56: Miles Grimshaw - Back Down the Mountain

Miles Grimshaw (X, LinkedIn) is an investor at Thrive Capital. He’s spent most of his career there, there, partnering with founders at the early stages of company building, including Cursor, Turbopuffer, Chai Discovery, Mesh Optical, Revel, XDOF, Socket, Benchling, GitHub, and many more. Miles was also briefly an investor at Benchmark before returning to Thrive in 2024.

The conversation focuses on Miles’ appetite for change and continuing to begin anew, again and again. That starts with “adventure racing” as a teenager, and continues through his career as an investor in search of world-changing companies.

We talk about how Miles proactively puts himself in position to work with great founders in a style that resembles courtship, his disposition of impatient patience, and why he loves change. The latter includes the dramatic shift in his primary domain: software. As the underlying assumptions for software businesses change due to AI, what traits will great companies have? And what moats if any will persist? Is software investing over?

Miles also talks through how great companies and founders go where they are looking, prioritizing customers that help you live in the future, the learned intuition of greatness, and joining the expedition squad alongside the founders Thrive partners with. Finally, we talk a bit about Thrive, his departure to and return from Benchmark, and endurance.

I hope you are inspired to find an infinite game where you are excited to see the stone roll back down the hill and begin to push again.

Transcript & links available at https://dialectic.fm/miles-grimshaw

Disclaimer: This podcast is for informational purposes only. The views expressed are the speaker's own as of the recording date and are subject to change. Thrive funds and their affiliates have investments in certain companies discussed in this episode. References to those companies are illustrative, do not represent all investments made by Thrive, and should not be viewed as recommendations or indications of future investment performance. Past performance is not indicative of future results.

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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
• (1:51:36) Outro