Dialectic

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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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion's custom agents are AI teammates that handle recurring work across your tools. Learn more about their new developer platform and workers here. Notion is hiring across product, storytelling, design, engineering, and more. You can learn more at notion.com/dialectic.

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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

“Art is For Seeing Evil” was published by Agnes Callard for The Point Magazine on July 15, 2022. My thanks to Agnes and The Point for permission to share this audio version of her essay on Dialectic’s feed.

https://thepointmag.com/examined-life/art-is-for-seeing-evil/

Agnes Callard (UChicago, Substack, X, Wikipedia) is a professor of philosophy at The University of Chicago, focused primarily on ancient philosophy and ethics. She also writes for The Point, The New York Times, and more. I particularly enjoyed her recent conversation with Derek Thompson on her theory of the “uni-context.”

This essay was shared with me by Nan Ransohoff, (Ep. 51). I hope you enjoy it!

Dan Lilienthal (X, LinkedIn) and José Chayet (X, LinkedIn) are childhood friends and cofounders of [untitled] (X, Instagram), a platform for musicians that they describe as a sacred place for work-in-progress music. It is where a song lives between recording and streaming. [untitled] is closer to the Photos app than to a social network: a private place to store, listen to, and slowly share demos, with no feed.

Dan and José are not trained musicians, engineers, or designers, but they have built a product artists love by “method acting” their way into deep empathy. The platform has grown to 50K paying users and now allows artists to share unreleased music directly with fans. Lorde recently released XRAYS on [untitled]: 49 demos and works in progress from her album Virgin, creating a kind of museum behind the record.

We discuss music as a form of communication and a connection to the divine; why they have resisted adding a feed; product inspirations like the iPod and Snapchat; how empathy and QA underpin their product philosophy; designing for 16-year-olds and superstars; AI as an instrument; which parts of the creative process are worth sharing; what it means for software to be sacred; and building a company with your best friend.

I hope you’re inspired to consider what is sacred, share and live with the things you make, seek out music that inspires you, and stay untitled a little longer than is comfortable.

Full transcript and all links: dialectic.fm/untitled

This episode on [untitled].

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

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Timestamps:

(0:00) Opening Highlights

(1:24) Intro to Dan & José & Thanks to Notion

(4:42) Start: Brackets, How Creativity Makes the World Bigger, and Music's Connection to the Divine

(20:40) Duchamp, Music as a Set of Choices, and The Museum Behind the Work

(27:52) [untitled]: A Medium for Music In-Progress

(45:03) From a Better Dropbox to a Creativity Company

(52:13) Empathy as a Product Philosophy and The Collaboration's Origins

(1:01:04) Scaling the Sacred Place and Product Intuition

(1:10:33) Lorde's XRAYS Drop and Designing for a Wide Range of Artists

(1:17:26) 10K Unheard Songs and Whether Process Should be Seen

(1:24:10) Brand, Trust, Alignment with Artists and the [studio]

(1:30:54) The Word "Sacred" and Resisting the Feed

(1:40:52) AI as an Instrument: Building Tools Artists Actually Want

(1:49:27) Building a Company with Your Best Friend

(1:56:31) Closing Questions: Dream Users, Rapid Fire Brackets, and Titles

(2:08:52) Thanks Again to Notion

Full transcript and all links and references: ⁠dialectic.fm/ian-rogers⁠.

Ian and I made a playlist with albums/songs mentioned here (Apple, Spotify).

Ian Rogers (X, LinkedIn) is Chief Human Agency Officer of Ledger, the Paris-based security company whose hardware wallets secure much of the world's crypto. He now focuses on how Ledger can enable us to work with AI agents while maintaining our secrets and value.

His career has spanned music, culture, brand, and "the technolog(ies) people are going to hate next." He built and ran the Beastie Boys web presence in the 90s before working on music on the internet for over a decade: file sharing Nullsoft (Gnutella and WinAmp), early streaming at Yahoo!, direct-to-fan commerce at Topspin, Beats Music, and finally Apple, as an abbreviated list. He then joined LVMH as its first Chief Digital Officer, working with Bernard Arnault and its many Maisons to bring them into the internet era. More recently, he joined Ledger to improve its product experience, including collaborating with Tony Fadell to create Ledger's flagship form factor, Ledger Stax.

