Claire Smilow has spent years scouting talented people before they become the next big thing in tech. That instinct paid off in 2019, when she was blown away by a sophomore at MIT who already had a strategic and commercial vision. Smilow played the long game in seeing his talents through—and it led to a billion-dollar payoff.
The investor first met Michael Truell while conducting case study interviews for her student VC firm, Dorm Room Fund. At the time, Truell hadn’t founded a company; but three years later, the venture capitalist persuaded her firm, BoxGroup, to invest in the Gen Z engineering savant’s nascent business. The firm poured $750,000 into the recent graduate’s little-known startup, an AI coding company called Cursor. And a couple follow-on checks and few years later, Cursor swelled into an industry sensation, with SpaceX eventually acquiring the business for $60 billion in 2026—a deal estimated to drive $1 billion in returns to BoxGroup.
