Airbnb
Brian Chesky & Joe Gebbia
In 2008, we were completely broke and drowning in thousands of dollars of credit card debt. VCs weren't biting on the idea of people renting out air mattresses to strangers. To fund the company, we noticed the Obama-McCain election was dominating the news cycle. We designed and printed 1,000 custom cardboard cereal boxes: "Obama O's" and "Cap'n McCains."
We bought cheap generic cereal at the grocery store, hand-glued the boxes together in our apartment, and sold them as limited-edition political memorabilia for $40 a box to collectors. We made $30,000, which literally kept our servers running.
Later, when we interviewed with Paul Graham at Y Combinator, he looked at a box and said, "If you can convince people to pay $40 for a $4 box of cereal, maybe you can convince them to sleep in each other's airbeds."