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How I Invest with David Weisburd

David Weisburd

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.

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  • #450
    Yesterday · 1 hr 5 min

    E450: Brijesh Jeevarathnam on Why Venture Is Eating Public Markets, Picking Great VCs, and the AI Boom

    What if just 7% of venture-backed companies generate all the gains, and the real skill is identifying the managers who can find them first? In this episode, I sit down with Brijesh Jeevarathnam, Partner and Global Head of Fund Investments at Adams Street Partners, to explore how institutional investors identify exceptional venture capital managers in an increasingly crowded market. Drawing on more than 20 years of experience evaluating venture and private equity funds, Brijesh explains why the best VCs think independently, how they earn access to extraordinary founders, and why past performance is often the least predictive part of manager selection. We discuss how Adams Street evaluates emerging managers, the role of information asymmetry in fund investing, and why venture capital is increasingly capturing value creation once available to public market investors. Brijesh also shares how AI is changing institutional due diligence and why the next generation of transformative AI companies may still be ahead of us. Highlights: Why the best venture capitalists see opportunities before they become consensus How the number of venture firms expanded from roughly 500 to 4,000 The three characteristics Adams Street looks for when selecting venture managers Why having a chip on your shoulder can be an advantage in venture capital How early LP commitments create lasting relationships with emerging managers Why information asymmetry remains a competitive advantage in fund investing How to identify exceptional managers before their investment returns materialize What separates founder whisperers from venture capitalists who simply provide capital Why venture capital is increasingly capturing value creation from public markets How Adams Street studies missed investments through its anti-portfolio Why just 7% of venture-backed companies generate all the gains How AI is transforming due diligence without replacing human judgment Why power-law returns may still exist in late-stage venture investing Why the AI investment cycle could still be in its earliest innings Guest Bio: Brijesh Jeevarathnam is a Partner and Global Head of Fund Investments at Adams Street Partners, a global private markets investment firm. He has more than two decades of experience evaluating venture capital and private equity managers, with a focus on identifying exceptional investment teams and building long-term institutional partnerships. Sponsor: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. **Stay Connected with David Weisburd: ** X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Brijesh Jeevarathnam: LinkedIn:https://www.linkedin.com/in/brijesh2075/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdpierce.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 Pierce. 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 Separates the World's Best Venture Capitalists? (4:28) Why Venture Capital Has Changed Dramatically in 20 Years (7:22) The Three Things Adams Street Looks for in VC Managers (12:45) How LP Relationships Create an Information Advantage (14:39) How Long Does It Take to Know if a VC Manager Is Good? (19:06) How to Identify a VC Who Can Win Over the Best Founders (27:43) Why Venture Capital Is Eating the Public Markets (38:03) How Adams Street Learns From Its Biggest Investment Mistakes (41:23) Why Just 7% of Startups Generate All the Gains (56:34) What Inning of the AI Boom Are We Really In?

    • Transcript
  • #449
    Friday · 48 min

    E449: Federated Hermes CEO on $400 Billion in Cash, the Private Markets Boom, and AI

    What if the most overlooked asset in your portfolio is the one that gives you the freedom to invest in everything else? In this episode, I sit down with Christopher Donahue, President, Chair and CEO of Federated Hermes, to explore how the firm manages approximately $700 billion in money market assets and why cash is far more than an idle allocation. Chris explains how liquidity creates financial flexibility, why trust and scale have concentrated the money market industry among a handful of firms, and what stablecoins can learn from decades of cash management. We also discuss how corporations manage their cash reserves, why AI could improve investment management without replacing employees, and how Federated Hermes plans to expand its private markets business. After more than 50 years at the firm, Chris shares the principles behind its longevity and why culture, trust, and disciplined risk-taking remain essential to building an enduring financial institution. Highlights: Why cash is one of the most misunderstood assets in an investment portfolio How Federated Hermes built a money market business managing approximately $700 billion Why liquidity, trust, and operational reliability matter more than chasing yield How regulation and size created an oligopoly in money market funds What stablecoin companies can learn from the money market industry Why Federated Hermes chose not to compete directly with its distribution partners How corporations, pension funds, and individuals should think differently about cash reserves The differences between Treasury, government, and prime money market funds Why Chris sees AI as an opportunity to improve quality rather than eliminate jobs How Federated Hermes built a culture that has endured for more than five decades Why the firm's private markets business could eventually become larger than its existing operations The importance of disciplined risk-taking and entrepreneurial confidence Guest Bio: Christopher Donahue is Chairman, President, Chair and CEO of Federated Hermes, a global investment management firm headquartered in Pittsburgh. He joined the company in 1972 and served as President and Chief Operating Officer from 1993 to 1998 before becoming CEO in April 1998.Under his leadership, Federated Hermes has expanded its investment management capabilities across money markets, equities, fixed income, and private markets while maintaining a focus on liquidity, client service, and long-term relationships. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. **Stay Connected with David Weisburd: ** X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. 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 Cash Is the Most Misunderstood Asset (2:02) How Federated Hermes Built a $700 Billion Money Market Business (3:45) Why Only a Handful of Firms Dominate Cash Management (5:39) What Stablecoins Can Learn From Money Market Funds (7:02) Why Federated Hermes Refuses to Compete With Its Customers (11:14) How Corporations Should Think About Cash Reserves (16:21) Treasury vs. Government vs. Prime Money Market Funds (20:34) How AI Is Changing the Future of Asset Management (24:38) The Secret Behind 50 Years of Leadership at Federated Hermes (37:06) Why Private Markets Could Become Federated Hermes' Biggest Business

