Invest Like the Best with Patrick O'Shaughnessy
Bill Gurley - The Gift and The Curse of Staying Private - [Invest Like the Best, EP.427]
10 Jun 2025
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
Full Episode
The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busywork. If you think about it, you become a finance leader because you love strategic work.
modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions. It's the opposite of leverage. This is exactly why I'm so bullish on what the team at Ramp has built.
Kareem and Eric understood that every minute spent on manual expense management is a minute stolen from high leverage work. So they automated all of it. Automatic categorization, receipt matching, spending controls that actually work. Check out ramp.com slash invest and see what happens when you eliminate the busy work. Cards issued by Sutton Bank, member FDIC. Terms and conditions apply.
To me, Ridgeline isn't just a software provider, it's a true partner in innovation. They're redefining what's possible in asset management technology, helping firms scale faster, operate smarter, and stay ahead of the curve. I want to share a real-world example of how they're making a difference. Let me introduce you to Brian.
Brian, please introduce yourself and tell us a bit about your role. My name is Brian Strang. I'm the Technical Operations Lead, and I work at Congress Asset Management.
How would you describe your experience working with Ridgeline?
Ridgeline is a technology partner, not a software vendor, and the people really care. I get sales calls all the time and I ignore them. Ridgeline sold me very quickly. We went from 7 billion to 23 billion and the goal is 50 billion. Ridgeline was the clear front runner to help us scale. In your view, what most distinguishes Ridgeline? They reimagined how this industry should work.
It was obvious that they were operating on another level.
It's worth reaching out to Ridgeline to see what the unlock can be for your firm. Visit RidgelineApps.com to schedule a demo. I'm excited to introduce our newest sponsor, Arcana.
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