We went door to door with cameras taking pictures of all these apartments to put them online. We got into Y Combinator in 2009, and when New York took off, we flew back every weekend. We sold collectible breakfast cereal and did other crazy things. We met all these investors and they just wouldn't invest.

How did you go from 'we have a great idea' to 'we're building a great business.' Because all you had to believe was, if I like it, I have to bet that I'm normal enough that other people will like it, too. From there, we pretty much believed in the idea. In January or February 2008, there were enough ordinary people who wanted to do this. When did you realize you had stumbled on something that could be massive? He said: 'Brian, I hope that's not the only thing you're working on.' And I remember telling him about the idea. There was a designer in LA who I looked up to. People said to your face: 'Brian, Airbnb is a really dumb idea'? We thought, 'This'll work for one weekend to pay the bills while we come up with The Big Idea.' People still said it was absurd. The moment when we thought this idea wasn't going to work was the moment we came up with it. THOMPSON: Was there a moment when you thought this idea was never going to work?ĬHESKY: Yes. This transcript has been edited for clarity.

We talked about the early years, advice for young entrepreneurs, what he's working on at Airbnb, and whether sharing is for everybody - and every business. Last week, I spoke to Chesky, now CEO of Airbnb, at length in New York City, where the company has run into trouble with a city law that makes Airbnb-type rentals technically illegal. Five years later, Airbnb is a $2.5 billion company used by an estimated 50,000 to 60,000 people a night and the keystone of the emerging 'sharing economy.' They made special-edition Cheerios boxes for both presidential candidates called 'Obama O's' and 'Cap'n McCains' with hot glue and cardboard, selling several hundred items for tens of thousands of dollars when investors refused to give them money.

In 2008, Chesky and his co-founders, desperate for cash but confident they had an idea worth pursuing, got into the cereal business. I've read it in so many places, it's practically an origin myth by now.īefore Airbnb became a giant online marketplace for sharing homes and spaces, it was a couple of air beds on a floor in San Francisco. 'You know the story right?' Brian Chesky asks me.