    • Transcript
  • #448
    Wednesday · 1 hr 13 min

    E448: Gavin Ezekowitz on AI Valuations, Asymmetric Returns, and Why Great Investors Fail

    How do you invest in generational companies like Anthropic, OpenAI, and SpaceX before everyone recognizes their potential? Gavin Ezekowitz is the Co-Founder and Chief Investment Officer of BFA Global Investors, an alternative investment firm providing access to private market opportunities. In this episode, Gavin explains how BFA gained exposure to Anthropic, OpenAI, and SpaceX through GP relationships, including its early Anthropic investment at a $17 billion valuation. Highlights: - How BFA gained exposure to Anthropic, OpenAI, and SpaceX - Why Gavin invested in Anthropic at a $17 billion valuation - The investment lesson Gavin learned from missing Cursor - Why great founders can disrupt their own businesses - How to underwrite companies when future markets are impossible to predict - Why fundraising ability alone does not make a great founder - What SpaceX reveals about mission-driven leadership and exceptional talent - Why venture capital should be viewed as a 20-year asset class - How portfolio construction preserves exposure to power-law outcomes - Why pacing and position sizing matter more than predicting market cycles - How smaller venture funds can outperform larger, established firms Guest Bio: Gavin Ezekowitz is the Co-Founder and Chief Investment Officer of BFA Global Investors, an alternative investment firm focused on delivering outstanding returns through disciplined processes and trusted relationships. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Gavin Ezekowitz: LinkedIn:https://www.linkedin.com/in/gavin-ezekowitz-966a29a/ 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 Pierce. 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 Gavin Invested in Anthropic, OpenAI, and SpaceX (1:08) Why Gavin Invested in Anthropic at a $17 Billion Valuation (3:52) The Investing Lesson Gavin Learned From Missing Cursor (10:42) How Do You Value a Generational AI Company? (14:08) Are the Best Founders Capital Magnets? (23:54) What SpaceX Reveals About Great Technology Entrepreneurs (28:39) Why Portfolio Construction Matters More Than Market Timing (34:20) Can Small Venture Funds Outperform the Biggest Firms? (41:54) Why the Best Investors Make Concentrated Bets (53:14) What Separates Exceptional Venture Capital Managers?

    • Transcript
  • #447
    October 26 · 1 hr 3 min

    E447: Anthropic at $2 Trillion? The AI Bubble, and Why the Best Startups Always Look Overvalued

    Are venture capitalists overpaying for the next generation of AI winners? Matthew Harris is a Partner at Bain Capital Ventures, where he invests in financial services and technology companies. In this episode, Matthew explains why the best venture investments often look overpriced, how valuation discipline can cause firms to miss power-law winners, and why today's AI market is increasingly driven by consensus. Highlights: - Why Bain Capital Ventures historically struggled to capture some power-law outcomes - How valuation discipline can cause investors to miss exceptional companies - Why the best startups often appear overpriced at every funding round - How consensus investing is changing venture capital - Why Matthew believes there are still undiscovered AI winners - The two investment themes driving Bain Capital Ventures' recent strategy - How AI-native services companies could disrupt insurance, law, and other industries - Why OpenAI and Anthropic may avoid competing directly with their largest customers - How access to compute could determine the next AI leader - Whether Anthropic could justify a $2 trillion valuation - Why AI agents could expand the market beyond eight billion human users - How consistent investment pacing protects against venture market cycles - Why personal agency matters more as AI makes knowledge and tools widely accessible Guest Bio: Matthew Harris is a Partner at Bain Capital Ventures, where he focuses on investments in financial services and technology. His investment interests include payments, specialty lending, fintech, asset management, trading systems, and insurance. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Matthew Harris: LinkedIn:https://www.linkedin.com/in/mattcharris/?isSelfProfile=false 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 Pierce. 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 Bain Capital Ventures Missed Some Power-Law Winners (3:13) Why the Best Startups Always Look Overvalued (6:51) Are There Still Diamonds in the Rough? (10:14) How AI Is Changing Bain Capital Ventures' Investment Strategy (16:10) Why AI-Native Services Could Beat Traditional Software (22:19) Will Compute Determine Who Wins the AI Race? (29:03) Is Anthropic Worth $2 Trillion? (36:12) Why AI Agents Could Expand the Market Beyond Eight Billion People (49:02) Are We in an AI Investment Bubble? (53:48) The Most Important Skill for Surviving the AI Era

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  • #446
    October 23 · 58 min

    E446: Vista Equity President: The Death of SaaS? AI Agents and the $3 Trillion Opportunity

