on to found and scale multiple companies across defense, technology, and frontier innovation. Fox is known for investing in high-impact sectors ranging from national security to healthcare and for his mission-driven approach to combining capital with meaningful global change. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

What if the best investments aren’t the riskiest—but the ones everyone else can’t own? In this episode, I sit down with Keri Findley, Founder and CEO of Tacora Capital, to discuss how she built one of the most differentiated credit strategies by focusing on illiquidity, not risk. Keri explains how dislocations are often driven by forced sellers and structural constraints, why the best credit opportunities come from creating assets rather than just finding them, and how she partners with startups to finance products banks won’t touch. We also explore portfolio construction, why scaling is the hardest problem in credit, and how incentives, ethics, and alignment ultimately determine outcomes. Highlights: Why illiquidity—not risk—creates the best credit opportunities How forced sellers and ratings constraints drive mispricing The difference between finding assets and creating them Why scaling a credit fund is harder than venture How one bad deal can destroy an entire credit portfolio Why alignment and ethics matter more than structure The hidden equity upside inside credit strategies Why solving real problems creates durable alpha Guest Bio: Keri Findley is the CEO of Tacora Capital, an investment firm focused on asset-based lending across fintech, insurtech, and specialty finance. She previously built and led the structured credit business at Third Point, one of the world’s leading hedge funds, and has spent her career investing in complex credit opportunities. Keri specializes in structuring and financing assets that fall outside traditional markets, partnering closely with founders to scale new financial products. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank @AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Keri Findley: LinkedIn:h

What if the biggest mistake in venture investing isn’t picking the wrong fund—but misunderstanding incentives and behavior? In this episode, I sit down with Ilya Strebulaev, Professor of Finance and Private Equity at Stanford GSB, to discuss how incentives, biases, and portfolio construction shape outcomes in venture capital. Ilya explains why fee structures matter less than how they’re designed, how carry changes risk-taking behavior, and why persistence in venture is real but often misunderstood. We also explore diversification, correlation across managers, and the hidden decision-making biases that drive both LPs and GPs, from escalation of commitment to style drift. Highlights: Why incentives—not fees—drive investment behavior How higher carry structurally increases risk-taking The difference between gross returns and net returns Why diversification works differently in venture The concept of style drift and why it destroys persistence How LPs underestimate correlation across managers Why follow-on decisions matter more than initial investments The bias that leads VCs to double down on bad investments Guest Bio: Ilya Strebulaev is a tenured chaired Professor of Finance and Private Equity at Stanford Graduate School of Business and a leading expert in venture capital, private equity, and innovation. He is the founder and faculty director of the Stanford GSB Venture Capital Initiative and has published extensively in top academic journals, with his work featured in major media outlets. Ilya teaches courses on venture capital and private equity at Stanford and has received the Distinguished Teacher Award, while also advising global investors and institutions on investment strategy and decision-making. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ilya

What if venture capital isn’t an asset class—but an access game where only a few managers matter? In this episode, I sit down with Nolan Bean, CIO at FEG Investment Advisors, to discuss how institutional investors are adapting to a world where companies stay private longer and AI is reshaping every asset class. Nolan breaks down why access to top-tier managers matters more than allocation, how venture portfolios are evolving to include both early-stage and multi-stage exposure, and why DPI, liquidity, and portfolio construction are becoming more complex. We also explore portable alpha, diversification myths, and how allocators think about risk in a world where everything is increasingly correlated. Highlights: Why venture is an “access class,” not an asset class How staying private longer is reshaping LP strategies The real tradeoff between DPI and long-term compounding Why diversification is harder than it looks in modern portfolios How small growth equity complements venture for earlier liquidity The difference between building companies vs scaling organizations Why AI exposure exists across every asset class How portable alpha changes the way institutions build portfolios Guest Bio: Nolan Bean is the Chief Investment Officer at FEG Investment Advisors, where he oversees portfolio strategy across public and private markets for institutional clients. He brings over two decades of experience applying an endowment-style investment approach, with a focus on manager selection, portfolio construction, and risk management. Nolan is actively involved in the broader investment community, serving in leadership roles across industry organizations and advising institutional investors on long-term capital allocation. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with

What if the real edge in venture capital isn’t picking companies—but helping them survive long enough to matter? In this episode, I sit down with Nigel Morris, Managing Partner at QED Investors and Co-Founder of Capital One, to discuss how fintech innovation actually happens and why most investors misunderstand the role of venture capital. Nigel explains why incumbents struggle to innovate despite massive advantages, how QED built one of the most successful fintech franchises by combining operating experience with investing, and why venture is not stock picking but hands-on company building. We also explore founder psychology, power laws, and how culture and talent ultimately determine outcomes more than strategy or capital. Highlights: Why venture capital is “day-to-day combat,” not passive investing The difference between fintech founders and traditional operators Why incumbents fail despite scale, data, and distribution How QED finds and avoids “mercenary” founders Why most venture outcomes are driven by a few extreme winners The concept of “threshold scale” in venture firms How geo-arbitrage creates repeatable fintech opportunities Why culture and people are the only true long-term advantage Guest Bio: Nigel Morris is the Managing Partner at QED Investors and Co-Founder of Capital One, where he helped pioneer data-driven financial services and scale the company into one of the largest credit card issuers in the world. At QED, he has led investments in over 200 fintech companies globally, building one of the leading venture platforms in the sector. With decades of experience as both an operator and investor, Nigel focuses on supporting founders in building transformative financial businesses at scale. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ni

