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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 adolescent business. The firm poured $750,000 into the recent graduate’s little-known start-up: an AI coding company called Cursor. And a couple follow-on checks and a 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.
That bet cemented Smilow as the student-founder whisperer—a VC whose early conviction in Truell helped deliver a roughly 650-fold return on the firm’s original investment, alongside high gains from subsequent financing. As a partner at BoxGroup and the Dorm Room Fund, the 36-year-old is continuing to chase that success at America’s elite schools. Smilow says she sets aside a “huge” amount of time mingling with the young AI natives, with an upcoming trip to Harvard University and MIT on the books—the second time she’s visited this year. After all, 588 U.S. alumni from the two colleges have built billion-dollar companies., representing roughly 13.1% of all of America’s unicorn founders, according to a July analysis from Stanford professor Ilya Strebulaev.
“[College] is a fantastic place to recruit for the portfolio, and I often bring portfolio founders with me to campus,” Smilow tells 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.”
Smilow says a few entrepreneurial trends are taking over college campuses. She’s been spending a lot of time looking into frontier tech, like robotics and quantum computing; and when roughly four out of 20 to 25 students brought up brain-computer interfaces (BCI) during a fall 2024 campus conversation, she took it as a signal to pay closer attention. Two years later, she says, early-stage BCI companies are already proliferating. For Smilow, the lesson is that listening to talented people can help investors spot promising markets before they become obvious.
The VC explains that her strategy is less about a founder’s age, and more about connecting with talent before they come into their own. Some may become founders later in life, while others may never venture into the entrepreneurial life—but she says that learning about the ambitious spaces talented people are exploring is “the most authentic way” to do her job.
Over her six-and-a-half years at the firm, BoxGroup has backed the likes of Ramp and Clay in their early stages—and now, both have reached multibillion-dollar valuations. Smilow says that the firm is founder-led, working with businesses that are almost “never proven.” She’s on the lookout for promising talent whose names repeatedly come up in conversations with their peers.
“I tend to think often the best founders don’t make the best interns,” Smilow said, adding that the 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.”
This story was originally featured on Fortune.com
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