    Is AI destroying the software industry, or creating its biggest investment opportunity yet? David Breach is President of Vista Equity Partners, a firm managing approximately $100 billion in assets. In this episode, David explains why the recent selloff in software stocks may be missing a much larger opportunity: AI-powered digital workers. We explore Vista's repeatable playbook for creating value in enterprise software, why mission-critical products and proprietary data remain competitive advantages, and how AI could expand software's addressable market into trillions of dollars in services. David also shares how Vista evaluates software companies amid AI disruption, why incumbents may be better positioned than startups to deploy AI agents, and the career lessons that took him from selling juice to leading one of the world's largest software-focused private equity firms. Highlights: - Why David left Kirkland & Ellis to help build Vista Equity Partners - How Vista grew from $13 billion to approximately $100 billion in AUM - The four pillars of Vista's repeatable software value creation playbook - Why David believes the SaaS selloff doesn't reflect software's long-term opportunity - How AI agents could unlock a $3 trillion services market - Why existing software companies may have an advantage over AI-native startups - The three characteristics Vista looks for in mission-critical software - Why recent customer retention data matters more than historical performance - How proprietary data and industry expertise create defensible competitive advantages - Why cybersecurity and data protection are central to enterprise AI adoption - How Vista approaches diversification and portfolio construction - The career lesson David believes matters more than intelligence or talent Guest Bio: David A. Breach is President of Vista Equity Partners. He serves on the investment committees for Vista's Flagship, Foundation, Endeavor and Perennial Funds and is Co-CEO of VistaOne, the firm's evergreen private equity vehicle. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with David Breach: LinkedIn:https://www.linkedin.com/in/david-breach/ 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 Pierce. 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 David Left Kirkland & Ellis to Join Vista Equity Partners (3:41) The Vista Playbook for Creating Value in Software Companies (7:12) Is AI Making Software Uninvestable? (11:08) Why AI Could Trigger a Major Revaluation of SaaS Companies (14:00) Will OpenAI and Anthropic Replace Enterprise Software? (20:03) The Three Things Vista Looks for in Software Investments (26:23) How AI Is Changing Software Investment Due Diligence (35:20) Why Data Security Could Determine the Winners in AI (41:13) How Vista Constructs Its Private Equity Portfolios (49:34) From Selling Juice to Leading Vista Equity Partners

    • Transcript
  • #445
    October 21 · 1 hr 1 min

    E445: AngelList: Why Picking Winners Is the Wrong Way to Invest in Startups

    What if the biggest advantage in venture capital isn't picking winners, but getting access to them? Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. Drawing on AngelList's extensive venture investment data, Erik explains why seed and growth investing operate like two different asset classes, why the best startups often command higher valuations from the beginning, and how access drives venture returns. We explore the power law, why doubling down on winners matters, the two strategies for building successful venture portfolios, and the challenges of selling investments in breakout companies. Erik also discusses how USVC aims to expand access to private markets as companies like OpenAI, Anthropic, and SpaceX create enormous value before going public. Highlights: - Why Erik believes venture capital is actually two different asset classes - Why access may matter more than picking winners at the seed stage - What AngelList's data reveals about startup valuations and future returns - Why venture's power law makes portfolio concentration so important - How the "Cathedral and Bazaar" framework explains winning VC -strategies - Why the middle market of venture capital may face structural challenges - How LPs can identify emerging managers with a genuine access advantage - Why investing across vintages matters more than timing the market - What Erik learned from an investment in Anthropic that was sold too early - Why selling shares can damage a VC's relationship with founders - Why individual investors struggle to access private-market value creation Guest Bio: Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. With more than eight years at AngelList, Erik works at the intersection of venture capital, investment management, and private-market access. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Erik Syvertsen: LinkedIn:https://www.linkedin.com/in/erik-syvertsen-334b1138/ 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 Pierce. 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 Actually Two Different Asset Classes (2:32) What AngelList's Data Reveals About Startup Valuations (5:21) Why Access Matters More Than Picking Winners (12:50) The Power Law Behind Venture Capital Returns (17:33) The Cathedral and Bazaar Model of Venture Investing (24:59) How to Find Emerging Managers With an Access Advantage (28:08) How Many Startup Investments Does It Take to Find a Winner? (32:15) The Anthropic Investment Erik Wishes He Had Held (38:08) Why Retail Investors Are Missing Private-Market Wealth Creation (52:54) How USVC Plans to Expand Access to Venture Capital

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  • #444
    October 19 · 53 min

    E444: NEPC President on AI Portfolio Risk, Finding Top Funds, and Preparing for a Downturn

    What if the biggest advantage in institutional investing isn’t finding better managers, but building an organization that can make better decisions over decades? In this episode, I sit down with Tim McCusker, President of NEPC, which advises on approximately $2 trillion in assets, to discuss what separates the best institutional investors from everyone else. Tim explains why even sophisticated endowments and pension funds fall into peer-driven investing, how governance and incentives shape long-term returns, and why the strongest allocators are willing to invest when others are retreating. Highlights: - What advising on nearly $2 trillion reveals about institutional investing - Why sophisticated investors still fall into herd behavior - How governance and investment committee support can determine long-term returns - Why the best LPs stay committed to managers during market downturns - How endowments and pension funds construct portfolios differently - Why the best co-investment programs focus on manager selection rather than re-underwriting every deal - Why venture capital deserves a place in portfolios beyond its return potential - How AI concentration, changing correlations, and portable alpha are reshaping portfolio risk Guest Bio: Tim McCusker is President of NEPC, an institutional investment consulting firm advising on approximately $2 trillion in assets across more than 400 clients, including pension funds, endowments, foundations, and healthcare organizations. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Tim McCusker: LinkedIn:https://www.linkedin.com/in/tim-mccusker-76174278/ 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 Pierce. 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 Advising on $2 Trillion Reveals About Investing (3:07) The Biggest Mistake Sophisticated Institutional Investors Make (7:15) Why the Best CIOs Stay in Their Seats for Decades (10:10) What Separates the Top Institutional Investors? (16:00) How the Best Endowments Construct Their Portfolios (20:14) The Biggest Mistake LPs Make in Co-Investments (25:48) How NEPC Finds the Next Generation of Venture Managers (31:22) Why Venture Capital Belongs in Institutional Portfolios (36:33) Is Portable Alpha Worth the Risk? (43:34) Why AI Concentration Keeps Tim Up at Night

