How Brian Chesky funded Airbnb selling Obama-branded cereal
In 2008, before YC, Airbnb was broke. The fix wasn't a pivot — it was 800 boxes of cereal, $40,000 in revenue, and the willingness to look ridiculous in front of investors.
Brian Chesky · 6 min read
Most people remember Airbnb's YC story as the moment Paul Graham looked at Brian, Joe, and Nate and asked, "Why are you wasting your time on this?" What they forget is what came next: Brian opened a cabinet and pulled out a box of Obama O's.
It was the summer of 2008. Airbnb had been live for nearly a year. Growth was flat. They had maxed out 15 credit cards across the three founders. The Democratic National Convention was coming to Denver, and the team had an idea, limited-edition political cereals. Obama O's ("The Breakfast of Change") and Cap'n McCain's ("A Maverick in Every Bite"). They convinced a designer friend to make the boxes for free and a local cereal company to fill them at cost.
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