Bill Gurley - The Gift and The Curse of Staying Private - [Invest Like the Best, EP.427]
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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** Ramp**⁠⁠⁠⁠). Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠** Ramp.com/invest**⁠⁠⁠⁠)** to sign up for free and get a $250 welcome bonus.**

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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.**

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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