    • Transcript
  • October 16 · 1 hr 2 min

    E443: Why the Next Trillion-Dollar Startup Won’t Be a Software Company

    What if AI makes software abundant and shifts venture capital’s biggest opportunities into the physical world? Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing across robotics, defense, energy, manufacturing, and other physical industries. Leo explains why AI is commoditizing software, why hardware may capture more value as a result, and why some of the best opportunities are hiding in industries with almost no startup competition. We also discuss how to underwrite deep tech before revenue, what separates exceptional founders, the infrastructure bottlenecks created by AI, and why the biggest risk to deep tech may be its dependence on continued funding. Highlights: - Why the best companies and investors need a lane uniquely their own - Why quantity of meetings can improve venture investment quality - How AI growth is changing the definition of exceptional traction - Why deep tech companies have a completely different revenue curve - What separates the best venture capitalists from average investors - Why Leo believes hardware investing is becoming more attractive - How to evaluate deep tech companies years before meaningful revenue - Why hardware may not be as capital intensive as investors assume - The founder traits that matter most when building physical products - Why Leo is cautious on investing directly in humanoid robotics Guest Bio: Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing 500K–1M in companies across robotics, bio, defense, energy, manufacturing, and other physical industries. He previously co-founded Susa Ventures, an early investor in companies including Robinhood, Flexport, and Stord. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest. AlphaSense: 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 alpha-sense.com/howiinvest to learn more. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Leo Polovets: LinkedIn:https://www.linkedin.com/in/lpolovets 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 Best Investors Need Their Own Lane (2:05) Why More Meetings Can Make You a Better Investor (6:14) What Separates the Best Venture Capitalists? (10:03) Why Leo Is So Bullish on Hardware (12:31) How Do You Underwrite a Deep Tech Startup? (16:08) Is Hardware Really More Capital Intensive? (22:38) Where Are Deep Tech’s Most Underrated Opportunities? (33:28) What Separates the Top 0.1% of Founders? (41:28) Why Leo Is Cautious on Humanoid Robotics (56:26) The Investing Lesson Leo Learned the Hard Way

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  • #442
    October 14 · 53 min

    E442: Nelson Mills on Building a $100 Billion Company, the China Threat, and the Future of War

    What happens when autonomous underwater vehicles become cheap enough to manufacture at scale? Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. Nelson explains why undersea autonomy has lagged aerial drones, how advances in AI, navigation, manufacturing, and autonomy are changing the economics, and why Vatn is building lower-cost systems designed to operate at scale. We also discuss raising $85 million for a hardware startup, the rise of asymmetric warfare, lessons from Anduril, and what it takes to build a new defense prime. Highlights: Why Nelson left venture capital to become a founder Why undersea autonomy is finally reaching an inflection point The navigation and communications problems that make underwater technology so difficult How Vatn raised its first $2 million pre-seed round in just 30 days Why hardware founders should start with the smallest viable version of their product Vatn’s plan to become a focused defense prime for the undersea market What Anduril proved about building defense technology differently How lower-cost underwater vehicles could change deterrence for smaller countries The biggest hiring lesson Nelson learned as a founder Why founders should always be building relationships for their next round Guest Bio: Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. After growing up on the water and spending roughly nine years operating at startups, Nelson moved into venture capital before leaving to build Vatn. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. **Stay Connected with David Weisburd: ** X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Nelson Mills: LinkedIn:https://www.linkedin.com/in/millsn/ 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 Pierce. 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 Growing Up on a Sailboat Led to Vatn Systems (1:18) Why Nelson Left Venture Capital to Become a Founder (6:08) Why Undersea Autonomy Is Finally Having Its Moment (8:20) What Needs to Happen for Underwater Drones to Scale? (11:13) How Do You Build a Company Everyone Says Is Impossible? (12:41) How Vatn Raised $2 Million on a Dream (20:53) How Vatn Went From Pre-Seed to $85 Million Raised (21:48) Can Vatn Become the Next Defense Prime? (27:42) How Defense Technology Could Change Global Deterrence (45:21) The Advice Nelson Would Give Himself as a First-Time Founder

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  • #441
    October 12 · 1 hr 16 min

    E441: Startup Investing When the Cost of Building Goes to Zero

    What if AI makes the founder more important, not less? John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented. John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented. Highlights: - Why John now believes the founder matters more than ever - The unusual question he uses to understand a founder’s emotional connection to their company - Why betaworks chose the venture studio model instead of a traditional fund - How betaworks combines accelerator programs with pre-seed investing - Why John focuses on proximity to products instead of traditional pattern matching - How AI is changing founders from builders into “steerers” - What betaworks saw in Hugging Face before transformers changed AI - Why John believes open and closed AI models need to coexist - The AI risks John thinks deserve more attention than existential risk Guest Bio: John Borthwick is the Founder of betaworks, which he founded in 2008 as a startup studio for building and investing in early-stage consumer technology companies. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with John Borthwick: LinkedIn:https://www.linkedin.com/in/jborthwick/ 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 Pierce. 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 John Now Believes Founders Matter More Than Ever (1:36) The Question John Uses to Identify Exceptional Founders (7:34) Why Betaworks Chose a Venture Studio Over a Traditional Fund (13:42) How John Finds 100x Venture Investments (15:45) Why AI Is Making Founders More Important (21:30) How Betaworks Found Hugging Face Before the AI Boom (29:03) Why Open-Source AI Still Matters (40:14) Why John Believes AI Was Discovered, Not Invented (56:13) Where the Biggest AI Opportunities Are Emerging (1:01:10) How to Make Your Career Antifragile to AI

