“I love the business of risk,” Jonathan Crystal tells me. He didn’t really have a choice. After a brief career as a consultant, he joined his family’s insurance brokerage firm, Crystal & Company, rising through the ranks to become CFO in 2014 before helping broker a sale to Alliant in 2018.

But despite spending his career in insurance, Crystal was always frustrated with how slow it moved, joking that the only thing his grandfather would be surprised by now about the industry would be email. So he decided to try out a different kind of risk, setting out to start a venture firm just as AI began to upend the staid sector. His new operation, the New York-based Crystal Venture Partners, just closed its first $33 million fund, backed by an array of family offices and global insurance companies.

Crystal’s decision to start an insurance-focused VC operation came at an opportune time, as he started making his first investments out of the fund in the months after OpenAI released ChatGPT to the world. Having started at his family’s company right around the dot-com bubble era, he felt like he’d experienced the craze before. “The gun goes off and everybody starts sprinting,” Crystal says.

He argues that makes his decades-long experience as an operator all the more valuable, able to root out the vertical software ideas that actually stand a chance of transforming the business of underwriting. For one, Crystal says he throws out any decks that include the buzzword “disrupt,” so founders beware. “It generally feels kind of naive when people start with that phrase,” he says. “It’s a very capital-intensive, highly regulated industry, and so there’s reasons, in some cases, why it’s conservative.”

But aside from the methodical approach, Crystal says that AI is already having a deep impact on how startups think about insurance. He points to several of his firm’s first investments. One, Bright Harbor, creates software designed to help people impacted by natural disasters, and has already raised (https://www.axios.com/pro/climate-deals/2025/08/26/bright-harbor-disaster-recovery-joel-wish) a $10 million seed round after Crystal Venture Partners’ initial investment. Another, Sixfold, uses generative AI to aid with insurance underwriting and raised (https://www.thesaasnews.com/news/sixfold-raises-15-million-in-series-a) a $15 million Series A after Crystal invested. His new fund has already announced six investments, with 15 total planned, though he says he’s not actively raising his next fund. “I didn’t go into this to stop at a Fund One,” he adds.

While insurance may seem like a narrow focus area, Crystal argues that it touches every sector, from healthcare to climate risk to cybersecurity. Still, for an industry that he says hasn’t changed much since his grandfather entered it, insurance is entering a period of massive flux. Now it’s his job to figure out where it’s headed—and to capitalize on the moment. “I’m inspired by what the future might hold,” Crystal says. “But I’m experienced enough to be cynical and skeptical about how quickly that’ll happen.”