I just saw a video from Brian Chesky, founder of Airbnb, where he is giving a lecture to a couple of Stanford University students on the time he hit rock bottom. He had no cash left and his company, Airbnb, was in lots of debt. His co-founder was thinking of moving to Boston - Airbnb was based in California - because he was getting engaged and his fiance wasn't sure if she wanted to remain on the west coast. Airbnb also wasn't getting enough bookings during this time to generate enough revenue to keep the business going.
So how did Brian survive? He sold cereal. The time was around the democratic and republican conventions for the 2008 election and he decided to make cereal that was going to be sold in boxes with two different brands: Captain McCains (for republican nominee John McCain) and Obama O's - "the breakfast of change" (for Barack Obama).
Brian called General Mills who thought he was crazy for thinking that they were going to work with him to sell unlicensed presidential themed cereal. He then called the mid-tier cereal makers who decided to work with him but they wanted a non-refundable check for $200,000. Not an easy check for Brian to write since he was in the hotel and lodging business, but resorted to selling cereal just so his business could survive.
But then Brian found a guy in Berkeley who agreed to print him 1,000 boxes as long as he got some royalties. Brian and his team folded 1,000 boxes of cardboard and packed it with cereal. They then sold the cereal for $40 a box and hand labeled each box to show their customers that the cereal was a limited edition. They made $30,000 to fund the company during this time.
Then after almost blowing through all of the $30,000 and being back in the same situation, they met Paul Graham of Y Combinator.
Paul hated the idea of Airbnb, but Brian's business partner, Joe, gave Paul Graham a box of the cereal that they made. Once Paul found out that they were selling each box for $40, he decided that if they could convince people to pay $40 for a box of cereal, then they might be able to convince people to stay in other people's homes.
He decided to invest and said Brian Cheskey was like a cockroach because of his ability to stick around. Brian said that Paul calling him a cockroach was the best compliment he got during those harsh times.