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  • #440
    October 9 · 1 hr 3 min

    E440: What Steve Jobs Taught Me About Great Founders

    What did Steve Jobs understand about building great companies that most founders miss? Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm based in New York City. Drawing on more than two decades as an operator and investor, including his time at Apple and Foursquare, Steven shares what he learned working directly with Steve Jobs, how he separates ambitious founders from delusional ones, what drew Oceans to Etched, and why AI is creating a technology cycle unlike anything he has seen before. Highlights: Why great technology companies always start with exceptional people How Steven separates founder ambition from delusion What great founders understand about attracting world-class talent What Steven learned from working directly with Steve Jobs Why Steve Jobs obsessed over details most CEOs would ignore How Apple sold $60 million of advertising before the product was live Why the founders of Etched immediately stood out The founder traits that remain constant across every technology cycle Why AI is moving faster than previous technology revolutions Why Steven believes both enormous winners and failures are coming What Foursquare taught him about valuations and paper gains Guest Bio: Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm headquartered in New York City. Previously, he held senior operating roles at Foursquare and Apple, joining Apple after its acquisition of Quattro Wireless. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Steven Rosenblatt: LinkedIn:https://www.linkedin.com/in/stevenrosenblatt/ 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 Pierce. 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 Great Technology Companies Have in Common (2:47) How to Separate Ambition From Delusion (6:57) What Steven Learned Working With Steve Jobs (16:10) What Steve Jobs Understood About Building Companies (27:26) How Apple Changed Steven as a Leader (37:30) What Made the Founders of Etched Stand Out (42:18) Do the Rules for Great Founders Change With AI? (47:39) Why This AI Boom Is Different From Every Previous Cycle (51:45) The Timeless Career Lesson Steven Would Give His Younger Self (55:30) Why New York Took Decades to Become a Tech Hub

    • Transcript
  • #439
    October 7 · 57 min

    E439: Ethan Thornton: The 22-Year-Old Building a $3.7 Billion Defense Company

    What if the future of warfare is determined by who can innovate faster, not who can spend more? Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company he started after dropping out of MIT. We break down how Mach went from experimenting with roughly 20 technologies to becoming a multibillion-dollar company, why Ethan believes asymmetric technology is reshaping modern warfare, and how Pentagon procurement is evolving. We also discuss China and Taiwan, lessons from Ukraine, autonomous warfare, recruiting exceptional talent, taking risk, and why Ethan believes great founders should empower their teams rather than make every decision themselves. Highlights: Why Ethan dropped out of MIT to build a defense company How Mach experimented with roughly 20 technologies before narrowing its focus Why building prototypes created an advantage over presenting slide decks How Pentagon procurement is changing for defense startups Why Ethan believes cost-plus contracting can create the wrong incentives Why venture capital matters for asymmetric technology How Mach recruits people around mission rather than persuasion Why Ethan doesn’t view Anduril as a zero-sum competitor How media fits into the strategy of a defense company Why Ethan believes founders should find people they trust and empower them What he misunderstood about “founder mode” Guest Bio: Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company focused on developing and manufacturing next-generation systems. Thornton began working on ideas for asymmetric technology as a teenager and started Mach after leaving MIT. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Ethan Thornton: LinkedIn:https://www.linkedin.com/in/ethan-thornton-74417024a/ 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 Pierce. 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 Ethan Thornton Dropped Out of MIT to Build Mach Industries (2:50) How an MIT Dropout Built a Multibillion-Dollar Defense Company (5:00) Why Mach Started by Building 20 Different Technologies (6:41) How the Pentagon Is Changing Defense Procurement (12:24) Could the U.S. Deter a Conflict Over Taiwan? (25:00) How Mach Chooses Which Defense Technologies to Build (32:47) How Mach Competes for the Best Engineering Talent (39:03) Why Ethan Believes Staying at MIT Was the Bigger Risk (43:55) The Leadership Lesson Ethan Wishes He Learned Earlier (46:02) What Ethan Misunderstood About “Founder Mode”

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  • #438
    October 5 · 1 hr 16 min

