Airbnb’s Brian Chesky is repositioning itself for a new era of travel

Airbnb announced several updates to its platform today. The company says the search overhaul and a new feature allowing people to split long stays are part of the “biggest change to Airbnb in a decade,” prompted in response to pandemic-era trends allowing more people to combine work and travel.

Although Airbnb was hit hard by the early months of the pandemic, the company has benefited from these changing trends over the past two years. In a quarterly announcement of results last week, Airbnb said total bookings had now surpassed pre-pandemic levels and long-term stays (lasting 28 days or more) had doubled since 2019.

Airbnb co-founder and CEO Brian Chesky spoke with “Marketplace” host Kai Ryssdal about the company’s decision to allow employees to “live and work anywhere” while maintaining their current salaries and those of Chesky own ad that he “now lives on Airbnb”. The following is an edited transcript of their conversation.

Brian Chesky: For the past two years, Airbnb has been isolated. I’m 40, I only live with a golden retriever. She has flexibility, I have flexibility, and I tell myself that life is short, I want to see a little more of the country. And so, in the last four months I’ve been around, I’ve probably stayed at a dozen Airbnbs and seen a bunch of countries. It was a lot of fun and it was a great experience.

Kai Rysdal: Okay, so there’s a lot to unpack there. But first, how’s the dog? Does she like to move every two weeks?

Chesky: She seems to like it, you know, I do my best to communicate. We choose houses with yards and she likes that. It’s a lot of fun and it was a great experience.

    Earlier this year, Airbnb CEO Brian Chesky announced that he had started
Earlier this year, Airbnb CEO Brian Chesky announced that he had started “living on Airbnb”, moving to a new city every two weeks. Above: Chesky and his dog Sophie in Ann Arbor, Michigan (Courtesy Airbnb/Jessica Chou)

Rysdal: Do you book your stays yourself via the application? Or do you have people doing it for you?

Chesky: I reserve it. And I don’t tell them who I am, although I don’t use a pseudonym either, so I’d say half the time they find out it’s me, half the time they don’t. And that’s great because you kind of see everything that’s good and, sometimes, not so good about your product, and that’s exactly how you get the feedback. I also think that anecdotes and first-hand experiences are often more useful than data alone.

Rysdal: I want to get to announcement you said people at Airbnb could be remote full time in a second, but I want to get back to you for a minute on when this pandemic started, when you and this company, you had what must be a Existential crisis. And I’d like you to think for a second about: Here we are two years later, and it looks like you’ve made it. How did you do that?

Chesky: Oh my God. Well, Kai, first let me say I’m 40, but I feel like I’m 50 or 60 after the last two years. You know, I’ve been lucky in my life to never have had a near-death experience. I’ve heard them describe them to me as, your life flashes before your eyes, and sometimes people describe that experience as giving them clarity. I certainly had what felt like a near death business experience as our business dropped 80% in eight weeks. And, by the way, when your business drops 80% in eight weeks, you don’t know if that’s the end of it or not. It could have dropped 99%. And it was like an 18 wheeler on a highway going 80 miles an hour and then you slam on the brakes. It’s very traumatic.

I remember that on March 15—it’s the Ides of March—we had a board meeting. And after the board meeting, I had a board member call me, he was a former CEO of Amex, and he said, you know, “This is your watershed moment as CEO.” And it was kind of like this bell in my head just rang and it was just kind of like, “Yeah, this is it. This is the moment of truth for me, and this is the moment of truth for the company. And we kind of got into the fox hole and we kind of rebuilt the company from the ground up. We had to make a lot of painful decisions. We laid off 1,900 people. We We closed most of our new initiatives. And something remarkable happened. People, even if they weren’t crossing borders and they weren’t traveling for business, they were getting in their cars and they were traveling, a full tank of gas from home, to stay in Airbnbs. And we were able to rotate the product to take advantage of that opportunity. I guess you could say we never looked back after that.

Rysdal: I mentioned we were on a Zoom, which I don’t usually do – I don’t usually see the people I interview – and it’s interesting that during this whole answer your head was down, you were scratching the forehead, you did not look up. It was just interesting to see.

Chesky: Well, I’ll tell you, there are a lot of emotions that run through my mind when I think of that time, I mean, both good and painful. You know, it was the most defining year, 2020, of my life. I didn’t think it would be possible after launching Airbnb. I kind of said to myself at that point, like, “This is the craziest thing I’ve ever experienced.” I had no idea what awaited me in 2020.

Rysdal: All right, some super quick stuff and then I’ll let you take over running the business. Wholesale announcement of you guys last [month]: Everyone at Airbnb can be remote, wherever they want, for as long as they want. You know, there are going to be in-person gatherings, but basically wherever you want to live and work, you can live and work. It’s a reasonable decision for you as the CEO of a company, I guess, because that’s what people want now, but also a reasonable decision for you as the CEO of Airbnb, for whom this future workforce is tailor-made.

Chesky: 100%. I mean, look, there were two reasons why I did this. First, because it benefits our business. If we can embrace remote work and have more people living and working in Airbnbs, and then we can popularize that for other businesses, that’s good for our business. But I’ll tell you, if we hadn’t taken advantage of it at all, I still would have, because, number one, we had the most productive two years in our history working remotely.

Second point: I generally like to predict the future by not looking at what larger or mature companies are doing, but what young companies are doing. Twenty years ago it was the young startups in Silicon Valley that popularized open floor plans, you know, in-person perks and all these different perks. And I think if you look at start-ups today, they’re embracing flexibility and remote working. And the third thing is that it seems like the best people now live everywhere. I think the best people aren’t just in Silicon Valley and we’ve decided not to lower people’s salaries if they move from San Francisco to Ohio. Let’s just try to be a little further ahead of the curve here.

Rysdal: Well, so about this salary thing, which is the other thing I wanted to ask you. So that’s great for Airbnb employees, but what do you say to somebody in, you know, Ottumwa, Iowa who’s trying to buy a house or whatever, and you have people earning salaries in Silicon Valley, when this is not the prevailing salary in this area? I mean, it seems like a challenge and doesn’t do much for the other parts of this economy outside of Airbnb.

Chesky: Well, actually, I mean, I can’t speak for all cities, but I think a lot of cities and a lot of mayors would like high-paying workers and high-tech people to come to their city. They frequent, they can provide more income for their markets. I will also say that I don’t think they will flood any particular area. What we’ve generally seen with our data at Airbnb is that there’s this massive redistribution of population. It used to be that people were really concentrated in certain cities (San Francisco, New York, Los Angeles) and now they are spreading to thousands of cities and communities. But I also think cities can decide, based on their own policies, who they want to live there and who they don’t.

Rysdal: Do you think you’re, you know, listen, you’re a big name company and you’re a big name guy. Do you think you’re setting a trend here for this all-remote workforce?

Chesky: Establishing a trend may be a slight exaggeration, but I think we are popularizing or accelerating a trend. I mean, sure, since we made that announcement, we’ve had over a million hits on our Careers and Jobs page. Now we only have 6,000 employees and we don’t hire that many people. So I don’t know, I just think as an indication that we’ve tapped into something, that’s what people want. And I think that’s inevitable because I think that after compensation, flexibility will probably be the most important benefit that employers will give to employees. This is my prediction.

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