Brian Chesky, CEO and co-founder of Airbnb, reflects on his company's 20-year journey in an interview at the San Francisco headquarters. At age 45, Chesky distinguishes himself as introspective within Silicon Valley by openly discussing his leadership style and past mistakes. The conversation touches on topics such as the importance of hiring well, the value of remote work policies, and the company's recent shift to include hotels in its offerings despite initial ideological opposition from Chesky himself.
Written by the local model on 2026-09-14,
using this article's own text rather than the other coverage of the
same event (that is the story summary below).
Next year, Airbnb will mark its 20th anniversary.
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Airbnb → mark → anniversary
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.
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it → place → 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.
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who → champion → character
“The primary weakness of me as a founder running a company was people had to pay for my immaturity in my thirties,” he told me during a recent interview at Airbnb’s headquarters in San Francisco for our new interview series, The CEO Moment.
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he → run → series
“But I said it was a good long-term bet,” We spoke as the company, called out by critics as contributing to rising housing costs in the cities where it operates, was set to announce a number of new housing initiatives.
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it → say → initiatives
You are one of three people who started the company in 2007.
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who → start → 2007
How do you think the fact that you founded this company shapes how you lead it today?
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you → think → it
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.
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they → build → authority
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.
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I → change → company
Somebody who is a professional manager, I don't think they would ever dare change the name of their company.
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they → think → company
They would feel like it's not theirs to change.
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it → feel → ?
You’ve said that you think CEOs think about hiring wrong.
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CEOs → say → ?
Because I thought about hiring wrong…When I was starting Airbnb…Sam Altman…said hiring should be 50% of your job.
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hiring → think → job
Has your thinking about the value of remote work shifted as we’ve gotten further from the pandemic?
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we → shift → 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.
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size → have → 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.
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leaders → ’re → reports
I think it's not only unnecessary, it's probably inferior.
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it → think → ?
And if you go through the list of great CEOs, almost none of them that I'm aware of do recurring one-on-ones…
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I → go → ones
Now you can get a hotel on Airbnb.
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you → get → Airbnb
In fact, I think our first tag line was “forget hotels.”
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line → think → hotels
So why would I ever offer them?
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I → offer → them
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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we → get → hotels
And ultimately I had to make a decision.
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I → have → decision
You know if you're a brand, just because your customer wants something doesn't mean you sell it to them.
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you → know → them
You can decide no, go somewhere else…
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You → decide → ?
But we noticed there were three types of people.
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we → notice → people
There are people that only book Airbnbs.
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that → be → Airbnbs
There are people that only book hotels, but most people are willing to book both.
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people → be → both
You're building your own AI frontier lab separate from Airbnb.
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You → build → Airbnb
Why not build that within Airbnb and what will be the relationship between the two?
I thought about building inside of Airbnb…
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I → build → Airbnb
.I like to think that our shareholders know what they get themselves into, and I never sold them on us being a frontier company and spending billions and billions of dollars of capital expenditure and then spending huge sums recruiting these engineers or these AI researchers…
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us → like → engineers
benefit to Airbnb and to me is I'm gonna learn a lot about AI, but it's also a totally different kind of culture.
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it → go → culture
So I wanted to keep them separate.
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I → want → them
You’re announcing a number of new initiatives around housing.
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You → announce → housing
People say Airbnb makes cities more expensive.
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cities → say → ?
What role do you want the company to play in making places more affordable?
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places → want → role
I think Airbnb has been a place people pointed to over the last 15 years, especially the last decade…for reasons why cities are expensive.
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cities → think → reasons
And so we have wanted to be part of the solution, not part of the problem.
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we → want → problem
We're creating a $250 million fund to house the last dollar for projects.
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We → create → projects
There's about 750,000 homes in America development projects that are stalled because they don't have the last dollar of completion ...
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they → be → completion
…and 3 more, not listed.