    E438: Will Robbins on Elon Musk, AI & the Future of Silicon Valley

    What if the biggest edge in venture capital is identifying an exceptional founder before everyone else does? Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at formation. Previously, Will joined Contrary as its first employee and helped grow the firm to more than $250 million in AUM. In this episode, Will explains why traditional VC brands may matter less in an AI-driven world, how he identifies exceptional founders before they have traction, why the best startups often pivot, and why reputation with founders may be the most important asset a venture investor can build. Highlights: Why traditional VC brands may be losing their edge How AI could fundamentally change the economics of seed rounds Why founders may need dramatically less capital to reach product-market fit How two 17-year-old founders built Zepto into a massive retailer Why college dropouts can produce disproportionately large venture outcomes The elusive “X factor” Will looks for in exceptional founders Why a founder’s social graph can reveal signals a pitch meeting cannot Why extreme focus may be one of the most important founder traits The small group of business models behind many of venture’s biggest outcomes Why Will remains optimistic about software despite AI disruption Why 50% of Will’s successful early-stage investments pivoted The one asset Will believes matters most for a long-term venture career Guest Bio: Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at company formation. Prior to investing under his own name, Will joined Contrary as its first employee and helped grow the firm from the ground up to more than $250 million in AUM. Early-stage companies Will was responsible for backing now have a combined market capitalization of over $10 billion. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Will Robbins: LinkedIn:https://www.linkedin.com/in/whrobbins/ 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 Pierce. 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 VC Brands May No Longer Matter (5:05) What Happens to Seed Rounds When Software Gets Cheap? (10:40) How Two 17-Year-Olds Built Zepto (16:00) Why College Dropout Founders Keep Producing Outliers (21:53) What Will Looks for in Exceptional Founders (23:52) Can You Actually Identify the Founder “X Factor”? (29:20) The Founder Signal That’s Almost Impossible to Fake (41:11) Which Business Models Create Venture’s Biggest Outcomes? (54:41) Why So Many Great Startups Pivot

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  • #437
    October 2 · 41 min

    E437: Doug Beyer on Raising Capital, LP Psychology & GP Stakes

    What if the biggest opportunity in private markets isn’t backing companies—but backing the next generation of investment firms? In this episode, I sit down with Douglas Beyer, managing partner and founder of Roaring Brook Holdings, to discuss why emerging managers remain one of the most undercapitalized opportunities in alternative assets. Douglas explains how anchor capital changes fundraising dynamics, why LP relationships determine whether firms survive, and how the best emerging managers build trust through transparency and execution. We also explore GP seeding, organizational durability, and why fundraising momentum matters more than most managers realize. Highlights: Why emerging managers face a structural capital gap How anchor investors solve the “cold start” problem Why LP relationships are built years before capital is deployed The hidden importance of communication and transparency How fundraising momentum determines fund survival Why many great investors fail at building firms The difference between raising capital and building a franchise How secondary markets are reshaping private equity liquidity Guest Bio: Douglas Beyer is managing partner and founder of Roaring Brook Holdings, a firm providing seed, acceleration, and GP solutions to the next generation of private market investment firms. He spends his days evaluating opportunities where their capital, relationships, and strategic involvement can catalyze and improve the success of a firm. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Douglas Beyer: LinkedIn:https://www.linkedin.com/in/douglas-beyer-2944bb1a/ 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 Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why He Left a Prestigious Family Office to Back Emerging GPs (2:00) The Hidden Value Most Investors Miss in Asset Management Firms (5:27) Why LP Relationships Matter More Than Most GPs Realize (9:10) The Gold Standard for Managing LP Communication (14:08) The Anchor Investor Problem Breaking Emerging Managers (17:23) The Silent Risk LPs Fear Most in New Funds (22:26) Why the Best GPs Add Value Before Asking for Capital (29:26) Why Emerging Managers Still Matter in a Mega-Fund World (34:17) The One Thing Every New Fund Needs to Survive

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  • #436
    September 30 · 1 hr 7 min

    E436: Nnamdi Okike on Billionaires, Founder Psychology & the Venture Capital Bubble

    Can venture capital really be turned from instinct into science? Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he leads Seed and Series A investments in software and software-enabled companies. We discuss why Nnamdi believes venture investing is driven by the totality of an investor’s experiences rather than pure instinct, how 645 quantifies founder qualities, and why missionary and “non-central casting” founders can become exceptional investments. We also explore why startups need the right market inflections, how stablecoins and agentic commerce are reshaping fintech, what Nnamdi has learned across five fund vintages, and why raising too much capital at Seed can actually hurt a company. Highlights: Why venture investing may be more science than instinct How 645 Ventures quantifies founder potential Why Nnamdi prefers missionaries over mercenaries What separates “non-central casting” founders Why great founders still need the right market inflection Why VCs can mistake themselves for the customer How to tell whether founder confidence is actually justified Why stablecoins could transform global financial infrastructure How AI and programmable money could enable agentic commerce Why market cycles should influence venture deployment Why patience and truth-seeking are core values at 645 Ventures Why massive Seed rounds can damage startup culture Guest Bio: Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he partners with founders building vertical and horizontal software and software-enabled companies. 645 Ventures leads Seed and Series A rounds and works closely with exceptional teams as they scale toward the growth stage. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Nnamdi Okike: LinkedIn:https://www.linkedin.com/in/nnamdiokike/ 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 Pierce. 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 Investing Isn’t About Instinct (3:36) How 645 Quantifies Founder Potential (5:41) Why the Best Founders Think Differently (9:14) What Really Predicts an Exceptional Founder (13:29) The Inflection Points Behind Great Startups (17:35) The Hidden Failure Mode in Early-Stage Investing (23:51) Why Harder Markets Require Different Founders (31:53) Where Fintech’s Next Opportunities Are Emerging (44:38) The Biggest Lessons From Four Venture Funds (57:03) Why Too Much Seed Capital Can Hurt Startups

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  • #435
    September 28 · 43 min

