Brian Chesky Story and Lessons - How a Cash-Strapped Startup Became a Global Vacation Rentals Powerhouse & 9 Startup Lessons #933761

There's a particular kind of desperation that comes from not being able to pay rent. It's not romantic. It's not the kind of struggle we celebrate in startup mythology until it works out. When you're there, living it, maxing out credit cards and wondering if you made the biggest mistake of your life by leaving a steady job, desperation feels like the opposite of opportunity.
This is where Brian Chesky found himself in 2007, living in a cramped San Francisco apartment with his design school friend Joe Gebbia. They had moved to California chasing dreams – the kind of dreams you have when you're young and idealistic, convinced that designers really can change the world. But dreams don't pay bills. The rent was due, and they were short.
What happened next sounds almost too convenient to be true. A design conference was coming to San Francisco, and every hotel room in the city was booked. These two broke designers looked at each other and their empty living room, and they did something genuinely audacious. They bought a couple of air mattresses, posted an ad online offering accommodation for the weekend, and waited to see if anyone would respond.