This Week in Startups · Thursday, October 1, 2026
Brian Chesky detailed Airbnb's Y Combinator interview, where they were initially met with skepticism. Paul Graham questioned the concept and suggested they create Stripe instead. However, the Airbnb founders' resourcefulness, particularly their creation and sale of politically themed Obama-Os cereal boxes to fund their venture, ultimately convinced Y Combinator. They were admitted due to their perceived resilience, described as 'cockroaches' that would survive any market downturn.
“And the first question Paul Graham asked me is people are actually doing this. And I said, "Yes." His second question was, what's wrong with them?”
“And Joe takes out a box of Obama-Os. And he hands it to Paul Graham. And Paul Graham's like, looks like he just got a novelty gift. He's like, all right, thank you. Yeah. And and we go, He goes, what's the story? He goes, this is how we fund the company.”
“And he said something like, I guess if you can convince people to pay $40 for a $4 box of cereal, then maybe you can convince at least some people to stay in each other's homes.”
“And I remember Paul and Jessica said later they thought we were like cockroaches, and I think they mean it in a good way, that it was like an investment in nuclear winter, and in a nuclear holocaust, the only thing that survives are cockroaches. And the only thing that would survive an investment in nuclear winter would be the founders of Airbnb. We said, "We won't die no matter what happens."”