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Airbnb CEO Brian Chesky on keeping a startup vibe as his company grows

The Airbnb CEO talks about working with Apple legend Jony Ive, the trouble with most companies’ structure, and how he’s emulating Robert Oppenheimer on the latest episode of the ‘Rapid Response’ podcast.

Airbnb CEO Brian Chesky on keeping a startup vibe as his company grows
[Source photo: Jesse Grant/Getty Images for Airbnb]

Don’t bet on chat or voice as the future of AI, argues Airbnb CEO Brian Chesky. Chesky gives an inside peek at his partnership with legendary Apple designer Jony Ive to explore a new interface for engaging with tech. Chesky also shares details of how he operates Airbnb—like planets orbiting the sun—and how once all those pieces of his plan fit together, Airbnb will be a very different company.

This is an abridged transcript of an interview from Rapid Response, hosted by the former editor-in-chief of Fast Company Bob Safian. From the team behind the Masters of Scale podcast, Rapid Response features candid conversations with today’s top business leaders navigating real-time challenges. Subscribe to Rapid Response wherever you get your podcasts to ensure you never miss an episode.


How is AI being used at Airbnb now? Does AI apply less to your business because it’s a physical-experience company or more because it’s a digital platform?

AI is going to affect digital things more than physical things in the near term. Go to a Hilton or Marriott five years from now, it is not different because of AI. So AI is going to affect us much more than hotels.

For instance, we have very complicated customer issues. You might have a traveler from Japan staying with a host in Italy that calls a call center somewhere else. Customer service in our business, it’s not impossible, but it’s very, very difficult. AI can read all the documentation, can speak every language, and look at the last thousand times this happened. What was the most likely course of action that led to a resolution?

It doesn’t mean AI will do all the customer service. These bots, these models, are not autonomous. They’re not even close. But they become a powerful tool for the agents. So, the near term is they’re going to allow agents to be more personal.


That’s only the start, right? Where are you taking AI from here?

One of the designers that I work with is Jony Ive, who designed every Apple hardware device from the iMac until he left in 2019. Airbnb and Ferrari are his two anchor clients.

Even before ChatGPT launched, Jony said, “It’s weird that I open all these apps and none of them know me.” Even our app, there’s a search box and you have to enter a destination. We’re all stuck in this Amazon, eBay, 1997 paradigm, this internet era interface. And everyone’s waiting for a new interface paradigm.

I don’t think that interface paradigm is the Vision Pro. There’s an interface paradigm that’s going to be powered by AI, and it’s not a chatbot. Jony Ive doesn’t think so. I don’t think so. No great designer I respect thinks a chat interface is the best interface. You want a chat interface for chatting. But you don’t want a chat interface for a calculator or to find the weather. Every application wants a different interface.

What we are working on with Jony and others is, what is a new interface paradigm for this new age? I think it’ll be more dimensional. I think flat design is over. We lived in skeuomorphism design in the 2000s, we went to flat design. I think we’re entering a more three dimensional design again, but not so literal representation.

The second thing, the application layer is going to be much more personal. You’re going to open an app and it’s going to learn about you. It’s going to understand you. We had this vision before ChatGPT launched. Like the ultimate concierge. It could recommend where to travel, what to do, who to meet. But we didn’t have the technology available. And then when ChatGPT launched, we’re like, “Oh my God”. Now, GPT4 is not strong enough. Even GPT5, which is coming out soon, isn’t strong enough. But probably by the GPT 6 era, the technology will be there.

Anyone watching this or listening to this, open your phone, and look at your home screen. Ask yourself, “how has generative AI changed any of those apps in the last 12 months?” Every app’s basically the same as it was before ChatGPT launched. So we haven’t yet figured out what the application layer is for AI. I think it’s dimensional. It’s personal. It’s more conversational. But it’s not chat.

Will it talk to you?  Are you talking about voice? 

The future is absolutely not voice. Not voice alone. This is another thing that I talked to Jony about. There’s a lot of problems of voice. Words are not the most comfortable way for the average person to express their preferences and desires. If it was, Twitter would have billions of users and no one would use TikTok or Instagram. A lot of people are visual, and I think people in Silicon Valley who aren’t as visual tend to build the things they want. Well, you’re not everyone.

