Exclusive: Meet the 38-year-old founder who left Wall Street for love and created an AI insurance unicorn a decade later

Gage Caligaris said he decided to marry his wife on their first date, during his last month at Harvard. A few years later, he made another consequential decision: leaving Wall Street and starting over as an insurance intern to get closer to her family in Boston. The math graduate had been trading exotic derivatives in New York, a career he describes as fast-paced and fun. (His LinkedIn profile shows three trader roles, including one at Barclays Capital in New York.) Originally from Yardley, Pa., Caligaris recalled spending a year in a long-distance relationship, riding Chinatown buses between New York and Boston before his future wife moved south to join him. “I took so many Chinatown buses,” he told Fortune. And he still supports the Philadelphia Eagles. But her parents lived in Boston, and after about three years on Wall Street, he wanted a route north. He had been considering business school when his younger sister, who had interned in Travelers’ actuarial program, suggested a profession he said he had never heard of. “She…