Brian Chesky

The move

2008. Brian Chesky and Joe Gebbia are flatmates in San Francisco who can't make rent. They blow up three air mattresses, make breakfast, and put up a site called airbedandbreakfast.com for people at a design conference who can't find a hotel. Three guests.

People laugh at the idea. Strangers sleeping in your house is the kind of pitch that ends a meeting. Investors say no. In 2008 Chesky and Gebbia keep the company going by selling election-themed cereal boxes. Obama O's. Cap'n McCain's. $40 each. They pay off the credit cards and keep building.

Y Combinator takes them in 2009. Airbnb grows on one rule Chesky still uses twenty years later. Do things that don't scale. He stays with hosts in New York himself. Photographs the listings. Redoes the profiles. The company was obsessed with its customers before that was something people said.

Airbnb goes public in December 2020, in the middle of a pandemic that had wiped out 80% of its bookings six months earlier. The IPO values it at $86.5B. More than Marriott, Hilton and Hyatt put together. The strangers-in-your-house pitch became the biggest hospitality company in the world.

Why it was risky

There was nothing like it. No insurance. No rules. No way to trust anyone. Nobody rented a stranger's flat. Chesky and Gebbia spent five years just proving people wanted it. Then ten more convincing cities, regulators and the big hotel groups that it should be allowed.

The numbers

From three air mattresses to the biggest hospitality company on earth. Every step was a choice to keep doing the stuff that doesn't scale, for as long as it took.

The lesson

The platform wasn't the risk. Being the founder people laughed at for six years straight was. Chesky and Gebbia built Airbnb on a simple idea. If the category doesn't exist, make it yourself. Take the photos. Host. Design. Answer the emails. R.I.S.K. is for founders ready to keep doing the unscalable long after people stop laughing.