How Did COVID Change the Way Brian Chesky Runs Airbnb?

Brian Chesky says the pandemic was the first moment he had to be a good chief executive, because it was life or death. Before that, being better at the job was a nice-to-have that might have made Airbnb grow faster and feel less chaotic. In the crisis, either he was a good chief executive and the company survived, or he was a bad one and the company died. Guy Raz, earlier in the episode, quotes him from 2020 saying Airbnb lost 80% of the business, and Chesky puts that drop at eight weeks. He was about 38 or 39, about 12 or 13 years in, and he says he is good in a crisis.

Hands-on work, which he calls founder mode, came only from that crisis. He had not thought about Steve Jobs for eight or nine years after Jobs died. When people thought Airbnb was going out of business, he asked who else had nearly gone out of business, and the answer was Steve Jobs. Hiroki Asai, a creative director at Apple, and Jony Ive, an industrial designer who worked with Jobs, told him the stories. Jobs, about 12 weeks from bankruptcy, got into the details, cut projects, simplified, stayed present, said no more than yes, and watched every pixel and every word.

Chesky says he then ran Airbnb hands-on for the first time in 15 years, in the foxhole with the team. When employees wanted the old distance back, he refused.