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 told me it’s a bunch of math tests. You can become an insurance executive if it pans out,” said Caligaris, who studied applied mathematics in undergrad. “And so, armed with those two sentences, I did some Googling.”

That search led him to Liberty Mutual, where he joined as an intern in 2014. Today, the 38-year-old runs Ledgebrook, a Boston-based, AI-native specialty insurance platform, and he has just raised a $200 million financing round co-led by Allianz X and Rockefeller Capital Management. The deal values the company at $2.6 billion after the investment, according to a source close to the company, taking it into unicorn territory for the first time.

The family calculation worked out, too.

“My in-laws still watch the kids every weekend,” said Caligaris, now a father of three. “So that part worked out.”

Founded in 2022, Ledgebrook provides insurance for midsized businesses with complex or hard-to-place risks. It sells exclusively through wholesale brokers, offering coverage including general liability and professional liability. Its technology helps underwriters assess those risks and decide what to charge, with the company saying it can often provide quotes in hours rather than weeks.

It operates in what the industry calls the excess and surplus, or E&S, market—the home for risks standard insurers won’t take. Caligaris puts the market at $143 billion in premiums last year, growing about 10%. Average policy size at Ledgebrook is “well over” $100,000, he said, and some run into the millions.

Plenty of startups pitch AI-powered insurance. Caligaris argues that in his corner of the market—big policies placed through wholesale brokers—”there’s really not a tech competitor.” The reason, he said, is that reinsurers are careful........

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