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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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- 2 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.
- 2 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.
- 2 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.
- 3 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.
- 3 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.
- 3 weeks ago1h 2m
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.
- 4 weeks ago53 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.
- Oct 12, 20261h 16m
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.
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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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