What if the biggest opportunity in AI isn’t intelligence—but the missing data layer for the physical world? In this episode, I sit down with Daniel Jacker, CEO and Co-Founder of ZaiNar, to discuss why physical AI could become a $50 trillion market and the infrastructure required to make it work. Daniel explains how turning wireless networks into a real-time sensing layer unlocks entirely new capabilities across industries, why the absence of physical-world data is the biggest bottleneck in AI today, and how his company spent nearly a decade in stealth building a foundational technology before scaling. We also explore swarm intelligence, robotics, and where value will accrue as AI moves from digital to physical environments. Highlights: Why physical AI lacks the equivalent of the internet’s data layer How wireless networks can become a global sensing system What most people misunderstand about robotics and automation Why swarm intelligence matters more than individual robots How ZaiNar stayed in stealth for nine years while building a moat Where value accrues in AI beyond applications and models The real bottleneck preventing AI from entering the physical world Why data, not robots, may be the biggest investment opportunity Guest Bio: Daniel Jacker is the CEO and Co-Founder of ZaiNar, a 5G positioning technology company focused on real-time, high-precision location intelligence for physical AI applications. He earned his MBA from Stanford GSB and is a General Partner at Magic City, a seed fund backing Stanford founders, as well as an active mentor at StartX and other leading accelerators. Prior to ZaiNar, he worked at Accenture on emerging technology strategy and founded The 3D Printing Company. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Daniel Jacke

What if venture capital isn’t really an asset class—but a game where only a handful of managers actually matter? In this episode, I sit down with Ian Sigalow, Co-Founder and Managing Partner of Greycroft, to discuss why venture returns are driven by a small group of firms with consistent access to the best companies. Ian explains why diversification often hurts venture outcomes, how the industry splits between “access” and “craft” investing, and why conviction, not consensus, drives results. We also explore what defines great founders in the AI era, how venture firms build brand and culture over decades, and why the intersection of multiple skill sets is becoming the foundation for generational companies. Highlights: Why venture is “manager selection masquerading as an asset class” The difference between access investing and craft investing Why diversification can actually reduce venture returns What makes a founder a “master of two domains” How top firms consistently access the same small set of winners Why conviction beats consensus in investment decisions The role of brand in winning competitive venture deals How AI is changing both company building and venture workflows Guest Bio: Ian Sigalow is the Co-Founder and Managing Partner of Greycroft, a $4B+ venture capital firm investing from seed through growth stages. He has over two decades of experience backing companies across fintech, enterprise software, consumer, and healthcare, and has built Greycroft into a leading platform spanning both early-stage “craft” investing and later-stage access investing. Ian focuses on partnering closely with founders to help scale businesses, combining deep operating insight with long-term venture experience. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ian Sigal

What if the biggest breakthroughs in biotech don’t come from more capital—but from building better systems for innovation? In this episode, I sit down with Errik Anderson, biotech entrepreneur and founder behind multiple billion-dollar companies, to discuss how building infrastructure, not just drugs, is reshaping the future of healthcare. Errik explains why most biotech companies fail the same way, how reducing the cost and time of experimentation unlocks more innovation, and why staying private longer enables better long-term decision making. We also explore compounding in biotech, the limits of scaling creativity, and how conviction, mission, and talent ultimately determine which companies change the world. Highlights: Why most biotech companies fail the same way How lowering experiment costs increases innovation The difference between building drugs vs building infrastructure Why great companies stay private longer than expected How compounding works in biotech beyond capital Why you can’t scale creativity by adding more money The real bottleneck in drug discovery today Why mission-driven teams outperform over long time horizons Guest Bio: Errik Anderson is a biotech and technology entrepreneur, investor, and founder of multiple billion-dollar companies, including Alloy Therapeutics. He focuses on building platforms that accelerate drug discovery and innovation across the healthcare ecosystem. In addition to founding and scaling companies, he is an active mentor and investor, driven by a long-term mission to create transformative solutions in health and science for future generations. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Errik Anderson: LinkedIn: https://www.linkedin.com/in/errik

What if the real edge in venture isn’t price—but who you choose to partner with for a decade? In this episode, I sit down with Jamie Montgomery, Co-Founder and Managing Partner of March Capital, to discuss how long-term relationships, not transactions, drive venture outcomes. Jamie explains why asymmetric upside matters more than negotiating the last percentage point, how conviction and discipline shape follow-on decisions, and why understanding your own biases is critical when doubling down. We also explore capital cycles, liquidity dynamics, and how AI is forcing every company to either reinvent itself or fall behind. Highlights: Why relationships outperform transactions in venture over time The “turkey sandwich test” for choosing founders How to actually decide when to double down on a company Why most investors misunderstand capital cycles and liquidity The hidden biases that distort follow-on investment decisions How AI is forcing a full reset across portfolio companies Why venture returns come from asymmetric outcomes, not pricing The real competition for capital most VCs ignore Guest Bio: Jamie Montgomery is the Co-Founder and Managing Partner of March Capital, a leading technology investment firm focused on growth-stage companies. He previously founded Montgomery & Co., where he advised and financed hundreds of companies and took dozens public, building deep experience across capital markets and entrepreneurship. At March Capital, he has led investments in category-defining companies such as CrowdStrike and ThoughtSpot, and continues to focus on backing disruptive technologies with long-term compounding potential. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. 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 Montgomery: LinkedIn:<a href="https://www.linkedin.com/in/jamiemontgomer

What if the biggest edge in investing isn’t capital or strategy—but how clearly the world understands you? In this episode, I sit down with Jennifer Prosek, Founder and Managing Partner of Prosek Partners, to discuss how branding, narrative, and communication have become core drivers of success in financial services. Jennifer explains why firms went from ignoring marketing to depending on it, how “efficiency and preference” directly impact fundraising and deal flow, and why owned media and the “digital blink” now shape first impressions. We also explore how founders should think about storytelling, differentiation, and building long-term trust in an increasingly competitive capital landscape. Highlights: Why branding went from irrelevant to essential in finance The concept of “efficiency and preference” in fundraising Why most first meetings are actually second meetings How the “digital blink” shapes investor perception instantly Why owned media is the highest ROI strategy today The biggest mistake GPs make when going on podcasts How to compete for retail capital without massive budgets Why narrative clarity is the foundation of all marketing Guest Bio: Jennifer Prosek is the Founder and Managing Partner of Prosek Partners, a leading global marketing and communications firm specializing in financial services. She has built the firm into one of the most influential platforms in the industry, advising top asset managers, private equity firms, and financial institutions worldwide. Jennifer is also a published author, board member, and active investor in communications technology, with deep expertise at the intersection of brand, capital markets, and reputation. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Jen Prosek: LinkedIn:<a href="https://www

