Brian Chesky interview: AI agents need their own operating system

Airbnb rolled out its new AI-powered search this week as part of its fall update, a significant step for a company that has been slow and deliberate about AI. Co-founder and CEO Brian Chesky has said in the past that a chatbot-only interface is not fit for travel discovery. With more AI on the way to the Airbnb app, I caught up with Chesky over Zoom to talk about how the company is approaching it, where interfaces are headed, why consumer AI still isn’t working, and what role voice will play.

Chesky hasn’t changed his mind on chatbots. He said they aren’t good for browsing or shopping because they give you a few options at a time, and you have to take multiple turns before reaching a result. But he doesn’t see the current version of Airbnb’s search as the final form either: it’s interface will evolve over time.

“I think that I’ve believed for a long time that a chatbot isn’t the right interface for e-commerce. I think what you’re seeing today is also not the endgame for e-commerce or for travel or shopping. I think that there’s going to be some interface that is, you know, I don’t want to call it a midpoint, but something between a chatbot and what you see in the first version we shipped,” he said.

Continued Chesky: “You know, a lot of people want some things people want to be fast and easy, like ‘Book me a flight, I don’t want to look at it.’ With Airbnb, they enjoy looking at the product. Travel studies show that people actually derive more pleasure in planning and anticipating travel than they do traveling. So you don’t want to take the inspiration and the browsing and the library experience of dreaming away.”

Chesky sees a second problem with chatbots, which is that they are built for one person. He feels that they aren’t a collaborative interface, which matters for a product that people often use with family and friends. Over the next three to six months, the company’s task is to explore interfaces that enable “multiplayer” AI, meaning AI that several people, such as a group planning a trip together, can use at once.

Airbnb isn’t the only one rethinking what an AI interface should look like. As AI tools evolve, new interfaces are also showing up in apps. Startups like Monogram and, more recently, Wabi are experimenting with “generative” interfaces, which are screens an AI builds on the fly rather than ones a designer fixed in advance. Chesky thinks people will see a mix of deterministic (pre-designed and predictable) and generative interfaces.

I asked Chesky how Airbnb is preparing for consumer AI agents, which are tools like Instinct and Muse that carry out tasks on a person’s behalf. Agents will need robust software infrastructure on Airbnb’s end, he said, and the company wants to make itself more agent-friendly. In his view, they could be good lead generators.

“I don’t necessarily know if I believe in a world that there’s apps in the future, but I don’t believe in a world where the apps become data layers of a universal simple UI because when you open your iPhone, there is a reason Airbnb’s app is a different design than DoorDash, Shopify, and Amazon. Our interfaces should be adaptive to the utility and the function that we’re doing. We want to make our app more agentic, and we want to build a lot more user interface controls,” he said.

“If I have an agent, but I also want like really great browse functionality, if I want to be able to message the host like an Airbnb, if I want to be able to compare, if I want to be able to verify my identity, if I want to be able to use a map feature, if I want to then be able to add other items, then if I want to stay in the platform, then either the agent has to do a handoff or the agent application would need to build a bit more of, I think, a robust software developer kit to bring the app to you, so to speak.”

Chesky thinks that there were concerns around AI tools cutting companies like Airbnb out of the customer relationship, but he said that chatbots has proven to be good at lead generation.

The Airbnb CEO is also planning for agent-to-agent interactions through the platform. He explained there might be some interactions within the platform and some with agents of other apps. His thesis is that apps have not always interoperable unless companies struck a business deal. On the other hand, agents are like “apps with faces,” and when they talk to each other, all apps can become interoperable.

“I think of the Airbnb app as one day becoming an agent, you know, where basically the explore tab has an agent, our customer service has an agent, we’re developing another agent in another service area. Probably eventually there’s going to be a macro Airbnb agent. And that will probably be interoperable with MCP [a standard that lets AI agents connect with other software] to other agents,” Chesky noted.

Chesky argues the bigger problem is that the industry lacks a true operating system built for AI. Right now people are building AI apps for iOS, macOS, and Windows that are not “AI operating systems.” He thinks that in an ideal world, AI would be operable at the kernel level — the core of an operating system — and all components like agents would interact with each other. Right now, he said, the race is to be the “quarterback,” or primary AI agent that users go through for everything.

“The problem with that model [of trying to become primary agent] is no one is developing a full operating system software developer kit. I’ll give you an example,” he continued. “ChatGPT, at the beginning of last year, tried to do their little app store. And I told Sam [Altman]: if you want to be an app store like the iPhone, you need to have a software developer kit and an operating system like the App Store. Otherwise, none of our functionality is going to exist. And of course, it didn’t work very well,” Chesky said.

“I’ve used Airbnb on Muse and Instinct,” he went on. “And it doesn’t work very well. I mean, even hotels don’t work that well, but Airbnbs work even worse. So I don’t think we’ve cracked consumer AI. And for consumer AI to be cracked, we have to crack at a lower substrate, and we need to make the agents- apps; all apps need to become agents; all must be interoperable; and all must have much richer user interfaces.”

Chesky thinks that there are two misconceptions in Silicon Valley: first, that the interface is going away and people will just talk and type; second, that software will be completely generative. His argument is that a designer can prompt better software than a consumer can.

He also thinks that as long as the iPhone remains dominant and Apple and Google control the major platforms, apps will likely remain a central fixture.

“It’s really up to Apple or Google, or somebody, to build a new platform for us to really make the true shift from apps to agents. Otherwise, we’re going to have apps that have agents inside them, rather than the whole app being a robust agent that’s interoperable with other agents,” he said.

Before we wrapped up, I asked Chesky about voice, which is gaining ground as apps like Wispr Flow, Willow, and Superwhisper, a new wave of note-taking apps, and built-in dictation in AI tools get people talking to their devices more. He thinks people will eventually speak to computers more than they type. Voice, he said, will play a key part for Airbnb in search and customer service, and the company plans to roll out voice agents this fall to help users.

The company has been seeing big gains from using AI to ship features faster, he volunteered. On a personal level, Chesky said AI has helped him get information faster, freeing him from so many meetings.

“I think AI is reducing communication layers. One of my jobs as CEO is try to get information. And the way I used to get information was having meetings. Now, I can just ask my AI and I don’t need to have as many,” he said.