Jackson Dahl@jacksondahlSep 1

Dialectic 56: Miles Grimshaw @milesgrimshaw is an investor at @ThriveCapital. He has spent his life hunting change: from "adventure racing" to finding and working with the world's most ambitious companies. His favorite part: getting to go back down the mountain and begin again. I talked to Miles about playing infinite games, seeing greatness up close, and the biggest change he's seen so far: After a career of software investing, all of the underlying assumptions for venture-backed software startups are in question. What moats will persist? Is software over? We also discuss: - Impatient patience: flying to Ottawa for dinner with @Sirupsen and waiting a year to invest in @turbopuffer - Two fundamental questions: "what is it?" and "who cares?" - Software's barbell future: Benioff building "sales city" and "the champagne region of Palantir" - Founder Vision: "you go where you look" and what @mntruell saw for @cursor_ai - Getting up to speed as a generalist: "I don't know" and "I'll figure it out" - Intuition for great: committing to SpaceX laser engineers (@meshoptical) in 48 hours, with no domain expertise - Humility and conviction: leaving Thrive after a ~decade for Benchmark, and coming back Timestamps: (0:00) Opening Highlights (1:37) Intro: Miles Grimshaw (4:30) Infinite Games, Adventure Racing, and Starting Anew, Over and Over (11:01) Staying Hungry: Proactive Hunting and the Turbopuffer Story (17:35) Impatiently Patient: Courtship, Cursor, Recruiting, and Joining the Team (25:33) Loving Change: London to America, the Himalayas, and Learning New Sports (31:36) The Genetics of Companies: "What Is It?" and "Who Cares?" (38:08) House Cats & Tigers: Where Is the Founder Looking? (47:00) Confidence in Uncertainty and Customers That Pull You Into the Future (54:25) What Remains for Software: Moats, Cities, Wall-Clock Time, and the Barbell of Scale & Luxury (1:04:54) Craft, Trust, and Why Software Isn't Over (1:11:13) Intuition: Gradient Descent and Seeing Greatness Up Close (1:18:07) "I Don't Know" and "I'll Figure It Out" (1:22:12) Commitments, Not Bets: Closing People and Board Work (1:29:06) Joining Thrive, Being a Punk, and Music Studios over Jury Trials (1:36:18) Leaving for Benchmark and Returning to Thrive (1:43:18) Dream Bigger: Lessons from Josh, Teaching Agency to Kids, and Going the Distance @DialecticPod 56: Miles Grimshaw - Back Down the Mountain - is out now below and on all platforms.