The education of Brian Chesky

Brian Chesky is drawing intently on a napkin. We’re sitting in the President’s Room at Airbnb’s airy, ultra-chic headquarters in the SoMa neighborhood of San Francisco. Other meeting spaces in the historic building, which the company moved to in 2013, are designed to replicate an Airbnb rental in Fiji or the war room from the movie Dr. Strangelove. With its wood-paneled walls, leather club chairs, and a model of a ship on the coffee table, the President’s Room retains the feel of the original executive quarters from 1917, when the building was built to house a battery factory. After a moment of serious sketching, Chesky holds up the napkin to show me his picture: It’s a boat. And, it must be said, for a graduate of the Rhode Island School of Design it’s a rudimentary-looking vessel. But the quality of the drawing is not the point. I’ve just asked Chesky how his management style has evolved, and the boat is his answer.

“If you think about it, Airbnb is like a giant ship,” he says, holding up the napkin. “And as CEO I’m the captain of the ship. But I really have two jobs: The first job is, I have to worry about everything below the waterline; anything that can sink the ship.” He points to the scribbled line of waves that cuts the boat in half, and below that, two holes with water rushing in.

“Beyond that,” he continues, “I have to focus on two to three areas that I’m deeply passionate about—that aren’t below the waterline but that I focus on because I can add unique value, I’m truly passionate about them, and they can truly transform the company if they go well.” The three areas he’s picked: product, brand, and culture. “I’m pretty hands-on with those three,” he says. “And with the others I really try to empower leaders and get involved only when there are holes below the waterline.”

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