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Back to Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”, with Brian Chesky.

What Is Airbnb.org's Plan for Free Housing?

Brian Chesky says Airbnb.org is going to try to provide a million nights of free housing a year, for five years, for people in crisis. The nonprofit's leader put the biggest operable scale at a million nights in a few years, which Chesky thinks would pass Ronald McDonald House and any government. The cost he was given was about half a billion dollars of the company's money. He says a public company had to be able to do that responsibly for shareholders, that doing good is good business, and that this may be one of the most important things Airbnb does.

The idea is older than the company. In 2008 he emailed his co-founders with the subject line Airbnb.org, before Airbnb had launched, already thinking about housing. Nothing happened for four years. In 2012, after Hurricane Sandy, a woman asked to host a disaster evacuee for free, and Airbnb had to change its system to allow it. Some hosts opened their homes for free. When a stay had to be paid, Airbnb raised money or used its own money so the guest still paid nothing.

He says the nonprofit now responds to about 170 disasters a year. It housed 20,000 Afghan refugees, 100,000 refugees from Ukraine, and 70,000 free nights during the Los Angeles fires. It also covers medical stays and housing for people leaving domestic violence. His parents' lesson was to be useful, and housing is what Airbnb knows how to do.

Transcript

Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO” ·

How I Built This with Guy Raz

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  1. Why Did Brian Chesky Feel Lonely After Airbnb Went Public?Brian Chesky says he felt lonely the day after Airbnb went public because the rush ended and his life felt no different than the day before.
  2. Why Does Brian Chesky Say He Was a Great Founder but a Terrible CEO?Brian Chesky says he was naturally a great founder and naturally a terrible chief executive. He calls that a classic story.
  3. Why Does Hiring Great People and Getting Out of Their Way Fail?Brian Chesky says hiring great people, trusting them, and getting out of their way is what a mature company does, and it is a death sentence for a young…
  4. Why Can't a Company Grow Faster Than Its Chief Executive?Brian Chesky says a company cannot grow faster than its chief executive's learning curve, and he believed the limit of Airbnb's potential was the limit of him.
  5. What Did Barack Obama Tell Brian Chesky About Loneliness?Brian Chesky says the chief executive job can be lonely in a way founding was not.
  6. Why Does Brian Chesky Watch How People Treat His Assistant?Brian Chesky asks his assistant how nice people are to her, because success makes everyone nicer to him and he becomes a bad read of character.
  7. Why Did Fast Success Make Airbnb Sloppy?Brian Chesky says fast success made Airbnb sloppy because the company forgot how hard the first product was to create.
  8. 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.
  9. Why Does Brian Chesky Talk to Employees Who Do Not Report to Him?Brian Chesky talks to employees two or three layers below his direct reports so he hears from the people doing the work, not only from the executives above…
  10. How Does Brian Chesky Get Honest Pushback?Brian Chesky gets honest pushback at Airbnb by keeping people who can afford to tell him the truth, then by taking the opposite side of his own idea so the…
  11. Why Is Killing a Project After Six Months a Leadership Failure?Brian Chesky calls it a failure of leadership when a team spends six months on a project and he has to kill it.

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