What if the biggest edge in managing $390 billion isn’t picking assets—but controlling risk and liquidity when markets break? In this episode, I sit down with Scott Chan, Chief Investment Officer of CalSTRS, to discuss how one of the largest institutional investors in the world is positioning for a period of massive structural change. Scott breaks down how AI, deglobalization, and the energy transition are driving a multi-decade investment cycle, why traditional diversification is breaking down, and how liquidity and dynamic allocation become critical in volatile markets. We also explore structural alpha, co-investing at scale, and how governance and partnerships enable CalSTRS to generate returns without taking incremental market risk. Highlights: Why stocks and bonds may no longer provide true diversification How liquidity becomes the biggest advantage during market dislocations What “structural alpha” looks like at a $390B portfolio Why infrastructure is a multi-decade opportunity How CalSTRS scaled co-investments from 2% to 30%+ of the portfolio The real edge of governance and delegated decision-making Why AI is driving a fixed asset investment boom The mistake most investors make during market recoveries Guest Bio: Scott Chan is the Chief Investment Officer of CalSTRS, one of the largest pension funds in the world with approximately $390 billion in assets under management. He previously served as Deputy CIO and now oversees a team of more than 200 investment professionals across public and private markets. Scott is a board member of the Toigo Foundation, co-chair of the Institutional Investors Roundtable, and serves on multiple advisory boards including the Milken Institute, AIMA, and CAIA, with a focus on advancing diversity and innovation in asset management. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https

What if the next source of alpha in private equity isn’t funds—but individual deals? In this episode, I sit down with Rohan Parikh, Vice President at Houlihan Lokey, to discuss the rapid rise of co-investments and why they are becoming a core part of institutional portfolios. Rohan explains how extended fundraising cycles, larger deal sizes, and slower distributions have created a “perfect storm” for deal-by-deal capital, why LPs are increasingly treating co-investments as a standalone asset class, and how independent sponsors are reshaping the market. We also explore underwriting frameworks, alignment, and how relationships, not just returns, drive long-term success in this segment of private markets. Highlights: Why co-investments have doubled to a $300B+ market in just a few years The “perfect storm” driving deal-by-deal fundraising Why LPs now treat co-investments as a standalone asset class How independent sponsors are competing with traditional PE firms What separates a fund track record from a co-invest track record Why alignment is often stronger in co-investments than funds How deal vs sponsor underwriting shifts based on control The real risk of adverse selection—and how to avoid it Guest Bio: Rohan Parikh is a Vice President at Houlihan Lokey, where he focuses on direct placements and co-investment fundraising within the firm’s Equity Capital Solutions business. He previously worked at PJT Park Hill in co-investment fundraising and began his career at Citi in leveraged finance. Rohan specializes in structuring and raising capital for sponsor-backed single-asset transactions and works closely with GPs and LPs across private markets. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Rohan Parikh: LinkedIn:<a href="https://www.linkedin.com/

What if the best investments aren’t found in chaos—but in having the discipline to act when others can’t? In this episode, I sit down with Darren Fisk, Founder of Forum Investment Group, to discuss how he scaled from early syndication deals to a fully integrated multifamily investment platform managing billions. Darren breaks down how he leaned in during the 2008 financial crisis to acquire 9,000 units, why focusing on distressed capital structures rather than distressed assets created asymmetric opportunities, and how flexibility across the capital stack allows investors to generate returns in any market. Highlights: How buying distressed capital stacks created outsized returns in 2008 Why conviction matters more than timing in volatile markets The difference between allocating capital and truly investing How flexibility across debt and equity drives consistent returns Why the best opportunities are often “below the headline” The hidden advantage of operating assets, not just owning them Why doing nothing can be the highest returning decision How market cycles create obvious opportunities most investors miss Guest Bio: Darren Fisk is the Founder of Forum Investment Group, a multifamily-focused investment platform with over two decades of experience across real estate equity, debt, and structured finance. He built the firm from early syndication deals into a fully integrated asset manager investing up and down the capital stack. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. . We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Darren Fisk: LinkedIn:https://www.linkedin.com/in/dfiskforumre/ Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

What if venture capital isn’t about finding unicorns—but about consistently making good investments? In this episode, I sit down with Eric Scott, Co-Founder and Managing Partner at Overlook Capital, to discuss how his approach to venture evolved from chasing power laws to focusing on fundamentals. Eric explains why most venture frameworks only make sense in hindsight, how thinking like a value investor can improve early-stage decision-making, and why founder quality is ultimately revealed through execution, not narratives. We also explore concentrated markets, late-stage venture dynamics, and how reputation, conviction, and timing shape outcomes across cycles. Highlights: Why venture “power laws” don’t help you pick winners in real time How value investing principles apply to early-stage companies What most investors misunderstand about founder selection Why great companies don’t come from A/B testing alone How venture markets became structurally concentrated Why smaller funds can outperform in overlooked segments The hidden role of reputation and signal in fundraising Why being wrong—and correcting it—is a core investing skill Guest Bio: Eric Scott is Co-Founder and Managing Partner at Overlook Capital, where he focuses on investing in category-leading growth companies. He previously worked at Founders Fund and 8VC, gaining experience across early and growth-stage investing, and has also held roles in healthcare and technology startups. Eric began his career after founding a company out of college and brings a cross-functional perspective shaped by both operating and investing experience. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Eric Scott: LinkedIn: https://www.linkedin.com/in/eric-sc

