Podcast
How I Invest with David Weisburd
Hosted by David Weisburd · EN
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
277episodes
Episodes
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E380: How Billionaire Family Offices Actually Invest
Today00:45:52Summary readyWhat 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 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 Eric Becker: LinkedIn:https://www.linkedin.com/in/ebecker1/ 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 Billionaire Founders Were Disappointed by Private Banks (3:45) The Hidden Conflicts Inside Traditional Wealth Management (7:16) How Crescent Avoids the Incentive Problems Most RIAs Have (9:30) What Family Offices Actually Do Beyond Investing (15:05) Why “Wealth Preservation” Often Fails by the Third Generation (18:13) The Most Underrated Alpha in Investing: Structure and Taxes (22:25) The Asset Classes Smart Family Offices Are Quietly Buying (28:40) What 200-Year-Old Companies Understand That Startups Don’t (37:56) Why Building for the Long Term Creates Faster Growth (41:21) The Strange Paradox Behind Great Founders and Wealth
Summary
E379: Why Great Investment Firms Eventually Stop Performing
3d ago00:36:57Summary readyWhat 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
Summary
E378: Why LPs Keep Selling Their Highest-Quality Funds
4d ago00:26:57Summary readyWhat 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
Summary
E377: Midas List VC: Why Most VCs Miss the Biggest Companies
5d ago00:43:30Summary readyWhat 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
Summary
E376: The $3 Trillion Liquidity Problem in Venture Capital
6d ago00:37:25Summary readyWhat 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
Summary
E375: Why Tax Alpha Could Matter More Than Investment Returns
1w ago00:47:18Summary readyWhat 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
Summary
E374: Why the Best Investors Prepare for Crashes Before They Happen
2w ago00:31:44Summary readyWhat 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
Summary
E373: What Most CIOs Get Wrong About Alpha
2w ago00:46:47Summary readyWhat 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
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E372: Why the Best Venture Investments Look Wrong Early
2w ago00:48:58Summary readyWhat 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
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E371: Midas List VC: Why AI Models Will NOT Become Commodities
2w ago00:28:43Summary readyWhat 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
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