How Brian Chesky funded Airbnb selling Obama-branded cereal

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.

They sold 800 boxes at $40 each. That's $32,000. They ate the Cap'n McCain's themselves for the next year.

When Paul Graham heard the story, his reaction wasn't "that's clever marketing." It was: "If you can convince people to pay $40 for a $4 box of cereal, you can probably convince them to sleep in a stranger's house." That single anecdote — the willingness to do something undignified to keep the company alive — is what got them into YC W09.

The lesson founders take from this is usually the wrong one. It's not "do PR stunts." It's that the cereal wasn't a stunt. It was rent. It was payroll. It was the only thing standing between three guys and going back to design jobs.

Years later, when Airbnb was worth $100B, Brian kept a box of Obama O's on his desk. Not as nostalgia. As a reminder that the difference between companies that survive 2008 and companies that don't is usually one weird decision that no business school would teach.