What if the biggest opportunity in healthcare isn’t new drugs—but reinventing how the entire system works? In this episode, I sit down with David Berry, Founder of over 20 companies including seven $1B+ businesses, to discuss why the traditional biotech model is breaking and where the next wave of innovation in healthcare is emerging. David explains how pricing pressure, rising costs, and global competition are compressing returns in drug development, while AI, data, and new business models are unlocking entirely new ways to deliver care. We also explore how technology is transforming clinical trials, why healthcare is shifting beyond pharmaceuticals, and how investors can find opportunity in mispriced parts of the market. Highlights: Why biotech returns are structurally declining despite innovation How AI is changing clinical trials and drug development timelines The unappreciated impact of China on global biotech competition Why healthcare is a $5T opportunity beyond pharmaceuticals How data and longitudinal patient insights unlock new discoveries The next frontier in longevity, wearables, and personalized health Why the middle stage of venture is undercapitalized today How supply-demand imbalances create the best investment opportunities Guest Bio: David Berry is a founder, entrepreneur, and investor who has built over 20 companies, including seven valued at over $1 billion. He spent nearly two decades at Flagship Pioneering, where he helped create and scale leading biotech companies, and later founded Valo Health. He is now the founder of Averin Capital, where he focuses on the technology-driven transformation of healthcare and investing in companies at the intersection of biology, data, and innovation. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected wit

What if the best venture returns come from avoiding trends—not chasing them? In this episode, I sit down with Colin, Co-Founder of Narya, to discuss how he approaches investing in frontier sectors without falling into mimetic behavior. Colin explains why the best opportunities are often “hidden in plain sight,” how mission-driven investing can still generate venture-scale returns, and why concentration, not diversification, drives outcomes in venture. We also explore defense, space, and advanced manufacturing, and how timing, business model innovation, and founder quality ultimately determine success. Highlights: Why chasing popular sectors often leads to worse outcomes How to identify “hidden in plain sight” opportunities Why venture returns are driven by a few concentrated bets What most investors misunderstand about deep tech investing How mission-driven companies can still deliver top-tier returns Why too much capital can hurt startups more than help The traits that define world-changing deep tech founders Why business model innovation matters as much as technology Guest Bio: Colin is a Co-Founder of Narya, where he focuses on investing in early-stage companies across sectors such as defense, healthcare, and advanced manufacturing. He previously served as a Managing Director at Mithril and held senior roles across leading venture platforms, investing in companies spanning biotechnology, neuroscience, and enterprise software. Colin also serves as an advisor to multiple investment and accelerator platforms, and has built a career backing founders working on complex, high-impact problems. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Colin Greenspon: LinkedIn: https://www.linkedin.com/in/co

What if the biggest edge in investing isn’t picking better assets—but structuring them better for taxes, incentives, and control? In this episode, I sit down with Michel, Founding CIO of a16z Perennial, to discuss how institutional investing frameworks translate to individual portfolios. Michel breaks down why most wealth management fails at true investment management, how misaligned incentives shape outcomes, and why scale, access, and structure matter more than traditional asset allocation. We also explore concentrated portfolios, tax alpha, and how psychology ultimately determines whether a strategy succeeds or fails. Highlights: Why wealth management and investment management are fundamentally different How scale actually benefits LPs, not just GPs What most investors misunderstand about diversification Why a 90/10 portfolio may not be irrational for the right investor How tax alpha can outperform investment alpha The hidden cost of fund-of-funds and fee layering Why access to top managers drives most institutional returns How psychology, not strategy, determines long-term outcomes Guest Bio: Michel is the Chief Investment Officer at a16z Perennial, where he leads multi-asset portfolio construction for founders and large individual investors. Prior to a16z, he was CIO at Jordan Park, managing approximately $17 billion across global asset classes, and a Managing Director at Makena Capital Management. Earlier in his career, he worked at Scion Capital and McKinsey, and holds advanced degrees from Stanford and Cambridge, including a PhD in Management Science and Engineering as a DARPA fellow. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Michel Del Buono: LinkedIn: <a href="https://www.linkedin.co

Is the real edge in investing not picking assets but structuring how you allocate capital? Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity provider during market stress is one of the most powerful strategies. We also discuss concentration risk in public markets, the evolution of private markets, and how allocators can think about illiquidity, secondaries, and niche opportunities. Highlights: Why single family offices have a structural edge over multifamily offices Total portfolio approach vs traditional asset allocation Competing strategies for capital across the portfolio Why liquidity is critical during market dislocations Concentration risk in large cap equities Structural changes in small cap and private markets The impact of retail capital flowing into private equity How misaligned liquidity structures can hurt returns Where illiquidity premium still exists Underrated opportunities in small buyout and niche credit The role of behavioral bias in asset allocation Why risk tolerance should match the capital base Guest Bio: Terence Thompson is a Vice President of Investments at DF Enterprises, a single family office where he oversees investment strategy, portfolio construction, and manager selection across public and private markets. He has over a decade of institutional investment experience, including managing assets at Blue Cross Blue Shield of Arizona. Terry is a CFA charterholder, USAF veteran, and an active member of several investment and policy organizations. He focuses on building resilient portfolios that balance liquidity, risk, and long-term compounding. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linked

What if the biggest edge in venture today isn’t picking companies—but owning the entire lifecycle of capital? In this episode, I sit down with Paris Heymann, Co-Managing Partner of Technology Investing at J.P. Morgan Private Capital, to discuss how the boundaries between public and private markets are breaking down. Paris explains why companies are staying private longer, how value is increasingly accruing to private investors, and why multi-stage platforms are becoming the new model for capturing returns. We also explore how AI is shifting business models from selling software to selling work, why founder quality still drives outcomes, and how power laws continue to dominate both private and public markets. Highlights: Why the line between public and private markets is disappearing How J.P. Morgan competes using platform, not just capital Why companies are staying private for 15+ years What changes when companies start selling “work” instead of software Why valuation matters less than quality and compounding How power laws dominate even in growth and public markets Why founder-market fit matters more than ever in AI The real advantage of multi-stage investing platforms Guest Bio: Paris Heymann is Co-Managing Partner for Technology Investing within J.P. Morgan Private Capital, a division of J.P. Morgan Global Alternatives in J.P. Morgan Asset Management. Paris joined Private Capital from Index Ventures in 2024 where he served as Partner and helped to establish the firm’s New York office. Before Index, Paris was Partner at Arena Holdings where he invested globally in public and private technology companies. He began his career at Bain Capital within the North American Private Equity group. Paris holds a B.A. in Political Economy from Williams College. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank @AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapita

