The Minutes of Bill Gurley on investing https://minutesof.com/bill-gurley/on/investing/ Everything Bill Gurley has said on investing: 17 verbatim quotes between July 2019 and August 2026, each with a timestamp and a link to the recording it… en Sun, 30 Aug 2026 16:21:59 +0000 Gurley explains venture capitalists live in fear of missing the one or two asymmetric deals each year. https://minutesof.com/q/bb27b2e4-358f-4d96-bd9f-4161b22aa2cd/ https://minutesof.com/q/bb27b2e4-358f-4d96-bd9f-4161b22aa2cd/ “Once again, because of this asymmetric outcome thing, live in fear of missing this one or two deals a year. There's like, how could you possibly minimize the chance of not finding that?” — MIT Sloan VCPE Mon, 11 May 2026 19:59:13 +0000 investing Gurley cites Uber shifting from burning $2B yearly to generating $10B in free cash flow through unit economics https://minutesof.com/q/f6c24726-1992-4b0d-a107-884385704465/ https://minutesof.com/q/f6c24726-1992-4b0d-a107-884385704465/ “I mean, Uber was burning 2,000,000,000 a year and Dara had 10,000,000,000 in free cash flow last year. Being able to make that shift, it's gonna require an innate understanding of your true unit economics.” — MIT Sloan VCPE Mon, 11 May 2026 19:59:13 +0000 investing Gurley says venture capital requires breaking your own rules or you'll say no to everything. https://minutesof.com/q/ca3a2602-6846-4e3b-bc4e-2abd25f17632/ https://minutesof.com/q/ca3a2602-6846-4e3b-bc4e-2abd25f17632/ “venture capital is a game where you have to one of the reasons, group decision making works so well is you're you're gonna have to break one of your rules or you're gonna say no to everything.” — Afford Anything Podcast Fri, 13 Mar 2026 19:00:04 +0000 investing Gurley found Dell trading at six times earnings after laptop fire and option hedging problems. https://minutesof.com/q/3e460770-4958-4a5f-8d92-fd49cdb4a8b4/ https://minutesof.com/q/3e460770-4958-4a5f-8d92-fd49cdb4a8b4/ “It was trading at six times earnings. Their laptop had caught on fire, and they had this option hedging strategy gone awry Uh-huh.” — Bill Gurley Fri, 06 Mar 2026 02:57:59 +0000 investing Gurley emphasizes the person matters more than the concept, citing founders who pivoted 180 degrees. https://minutesof.com/q/f2d02a58-afd8-4623-bd75-15ed6a3f8a86/ https://minutesof.com/q/f2d02a58-afd8-4623-bd75-15ed6a3f8a86/ “And we've seen incredible businesses be built by great founders who have pivoted a 180 degrees from the original idea.” — BigDeal by Codie Sanchez Wed, 04 Mar 2026 15:00:36 +0000 investing Gurley warns retail investors that 100x AI returns already happened; current odds are very low. https://minutesof.com/q/bd5b05d6-34a6-4b5a-b236-2f88b007c06d/ https://minutesof.com/q/bd5b05d6-34a6-4b5a-b236-2f88b007c06d/ “And that's not to say there won't be an incremental AI investment that makes money, I think there will. But your odds right now of that being the case are really, really low.” — Tim Ferriss Wed, 17 Dec 2025 16:45:52 +0000 investing Gurley argues increasing returns vary in strength, with some linear and some exponential, forming a scale of n https://minutesof.com/q/060ae2c0-40b0-4edf-ba65-806ffed62d77/ https://minutesof.com/q/060ae2c0-40b0-4edf-ba65-806ffed62d77/ “It's arguable there are levels of increasing returns. Like, you could come up with some kind of scale or index because some of them are more linear and some of them can go exponential.” — Invest Like the Best Tue, 23 Apr 2024 08:00:00 +0000 investing Gurley admits pattern recognition led VCs to miss HubSpot, Shopify, and Twilio due to anti-small-business bias https://minutesof.com/q/d497c52b-1752-4e58-8b3a-1c22a6659054/ https://minutesof.com/q/d497c52b-1752-4e58-8b3a-1c22a6659054/ “And so you develop this anti small business mindset, which keeps you out of HubSpot and Shopify and Twilio. Then miss massive amounts.” — Invest Like the Best Tue, 23 Apr 2024 08:00:00 +0000 investing Gurley says all investors must hold strong opinions loosely because variables constantly change. https://minutesof.com/q/7d12c629-8bb6-490c-8c87-22199fbb5e85/ https://minutesof.com/q/7d12c629-8bb6-490c-8c87-22199fbb5e85/ “And Yes. I think I think all investors have to work within that framework because things change.” — Tim Ferriss Thu, 26 Jan 2023 19:45:00 +0000 investing Gurley discovered Dell had 20-to-1 ROIC advantage versus competitors using return on invested capital framewor https://minutesof.com/q/19c858a7-a0ae-45ba-85d9-70a9ca6dba21/ https://minutesof.com/q/19c858a7-a0ae-45ba-85d9-70a9ca6dba21/ “It turned out just by happenstance that Dell stood out like a sore thumb with ridiculously high ROIC numbers versus the rest of the industry. Like, night and day, like, 20 to one.” — Tim Ferriss Thu, 26 Jan 2023 19:45:00 +0000 investing Gurley found Dell's return on invested capital was 20 times higher than competitors, initially unbelievable. https://minutesof.com/q/5834e02b-5116-49b3-8aec-6e2d797860c7/ https://minutesof.com/q/5834e02b-5116-49b3-8aec-6e2d797860c7/ “Like, night and day, like, 20 to one. Wasn't even close. And in fact, it was so ridiculous.” — Tim Ferriss Thu, 26 Jan 2023 19:45:00 +0000 investing Gurley believes Facebook's stock would double if they shut down VR, which costs $5-10 billion annually. https://minutesof.com/q/26d4b192-2680-4555-b3e8-a4c01d36376d/ https://minutesof.com/q/26d4b192-2680-4555-b3e8-a4c01d36376d/ “Wall Street's on my side on this one. I think if they shut down the VR effort, not only will the profitability would soar because they're spending real money, like 5 to 10,000,000,000 a” — Tim Ferriss Thu, 26 Jan 2023 19:45:00 +0000 investing Gurley criticizes VCs who think cheap capital enables them to pursue low-return businesses in new industries. https://minutesof.com/q/91a7bb16-6d51-4980-8548-69b7ced6e390/ https://minutesof.com/q/91a7bb16-6d51-4980-8548-69b7ced6e390/ “But I overheard a VC on a panel say that now that capital's become so cheap, we as venture capitalists get to go after all these new industries.” — Invest Like the Best Tue, 02 Jul 2019 09:30:00 +0000 investing Gurley argues that VCs using cheap capital to enter new industries are actually funding low-return businesses. https://minutesof.com/q/348a68f1-9d14-4cb1-a949-1312117e8e38/ https://minutesof.com/q/348a68f1-9d14-4cb1-a949-1312117e8e38/ “I overheard a VC on a panel say that now that capital's become so cheap, we as venture capitalists get to go after all these new industries.” — Invest Like the Best Tue, 02 Jul 2019 09:30:00 +0000 investing