Chesky grew up in Niskayuna, N.Y., north of Albany. He was into hockey, and he also liked to draw and design new versions Nike sneakers, which turned into an interest in art.
In 1999, Chesky attended Rhode Island School of Design, where he served as captain of the hockey team and studied industrial design.
At RISD, Chesky met Joe Gebbia, who would eventually cofound Airbnb.
Gebbia told Fortune that after graduation, he pulled Chesky aside and said: "Before you get on the plane, there’s something I need to tell you. We’re going to start a company one day, and they’re going to write a book about it."
In his early 20s, Chesky was a competitive bodybuilder. He's described as still having "16-inch biceps."
In a Fast Company profile from 2014, Chesky is described as an imposing figure: "A former hockey player and bodybuilder with 16-inch biceps, the CEO commands attention. His boomerang grin and slant nose work to sharply focus his attention on you. Rather than turn his head toward me, he physically picks up his chair and pivots it directly so we're eye to eye."
But shortly thereafter, he moved to San Francisco with Gebbia. When a design conference came to town in 2007 resulting in all the hotels being sold out, Gebbia pitched Chesky the idea to rent out space for those who couldn't find a place to stay.
Here is the email that started Airbnb. Shown onstage at #TED #TED2016 pic.twitter.com/A2ZF9Epcxj
— Bill Gross (@Bill_Gross) February 16, 2016
Along with a third cofounder, Nathan Blecharczyk, Gebbia and Chesky started what was at the time called Airbedandbreakfast.com.
Since then, Airbnb has not only shortened its name, but has expanded to more than 34,000 cities and as of 2016, had been used by more than 60 million guests. The company is currently the second-highest valued startup in the U.S.
According to Forbes, Chesky owns a 13% stake in Airbnb and his personal net worth is $3.3 billion, landing him at #7 on the list of the world's wealthiest entrepreneurs under 40.
All three of Airbnb's founders have publicly pledged to donate more than 50% of their wealth to the Giving Pledge, a philanthropic initiative started by Warren Buffet and Bill and Melinda Gates.
Chesky is currently dating artist Elissa Patel, who he met on Tinder two years ago.
Chesky and Patel do yoga together each week and book staycations in Airbnb's throughout San Francisco.