Is private equity alpha really about picking great deals—or about executing the same playbook better than everyone else? In this episode, I discuss with Monty Yort, Managing Partner at GenNx360 Capital Partners, about how disciplined execution and consistency drive long-term outperformance in private equity. We break down how GenNx360 approaches proactive sourcing, why lower middle market investing creates structural advantages, and how operational improvement and buy-and-build strategies compound value over time. Monty also shares lessons on leadership, mentorship, and why the best firms continuously refine their process rather than chase new strategies. Highlights: Why proactive sourcing leads to better deals and more opportunities The shift to industrial services and fragmented markets Buy-and-build as a repeatable value creation strategy Why organic growth is the primary driver of returns How to evaluate founders and build leadership teams The importance of discipline in fund size and strategy Why continuation funds extend the best investments How repetition and consistency outperform complexity The role of mentorship in accelerating careers Why private equity is about people as much as process Guest Bio: Monty Yort is a Managing Partner at GenNx360 Capital Partners, a New York–based private equity firm with $2.5 billion in assets under management focused on middle-market industrial and business services companies. He has more than two decades of experience leading acquisitions and recapitalizations totaling over $3 billion, specializing in operational improvement and growth in fragmented industries. Prior to joining GenNx360 in 2009, Monty was a Managing Partner at Schroder Ventures and a Principal at Aurora Capital Group, with earlier roles at Morgan Stanley and Salomon Brothers. He holds an MBA from UCLA Anderson and serves on multiple portfolio company boards Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: <a href="https://www.linkedin.com/in/

How do you manage a $26 billion public fund while keeping every investment decision disciplined, every team member calibrated, and every partner accountable? In this episode, I sit down with Mark Steed, Chief Investment Officer of AZ Public Safety Personnel Retirement System, to explore how super forecasting and probabilistic thinking shape portfolio management. Mark shares how lessons from Dr. Phil Tetlock's the Good Judgment Project inform every investment decision, why intellectual humility and calibrated confidence drive better outcomes, and how simplifying portfolios into broad buckets creates flexibility and competition for capital. He also unpacks the role of co-investments, structural alpha, and first principles thinking in public markets. Highlights: How PSPRS uses probabilistic forecasts and Briar Scores to track accuracy and improve decision-making Why intellectual humility and calibration are as important as market knowledge Simplifying complex portfolios into three broad buckets: capital appreciation, contractual income, and diversifying strategies The growing role of co-investments and capturing structural alpha with trusted partners Benchmarking against the S&P 500 while managing expectations for thousands of police and fire pensioners Distinguishing between “investing,” “allocating,” and truly “owning” assets Lessons from super forecasting on evaluating GPs and reducing overconfidence in a complex market environment Guest bio: Mark Steed is Chief Investment Officer of AZ Public Safety Personnel Retirement System, overseeing approximately $26 billion for police and fire pensions. He has implemented super forecasting and probabilistic investment methodologies at scale, transforming decision-making, portfolio construction, and team dynamics. Known for his focus on calibration, intellectual humility, and first principles thinking, Mark combines behavioral science with traditional investment rigor to deliver disciplined, long-term results. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter:

How do you build a $7 billion portfolio that performs across decades while keeping every client aligned and every manager motivated? In this episode, I sit down with Karen Welch, Chief Investment Officer at Spider Management Company, to explore the evolving role of a CIO in today’s complex investment landscape. Karen shares how lessons from Stanford’s endowment shaped her approach, why the best investment edge comes from people and relationships, and how Spider leverages both to generate top-tier returns. She also unpacks how to navigate private markets, assess the illiquidity premium, and structure portfolios to balance opportunity with risk. Highlights: Why the most important skill for investors isn’t modeling—it’s building relationships with teams and managers How AI is reshaping portfolio management and why human judgment remains critical Playing offense and defense in a portfolio: spotting dislocations and leaning into opportunities Lessons from the endowment model: what still works, what needs evolution, and why illiquidity premiums aren’t guaranteed Strategies for accessing top-tier venture managers without decades of reputational capital The advantages of Spider’s single portfolio model across multiple clients and the “razor” it creates for disciplined investing Practical advice for career longevity: loving your work and balancing networking with building something meaningful Guest bio: Karen Welch is Chief Investment Officer at Spider Management Company, overseeing approximately $7 billion for the University of Richmond and affiliated nonprofit partners. Previously, she spent nearly a decade at Stanford’s endowment, where she honed her approach to portfolio construction, manager selection, and long-term investing. Known for her focus on relationships, strategic thinking, and disciplined portfolio management, Karen combines decades of endowment experience with a modern approach to private and public markets. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: <a href="https

What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact? In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and personal stakes. He discusses the lessons he learned from fundraising in both up and down markets, why creating momentum and scarcity is critical, and how setting boundaries transformed the outcome for him and his team. Highlights: The most difficult capital raise of Scott’s career and how he overcame repeated setbacks Persistence as a strategic tool: staying the course through 21 months of volatility Managing personal and professional stakes: balancing debt, family, and team morale Compartmentalizing bad news to make clear-headed decisions under pressure Using scarcity and deadlines to drive investor action in risk-off environments Learning from elite entrepreneurs like Elon Musk and applying resilience in real time Turning adversity into anti-fragility: lessons on confidence, focus, and long-term success Guest bio: Scott Painter is a serial entrepreneur and long-time leader in automotive technology, widely recognized for shaping how consumers buy, finance, and access vehicles. He founded TrueCar in 2005 to help car buyers save time and money with technology. Under his leadership, TrueCar went public in 2014. In January 2026, Painter re-acquired the company and returned as CEO to continue advancing its original mission. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Scott Painter: LinkedIn:https://www.linkedin.com/in/spai

