The strange business detour that saved Airbnb before it became a $100 billion company

Today Airbnb is worth tens of billions of dollars and operates in more than 220 countries and regions. But one of the company’s defining moments had nothing to do with technology or hospitality — it involved packaging ordinary breakfast cereal inside collectible political boxes to survive a period when almost nobody believed in the idea.

In 2008, founders Brian Chesky, Joe Gebbia and Nathan Blecharczyk faced a company with very little revenue and a string of fundraising rejections. Their short-term rental platform, then called AirBed & Breakfast, wasn’t generating enough to keep operating. So they created two limited-edition, election-themed cereals, Obama O’s and Cap’n McCain’s, selling each for $40 with only 500 boxes of each produced. As first reported by Yahoo Finance, the campaign brought in roughly $30,000.

That money, according to Airbnb’s official company timeline, provided the financial runway that helped the founders survive until they were accepted into startup accelerator Y Combinator in early 2009. The cereal campaign also attracted unexpected media attention, and later became a key part of the company’s pitch to investors.

In The Airbnb Story, later excerpted by WIRED, author Leigh Gallagher recounts how Gebbia brought one of the cereal boxes to the founders’ Y Combinator interview. Investor Paul Graham, initially unconvinced by the business idea, changed his mind after hearing how the founders had self-financed through cereal sales, later calling them “cockroaches” who simply refused to die — a phrase that stuck as a compliment describing their resilience. Airbnb was accepted into Y Combinator shortly after, marking its first major institutional backing.