Ian's roots are skateboarding and music, which formed alongside a punk rock ideology while growing up in Indiana in the 1980s. I am glad to have captured a long conversation that covers the many flavors of Ian, and the threads that have persisted through his many lives. That includes: individuality; being a participant, not a spectator; what makes a scene; building brands; trying to help Kanye; and why new culture is always being made—it's just that you have to find the 1% that's awesome. Also: ushering forward and translating frontier technologies; being pushed by Jimmy Iovine; why security matters in the AI era; why AIs aren't people; what he wants to automate; learning to fail; advice on relationships across work, parenting, and love; and a whole lot of love for music—from his 2026 pick Twisted Teens to his desert island albums to tea with Paul McCartney.

I hope you're inspired to participate in the world and make great things. Thanks to our friends at Ledger for hosting me.

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

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Timestamps

(0:00) Opening Highlights

(1:37) Intro to Ian & Thanks to Notion

(5:22) Start: Tattoos, Individuality, and Punk Rock: Spectator vs Participant

(16:44) What Makes a Scene?

(25:24) New Culture, 99% of Everything is Garbage, Finding the 1%

(40:09) Niche, Quality, and The Blockbuster vs. The Snowball

(53:35) Brand, Selling Culture Before Product, and The Age of the Individual

(1:08:12) Aggression, Patience, and Being Pushed

(1:16:52) Translating New Technologies, Empowerment, and Agency

(1:25:19) Interfaces, Ledger, Security, and Ideology

(1:39:56) Ian's New Role: Chief Human Agency Officer

(2:06:03) Seeing What is Real, Comfort Being Wrong, Chasing What's Fun and Cool

(2:13:45) Lessons from Skateboarding and Favorite Albums

(2:22:56) Working with Your Friends, Parenting, Love, and Remembering to Stay a Participant

(2:35:47) Thanks Again to Notion

Zhengdong Wang (Website, X, LinkedIn) is an AI researcher based in London.

He writes annual letters (inspired by Dan Wang), mainly about AI progress, and his 2025 letter blew me away and inspired me to meet him. In it, he describes his ‘compute theory of everything,’ and makes the case that it would be stranger if AI progress slowed down than if it continued. Put a different way, reading his letter helped me get closer to truly feeling the wave of AI progress.

It took Zhengdong a long time to become “AGI-pilled,” despite years of feeling like he was late to AI and working as a research engineer for the last five. I talked to him about what it will take for the rest of us to see what he sees, and feel what he feels. We also discuss why AGI may be a hazier target than simply seeing AI progress as “the model does the eval,” and why recursive self-improvement may be both happening and less fantastical than it may seem. ZD makes the case that based on the rate of progress and scaling, skeptics will simply be proven right or wrong soon. We talk a bit through what narrative and political challenges the AI industry faces ahead of this transition.

Then there are the implications of all of this—namely how AI progress accelerates the question of what we each value, how we will spend our time, and where we will find or create meaning. ZD takes a stab at some of those impossible questions and shares some other favorite miscellanea that is reflective of the range of his letters.

I hope this conversation helps you feel the wave a bit yourself, and that you remember that, regardless of how much change lies ahead, we still get to make our meaning. We get to choose.

Full transcript and all links: dialectic.fm/zhengdong

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

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Timestamps:

(0:00) Opening Highlights

(1:16) Intro to Zhengdong & Thanks to Notion

(4:33) Start: Why Research: "I Just Want to Know"

(12:25) The Model Does the Eval: AGI as a Moving Target, RSI, and Laser Beams

(33:17) The Compute Theory of Everything and Feeling the Wave

(53:17) The Myths AI Needs, Competition vs. Power Concentration, and Whether Progress Is Inevitable

(1:13:42) "Who Could Possibly Compete?": Post-AGI Meaning, Work, and Questing

(1:29:28) Are You Having Fun? Vacations, Mattering, and How to Live

(1:47:13) Annual Letters, Economist Obituaries, London, and Burke

(2:06:33) Closing & Thanks to Notion