What if the families with the largest fortunes generate the highest returns not by chasing hot sectors, but by pacing capital, managing liquidity, and investing with a multi-decade horizon? In this episode, I sit down with Douglas Evans, Chief Investment Officer & Partner at Callan Family Office, to explore how a $10B family office approaches private markets like an institutional investor. Doug shares how private capital pacing, vintage year diversification, and strategic GP partnerships drive consistent performance, why continuation vehicles and secondary markets are reshaping liquidity, and how focusing on underlying assets rather than labels helps families build repeatable, long-term returns. Highlights: Managing private capital pacing to capture the best vintages Balancing taxable versus non-taxable investment strategies Navigating declining DPI in venture and growth funds Continuation vehicles and secondaries as tools to unlock liquidity and optimize returns Building strategic GP relationships for first-look co-investment opportunities Investing in underloved sectors like enterprise security and infrastructure Doug’s advice: focus on alignment, patience, and long-term perspective to generate outsized outcomes Guest bio: Douglas Evans is Chief Investment Officer & Partner at Callan Family Office, overseeing $10B in assets for ultra-high-net-worth families. He specializes in portfolio construction across public and private markets, private capital pacing, tax-aware investing, and cultivating long-term GP relationships to deliver repeatable, institution-like performance. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Douglas W. Evans: LinkedIn:https://www.linkedin.com/in/douglas-evans-733723

What if the biggest edge in portfolio construction isn’t picking better assets but structuring a portfolio you can actually stick with through cycles? In this episode, I sit down with Chaya Slain, President and CIO at Virtera Partners LLC, to unpack how families can access institutional-quality investing without building a full family office. Chaya explains why alternatives are often the true driver of outperformance, how trend following can reshape risk and return, and why behavioral discipline matters more than perfect asset selection. Disclaimer: The information discussed in this podcast is for informational and educational purposes only and should not be considered investment advice or a recommendation or offer to buy or sell any security. Nothing discussed in this podcast should be construed as creating an advisory relationship with any listener. Highlights: Why building a traditional family office is inefficient below $100M to $1B in assets The real challenge in alternatives is access, diligence, and fee structure, not just sourcing How FOMO drives overexposure to “hot” private deals without understanding price Trend following explained simply and why it thrives during market dislocations Historical performance: how combining trend and equities improves returns and reduces drawdowns Why bonds may fail as protection and what can replace them in modern portfolios Behavioral investing: why structure and discipline outperform individual decision-making Lower middle market private equity: less competition, better entry prices, and multiple expansion potential Venture capital challenges: access, long time horizons, and wide dispersion of returns How misaligned incentives and layered fees can quietly erode returns Guest Bio: Chaya Slain is the President and CIO at Virtera Partners LLC, an investment firm focused on helping families access institutional-quality alternative investments. She previously worked at a leading family office where she identified gaps in access to private markets for sub-billion-dollar portfolios. Chaya specializes in portfolio construction, manager selection, and integrating strategies like trend following to improve long-term risk-adjusted outcomes. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most

What if the real edge in venture isn’t picking the hottest companies, but structuring your portfolio, pacing capital, and building relationships in a way most investors never do? In this episode, I sit down with Jamie Melzer, Founder and Managing Partner of Altra Venture Partners, to break down how she built a firm focused on late-stage venture and secondaries at the height of market dislocation. We discuss why rising interest rates in 2022 created a rare entry point, how buying private tech companies at 40 to 80 percent discounts reshaped the opportunity set, and why transaction risk often matters more than company risk in secondary markets. Jamie explains her concentrated, power-law-driven portfolio strategy, how she sources deals in an opaque and relationship-driven ecosystem, and why access, not awareness, is the true barrier in private markets. Highlights: Why 2022 to 2023 created a once-in-a-generation opportunity in venture secondaries How liquidity constraints, not fundamentals, drove massive valuation resets The difference between single-asset secondaries and portfolio acquisitions Why transaction risk, not company risk, is often the biggest constraint How Altra builds concentrated exposure to top private tech companies Creative deal structures like equity swaps and co-investment partnerships The reality of information asymmetry in private secondary markets Why late-stage private companies now resemble public market equivalents Guest Bio: Jamie Melzer is the Founder and Managing Partner of Altra Venture Partners, with over 20 years of experience across credit, public equities, and venture capital. Drawing on her background investing through multiple market cycles, she applies a public markets lens to late-stage and secondary investments in pre-IPO technology companies. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: <a href="https://www.weisburdcapital

What if the best venture returns come from the LPs that are most patient and most strategic? In this episode, I sit down with Scott Voss, Partner at HarbourVest, to explore how the $150B multi-manager firm generates consistent outperformance across venture, growth equity, buyouts, and secondaries. Scott shares how consensus risk, vintage year timing, and strategic co-investing shape returns, why continuation vehicles and evergreen structures are transforming private markets, and how long-term relationships with GPs create first-look access to top deals. Highlights: Consensus risk and why groupthink in hot sectors can distort valuations How venture returns correlate with capital deployment: less raised often equals higher performance Timing matters: investing through cycles, not just in peak years, compounds long-term alpha Continuation vehicles and secondaries as tools to capture liquidity and enhance returns Evergreen funds as a way to reduce cash drag and deliver smoother, long-term exposure Strategic GP partnerships: how trust, transparency, and co-investing unlock first-look deals Balancing diversification across funds, portfolio companies, and vintage years to reduce risk Scott’s advice: focus on alignment, persistence, and playing the long game for outsized outcomes Guest Bio: Scott is a Managing Director at HarbourVest with over 25 years of experience across the U.S. and Asia. He previously served two terms as Chair of the Global Primary Investment Committee and now focuses on venture capital, where his career began. He currently serves as Senior Market Strategist, analyzing trends across the private markets ecosystem and sharing insights through client engagement, public speaking, and thought leadership. Earlier in his career, he led international sales and distribution for Cannondale Corporation. He holds a BS from Bryant College and an MBA from Babson College. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: <a href="https://www.linkedin.com/in/dweisbur

