Always Another Adventure: Miles Grimshaw on Software’s 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 Camus’ classic essay imagining Sisyphus happy. He’s internalized it with regard to his infinite game as a venture investor: “I love going back down and looking at new summits and going, ‘Can we go do that one?’”
Courtship starts before the round exists. Miles flew to Ottawa after one call with Turbopuffer’s 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. “Our challenge is to be impatiently patient.”
Underwrite the person before the model. Miles invested in Cursor after getting rough numbers over dinner without ever receiving detailed revenue numbers. “It never starts with a spreadsheet. It starts with that person, the future that they see.”
Investing is enlisting. Miles treats early investment like joining the team and working for that ownership over the next decade. After Cursor’s Series A, Thrive went all-in on recruiting for them through the Series B. The relationship is working when a founder thinks, “Sure, I want to raise money from these people, but actually, I kind of want them on the team.”
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, “There are infinite ways this can go wrong that I can enumerate. Our job is to figure out the path of it going right.”
What is it? And who cares? Two questions underpin Miles’s 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; Cursor’s Michael Truell was looking beyond the IDE toward new abstractions for coding. “In driving and biking, you go where you look… I think that is really true for companies, too.”