A lot of people start with a vision, but give up because it’s too big,” says Airbnb CEO Brian Chesky. “Or they edit their vision, so it’s more attainable. But as Walt Disney once said, ‘If you can dream it, you can do it.’ ”
The dream that became Airbnb began as a quick-cash boondoggle in the fall of 2007, after Chesky, a 27-year-old graduate of the Rhode Island School of Design, decided to move to San Francisco following a brief stint at a design firm in LA. “After a while I started to feel unfulfilled designing products that would eventually end up in a landfill,” he says of the job. “I wanted to build something that would last.”
Auspiciously, his friend Joe Gebbia, a fellow RISD alum, had room for him to stay at his place. “Everyone has one or two moments when they make a decision and it changes their life forever,” says Chesky, now 34. “Almost every decision I’ve made is a chain reaction
from that moment I decided to move to San Francisco.”
Having packed all of his possessions into the back of a Honda Civic, Chesky arrived with everything but enough money to make his first month’s rent. A major design conference was coming to town, and the city’s hotels were at capacity. So he and Gebbia came up with a plan, inflated three air mattresses in their living room and registered a website, airbedandbreakfast.com. Within a week, they had three strangers paying to sleep on their floor—and the sharing economy was born. Well, almost.
“No one wanted to invest in us,” Chesky admits of the company’s infancy. He remembers one meeting with an investor who got up and left the room midway through the pitch without saying goodbye. “I thought he was going to feed the parking meter, but I’ve never seen him again,” he says. Deep in debt and living off credit cards, Chesky and Gebbia became so desperate they started selling collectible cereals inspired by the 2008 presidential election. The $30,000 they made from Obama O’s and Cap’n McCain’s was enough to sustain them until the start-up incubator Y Combinator took a chance on their pitch in 2009.
Since then, in a little over six years, Chesky and Gebbia’s homegrown scheme has exploded into a $25.5 billion juggernaut, with some two million homes available to rent in more than 190 countries. And to Chesky, whose net worth now exceeds $3.3 billion, one of the most rewarding aspects of the business is that it gives regular individuals a chance to become micro-entrepreneurs just by putting their home, or part of it, on the site. A recent study estimates that those who lease out space through Airbnb increase their annual income by about 14 percent. “This means they have more financial freedom, extra money to pay the rent, fund a vacation or even start a new business,” he says.
The model also gives users, or “guests,” a richer—and typically more economical—way to see the world. “When you travel to a new place, you usually feel like an outsider,” Chesky explains. “You go to a city, see the landmarks and tourist traps, but you don’t meet any locals, or experience the way people actually live. With Airbnb, you’re an insider.”
Chesky believes that nurturing a strong, trusting culture at the company, which adds hundreds of new employees each month, is critical to maintaining its success and, as he puts it, positioning them to “take the next moonshot.” He conducts extensive research on
the corporate culture of companies like Zappos, Disney, Nike and Apple, often personally interviewing their employees to get at the heart of what works.
One of those moonshots will be Airbnb’s push into China, whose citizens took around 109 million trips in 2014 and have been the world’s top spenders in international tourism since 2012. In the past year, Airbnb bookings by Chinese travelers going abroad shot up 700 percent—the company’s fastest growing market. Chesky is also working to bolster Airbnb’s business-travel program, which already has over 1,000 companies signed up for corporate accounts. And he’s looking at new ways to provide users with a better trip from start to finish.
To that end, Chesky has an insatiable appetite for new ideas. “If we could get any home in the world on Airbnb, which would it be?” he recently asked on Twitter. He even approached President Obama, with whom he had worked on encouraging entrepreneurship in Cuba, to inquire in earnest if he’d consider making the Lincoln Bedroom available on the site. (The president’s response: “I need
to check with Michelle.”)
So far, the most exceptional Airbnb property Chesky has stayed in is in Australia, a house suspended 130 feet over a beach. When he books through the exchange, he tries to keep his job title hidden from the hosts, with the hope of having an authentic experience, but he says they usually find out. “I do get a lot of ideas from my hosts,” he adds, “which I always bring back to the team.”
Chesky frequently credits his parents, both social workers from upstate New York, for giving him the tools that allowed him to build Airbnb into the culture-shifting, industry-defining powerhouse it is today. “We make decisions that aren’t just right for our business, but are right for our community and the places that we serve,” he explains. “We reinforce empathy for our guests and hosts, and believe that people are fundamentally good. I think all these principles were instilled in me from an early age.”
Without regard for limitations, Chesky seems to be having a blast pushing boundaries and conceiving new realities. “Our mission is to create a world where you can belong anywhere,” he says, before conceding that it’s an audacious aim. Still, as Walt Disney also once said, “It’s kind of fun to do the impossible.”