    E435: Why Most Companies Aren’t Ready for AI

    Which competitive moats will actually survive the AI era? SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. We break down what Mighty Capital learned from mapping 550 companies by defensibility, why traditional SaaS advantages like switching costs and data moats may be weakening, and why network effects and counter-positioning are emerging as powerful AI-era moats. We also discuss why SC disagrees with the conventional power-law approach to venture, how AI is transforming M&A and corporate innovation, the Product Alpha Effect behind Mighty Capital’s investment strategy, and what venture firms must change to survive the AI transition. Highlights: What Mighty Capital learned from analyzing 550 companies Why traditional SaaS moats may no longer work in AI Why network effects and counter-positioning are gaining importance Why the IPO threshold may now be closer to $30–50 billion Why SC disagrees with the conventional power-law approach to venture How AI is shifting M&A from financial engineering to product innovation Why the best companies treat leaders like resource allocators How the Product Alpha Effect turns product innovation into investment alpha How Mighty Capital uses signals from 600,000 product builders The two metrics SC believes investors should watch in AI companies Why AI could force companies to reinvent distribution Which venture capital firms could survive the AI transition Guest Bio: SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. She co-founded Mighty Capital around the Product Alpha Effect, a data-backed framework for investment outperformance, and has invested in companies including Amplitude, Netskope, and Groq. Earlier in her career, SC built products at Meta and Siebel Systems and authored an award-winning book on what makes a great product. She is a Stanford GSB alum, Kauffman Fellow, YPO member, and graduate of CentraleSupélec. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with SC Moatti: LinkedIn:https://www.linkedin.com/in/scmoatti/ 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 Pierce. 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) Which Moats Actually Survive AI? (1:37) How SC Stays Disciplined on Valuation (4:55) Why Power-Law Investing Can Become a Constraint (6:32) How AI Is Rewriting the M&A Playbook (14:11) The Product Alpha Effect Behind Mighty Capital (17:47) The Two AI Metrics Investors Should Watch (21:43) Why AI Could Reinvent Distribution (24:11) What Makes a Great Product in the AI Era? (30:30) Which Venture Firms Will Survive AI? (36:20) The Advice SC Would Give Her Younger Self

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  • #434
    September 25 · 1 hr

    E434: Warren Gibbon on How AI is Changing the Private Markets

    Are private markets still positioned to outperform public markets? Warren Gibbon is a Multi-Family Office Chief Investment Officer with deep experience across asset allocation, equity research, and portfolio management. We discuss why investors may need to re-underwrite their assumptions about private markets, how higher rates and growing competition have changed private equity, and why public-market earnings growth may be underappreciated. Warren also explains why he is more constructive on venture, what he looks for in emerging managers, the risks created by passive investing, and how he would deploy $100 million of fresh capital today. Highlights: Why investors should re-underwrite the case for private markets. What the endowment model’s historical returns may be hiding. Why Warren believes public-market value creation is underestimated. The risk behind today’s massive AI infrastructure spending boom. Why private equity faces a much harder environment going forward. How passive investing may be changing the behavior of public markets. Why “boring and hard” investments can remain structurally underfunded. How Warren would deploy $100 million of fresh liquidity today. Guest Bio: Warren Gibbon is a Multi-Family Office Chief Investment Officer with 14 years of investment management experience and a focus on U.S. and global equities. His expertise spans asset allocation, equity research, portfolio management, investment analysis, and valuation, with additional interests in behavioral finance and the construction of diversified portfolios across public and private markets. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest. AlphaSense: 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 alpha-sense.com/howiinvest to learn more. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Warren Gibbon: LinkedIn:https://www.linkedin.com/in/warren-gibbon-cfa/ 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 Pierce. 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) Will Private Markets Still Outperform? (4:00) Is the AI Spending Boom Sustainable? (7:00) Why Warren Is Cautious on Private Equity (13:00) Why Venture May Be More Attractive Today (18:00) Why “Boring and Hard” Can Be a Great Investment (21:00) Is Passive Investing Breaking the Market? (27:00) Why Liquidity Could Become Your Biggest Advantage (31:00) The Problem With Portable Alpha (34:00) How Warren Thinks About Venture’s Top Firms (40:00) How He Would Invest $100 Million Today

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  • #433
    September 23 · 36 min

    E433: AlphaSense’s Chris Ackerson on AI, the Future of Finance & Finding Alpha

    What happens to financial analysts when AI can do the work they used to spend all night doing? Chris Ackerson is SVP of Product at AlphaSense, where he focuses on applying information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery. We discuss how AI is changing the analyst role, why vertical AI can outperform general-purpose models in financial research, and why proprietary data may become one of the most important competitive advantages in AI. Chris also explains why LLMs hallucinate, how AlphaSense is using AI to conduct expert interviews, where humans still create investment alpha, and why the future of financial research may look less like software and more like an AI teammate that never sleeps. Highlights: How AI is changing the role of financial analysts How AlphaSense increased banker coverage by up to 15% in one case study Why vertical AI can outperform general-purpose models in financial research Why hallucinations remain a barrier to professional AI adoption Why proprietary data could become a defining AI advantage How AI agents are conducting expert interviews and channel checks What investment bankers and hedge fund analysts may do in five years Why human judgment becomes more valuable as AI improves Where investment alpha comes from if everyone has access to similar AI Why frontier AI models are becoming more specialized, not less How AI agents could become teammates that work 24/7 Why AI companies must constantly be willing to disrupt themselves Guest Bio: Chris Ackerson is SVP of Product at AlphaSense and an experienced product leader focused on applying innovations in information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Chris Ackerson: LinkedIn:https://www.linkedin.com/in/chris-ackerson-965b1313/ 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 Pierce. 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) Will AI Replace Financial Analysts? (3:00) Why Vertical AI Could Beat General-Purpose Models (6:28) Why Do LLMs Hallucinate? (7:50) Why Proprietary Data Matters More in AI (10:58) How AI Can Interview Human Experts (14:11) What Finance Jobs Could Look Like in Five Years (17:23) If Everyone Has AI, Where Does Alpha Come From? (20:32) Why AI Models Are Becoming More Specialized (27:16) What Happens When AI Agents Work With Other Agents? (30:57) The AI Lesson Chris Wishes He Learned Earlier

