How selling political cereal boxes convinced a top investor to fund Airbnb

When Airbnb’s founders walked into their Y Combinator interview in early 2009, they brought an unusual prop: a box of novelty cereal. That decision, according to a story recounted in Leigh Gallagher’s book The Airbnb Story and later excerpted by WIRED, helped change one investor’s mind about backing the struggling startup.

The cereal in question, Obama O’s and Cap’n McCain’s, wasn’t a marketing gimmick dreamed up for the pitch — it was a genuine survival tactic from months earlier. In 2008, with their short-term rental platform, then called AirBed & Breakfast, generating very little revenue and fundraising meetings largely ending in rejection, founders Brian Chesky, Joe Gebbia and Nathan Blecharczyk created two limited-edition, election-themed breakfast cereals, each sold for $40, with only 500 boxes of each produced. As first reported by Yahoo Finance, the campaign generated roughly $30,000, enough to keep the company operating while the founders searched for real investors.

Investor Paul Graham was initially unconvinced by Airbnb’s core business idea, but his view shifted after hearing how the founders had managed to finance themselves through the cereal sales. Graham reportedly described them as “cockroaches” that simply refused to die — considered high praise in startup circles, reflecting extraordinary resilience under pressure. Airbnb was subsequently accepted into Y Combinator, receiving its first major institutional backing.

According to Airbnb’s official company timeline, the cereal money provided the financial runway that carried the founders through to that acceptance. Nathan Blecharczyk later reflected on the episode in a letter published by Airbnb, recalling that he initially viewed the cereal boxes as a distraction from the company’s real mission — though he later acknowledged the story helped convince investors the founders had the determination needed to build a successful company.