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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E446: Vista Equity President: The Death of SaaS? AI Agents and the $3 Trillion Opportunity
Episode 446
Friday, October 23, 2026 • Duration 58:46
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.
E445: AngelList: Why Picking Winners Is the Wrong Way to Invest in Startups
Episode 445
Wednesday, October 21, 2026 • Duration 01:01:23
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.
E444: NEPC President on AI Portfolio Risk, Finding Top Funds, and Preparing for a Downturn
Episode 444
Monday, October 19, 2026 • Duration 53:44
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.
E443: Why the Next Trillion-Dollar Startup Won’t Be a Software Company
Friday, October 16, 2026 • Duration 01:02:28
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.
E442: Nelson Mills on Building a $100 Billion Company, the China Threat, and the Future of War
Episode 442
Wednesday, October 14, 2026 • Duration 53:04
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.
E441: Startup Investing When the Cost of Building Goes to Zero
Episode 441
Monday, October 12, 2026 • Duration 01:16:29
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.
E440: What Steve Jobs Taught Me About Great Founders
Episode 440
Friday, October 9, 2026 • Duration 01:03:56
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.
E439: Ethan Thornton: The 22-Year-Old Building a $3.7 Billion Defense Company
Episode 439
Wednesday, October 7, 2026 • Duration 57:05
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.
E438: Will Robbins on Elon Musk, AI & the Future of Silicon Valley
Episode 438
Monday, October 5, 2026 • Duration 01:16:57
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.
E437: Doug Beyer on Raising Capital, LP Psychology & GP Stakes
Episode 437
Friday, October 2, 2026 • Duration 41:28
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.