Hatched in 2008 on a whim, Airbnb is now a massive platform that has been used by 40 million people. Indeed, the past seven-plus years have been a combination of exhilarating, nerve-racking, and flat-out surreal for Chesky. “There’s no learning curve for people who are in war or in startups.” defense secretary to explain his own voracious pursuit of management knowledge. “It’s kind of like the old Robert McNamara saying,” says Chesky, referencing a comment about nuclear weapons by the controversial 1960s U.S. Others he’s reached out to for lessons include Berkshire Hathaway’s (BRK.A) Warren Buffett and Disney (DIS) CEO Bob Iger a long list of tech luminaries that includes Apple’s (APPL) Jony Ive, LinkedIn’s (LNKD) Jeff Weiner, and ’s (CRM) Marc Benioff and a separate group he’s taken posthumous lessons from, including Steve Jobs, Walt Disney, George Bernard Shaw, and Dwight D. But Tenet is just one of a long list of leaders Chesky has sought out since co-founding the home-rental website-some inside the box and some very far outside it. It may seem odd for Chesky, the CEO of the company that, along with ride-sharing giant Uber, has become the poster child for the so-called sharing economy, to seek advice from the man who signed off on the intelligence that led to the 2003 U.S. Chesky was introduced to Tenet a few years ago and asked to set up a meeting. 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. And in fact there is an outside source for this bit of wisdom, but it’s not what you might expect. It’s a high-level, strategic way of thinking about management, something that sounds more out of the playbook of Jim Collins or Peter Drucker than a 33-year-old first-time CEO. Watch: Airbnb’s founder on disrupting an industry “And with the others I really try to empower leaders and get involved only when there are holes below the waterline.” “I’m pretty hands-on with those three,” he says. “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. 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. “If you think about it, Airbnb is like a giant ship,” he says, holding up the napkin. I’ve just asked Chesky how his management style has evolved, and the boat is his answer. But the quality of the drawing is not the point. And, it must be said, for a graduate of the Rhode Island School of Design it’s a rudimentary-looking vessel. After a moment of serious sketching, Chesky holds up the napkin to show me his picture: It’s a boat. 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. 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. We’re sitting in the President’s Room at Airbnb’s airy, ultra-chic headquarters in the SoMa neighborhood of San Francisco. How the home-sharing site’s co-founder hacked leadership and taught himself to be a world-class CEO.īrian Chesky is drawing intently on a napkin.
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