Press Space to continue
Press Space to continue
Wrote out some of my favorite ideas and lessons from my conversation with @milesgrimshaw:
Jackson Dahl@jacksondahl8h ago
đ 21 Lessons from Dialectic with Thrive's Miles Grimshaw Always Another Adventure: Miles Grimshaw on Softwareâs Future, Enduring Companies, and Being Impatiently Patient Miles is drawn to beginnings: the new country, the unfamiliar market, the next mountain. I talked to him about how he finds and partners with exceptional people, which genetics shape enduring companies, what moats will survive in software, and beginning again, over and over. The reward for reaching one summit is another climb. A coach sent Miles Camusâ classic essay imagining Sisyphus happy. Heâs internalized it with regard to his infinite game as a venture investor: âI love going back down and looking at new summits and going, âCan we go do that one?ââ Courtship starts before the round exists. Miles flew to Ottawa after one call with Turbopufferâs CEO Simon, offered him a term sheet, got turned down, and spent more than a year helping out anyway. When the call finally came at 9:30 on a Monday night, Thrive was committed by 10:30. âOur challenge is to be impatiently patient.â Underwrite the person before the model. Miles invested in Cursor after getting rough numbers over dinner without ever receiving detailed revenue numbers. âIt never starts with a spreadsheet. It starts with that person, the future that they see.â Investing is enlisting. Miles treats early investment like joining the team and working for that ownership over the next decade. After Cursorâs Series A, Thrive went all-in on recruiting for them through the Series B. The relationship is working when a founder thinks, âSure, I want to raise money from these people, but actually, I kind of want them on the team.â Instinct comes from exposure to the best. Your read on great is only as good as the greatness you've seen up close. When Thrive met Mesh Optical (a team who built Starlink's laser interconnect at SpaceX), they went from first meeting on Friday afternoon to commitment by Monday, all in a domain they "had no business knowing anything about." Specific optimism is the job. He once told a candidate, âThere are infinite ways this can go wrong that I can enumerate. Our job is to figure out the path of it going right.â What is it? And who cares? Two questions underpin Milesâs investment analysis. You can say many words about a company, but if you can't simply define what the customer is actually buying and who values it enough to pay, nothing else matters. Vision is where the founder is looking. Patrick Collison was looking beyond payments toward the GDP of the internet; Cursorâs Michael Truell was looking beyond the IDE toward new abstractions for coding. âIn driving and biking, you go where you look⌠I think that is really true for companies, too.â Ask what a companyâs growth is made of. Investors love to use a companyâs ARR growth as a scorecard: how fast to $10M or $100M? Miles is less interested: âThat's a phenotypic expression of an underlying set of genetics.â A handful of large contracts or a long tail of small customers might both have strong ARR, but will grow into completely different organisms. Pick the customer that helps you live in the future. For early-stage companies, he cares more about demanding, innovative customers than pure revenue. They force the product and the organization to adapt to a changing market. "I think Stripe would be a very different company if Delta was its first customer instead of Shopify or Lyft." A great product can outrun its sales team. When he began working with Cursor, it got to tens of millions in ARR with zero salespeople. The sales team remained very small until early 2026. Michael relied on his teamâs feedback and individual user conversations because âthey had a very strong purity to delivering a great product.â Copy the cause of success, not its privileges. Googleâs core business was so powerful that 20% time could look like a management principle instead of something Google could uniquely afford. âIn some sense, it was the wrong thing to learn the lesson of from that company.â Softwareâs hidden moat was wall-clock time. Switching costs mattered, but Miles thinks the undercounted advantage of software was the years spent building a place where customers, integrations, expertise, and mindshare naturally gathered. âThe great software companies basically built a city... If you're Benioff and you're building a CRM, sure, you're building a CRM, but you're kind of building the City of Sales.â Get big or go luxury. AI has compressed the build time that protected incumbents in software, threatening the middle. Miles suggests a lesson from ecommerce: either cover enormous surface area or be nimble enough to build bespoke, white-glove products. Craft creates trust. Customers may not consciously notice every product decision, especially as software becomes more like services. But they feel the accumulated attention to detail and infer that the invisible details have been handled with equal care. âI donât knowâ is only half the answer. The follow-up is "I'll figure it out." Learning requires enough humility to say âSorry, I just donât understand thatâ and enough self-confidence to believe you can reach the ground truth. Instinct must become legible before it becomes useful. Repetition improves Milesâs intuition, but an investment team cannot act on a feeling trapped inside his head. âIf I canât communicate it to the people who trust me the most⌠how is the rest of the world going to do that?â Raise the ceiling in good times and absorb the shock in bad ones. A lesson from Sequoiaâs Sir Michael Moritz. Success gives a company the capacity for the exceptional recruit, ambitious customer, or defining move: âwhen things are working, you need to set your eyes further out.â In adversity, the founder has already felt every problem more deeply than the board will, so constructive support is more useful than drilling on known problems. Hold jam sessions, not jury trials. He rejects the investment committee as a jury trial where one person presents, and everyone else looks for guilt. âThe best version of investment team conversations⌠is like being in the music studio making music together.â Stable foundations make larger adventures possible. Miles spent much of his life associating the next adventure with leaving: England, the US, India, China, a new major at the end of college, then Thrive for Benchmark. Returning taught him something else: âIâve come to find a lot more of the magic that gets unlocked by a strong foundation.â Endurance grows from evidence, not encouragement. Miles ran his first marathon at seventeen because he wanted to do it before turning eighteen; years later, he and his wife completed a 150-mile race in New Zealand that half the field did not finish. Belief follows proof: âOnce you know you can, you can.â Other platforms: Transcript & links Spotify Apple Subscribe on Substack YouTube https://x.com/i/article/2095147529155321âŚ