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  • #432
    September 21 · 47 min

    E432: $24 Billion Investor on Private Credit, the Psychology of Winning & Fear of Failure

    Is private credit really in a bubble, or are investors looking for risk in the wrong place? Theodore “Ted” Koenig is Chairman and CEO of Monroe Capital, a $24 billion private credit firm. We break down how private credit grew from a niche alternative to a $2 trillion asset class, why financing shifted from banks to private credit after the financial crisis, and the two ways Ted believes lenders can generate alpha. We also discuss the flood of retail capital into private credit, why Monroe focuses on the lower middle market, the dangers of prioritizing AUM growth over investor returns, and the personal drive and tradeoffs behind building Monroe. Highlights: How Ted spotted the opportunity in private credit before it became an asset class. Why the financial crisis permanently shifted lending away from banks. The two ways Ted believes private credit managers can generate alpha. Why Monroe built its moat around lower middle-market companies. Why Ted expects private credit to grow from $2 trillion to $5 trillion. What the surge of retail capital means for the future of private credit. Why Ted believes the greater risk today may actually sit in private equity. The personal tradeoff Ted made while building Monroe Capital. Guest Bio: Theodore L. “Ted” Koenig is Chairman and CEO of Monroe Capital LLC. He founded Monroe in 2004 after previously serving as President and CEO of Hilco Capital LP. Ted also co-founded HOPE Chicago and has received lifetime achievement recognition from the Association for Corporate Growth Midwest and SFNet, as well as recognition from Private Debt Investor as one of the top changemakers in private credit. He earned a B.S. in accounting with high honors from Indiana University’s Kelley School of Business and a J.D. with honors from Chicago-Kent College of Law. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Ted Koenig: LinkedIn:http://linkedin.com/in/theodore-koenig 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 Pierce. 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 Ted Saw Private Credit Before Everyone Else (3:18) What Keeps Him Building After $24 Billion (5:30) Why the Best Entrepreneurs Never Stop Competing (9:09) The Story Behind Ted’s Relentless Drive (13:36) How Private Credit Became a $2 Trillion Market (20:50) The Only Two Ways to Generate Alpha in Private Credit (24:16) Is Private Credit Actually in a Bubble? (30:30) Why Retail Investors Are Flooding Into Private Credit (35:13) The Problem With Chasing AUM Instead of Returns (42:46) The Personal Cost of Building a $24 Billion Firm

    • Transcript
  • #431
    September 18 · 1 hr 15 min

    E431: Marty Kausas on AI, Trillion Dollar Startups & Founder Psychology

    What if the best reason to start a company isn’t to change the world, but simply because you love the game? In this episode, I sit down with Marty Kausas, CEO of Pylon, to unpack how he thinks about building an ambitious company from first principles. Marty explains why Pylon started with a goal of reaching $1 billion in revenue, why market size can matter more than the quality of the founding team, and why the rise of AI has pushed his definition of a generational company even higher. Highlights: Why Marty started Pylon for “fun and adventure.” Why market selection can matter more than the founding team. How Pylon’s ambition grew from $1B in revenue to a $1T valuation. Why Marty believes AI replacement is the wrong startup thesis. What it really means for a support team to “go agentic.” Why great founders may be overestimating incumbent software companies. How category creation can become a company’s biggest marketing advantage. Marty’s biggest mistake transitioning from engineer to CEO. Guest Bio: Marty Kausas is CEO and Co-Founder of Pylon, where he is building a next-generation customer support platform for B2B companies and helping support teams transition toward agentic workflows. Before founding Pylon, Marty held an engineering role at Airbnb, invested through Andreessen Horowitz’s scout fund, and completed software engineering internships at Yelp and Qualcomm. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest. AlphaSense: 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. AlphaSummit Discount Code: AS26HII50 Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Marty Kausas: LinkedIn:https://www.linkedin.com/in/martykausas/ 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 Pierce. 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 Marty Started Pylon for “Fun and Adventure” (4:00) Why Market Matters More Than the Founding Team (8:00) The Greatest Gift a Founder Can Give Their Company (12:00) Why Building a Huge Company Can Actually Be Easier (16:00) Pylon’s New Goal: Build a Trillion-Dollar Company (20:00) Why Marty Thinks AI Won’t Replace Humans (24:00) What It Really Means to “Go Agentic” (31:00) Why the Best Startup Ideas Don’t Sound Serious (36:00) The Underrated Trait Marty Looks for When Hiring (44:00) Marty’s Biggest Mistake as a First-Time CEO

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