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How I Invest with David Weisburd: Daily Summaries Delivered
by 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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- Yesterday56 min
E451: Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia
What if the best venture capital opportunities are hiding in the 47 states Silicon Valley largely ignores? In this episode, I sit down with Jack Selby, Managing Director at Thiel Capital and an early member of the PayPal Mafia, to explore why he believes venture capital has become dangerously concentrated in Silicon Valley and overpriced AI startups. After working alongside Peter Thiel for 27 years, Jack is pursuing a contrarian strategy through Copper Sky, investing in promising technology companies outside California, New York, and Massachusetts. Jack explains why he can invest at roughly one-tenth of Silicon Valley valuations, how the next Carvana could emerge from cities like Phoenix or Milwaukee, and why venture capital's obsession with trillion-dollar outcomes may be hurting LP returns. We also discuss the hiring culture behind PayPal's extraordinary alumni network, why struggling venture firms have become zombies, and Jack's conviction that today's AI investment boom is a bubble.
- 3 days ago1h 5m
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.
- 6 days ago48 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.
- 1 weeks ago1h 13m
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.
- 1 weeks ago1h 3m
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.
- 1 weeks ago58 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.
- 2 weeks ago1h 1m
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.
- 2 weeks ago53 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.
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About How I Invest with 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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