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.

Miles is being far too modest here. What he saw in this team, and how early he saw it, will go down as one of the great venture investments of all time.

So sad - one of the sweetest souls, someone who thrived on the optimism of ideas, and who everyone called “friend.” om.co/2026/06/24/1966-2026/