How I Invest with David Weisburd

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 david@weisburdcapital.com . 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 Luke Sarsfield: LinkedIn: https://www.linkedin.com/in/luke-sarsfield/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The Asset Management Incentive Problem Ridgepost Is Trying to Fix (1:31) Why Carry Creates Better Investors Than Management Fees (3:03) The Hidden Correlation Risk Inside Private Equity Portfolios (4:45) Why Public Markets Assign Almost Zero Value to Carry (7:09) The Surprising Reason Great Managers Eventually Scale Anyway (9:38) Why Finance Quietly Rewards Short-Term Thinking (12:33) How a Public Company Can Still Think in Decades (17:57) What Asset Management Firms Are Actually Worth Today (23:33) The Common Pattern Across Every Great Asset Manager (31:53) The Most Important Career Decision Most People Get Wrong

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 david@weisburdcapital.com . 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 Levitt: LinkedIn: https://www.linkedin.com/in/ryan-levitt/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Secondaries Quietly Outperform Traditional Buyouts (2:22) The Hidden Problem Breaking Modern Buyout Returns (4:14) The DPI Crisis Forcing LPs Into the Secondary Market (7:45) Why LPs Sell Their Best Assets Instead of Their Worst (9:27) The Incentive Problem Quietly Driving Secondary Deal Flow (11:33) Where the Best Secondary Opportunities Exist Right Now (14:18) The Real Source of Alpha in Secondaries: Information and Access (18:37) Why There Still Isn’t Enough Capital in the Secondary Market (22:03) How ICG Scaled to $127B Without Burning GP Relationships (25:16) The Career Advice That Matters More Than Compensation

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 david@weisburdcapital.com . 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 Niko Bonatsos: LinkedIn: https://www.linkedin.com/in/bonatsos/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why 50% of Venture Profits Are Made Before a Market Has a Name (2:27) Why Most VCs Are Just Following the Herd (3:30) The Brutal Reality of Scaling Early-Stage Venture (5:14) How He Finds Markets Before Anyone Else Believes (6:26) What Makes a Founder a “Freak” (8:43) Why Most Smart VCs Don’t Take Enough Risk (12:41) Why AI and American Dynamism Are Already Overhyped (16:51) The Contrarian Founder Archetype Most VCs Ignore (21:30) Why Nobody Wants to Fund Gaming Right Now (36:13) The Biggest Problem Inside Venture Capital Today

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 david@weisburdcapital.com . 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 Jared Carmel: LinkedIn: https://www.linkedin.com/in/carmel/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The $3 Trillion Problem Locked Inside Venture Capital (1:18) Why Great Companies Stay Private for 20 Years (2:41) Why DPI Suddenly Matters More Than IRR (5:16) How the Secondary Market Became Institutional (7:48) The Hidden Risk in Retail Secondary SPVs (12:29) How MVP Competes in One of the Hardest Markets (14:45) Why Continuation Vehicles Could Fix Venture’s DPI Problem (19:04) The Trust That Built a $3B Secondary Platform (26:47) What MVP Could Become in 10 Years (28:12) The Advice That Would Have Changed Everything

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 david@weisburdcapital.com . 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 Brent Sullivan: LinkedIn: https://www.linkedin.com/in/brntsllvn/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Tax Alpha Became the “Boring” Edge Investors Miss (4:03) The Strategy Making Tax Loss Harvesting Explode (7:03) Where These Massive Tax Losses Actually Come From (12:28) The Biggest Players in Tax Loss Harvesting 3.0 (14:36) The Hard Part No One Talks About: Unwinding the Trade (19:39) Why Some Families Never Unwind These Strategies (23:12) The Hedge Fund Tax Strategy Quietly Gaining Momentum (29:15) How Tax Alpha Strategies Can Fail (36:54) Why Tracking Error Isn’t Always a Bad Thing (43:11) Why He Wishes He Went Independent Much Earlier

