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.
312episodes
Episodes
Newest firstAll episodes
E365: Stanford GSB Professor on Venture Capital’s Manager Incentives
May 800:47:11Summary readyWhat 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
Summary
E364: $90B Limited Partner: Why We're (Still) Bullish on Large VC Funds
May 700:39:19Summary readyWhat 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
Summary
E363: How Nigel Morris Built QED into a Fintech Powerhouse
May 600:58:43Summary readyWhat 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
Summary
E362: Why Jensen Huang Believes Physical AI will be a $50 Trillion Market
May 500:31:52Summary readyWhat 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
Summary
E361: Why Venture Capital is Not an Asset Class
May 400:42:29Summary readyWhat 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
Summary
E360: The Hardest Lessons I Learned from Building 4 Unicorns
May 100:54:13Summary readyWhat 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
Summary
E359: What Charlie Munger Taught Me About Venture Capital
Apr 3000:33:41Summary readyWhat if the real edge in venture isn’t price—but who you choose to partner with for a decade? In this episode, I sit down with Jamie Montgomery, Co-Founder and Managing Partner of March Capital, to discuss how long-term relationships, not transactions, drive venture outcomes. Jamie explains why asymmetric upside matters more than negotiating the last percentage point, how conviction and discipline shape follow-on decisions, and why understanding your own biases is critical when doubling down. We also explore capital cycles, liquidity dynamics, and how AI is forcing every company to either reinvent itself or fall behind. Highlights: Why relationships outperform transactions in venture over time The “turkey sandwich test” for choosing founders How to actually decide when to double down on a company Why most investors misunderstand capital cycles and liquidity The hidden biases that distort follow-on investment decisions How AI is forcing a full reset across portfolio companies Why venture returns come from asymmetric outcomes, not pricing The real competition for capital most VCs ignore Guest Bio: Jamie Montgomery is the Co-Founder and Managing Partner of March Capital, a leading technology investment firm focused on growth-stage companies. He previously founded Montgomery & Co., where he advised and financed hundreds of companies and took dozens public, building deep experience across capital markets and entrepreneurship. At March Capital, he has led investments in category-defining companies such as CrowdStrike and ThoughtSpot, and continues to focus on backing disruptive technologies with long-term compounding potential. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at 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 Jamie Montgomery: LinkedIn:https://www.linkedin.com/in/jamiemontgomery/ 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) What Weekly Meetings With Charlie Munger Actually Taught Him (1:24) The One Investing Rule Most People Quietly Break (3:20) Why Transactional Thinking Never Builds Real Wealth (5:53) The “Turkey Sandwich Test” That Filters Great Founders (9:09) The Dangerous Bias Behind Doubling Down on Investments (11:15) How a Small Conference Became a Global Power Network (16:07) Why One Great Asset Eliminates the Need for Fundraising (17:05) The $200B Opportunity Most Investors Are Ignoring (20:55) Why Doubling the Economy Still Doesn’t Fix Inequality (27:03) The Surprising Way AI Is Saving Venture Capital (31:29) Why Venture Liquidity Might Be About to Disappear
Summary
E358: The Woman Behind the World's Top GP Brands | Jen Prosek
Apr 2900:36:35Summary readyWhat if the biggest edge in investing isn’t capital or strategy—but how clearly the world understands you? In this episode, I sit down with Jennifer Prosek, Founder and Managing Partner of Prosek Partners, to discuss how branding, narrative, and communication have become core drivers of success in financial services. Jennifer explains why firms went from ignoring marketing to depending on it, how “efficiency and preference” directly impact fundraising and deal flow, and why owned media and the “digital blink” now shape first impressions. We also explore how founders should think about storytelling, differentiation, and building long-term trust in an increasingly competitive capital landscape. Highlights: Why branding went from irrelevant to essential in finance The concept of “efficiency and preference” in fundraising Why most first meetings are actually second meetings How the “digital blink” shapes investor perception instantly Why owned media is the highest ROI strategy today The biggest mistake GPs make when going on podcasts How to compete for retail capital without massive budgets Why narrative clarity is the foundation of all marketing Guest Bio: Jennifer Prosek is the Founder and Managing Partner of Prosek Partners, a leading global marketing and communications firm specializing in financial services. She has built the firm into one of the most influential platforms in the industry, advising top asset managers, private equity firms, and financial institutions worldwide. Jennifer is also a published author, board member, and active investor in communications technology, with deep expertise at the intersection of brand, capital markets, and reputation. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at 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 Jen Prosek: LinkedIn:https://www.linkedin.com/in/jennifer-prosek/ 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 the Financial Crisis Created a Marketing Boom No One Expected (1:50) How Branding Went From Useless to Mandatory Overnight (3:49) The Real Reason Private Markets Are Chasing Retail Investors (5:29) How Smaller Firms Compete Against Blackstone and KKR (8:01) Why Getting on a Platform Means Nothing Without Demand (9:27) The Hidden ROI of Brand: Efficiency and Preference (12:03) Why Podcasts Are the Most Powerful Asset in Finance Today (14:50) The Biggest Mistake GPs Make Before Doing Media (16:23) The Lowest-Cost Strategy That Actually Builds a Brand (18:30) Why Your Reputation Is Now Controlled by AI
Summary
E357: CalSTRS CIO: Where Do You Invest $390 Billion Today?