The other thing is that you’re not going to walk down the street talking like in the movie Her, whispering on the subway or in the bathroom stall. There’s big privacy concerns.

And so we think voice is part of the future, but it’s multimodal: it’s voice, it’s photo, it’s visual . . . see, I’m proving my point. I can’t with words express what I’m trying to communicate to you!


You talked about the difference between a startup and a mature company. Do you still think of Airbnb as a startup?

At what point does a company cease to be a startup? Some people say it’s when you go public. Some people say it’s some arbitrary scale threshold. But I have an ambition ’til the day I’m no longer running this company, which is hopefully decades from now, that Airbnb is the biggest startup in the world.

We’re one of the only companies in the Fortune 500 organized to be functional. Almost every startup starts with an engineering department, a design department, a marketing department. And at some point, they divisionalize. The engineering department has too many requests, so they create separate engineering teams

We’ve chosen not to do that. Everyone says, “If you don’t divisionalize, decision making is going to screech to a halt.” But we had a theory that if we stay functional, we’ll have as few employees as possible. We’re not going to be the Navy. We’re going to be the Navy SEALs. We don’t have a lot of junior people at the company. Almost everyone joins experienced. People don’t have their own goals. People don’t have their own priorities. All priorities are shared.

How do you keep people from becoming siloed? 

I’m in all the details of the company. The main downside to the model I’m describing is not that it’s slower, it’s actually faster. You can ship faster, people feel more empowered, not less empowered. The primary downside, you can’t do disparate things. You can do a lot of things, as long as they require the same functional capability.

So it enforces a certain kind of discipline.

We can’t be in more details than I can be in. Most of what I do all day is I review the work. Everything in the company is reviewed every one week, two weeks, four weeks, eight weeks, twelve weeks, six months, annually. Everything’s on a rhythm.

I’m not deciding on everything. I’m mostly signing off on decisions. But what I often do is I’m pushing. I’m getting everyone to talk. Most CEOs don’t do this. They think, “I don’t have time to do all the work.” And “I’m meddling, you’re closer to the customer.” The CEO, you have to be close to the customer.  You have to be like an orchestra conductor.

My approach isn’t to push decision-making down, it’s to pull decision making in. If I am like the sun of the solar system, my job is to pull the planets close to me. Now, it gets hot close to the sun. And as long as you’re okay with a little sun tan, you’ll do just fine. The downside, it’s very intense to work this way.

It goes back to the fact that I’m a designer by training, and I try to think about how you can design a company differently. CEOs are always reacting, and they don’t know what’s going on, and they create all these processes and these rules. And I just thought—modern corporate America and the modern way a tech company is designed is suboptimal. So what if we could design it differently and better?


You’re very confident. And a lot of these decisions come down to you. How do you check yourself? 

Gotta check yourself before you wreck yourself. I’ve wrecked myself more than a few times. Between 2014 and 2020, I greenlit and pursued a lot of things that did not work out. I grew fairly just detached and disconnected. So I studied Steve Jobs, Walt Disney.

Now I don’t make the decisions alone. If I’m in a meeting, I often speak last. I don’t always do that. But at least half the time. Tip number two: I change my mind. Sometimes I genuinely change my mind. But sometimes I’ll wear a different hat on.

So you’ll change your mind almost as a tool? 

As a tool. I mean, it can sound manipulative, but I’ll tell people I’m doing this. It’s almost like you try on a shoe and you’re like, “this fits really well.” You’re like, well, “let me at least try on the other shoe.” We call it trying on ideas.

I’m also not delegating understanding. Robert Oppenheimer, I studied him, he basically kept the whole bomb in his head. I think it’s important that a leader pulls everything into their head, not pushes everything out of their head. If you do it this way, it’s like a bicycle riding down the hill, it eventually gains speed.

Now, all designs must have design flaws acknowledged. This momentum can be a runaway train. And this is not good for disparate things. One of those disparate things might be the next big opportunity we miss. All designs have to acknowledge the trade-off. But we’ve just chosen that knowing those trade-offs, we’re going to go this direction.

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Robert Safian is the editor and managing director of The Flux Group. From 2007 through 2017, Safian oversaw Fast Company’s print, digital and live-events content, as well as its brand management and business operations. More

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