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 david@weisburdcapital.com . 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 Doug Hanly: LinkedIn: https://www.linkedin.com/in/doughanly/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Short-Term Government Bonds Are His Favorite Asset Class (3:41) The Contrarian Advantage of Holding Cash During Crashes (7:17) Why Asset Management Is Basically Exposure Therapy (10:01) The Slow-Motion Strategy That Protects LPs From Disaster (13:06) Why Smaller Funds Often Generate More Alpha (17:43) The Hidden Power of Simplicity in Investing (20:14) Why Quantity Quietly Creates Better Investors (22:25) The Surprising Benefits of a “Boring” Portfolio (25:10) The Consultant Strategy Most LPs Completely Miss (26:56) The One Simple Question That Can 10X Results

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 david@weisburdcapital.com . 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 Raphael Schorr: LinkedIn: https://www.linkedin.com/in/raphaelschorr/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The Secret Behind “Beautifully Inefficient” Markets (4:21) How Great Investors Decide Which Markets Are Worth Playing (7:54) Why Alpha Lives in “Boring and Hard” Investments (12:11) Is the Endowment Model Quietly Breaking Down? (16:08) Why Continuation Vehicles Could Reshape Private Markets (20:51) The Hidden Flaw in Traditional Private Equity Holding Periods (25:23) The Contrarian Bet That Could Define the Next Decade (29:11) Why the Best Venture Investments Always Look Wrong at First (37:28) Why Market Timing Might Be Fundamentally Impossible (43:52) The Diversification Myth Most Investors Still Believe

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 david@weisburdcapital.com . 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 Maya Bakhai: LinkedIn: https://www.linkedin.com/in/mayabakhai/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) How Kevin Durant Became an Early Silicon Valley Power Player (5:23) Why Following Tier 1 VCs Can Actually Hurt Returns (9:41) The Painful Truth About Learning to Pick Great Founders (12:59) Why “High IQ Investing” Often Misses Massive Opportunities (19:00) The Dangerous Side of Pattern Recognition in Venture (23:48) How She Made Her First Million Betting on Crocs (27:52) The Narrative Premium That Quietly Drives Venture Capital (32:42) Where Real Alpha Comes From in an AI World (41:01) The Founder Trait That Matters More Than Intelligence (43:19) The Biggest Investing Mistake She’d Never Make Again

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 david@weisburdcapital.com . 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 Hans Tung: LinkedIn: http://linkedin.com/in/hans-tung Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why He Chose Anthropic Over OpenAI (2:03) The Consumer Internet Signal Hidden Inside Anthropic (4:37) Why “Values” Can Become a Competitive Advantage (7:27) The Brutal Reality of Taking a Company Public (11:03) Why Immigrants Build So Many Billion-Dollar Companies (14:08) The VC Skill Most Investors Completely Fail At (18:25) The Problem Every AI App Founder Is Secretly Worried About (20:30) Why Physical AI Could Create Entirely New Winners (23:02) The Network Effect Hidden Inside LLMs (26:48) The “Prosumer” Pattern That Predicts Massive Companies Early

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 david@weisburdcapital.com . 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: https://www.linkedin.com/in/shangchou/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Tax Alpha Became One of the Biggest Edges for Investors (2:42) Why Volatility Makes Tax Loss Harvesting More Powerful (4:44) The Hidden Differentiator Between Tax Alpha Managers (7:27) The SpaceX Problem: Should You Ever Sell a Huge Winner? (11:13) Why Deferring Taxes Can Compound Into Massive Wealth (13:52) The Dangerous Mistake Investors Make With “Tax Strategies” (16:14) What Actually Matters When Choosing a Tax Alpha Manager (19:34) The Hedge Fund Strategy Quietly Reducing W-2 Taxes (30:34) Why Most New Tax Products Are Probably Bad Investments (35:00) How SpaceX Could Trigger One of the Biggest Passive Buying Waves Ever

