THOMPSON: Was there a moment when you thought this idea was never going to work?
CHESKY: Yes. The moment when we thought this idea wasn't going to work was the moment we came up with it. 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.
People said to your face: "Brian, Airbnb is a really dumb idea"?
There was a designer in LA who I looked up to. And I remember telling him about the idea. And he said something I'll never forget. He said: "Brian, I hope that's not the only thing you're working on."
When did you realize you had stumbled on something that could be massive?
In January or February 2008, there were enough ordinary people who wanted to do this. From there, we pretty much believed in the idea. 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.
How did you go from "we have a great idea" to "we're building a great business."
We met all these investors and they just wouldn't invest. So we started funding it ourselves. We sold collectible breakfast cereal and did other crazy things. We got into Y Combinator [the San Francisco-based incubator led by Paul Graham] in 2009, and when New York took off, we flew back every weekend. We went door to door with cameras taking pictures of all these apartments to put them online. I lived in their living rooms. And home by home, block by block, communities started growing. And people would visit New York and bring the idea back with them to their city.
Today, you're perhaps the most famous company to come out of Y Combinator. What was the best advice Paul Graham gave you?
"Do things that don't scale." It's better to have 100 people love you than to have 1,000,000 people like you. Go to New York to build your company, he said. Don't stay in Mountain View. Go to New York. That was the best advice we ever got.
"Do things that don't scale." What does that mean?
Create the perfect experience however you need to do it, and then scale that experience. Every company that makes something is just two things. It's creating an experience. And then it's multiplying them. We care about just two things: How great that one experience is and how many we make. Too many people start in technology with "how many you sell" and then they try to make it better. A lot of movements start with a small set of evangelists.
ON AIRBNB TODAY
How has the company changed since you first came up with this allegedly stupid idea that everybody warned you was stupid?
It was literally named Air Bed & Breakfast. It was literally supposed to be all about air beds. Today we have 123 people staying in castles.
At first, we thought, surely you would never stay in a home because you wanted to, you would only stay there because it was cheaper. But that was such a wrong assumption. People love homes. That's why they live in them. If we wanted to live in hotels, more homes would be designed like hotels.