Through its evolution—from a few air mattresses placed on an apartment floor to one of America’s best-known American technology companies—it has been led by Brian Chesky. And at a time when Silicon Valley doesn’t champion introspection, Chesky, 45, is an outlier: someone who has become a prominent voice on company leadership and a frequent investigator of his own character. You are one of three people who started the company in 2007.
There aren't that many founders leading Fortune 500 companies. How do you think the fact that you founded this company shapes how you lead it today?The people that build companies tend to be more in the details, more decisive, bigger authority, …They tend to take bigger, bolder risks partly because they have the moral authority to. For example, I could—I wouldn't—but I could change the name of the company because I came up with the name of the company.
Somebody who is a professional manager, I don't think they would ever dare change the name of their company. They would feel like it's not theirs to change. You’ve said that you think CEOs think about hiring wrong.
Why is that?Because I thought about hiring wrong…When I was starting Airbnb…Sam Altman…said hiring should be 50% of your job. I'm not even sure it was 50% of his job. Has your thinking about the value of remote work shifted as we’ve gotten further from the pandemic?I have a view that if your office policy's is easy to explain, it might be wrong because it might be one size fits all.
You’re vocal about the fact that you think leaders don’t need to have regular one on one meetings with their direct reports.I think it's not only unnecessary, it's probably inferior. And if you go through the list of great CEOs, almost none of them that I'm aware of do recurring one-on-ones… Now you can get a hotel on Airbnb. Why?I was ideologically against hotels.
In fact, I think our first tag line was “forget hotels.” So why would I ever offer them? And so that was my party line for probably 10 years. In 2018, 2019 my stubbornness got the best of me and many of our customers told us that we want hotels.
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