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Why Does Hiring Great People and Getting Out of Their Way Fail? · How I Built This with Guy Raz

How I Built This with Guy Raz

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

Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time. But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company…

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Notes

  1. Why Did Brian Chesky Feel Lonely After Airbnb Went Public? at 3:23

    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. Full answer

  2. Why Does Brian Chesky Say He Was a Great Founder but a Terrible CEO? at 11:28

    Brian Chesky says he was naturally a great founder and naturally a terrible chief executive. He calls that a classic story. Full answer

  3. Why Does Hiring Great People and Getting Out of Their Way Fail? at 12:32

    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… Full answer

  4. Why Can't a Company Grow Faster Than Its Chief Executive? at 18:01

    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. Full answer

  5. What Did Barack Obama Tell Brian Chesky About Loneliness? at 23:42

    Brian Chesky says the chief executive job can be lonely in a way founding was not. Full answer

  6. Why Does Brian Chesky Watch How People Treat His Assistant? at 32:26

    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. Full answer

  7. Why Did Fast Success Make Airbnb Sloppy? at 35:56

    Brian Chesky says fast success made Airbnb sloppy because the company forgot how hard the first product was to create. Full answer

  8. How Did COVID Change the Way Brian Chesky Runs Airbnb? at 40:07

    Brian Chesky says the pandemic was the first moment he had to be a good chief executive, because it was life or death. Full answer

  9. Why Does Brian Chesky Talk to Employees Who Do Not Report to Him? at 43:23

    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… Full answer

  10. How Does Brian Chesky Get Honest Pushback? at 53:38

    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… Full answer

  11. Why Is Killing a Project After Six Months a Leadership Failure? at 56:21

    Brian Chesky calls it a failure of leadership when a team spends six months on a project and he has to kill it. Full answer

  12. What Is Airbnb.org's Plan for Free Housing? at 1:01:19

    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. Full answer

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