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Brian Chesky: The Hero's Journey: Part One

This is one of Brian's first public conversations since the pandemic hit. It is also the first time Brian publicly discusses the layoffs and why they took the approach they did. They also discussed Brian's approach to crisis leadership and the importance of love and compassion. There was a lot to cover, so I decided to release this in two parts.

Updated on July 18

Key Smash Notes In This Episode


In the earliest weeks of Covid19, sometimes around March 2020, Bryan saw their user base in Europe started to shrink, an event that had not happened in the history of the company. That same week, big sports events started to get cancelled. That's when Brian new they were heading in a bad direction.


0. Setup a war room. Make sure that your board and executives meet on regular basis. Communicate extensively. Then, focus on the following:

1. Be decisive. 2. Preserve cash. 3. Act with all stakeholders in mind. 4. Emerge on the right side of history. 5. Play to win the next season 6. Don't trade in the future, think long-term.


In the face of the crisis, it was important that Airbnb as a company was going to survive. Although it was so painful for Brian to let go of the people, there were many more employees and customer that depended on Airbnb's future success.

No one knew how long the crisis was going to last, and the new round of funding was simply a bandaid meant to help in transition. It alone was not going help without serious cost-cutting.


Instead of making decisions based on circumstances, choose a principle that will be your guiding star, and make decisions based on it.

In Airbnb's case, Brian knew that by overwriting hosts' cancelation policy to return money to his guests was going to be a big challenge, but choose "health and safety" as the guiding principle had enabled him to justify it as the right path forward.

To smooth out the impact, Airbnb then ended up using their cash on hand to partially reimburse the hosts who lost out on income.

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