Insurance Founder Aims to Help the World “Become More Fair”

The son of a Chinese immigrant mother and Jewish father, Jonathon Grayson ’97 grew up in a rural New York town of 2,500. He realized at a young age that being different was difficult, and yet it made him yearn for a more equal world. 

His dad often drove him 30 miles to the nearest Jewish temple or more than 150 miles to New York’s Chinatown to visit his grandparents, making him “aware of a much larger world out there,” he says. To him, that wider world seemed more diverse and accepting than his small town and left him with the deep sense that everyone deserves fairness.

Now Grayson is CEO and cofounder of Surround Insurance, which “helps the world become more fair,” he says, by providing new kinds of coverage. Grayson is using technology, data, and design to build insurance around people’s activities, not just their assets—policies aimed at millennials and Gen Zers. He created the business to address a paradigm shift, he says.

The American dream after World War II was owning a house and car because it signaled success. But the cost of houses and cars in the decades since has become prohibitive, and consumers are now more aware of the environmental impact of driving. So many young people today are beginning their adult lives by biking and sharing cars and houses. 

Surround offers non-owner auto insurance for those driving a borrowed or rented car; renter’s insurance for personal property and accidents; biking insurance that covers stolen or damaged bikes as well as injuries and lost wages if you’re hit by a car; and freelancing insurance for errors in service or failure to provide service. After a customer answers online questions, an algorithm designs an individualized, affordable package.  

“Young people have more risk than their parents, who often spent a career in the same job,” says Grayson, citing surveys showing that nearly half of employees in their 20s are freelancing. “They also worry about burdening parents with student loans, supporting themselves if out of work, and paying bills after an accident. And with the pandemic, life became even riskier.”

Grayson founded Surround after 14 years at Liberty Mutual Insurance, where he oversaw the customer experience of 12 million policyholders representing $18 billion in revenue. His SB in economics from MIT and an MBA from Cornell also helped prepare him to launch his own company. “MIT taught me grit,” he says. “As a startup, we’ve had very difficult moments, but I learned you just figure it out.”

He lives near Boston with his wife, Amy Grayson ’97, PhD ’03, and their two sons.

This article also appears in the January/February 2023 issue of MIT News magazine, published by MIT Technology Review.