Bill Gurley - The Gift and The Curse of Staying Private

**Patrick O'Shaughnessy** (0:00)
Something I speak about frequently on Invest Like the Best is the idea of life's work. A more fun way to think about it is that I'm looking for maniacs on a mission. This is the basis for our investment firm PositiveSum, and it's the reason why I'm so enthusiastic about our presenting sponsor, Ramp. Not only are the founders, Kareem and Eric, life's work level founders, certainly maniacs on a mission, they have created a product that is effectively an unlock for founders and finance team to do more of their life's work by streamlining financial operations, saving everyone their most precious resource, time. Ramp has built a command and control system for corporate cards and expense management. You can issue cards, manage approvals, make vendor payments of all kinds, and even automate closing your books all in one place. Speaking from my own experience using Ramp for my business, the product is wildly intuitive, simplistic, and makes life so much easier that you'll feel bad for any company who hasn't yet made the switch. The Ramp team is relentless and the product continues to evolve to save you time that you would never have dreamed of getting back. To me, there is nothing more interesting than technologies that reduce friction for other entrepreneurs to be able to build the thing that they want to. So much attention has gone to cloud computing, APIs, and other ways of making life easy for founders. What Ramp has done and is doing is build yet another set of tools in this category. To get started, go to ramp.com. Cards issued by Celtic Bank and Sutton Bank, member FDIC. Terms and conditions apply. Ridgeline gets me so excited because every investment professional knows the core challenge that they saw. You love the core work of investing, but operational complexities eat up valuable time and energy. That's where Ridgeline comes in. Ridgeline is an all-in-one operating system designed specifically for investment managers, and their momentum has been incredible, with about $350 billion now committed to the platform, and a 60% increase in customers since just October. Firms are flocking to Ridgeline for good reason. They've been leading the investment management tech industry and AI for over a year with 100% of their users opting into their AI capabilities, putting them light years ahead of other vendors thanks to their single source of data. And they recently released the industry's first AI agents, digital coworkers that can operate independently. Their customers are already using this highly innovative technology and calling it mind-blowing. You don't have to put up with the juggling multiple legacy systems and spending endless quarter ends compiling reports. Ridgeline has created a comprehensive cloud platform that handles everything in real time, from trading and portfolio management to compliance and client reporting. It's worth reaching out to Ridgeline to see what the experience can be like with a single platform. Visit ridgelineapps.com to schedule a demo. I'm excited to introduce our newest sponsor, Arcana. Arcana is the world's most advanced portfolio intelligence platform trusted by institutional investors managing trillions in assets under management, including market-neutral, long-short, long-lonely, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and IDEO, construct optimal portfolios, and decompose performance at incredible granularity. Arcana is the only real-time, intraday system in the market with extensive live scenario analysis, custom screening and tagging, and a slate of one-click, lightning-fast portfolio construction tools, mock portfolio trackers, reporting, and single-stock crowding. This is the kind of tool I wanted when I was managing public equities, and I am sure you will benefit from the insights the system has to offer. Visit arcana.io to request a demo and learn more.
Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.

**SPEAKER_2** (3:56)
Patrick O'Shaughnessy is the CEO of PositiveSum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit PSUMVC.

**Patrick O'Shaughnessy** (4:25)
I guess today is Bill Gurley. Bill was a general partner at Benchmark Capital. He joins me for his sixth time on Invest Like the Best and 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 longer. He also walks through I know one from GPs to LPs to founders as proper incentives to mark assets accurately, creating a system-wide coordination problem. We dig into the investment implications of AI as a platform shift ranging from evaluating AI revenue quality to international competitive dynamics. Bill offers a crucial perspective on playing the game, both as it exists today and as it may evolve. Please enjoy my conversation with Bill Gurley.