Airbnb CEO Brian Chesky Thinks He Can Make Cities More Affordable - Time Magazine

Next year, Airbnb will mark its 20th 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. 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. “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. “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.

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. And ultimately I had to make a decision. You know if you're a brand, just because your customer wants something doesn't mean you sell it to them. You can decide no, go somewhere else…But we noticed there were three types of people. There are people that only book Airbnbs. There are people that only book hotels, but most people are willing to book both. 

You're building your own AI frontier lab separate from Airbnb. Why not build that within Airbnb and what will be the relationship between the two?I thought about building inside of 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….The 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. So I wanted to keep them separate.

You’re announcing a number of new initiatives around housing. People say Airbnb makes cities more expensive. What role do you want the company to play in making places more affordable?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. And so we have wanted to be part of the solution, not part of the problem. 

We're creating a $250 million fund to house the last dollar for projects. There's about 750,000 homes in America development projects that are stalled because they don't have the last dollar of completion ... .We want to do something called the City Index. We want to open source data around cities, policies, the cost of living, permitting  to basically show the cities that are most successful at lowering housing costs by having the best policies….We want to do the housing prize where we're going to do a million dollar prize every year for five years for any company, private or or nonprofit that has ideas around technology that can make housing development easier.