What if building a portfolio for high-net-worth investors is more about managing downside risk than chasing returns? In this episode, I sit down with Damien Bisserier, Managing Partner and Co-CIO at Evoke Advisors, to explore how he constructs diversified portfolios for ultra-high-net-worth families. Damien shares why after-tax returns, alternative assets, and private markets matter more than concentrated US stock bets, and how behavioral insights and client-centered thinking drive long-term compounding. He also dives into venture capital, the importance of relationships, and the nuanced ways to identify managers who deliver repeatable alpha. Highlights: How incorporating multiple, uncorrelated return streams improves consistency beyond US equities Why after-tax returns are often overlooked and how understanding tax implications enhances portfolio outcomes The evolution of private credit and alternative vehicles for high-net-worth investors Venture capital as a network-driven asset class and strategies to access top-tier managers Using private markets, real estate, and active management to generate tangible alpha The importance of GP alignment, skin in the game, and repeatable sources of outperformance Marrying portfolio engineering with client comfort and behavioral considerations Timeless advice: protect on the downside, focus on compounding, and listen more to learn faster Guest Bio: Damien Bisserier is Managing Partner and Co-CIO at Evoke Advisors, recognized by Forbes as the top RIA four years in a row. He previously worked at Bridgewater, building systematic investment frameworks, and now focuses on constructing diversified portfolios that balance private and public markets, tax efficiency, and behavioral factors for high-net-worth families. Damien specializes in portfolio design, alternative assets, venture capital diligence, and aligning manager incentives to capture repeatable alpha. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: <a href="https://www.linkedin

What happens when AI turns a $40B legal software market into a $1T opportunity? In this episode, I talk with David Eckstein, CFO of Legora, about scaling one of the fastest growing enterprise AI companies in history. David explains how Legora went from zero to $100M in 18 months, why AI is expanding markets rather than just disrupting them, and how the role of CFO is evolving into a strategic operator across every part of the business. We discuss vertical vs horizontal AI, why AI companies must focus on workflows instead of prompts, and how talent density and culture become the ultimate differentiators in high growth environments. Highlights: How Legora scaled from 0 to $100M in 18 months Why legal tech is a $1T opportunity, not just $40B Vertical AI vs horizontal AI and why workflows matter Why AI expands TAM rather than just disrupting it CFO as operator, not just finance leader How AI changes pricing, margins, and business models Talent density as the most important investment Why culture and intensity drive execution speed Lessons from Box and transitioning into venture The importance of moving fast in emerging markets Guest Bio: David Eckstein is the Chief Financial Officer at Legora, where he leads financial strategy, operations, and scaling for one of the fastest growing AI companies globally. Prior to Legora, he served as CFO at Vanta and Menlo Security, helping both companies scale rapidly and raise significant capital. Earlier in his career, he held leadership roles at OpenDNS and Box, including through OpenDNS’s $635M acquisition by Cisco, and began his career in technology investment banking at Barclays Capital. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with David Eckstein: LinkedIn: <a href="https://www.linkedin.co

Is AI the biggest risk to equity portfolios or the biggest opportunity? In this episode, I talk with Christopher Vogt about how institutional investors think about risk, portfolio construction, and manager selection across public and private markets. We discuss AI disruption, why governance and structure matter more than asset labels, and how to evaluate managers using both quantitative and qualitative frameworks. Chris also shares lessons from building an endowment style portfolio from scratch, why patience matters in private markets, and how position sizing can make or break long term outcomes. Highlights: Why AI is both a major risk and opportunity across equities Concerns around SaaS disruption and software private equity Structurally higher inflation and long term interest rate outlook Organizing portfolios by risk instead of asset class Building an endowment style portfolio with conservative risk Quant vs qualitative manager selection Why models are useful but always flawed Reference calls as the most important diligence tool Culture and turnover as leading indicators of manager quality Vintage diversification and capital pacing in private markets The reality of longer venture fund durations Quant strategies vs fundamental investing in public markets Why position sizing matters more than being right Guest Bio: Christopher Vogt is an institutional investor at the Margaret A. Cargill Philanthropies where he oversees public and private equity investments. He has extensive experience across asset allocation, manager selection, and portfolio construction, with a focus on building long term, endowment style portfolios. His approach combines quantitative rigor with deep qualitative judgment, emphasizing governance, culture, and risk management as key drivers of investment success. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the market intelligence platform trusted by 85% of the S&P 100 that helps you make confident, data-driven decisions faster than your competitors. With powerful search capabilities designed for hedge funds, mutual funds, and private equity investors, AlphaSense gives you the edge to elevate your research. Visit: alpha-sense.com/howiinvest. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Christopher Vogt: LinkedIn:<a href="https://www.linkedin.com/in

What does investing look like in a world dominated by AI? In this episode, David Weisburd talks with Alex Wissner-Gross about the profound implications of technological singularity and the evolution from LLMs to reasoning models. They discuss AI personhood, economic rights, and the rise of AI agents, as well as strategic investment approaches in a post-singular world. The conversation delves into Elon Musk's visions for massive compute capabilities, the role of science fiction in predicting technological advancements, and strategies to prevent technological unemployment. The episode concludes with a look towards the future and a call to action for listeners. Highlights: Why Alex thinks AGI may already be here and the singularity is underway Recursive self-improvement and AI building smarter AI The move from LLMs to reasoning models and its impact on science and math How AI agents already dominate parts of the economy Humans as front-ends for AI—the “secret cyborg effect” A post-scarcity world as intelligence, energy, and labor costs approach zero Rethinking investing when traditional economic assumptions fail AI rights, economic personhood, and the need for agent bank accounts Why the most transformative future companies may resemble science fiction A vision where individuals run billion-dollar AI-powered companies Guest bio: Dr. Alexander D. Wissner-Gross is an award-winning computer scientist, entrepreneur, and investor, serving as Founder and Managing Partner of Reified and a former instructor at Harvard and MIT. He has earned numerous honors, authored dozens of publications and patents, and has been involved in over 40 technology companies. A top MIT graduate and Harvard Ph.D. in Physics, his work spans AI, machine learning, and cyber-physical systems. He is also a thought leader, author, TED speaker, and podcast host whose work has been widely recognized and featured globally. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twi

