BoxGroup's $750,000 Cursor Bet Turned Into Roughly $1 Billion

BoxGroup turned a $750,000 check written to a recent MIT graduate into an estimated $1 billion return, and the partner behind that relationship is now working the same play again on college campuses.

Claire Smilow met Michael Truell in 2019 while running case study interviews for Dorm Room Fund, the student VC firm where she is also a partner. Truell was a sophomore. He had not founded a company. But Smilow says she was blown away by a student who already had a strategic and commercial vision.

Three years later she persuaded BoxGroup to invest in his little-known start-up, an AI coding company called Cursor. The firm wrote the first check, followed with more, and Cursor grew into an industry sensation. In 2026, SpaceX acquired the business for $60 billion—a deal Fortune estimates drove $1 billion in returns to BoxGroup. That works out to a roughly 650-fold return on the original investment, before counting the gains from subsequent financing rounds.

The exit cemented Smilow's reputation as a student-founder whisperer. At 36, she is a partner at both BoxGroup and Dorm Room Fund, and she keeps returning to America's elite schools.

Why campuses?

Smilow says she sets aside a "huge" amount of time with young AI natives. She has a trip to Harvard University and MIT on the books—her second visit this year.

The numbers explain the travel budget. 588 U.S. alumni from the two schools have built billion-dollar companies, according to a July analysis by Stanford professor Ilya Strebulaev. That is roughly 13.1% of all of America's unicorn founders.

"[College] is a fantastic place to recruit for the portfolio, and I often bring portfolio founders with me to campus," Smilow told Fortune. "On campus you get a real sense of forward-looking technological market trends. You get to hear what students at a lot of these cutting-edge research institutions are interested in, what they're studying, what companies they want to work at…It's a fantastic pulse on the market and our technological shifts."

How student chatter becomes a deal signal

Smilow treats campus conversations as market research. She spends significant time on frontier tech such as robotics and quantum computing. In one fall 2024 campus conversation, roughly four out of 20 to 25 students brought up brain-computer interfaces. She read that as a signal to pay closer attention. Two years later, she says, early-stage BCI companies are already proliferating.

The lesson, in her telling: listening to talented people helps investors spot promising markets before they become obvious.

Her strategy targets talent, not age. Some of the people she meets will found companies later in life; others never will. Learning about the ambitious spaces talented people are exploring is, she says, "the most authentic way" to do her job.

What BoxGroup backs

Over Smilow's six-and-a-half years at the firm, BoxGroup has backed Ramp and Clay at early stages. Both companies have since reached multibillion-dollar valuations.

Smilow describes BoxGroup as founder-led, working with businesses that are almost "never proven." She hunts for promising talent whose names repeatedly come up in conversations with their peers.

That peer-first approach extends to how she evaluates people. Smilow skips the standard reference call with former employers when she can.

"I tend to think often the best founders don't make the best interns," Smilow said. Part-time gigs are often "boring" for young entrepreneurs. "They're not always the most empowered positions, so I spend less time—especially for early-in-their-career founders—talking to prior bosses. There's value in that, but I actually spend more time talking to their peers and understanding how their peers perceive them."

The Cursor exit proved the method once. With BCI startups multiplying and Smilow booking her second campus trip of the year, BoxGroup is running the same talent-scouting loop that produced its billion-dollar payoff.