Patrick Finnegan began his career as an entrepreneur while struggling to fit in at a Delaware boarding school. He started businesses as a way to cope (some above board, like building websites, and some less so, like selling fake IDs). He dropped out after hearing about the Thiel Fellowship, which awarded $100,000 to fellow dropouts under 22 years old. Though he didn’t make it to the finalist round after traveling out to Las Vegas, he remembers seeing Lucy Guo and hearing about Dylan Field, who had founded Figma. Finnegan decided to follow a similar path, moving to New York to start a budding startup career and meet other young people across the city’s tech and art scenes.
That may not seem like the foundation for a successful VC firm. Still, in today’s impossibly saturated attention economy—where every new product seems to have an A-list celebrity as an investor or spokesperson—finding authentic boosters is a hot commodity. It’s also why Finnegan partnered with Chris Hollod to build Second Sight Ventures, which is announcing the close of its $75 million first fund. Like Finnegan, Hollod built a career out of the celebrity-driven investment paradigm. Through his role as the managing partner at Ashton Kutcher’s A-Grade Investments, he really pioneered the model, though he started the firm around when Finnegan was still in middle school.
I asked whether Finnegan, now knocking on the doorstep of 30 years old, is worried about losing his edge. “Just being a student and knowing my place and just being a sponge,” he said, echoing his early experience trying out for the Thiel fellowship. “I don’t want to be the smartest person in the world.”