Apr 2800:29:45Summary readyWhat if the biggest edge in managing $390 billion isn’t picking assets—but controlling risk and liquidity when markets break? In this episode, I sit down with Scott Chan, Chief Investment Officer of CalSTRS, to discuss how one of the largest institutional investors in the world is positioning for a period of massive structural change. Scott breaks down how AI, deglobalization, and the energy transition are driving a multi-decade investment cycle, why traditional diversification is breaking down, and how liquidity and dynamic allocation become critical in volatile markets. We also explore structural alpha, co-investing at scale, and how governance and partnerships enable CalSTRS to generate returns without taking incremental market risk. Highlights: Why stocks and bonds may no longer provide true diversification How liquidity becomes the biggest advantage during market dislocations What “structural alpha” looks like at a $390B portfolio Why infrastructure is a multi-decade opportunity How CalSTRS scaled co-investments from 2% to 30%+ of the portfolio The real edge of governance and delegated decision-making Why AI is driving a fixed asset investment boom The mistake most investors make during market recoveries Guest Bio: Scott Chan is the Chief Investment Officer of CalSTRS, one of the largest pension funds in the world with approximately $390 billion in assets under management. He previously served as Deputy CIO and now oversees a team of more than 200 investment professionals across public and private markets. Scott is a board member of the Toigo Foundation, co-chair of the Institutional Investors Roundtable, and serves on multiple advisory boards including the Milken Institute, AIMA, and CAIA, with a focus on advancing diversity and innovation in asset management. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at 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 Scott Chan: LinkedIn:https://www.linkedin.com/in/chanscott/ 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 CalSTRS Is Positioning for an Era of Extreme Uncertainty (1:40) Why the Old 60/40 Portfolio May Be Quietly Breaking (4:00) The New Assets Scott Believes Can Actually Diversify Risk (6:30) Why Regional Investing Could Matter More Than Ever (8:10) How CalSTRS Built Structural Alpha at Massive Scale (12:00) The Hidden Edge of Owning More Control in Private Markets (16:40) Why Co-Investments Became One of CalSTRS’ Biggest Advantages (21:00) Why Venture Capital Has Become Strategic for the Entire Portfolio (25:00) The Asset Class Scott Thinks Could Win the Next Decade (28:40) The Mistake CalSTRS Made When Markets Rebounded
Summary
E356: Why Co-Investments Are Taking Over Private Equity
Apr 2700:34:38Summary readyWhat if the next source of alpha in private equity isn’t funds—but individual deals? In this episode, I sit down with Rohan Parikh, Vice President at Houlihan Lokey, to discuss the rapid rise of co-investments and why they are becoming a core part of institutional portfolios. Rohan explains how extended fundraising cycles, larger deal sizes, and slower distributions have created a “perfect storm” for deal-by-deal capital, why LPs are increasingly treating co-investments as a standalone asset class, and how independent sponsors are reshaping the market. We also explore underwriting frameworks, alignment, and how relationships, not just returns, drive long-term success in this segment of private markets. Highlights: Why co-investments have doubled to a $300B+ market in just a few years The “perfect storm” driving deal-by-deal fundraising Why LPs now treat co-investments as a standalone asset class How independent sponsors are competing with traditional PE firms What separates a fund track record from a co-invest track record Why alignment is often stronger in co-investments than funds How deal vs sponsor underwriting shifts based on control The real risk of adverse selection—and how to avoid it Guest Bio: Rohan Parikh is a Vice President at Houlihan Lokey, where he focuses on direct placements and co-investment fundraising within the firm’s Equity Capital Solutions business. He previously worked at PJT Park Hill in co-investment fundraising and began his career at Citi in leveraged finance. Rohan specializes in structuring and raising capital for sponsor-backed single-asset transactions and works closely with GPs and LPs across private markets. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at 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 Rohan Parikh: LinkedIn:https://www.linkedin.com/in/rohan-parikh-214818109/ 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 Co-Investments Are Exploding in Private Equity (2:04) The New Asset Class LPs Can’t Ignore (4:55) Why Blue-Chip Investors Are Becoming Independent Sponsors (6:30) The Alignment Signal LPs Care About Most (7:27) What Makes a Co-Investment Worth Taking Seriously (10:56) How Independent Sponsors Pull Off $500M Deals (16:41) Why the Best Currency Between GPs and LPs Is a Deal (21:05) How LPs Avoid Getting the Worst Co-Investments (25:15) Why Co-Investments May Be More Aligned Than Funds (31:29) Why Blind Pool Funds Are Losing Their Grip
Summary