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 david@weisburdcapital.com . 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 Moore: LinkedIn: https://www.linkedin.com/in/ryan-moore-7193372/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why He Walked Away From Traditional Venture Capital (1:38) The Hidden Edge in Venture Secondaries Most Investors Miss (3:13) Why Insider Investors Are the Real Competition (5:04) The Unusual Strategy of Turning 30 GPs Into LPs (7:58) Why First Investors Hold So Much Power Over Founders (10:48) The Trait That Matters More Than Ivy League Intelligence (16:22) Why Small Funds Quietly Beat Giant Venture Funds (17:23) Why He No Longer Chases Power Law Investing (21:38) The Biggest Problem With Modern Venture Capital (30:10) The One Signal That Predicts Startup Success Better Than Revenue

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 david@weisburdcapital.com . 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: https://www.linkedin.com/in/oscar-fahlgren-13654b2/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The $12B Deal Hiding in Plain Sight That No One Touched (1:00) Why Bigger Checks Mean Less Competition (Not More) (1:48) The Strategy of “Buying Complexity” for Alpha (3:12) Why Markets Miss Obvious Opportunities (5:31) The Advantage Only a Handful of Funds Actually Have (6:51) How Mubadala Writes Massive Checks Without a Massive Fund (9:59) The Model That Lets GPs Scale Without Becoming Asset Gatherers (13:21) Why the Best Partnerships Don’t Come From Competitive Processes (16:42) The Biggest Lie LPs Tell Themselves About DPI (19:23) When Continuation Vehicles Actually Make Sense (25:22) Why AI Investing Might Be the Wrong Focus Entirely

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 david@weisburdcapital.com . 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 L.R. Fox: LinkedIn: https://www.linkedin.com/in/lrfox/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why He Ignored the “Build Wealth First” Playbook (1:41) The Secret Most Investors Miss About Impact (5:06) Why Hard Problems Can Create the Biggest Returns (7:11) The Buy, Hold, Invest Framework for Building the Future (12:00) How a Brutal Childhood Became His Greatest Edge (15:50) Why Having No Safety Net Made Him More Dangerous (20:09) The One Trait That Predicts Success Better Than IQ (25:18) Why Most Family Offices Think His Portfolio Is Crazy (32:15) The AI Jobs Bet Most Investors May Get Wrong (40:24) Why He Doesn’t Think About “Cutting Losers”

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 david@weisburdcapital.com . 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: https://www.linkedin.com/in/keri-findley-4a974a10a/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Being Young Made Her a Better Trader During the Financial Crisis (2:04) The Real Edge Great Credit Investors Have (4:49) The “$100 Bill on the Ground” Trade No One Wanted (7:15) The Mortgage Bond Trade That Changed How She Invests Forever (12:39) Why You Don’t Always Need a Catalyst to Make Money (16:11) How Peter Thiel Became Her Largest LP (21:15) Why Scaling a Credit Fund Can Actually Hurt Returns (30:51) The Deal That Made Her Swear Off Equipment Financing Forever (37:07) Why One Tiny Equity Stake Can Become a Billion-Dollar Outcome (40:44) The Dangerous Trap of Trying to “Speed Run” Your Career

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 david@weisburdcapital.com . 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 Strebulaev: LinkedIn: https://www.linkedin.com/in/ilyavcandpe/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why “2 and 20 vs 2.5 and 30” Is the Wrong Question (2:43) How Higher Carry Quietly Changes Investor Behavior (4:15) The Hidden Risk Behind “Top Performing” Fund Managers (5:54) Why LPs Misunderstand Performance Persistence (8:16) The Dangerous Incentive Shift From 20% to 30% Carry (9:53) Why Great Investors Suddenly Change Strategy (Style Drift) (12:10) Venture Might Be the Only Asset Class With True Persistence (16:08) Why You Can’t Access the Best Venture Funds (Even If You Want To) (18:12) The Biggest Mistake LPs Make When Diversifying Venture (30:58) The One Bias That Destroys More VC Returns Than Bad Deals

