Founder and Chief Executive Officer, Clearcover
UW Majors: Supply Chain Management; Law
Kyle Nakatsuji didn’t follow the traditional path to entrepreneurship — he carved one of his own. A former football player at UW–Oshkosh with a political science degree, Nakatsuji arrived at UW–Madison for graduate school without a clear plan. He left with two degrees, a certificate in entrepreneurship, and a start-up mindset backed by tenacity, creativity, and the belief that an underdog can come out on top.
Nakatsuji is CEO and cofounder of Clearcover, a digital auto insurer leveraging technology to deliver affordable, convenient, and customer-centered experiences. Its scalable API (application programming interface) platform and proprietary system, ClearAI, power Clear Claims, which determines eligibility for expedited payments, enabling payouts on eligible claims in as little as 30 minutes, with a record of just seven minutes, making it one of the fastest claims experiences in the industry. Clearcover is now focused on delivering flexible, tech-driven solutions tailored to meet the needs of the nonstandard auto insurance market.
Under Nakatsuji’s leadership, the company has raised more than $560 million in funding and earned recognition from Inc., Deloitte, and CNBC.
The journey to leading one of the fastest-growing and most innovative insurance tech companies began with persistence and curiosity. Nakatsuji was, by his own admission, “a terrible applicant” to business school — lacking the coursework, credentials, and experience typically expected of an MBA candidate. But he kept showing up with new arguments and ideas and eventually, one admissions staffer took a chance on his doggedness.
He repaid that leap of faith with relentless initiative. While earning both a JD and an MBA, Nakatsuji dove headfirst into the start-up world, gaining experience with founders and real-world challenges through the UW’s Law and Entrepreneurship Clinic and the Venture Capital Investment Competition team, with whom he traveled to London to help a UW-based start-up pitch to investors.
“The school provided me with opportunities to meander and learn and explore,” he says. “It’s hard to imagine I’d get to do what I do today without the experiences I gained at the UW.”
After graduation, Nakatsuji joined American Family Ventures — the venture capital arm of American Family Insurance — where he helped shape the firm’s strategy by investing in early-stage start-ups. From there, he was ready to take a leap and launched Clearcover.
Nakatsuji’s leadership extends beyond the business world. He also mentors students and entrepreneurs through UW–Madison’s Creative Destruction Lab — a seed-stage program for science- and tech-based start-ups — with a special focus on teams exploring innovation in insurance and risk.
His journey from a political science major with no business experience to a dual-degree graduate, venture investor, and tech CEO reflects what can happen when courage meets opportunity (and when the UW alumni network is full of Badgers willing to offer advice over a cup of coffee).
And for Nakatsuji, the work is never done. “We’re eight years into building this company, and every day is a new challenge and a new adventure,” he says. He finds motivation in what his father called “the law of the farm” — the idea that growth takes patience and perspective. “If you look every day, it’s pretty hard to see the crops growing. But if you give yourself some time, slowly but surely the results will come.”