Bill Gurley - The Gift and The Curse of Staying Private - [Invest Like the Best, EP.427]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Investing, Business, Technology

4.8 • 2.4K Ratings

🗓️ 10 June 2025

⏱️ 81 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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.⁠⁠⁠⁠ ----- 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. – 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. – 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. ----- 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

Transcript

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0:00.0	Something I speak about frequently on Invest Like the Best is the idea of life's work.
0:04.5	A more fun way to think about it is that I'm looking for maniacs on a mission.
0:08.5	This is the basis for our investment firm, Positive Sum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp.
0:15.0	Not only are the founders, Karim and Eric, life's work-level founders, certainly maniacs on a mission.
0:20.0	They have created a product that is effectively an unlock for founders and finance team to do more of their life's work
0:25.5	by streamlining financial operations, saving everyone their most precious resource time.
0:30.9	Ramp has built a command and control system for corporate cards and expense management.
0:35.1	You can issue cards, manage approvals, make vendor payments of all kinds, and even automate
0:39.4	closing your books all in one place.
0:41.7	Speaking from my own experience using Ramp for my business, the product is wildly intuitive,
0:46.4	simplistic, and makes life so much easier that you'll feel bad for any company who hasn't
0:50.4	yet made the switch.
0:52.5	The Ramp team is relentless, and the product continues to evolve to save you time
0:56.0	that you would never have dreamed of getting back.
0:58.2	To me, there is nothing more interesting
1:00.0	than technologies that reduce friction for other entrepreneurs
1:03.7	to be able to build the thing that they want to.
1:06.2	So much attention has gone to cloud computing,
1:08.8	APIs, and other ways of making life easy for founders,
1:12.5	what RAMP has done and is doing is build yet another set of tools in this category.
1:18.0	To get started, go to ramp.com.
1:20.5	Cards issued by Celtic Bank and Sutton Bank, member FDIC, terms and conditions apply.
	...

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