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 david@weisburdcapital.com . 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 Nolan Bean: LinkedIn: https://www.linkedin.com/in/nolanbean/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Venture Is an “Access Class” (Not an Asset Class) (0:12) The Shift That’s Forcing Investors to Rethink Venture Strategy (2:52) Why Everyone Agrees Markets Changed—but Few Adapt (4:43) When “Asset Gatherers” Actually Start Making Sense (5:40) The Skill Gap Between $0→$100M and $100M→$1B Companies (9:04) The Real Truth Behind the DPI “Crisis” (12:40) Why Holding Winners Might Beat Chasing New Ones (14:43) The AI Risk That Could Break Venture Returns (19:09) Why Public and Private Markets Are Quietly Converging (34:48) The Strategy That Could Replace Traditional Stock Picking

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 david@weisburdcapital.com . 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 Nigel Morris: LinkedIn: https://www.linkedin.com/in/nigelwmorris/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) How Capital One Started as a “Crazy” Idea No One Believed (1:22) Why Incumbents Always Underestimate New Entrants (3:49) The Real Trait That Separates Entrepreneurs From Everyone Else (6:00) Why Big Institutions Are Designed Not to Innovate (8:55) The Hidden Advantage FinTechs Have Over Banks (10:48) Why Most Banks Don’t Understand Customer Lifetime Value (13:05) The Decision That Changed QED Forever (18:01) The Tradeoff No One Talks About When Scaling a Fund (20:43) Why Bigger Funds Usually Kill Returns (But Not Always) (23:01) The Strategy That Let QED Spot Winners Globally (53:53) How to Tell If a Founder Is a Missionary or a Mercenary

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 david@weisburdcapital.com . 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 Jacker: LinkedIn: https://www.linkedin.com/in/daniel-jacker/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The $50 Trillion Market Most Investors Still Don’t Understand (1:28) Why Physical AI Isn’t Just About Robots (3:07) The $120M Mistake Happening on Construction Sites Today (5:40) How They Turn Wireless Signals Into a “God View” of Reality (9:00) The Physics Breakthrough That Makes This Possible (12:38) How They Recruited World-Class Talent While in Stealth (17:09) Why They Stayed Quiet for 9 Years (And Why It Worked) (23:10) The Missing Dataset Blocking the Future of AI (31:48) Why Robots Will Work in Swarms, Not Alone (40:41) Where Smart Investors Should Actually Bet in Physical AI

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 david@weisburdcapital.com . 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 Sigalow: LinkedIn: https://www.linkedin.com/in/iansigalow/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Venture Capital Is Not Really an Asset Class (2:50) The Two Businesses Hidden Inside Venture Capital (4:10) Why Seed Investing Has Structural Alpha (9:44) The Builder vs Investor Split That Defines Every VC (12:38) How Greycroft Competes Against Sequoia and A16Z (16:25) Why Venture Firms Need Both Craft and Access (21:59) The Moment You Know a Startup Is Actually Working (24:15) The Rare Founder Trait AI Makes More Valuable (31:32) Why AI Could Make Companies Hire More, Not Less (37:57) How Greycroft Uses AI to Find Frontier Founders

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 david@weisburdcapital.com . 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/errikanderson/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) How He Built His Fourth Unicorn (And Why This One Is Different) (1:20) The Strategy Behind Building a “Biotech Infrastructure” Giant (3:30) Why You Should Build the Company You’d Never Want to Leave (6:00) The Real Test of Conviction: Would You Ever Sell? (10:00) Why Most Great Companies Should Stay Private Much Longer (15:00) The Hidden Advantage Private Companies Have Over Public Markets (20:00) Why Innovation Can’t Be Scaled Just by Adding Money (25:00) The Brutal Truth: Every Company Fails the Same Way (30:00) Why So Few People Actually Do the Hard Things (34:00) The Counterintuitive Rule: Quantity Creates Quality