How David Tisch's BoxGroup turned a $750K bet on Cursor into a $1 billion exit by breaking all the VC rules

David Tisch likes to say he is an “internet investor,” not a VC, and the Cursor deal makes that sound less like branding and more like doctrine. BoxGroup’s early $750,000 check to Michael Truell, plus two follow-ons, is now expected to return about $1 billion, according to a source familiar with the matter. That came after Cursor was acquired by Elon Musk’s SpaceX for $60 billion, which Fortune described as the largest VC-backed acquisition ever.

The striking part isn’t just the size of the win. It’s how BoxGroup got there. Tisch’s firm did not muscle for control, board seats or ownership points the way many bigger funds do now. It did not center itself in the story. It leaned on Claire Smilow, then a principal and now a partner, who had met Truell in 2019 and pushed BoxGroup to back him in 2022, even when his idea was still about AI for CAD.

Tisch’s whole pitch is that early investing is closer to collecting than empire-building. He grew up trading sports cards, loved the internet before it was fashionable, and built BoxGroup around being early, small and collaborative. The firm’s early-stage funds typically back 120 to 150 companies, far more than a traditional venture fund’s roughly 30, and Greg Rosen said the goal is simply to make it easier for both sides to say yes. Sometimes that means writing very small checks. Sometimes, as with Cursor, it means getting in before everyone else and staying out of the way.

That restraint has become BoxGroup’s edge. Jack Altman of Benchmark called it one of the last stalwarts of highly collaborative investing, and the Cursor outcome gives that claim some teeth. BoxGroup’s return from the deal may end up larger than all the LP capital the firm has ever raised. Not bad for a shop that seems almost suspicious of its own success.