Skip to Content
MIT News: Alumni profile

Insurance founder aims to help the world “become more fair”

Jonathon Grayson ’97

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. 

Jonathon Grayson ’97

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.

Keep Reading

Most Popular

A Roomba recorded a woman on the toilet. How did screenshots end up on Facebook?

Robot vacuum companies say your images are safe, but a sprawling global supply chain for data from our devices creates risk.

A startup says it’s begun releasing particles into the atmosphere, in an effort to tweak the climate

Make Sunsets is already attempting to earn revenue for geoengineering, a move likely to provoke widespread criticism.

10 Breakthrough Technologies 2023

Every year, we pick the 10 technologies that matter the most right now. We look for advances that will have a big impact on our lives and break down why they matter.

These exclusive satellite images show that Saudi Arabia’s sci-fi megacity is well underway

Weirdly, any recent work on The Line doesn’t show up on Google Maps. But we got the images anyway.

Stay connected

Illustration by Rose Wong

Get the latest updates from
MIT Technology Review

Discover special offers, top stories, upcoming events, and more.

Thank you for submitting your email!

Explore more newsletters

It looks like something went wrong.

We’re having trouble saving your preferences. Try refreshing this page and updating them one more time. If you continue to get this message, reach out to us at with a list of newsletters you’d like to receive.