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Bill Gurley - The Gift and The Curse of Staying Private
Invest Like the Best with Patrick O'Shaughnessy10 June 2025·1 hours 19 minutes
My guest today is Bill Gurley. Bill was the general partner at Benchmark Capital. He joins me for his sixth time on Invest Like the Best with his most comprehensive market analysis yet, examining the realities reshaping venture capital. Bill tackles the uncomfortable math underlying today's venture returns, with companies staying private for far longer. He also walks through why no one—from GPs to LPs to founders—has proper incentives to mark assets accurately, creating a system-wide coordination problem. And, we dig into the investment implications of AI as a platform shift, ranging from evaluating AI revenue quality to international competitive dynamics. Bill offers crucial perspective on playing the game both as it exists today and as it may evolve. Please enjoy my conversation with Bill Gurley.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform.
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This episode is brought to you by Arcana. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators.
Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit arcana.io to request a demo and learn more.
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Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).
Show Notes:
(00:00:00) Welcome to Invest Like the Best
(00:05:23) State of the Union: Venture Capital Edition
(00:07:58) The Rise of Mega VC Funds
(00:09:38) Zombie Unicorns: The Overvalued Giants
(00:17:29) The IPO and M&A Market Stalemate
(00:24:08) The AI Wave and Its Impact
(00:26:03) Private Markets and LP Liquidity Issues
(00:29:57) The Future of Capital Markets
(00:37:49) Advice for Founders in a Changing Landscape
(00:39:27) The High-Stakes Game of Capital Battles
(00:41:35) AI: The New General Purpose Technology
(00:42:57) Challenges and Opportunities in AI Revenue Models
(00:44:37) The Role of Founders in the AI Revolution
(00:46:44) The Impact of Time and Liquidity on Venture Capital
(00:50:35) Navigating the Future of Venture Capital
(00:58:45) International Dynamics in the AI Race
(01:13:58) Advice for Founders in the AI Era