Fortune magazine recently spent some time with Airbnb CEO Brian Chesky, chatting about everything from his ever-growing homestay business to his childhood obsession with hockey. The linterview is more than worth a read—take it all in here—but if you're looking for the abbreviated version, we pulled some interesting tidbits about the man behind the endeavor. Read on:
His Napkin Sketches Aren't Impressive, According to the Writer
"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."
He Sees Himself As The Captain of a Ship
"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. 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. Beyond that, 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."
He Gets Business Advice From a Former CIA Director
"There is an outside source for this bit of wisdom, but it’s not what you might expect. Chesky learned the boat theory from George Tenet, the director of the CIA from 1997 to 2004 and now a managing director at the investment bank Allen & Company. Chesky was introduced to Tenet a few years ago and asked to set up a meeting."
Airbnb Was Born Because Of a Rent Check
"In October 2007, Chesky and Joe Gebbia, two unemployed RISD graduates, were broke and staring at their rent due date. So they came up with the idea to pull some of Gebbia’s air mattresses out of the closet and sell sleeping space in their apartment to attendees of a sold-out design trade show. They called it the Air Bed and Breakfast. (The 'continental breakfast' consisted of untoasted Pop-Tarts.)"
He's a Bookworm
"For Chesky, a source may come in the form of a biography of a business hero such as Steve Jobs or Walt Disney. His primary book source on management technique is Andy Grove’s High Output Management. To learn the ins and outs of hospitality, he went to the Cornell Hospitality Quarterly, a scholarly journal published by the Cornell University School of Hotel Administration."
He's Inspired By Warren Buffett
"One of Chesky’s biggest source triumphs was his audience with [Waren] Buffett. A little over a year ago, Chesky reached out and asked if he could travel to Omaha to have lunch, in part to talk about how Airbnb might help expand the number of rooms available in town during Berkshire’s annual meeting weekend. The discussion ended up lasting 4½ hours. 'He’s literally in the center of Omaha,' Chesky says. 'There are no TVs anywhere. He spends all day reading. He takes maybe one meeting a day, and he thinks so deeply.' The experience made such an impact on Chesky that he went to the airport, and, afraid he would forget the conversation, immediately wrote a 3,600-word report and sent it to his team."
When He Finds a New Hobby, He Goes All In
"Chesky’s first passion was hockey. After he got a full set of gear for Christmas one year, he insisted on sleeping in it—pads, skates, stick, and helmet. Later a hobby of drawing and redesigning Nike sneakers grew into a passion for art. He would disappear to the local museum for hours to draw replicas of the paintings."
He Knows How Long It Takes to Set Up 6,000 Chairs
"His natural leadership potential surfaced at RISD, where he served as the captain of the hockey team and was eventually selected to be the commencement speaker at his graduation. Chesky threw himself into the task, studying every commencement speech he could find; to make the experience less intimidating, the night before his address he stood at the podium and watched as the staff set up 6,000 chairs one by one."
He Met His Girlfriend on Tindr
"Even as his profile rises, however, Chesky has been working on a new project: finding balance. He has learned that if he is going to stay in his job for the long run, he must develop techniques to 'refill the reservoir.' The key source in that effort is Elissa Patel, his girlfriend of two years (they met on Tinder), who recently left photo app Frontback to start her own venture. They do yoga together every Thursday morning. And since Chesky’s apartment is still listed on Airbnb—yes, you can Airbnb the CEO’s pad—the occasional guest joins in. He and Elissa often do 'staycations,' booking an Airbnb in a different neighborhood just to experience it."
Erika Owen is the Audience Engagement Editor at Travel + Leisure. Follow her on Twitter and Instagram at @erikaraeowen.
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