Brian Chesky and Joe Gebbia are living large these days.Their rent-apartments-instead-of-hotel-rooms company, Airbnb, is rumoured to be raising a $100 million round which would give it a billion-dollar valuation.
Entrepreneurship wasn’t always easy for these successful founders though. In fact, they were on the verge of shutting down completely before their startup had a chance to take off.
Justin.TV founder Justin Kan recalls meeting the founders in 2008 when they were down in the dumps. They had tried multiple times to get traction for AirBNB but to no avail. Airbnb contracted outside sales people to generate leads and “launched” at three different conferences including SXSW and the Democratic National Convention.
Each promotion brought fleeting traffic surges of one-time visitors.
“By fall, almost anyone could have justified throwing in the towel,” Kan says. “They had tried to make the product work multiple times, had accumulated tens of thousands in personal credit card debt, and were literally printing cereal boxes to try to make money. Even their lead (and only) engineer had moved back to Boston.”
Their big break came when they were accepted into Y Combinator later that year.
Two years later, they’re arguably the most valuable Y Combinator company and are the “darling of west coast startups.”
Not all startups have such happy endings though. General Assembly’s founders had all of the makings of a successful first venture in college but they let it slip through their fingers.
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