30 Under 30 Honorees of 2019

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Josh Stiles
Individual salesperson
Compass
Boston, MA
United States
US
Age: 
29
Individual volume: 
$22.1 million
Individual sides: 
12

A Love Match

Josh Stiles, GREEN, SRS, claims to “bleed yellow,” as in fuzzy yellow tennis balls. As soon as he was old enough to swing a racquet, he was out on the courts with his dad, and he’s been swinging ever since. A car accident at age 19 that broke both his legs didn’t stop him—four years later, while earning a bachelor’s degree in economics, he helped lead his stellar Kenyon College tennis team to win the National Men’s Team Indoor Championships. When Stiles, now 29, relocated to Boston, he was rejected by one brokerage for not knowing enough people. Once he did affiliate with a broker, he built a client base partly by joining the local tennis community in league play and philanthropic events. “My favorite part of tennis is being part of a team,” he says. “Real estate is similar. Many parties are working together to get to the finish line.”