Is private equity becoming an asset gathering business instead of a performance business? In this episode, I talk with Sam Tidswell-Norrish, Partner at Access Holdings, about how private equity is evolving across sourcing, value creation, and distribution. We discuss why performance is still the core product, how AI is reshaping deal flow and portfolio operations, and why the lower middle market remains one of the best places to generate alpha. Sam also shares how culture, curiosity, and relationships drive long term success in an increasingly competitive and automated industry. Highlights: Why performance should remain the core product in private equity The three layers of innovation across sourcing, value creation, and operations How AI is changing deal sourcing and portfolio management Why the lower middle market offers stronger alpha opportunities The role of culture in driving innovation inside firms Why curiosity is an underrated trait in investing Relationships as the ultimate long term advantage Guest Bio: Sam Tidswell-Norrish is a Partner at Access Holdings, a private equity firm focused on essential services in the lower middle market. He is a member of the investment and executive committees and works across sourcing, investing, and value creation. Prior to Access, he was part of the founding team at Motive Partners, a private equity firm focused on financial technology. He is also the founder of OPUS, a global community for early stage entrepreneurs, and an active investor across technology and private markets. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Sam Tidswell-Norrish: LinkedIn: https://www.linkedin.com/in/samtidswellnorrish/</a

What if your family office could invest like a founder and a VC at the same time? In this episode, I sit down with Shane Neman, founder of a multi-entity family office with $850M AUM, to explore how he approaches venture investing, deep tech, and portfolio construction. Shane shares how his two decades as a SaaS founder shape his edge as an investor, why transparency and founder relationships matter more than fund mandates, and how he balances high-conviction bets with a rational family office lens. He also dives into frontier tech, co-invest structures, and building a diversified yet opportunistic portfolio. Highlights: Why being a founder gives him insight most VCs lack How investing personal capital changes risk appetite and alignment The case for radical transparency in co-investing and syndicates Why he focuses on emerging managers for outsized exposure and insight How he structures “barbell” portfolios across deep tech and durable businesses Lessons from early crypto, AI, and frontier tech investing How portfolio construction balances spiky alpha with long-term growth Why founder relationships often trump pro rata rights in venture deals Guest Bio: Shane Neman is the founder of a multi-entity family office investing across venture, crypto, frontier tech, and real assets. Formerly a SaaS founder, Shane leverages his operational experience and technical background to identify exceptional companies, co-invest with emerging managers, and structure high-conviction, founder-aligned investments. His portfolio combines early-stage moonshots with resilient businesses, reflecting a thoughtful approach to alpha generation and family office growth. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Shane Neman:

Why buy an office when everyone else is selling? In this episode, I sit down with Tim Barrett, CIO of the Texas Tech University Endowment, to explore how he builds high-conviction portfolios across private equity, real estate, and hedge funds. Tim shares why governance, manager selection, and a generalist team structure drive consistent alpha, how he balances risk and upside with portable alpha, and why lower middle market investments can outperform flashy venture deals. He also dives into building team culture, aligning incentives, and using the endowment’s size and flexibility to access niche opportunities others can’t. Highlights: Why Tim sees opportunity in trophy office assets despite negative headlines How governance authority lets the team move fast and capture alpha Why lower middle market buyouts offer consistency over venture capital The role of manager selection, partnerships, and co-investment asymmetry How portable alpha works and why true alpha justifies hedge fund fees Why generalist teams improve total portfolio management and risk-adjusted returns How team culture and incentive design drive collaboration and long-term performance Guest Bio: Tim Barrett is the Chief Investment Officer at the Texas Tech University Endowment, overseeing public and private markets with a focus on private equity, credit, real estate, and hedge funds. With over 30 years in endowment and institutional investing, he emphasizes governance, manager partnerships, and team culture to drive consistent, risk-adjusted returns, while leveraging the endowment’s size and flexibility to access niche opportunities unavailable to larger allocators. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the market intelligence platform trusted by 85% of the S&P 100 that helps you make confident, data-driven decisions faster than your competitors. With powerful search capabilities designed for hedge funds, mutual funds, and private equity investors, AlphaSense gives you the edge to elevate your research. Visit: alpha-sense.com/howiinvest. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Tim Barrett: LinkedIn: https://www.linkedin.com/in/tim-barrett-cfa-45575528/ Questions or topics you want us to discuss on How I Invest? Email us at davi

Why do most institutional investors still allocate heavily to large private equity funds? Alex Abell of RCP Advisors explains why the lower middle market has consistently outperformed, driven by less competition, faster exits, and stronger value creation. He breaks down the structural reasons LPs stay in large buyouts, including access constraints, manager selection difficulty, and career risk. The conversation also covers how top LPs evaluate managers, what actually predicts performance, and where alpha exists in private markets today. Highlights: Why lower middle market private equity often outperforms large buyouts over decades How manager selection, pattern recognition, and “superpowers” drive repeatable returns The structural advantages of smaller funds and family-owned company transactions Why size can be the enemy of returns and disciplined capital deployment matters How first-time and emerging managers can create alpha despite limited track records The role of premium economics, fund discounts, and alignment in incentivizing performance Why thorough LP diligence, reference checks, and on-site visits are critical to uncovering top managers Alex’s approach to benchmarking deals, evaluating operational improvements, and measuring true outcomes Guest Bio: Alex Abell is the Managing Partner at RCP Advisors, a private equity firm managing about $19 billion in assets. With over 20 years of experience as a limited partner, including at Hewlett Packard’s pension fund, Alex specializes in identifying high-performing managers in the lower middle market. He focuses on fund selection, evaluating emerging and established managers, and analyzing deal performance to uncover consistent alpha in private equity investments. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected]. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www