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The Anxieties Of Airbnb CEO Brian Chesky

Airbnb CEO Brian Chesky charts his anxiety level since his rent-a-stranger's-apartment service began.

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October 2007
During early brain­storming sessions, "I didn’t know if this idea could succeed outside my own group of friends," Chesky says. "There just wasn’t any data."

May 2008
Just as things started to take off, cofounder and key programmer Nathan Blecharczyk moved to Boston. "I was really concerned about the team dynamic," says Chesky. "We didn’t know if we could succeed without Nate."

September 2008
Faced with a crashing economy, "all of our [potential] investors went radio silent," Chesky recalls. "Nate was gone, we were completely in debt, it wasn’t clear if we had a sustainable model."

January 2009
Joining the incubator Y Combinator "offered us the chance to get back together and refocus on Airbnb," says Chesky. The $20,000 in seed funding and added exposure on TechCrunch didn’t hurt either.

March 2009
"The day we became Ramen-profitable"—aka netting $1,000 a week in revenue—"we knew we had a real business," Chesky says. That impressed investors from Sequoia Capital.

November 2010
Airbnb nets its first major funding round, with $7.2 million. "I know this sounds crazy, but it didn’t feel like a milestone," says Chesky. "We were already succeeding, and we knew we were going to raise money. So it was more operational than emotional."

February 2011
It was a triumph; yet "growing fast comes with a whole new set of worries," says Chesky. "Can we maintain our culture? Will our quality stay high?"

July 2011
When news broke that a rented home had been ransacked and robbed, Chesky moved to do damage control but didn’t fear for the business. "That was one transaction," he says, "and we’ve had hundreds of thousands of amazing experiences."

Read more Airbnb articles

A version of this article appeared in the November 2011 issue of Fast Company magazine.