Airbnb introduced its new AI-powered search this week, marking a significant step for a company historically cautious about artificial intelligence. CEO Brian Chesky has consistently criticized chatbot-only interfaces as unsuitable for travel discovery. To discuss the company's strategy, the future of interfaces, and the challenges facing consumer AI, I spoke with Chesky via Zoom.
Chesky remains skeptical of chatbots for browsing or shopping, arguing they offer limited choices and require multiple turns to reach a result. However, he views the current Airbnb search as an evolving foundation rather than a final product.
"I’ve believed for a long time that a chatbot isn’t the right interface for e-commerce," Chesky remarked. "I think that there’s going to be some interface that is... something between a chatbot and what you see in the first version we shipped."
He noted that while consumers desire speed—such as asking an agent to "book a flight"—they also derive pleasure from browsing and dreaming about travel. Removing the inspiration aspect would negatively impact the user experience.
Another weakness of chatbots is that they are designed for single users, whereas Airbnb is often used collaboratively. The company aims to develop "multiplayer" AI interfaces over the next few months to support groups planning trips together.
Startups like Monogram and Wabi are experimenting with "generative" interfaces that AI builds dynamically. Chesky anticipates a mix of these generative screens and traditional pre-designed interfaces.
Regarding consumer AI agents like Instinct and Muse, Chesky acknowledged that Airbnb must build robust software infrastructure to be agent-friendly. These agents could prove valuable as lead generators.
"I don't necessarily know if I believe in a world that there’s apps in the future... Our interfaces should be adaptive to the utility and the function that we’re doing," Chesky explained. He emphasized that agents must support handoffs for features like messaging a host or comparing listings.
Despite concerns that agents might displace companies like Airbnb, Chesky pointed out that chatbots have actually been effective at generating leads.
Chesky also envisions agent-to-agent interactions within the platform. Since apps are rarely interoperable without business deals, he sees agents—described as "apps with faces"—as the key to universal interoperability.
"The Airbnb app as one day becoming an agent... interoperable with MCP [a standard that lets AI agents connect with other software]," Chesky noted.
The most significant challenge, however, is the lack of a true operating system built for AI. Current apps on iOS, macOS, and Windows are not "AI operating systems."
Chesky argued that for AI to function at the kernel level like a traditional OS, all components must interact seamlessly. Currently, companies are racing to become the primary "quarterback" agent, but without a software developer kit and a full operating system, this model fails, as evidenced by the struggles of ChatGPT's app store.
"I’ve used Airbnb on Muse and Instinct... And it doesn't work very well," Chesky admitted. He believes consumer AI will only succeed when apps become interoperable agents with rich user interfaces.
Chesky also challenged the Silicon Valley view that interfaces are disappearing or that software will be entirely generative. He believes designers can prompt better software than consumers and that apps will remain central as long as Apple and Google control the dominant platforms.
Finally, Chesky highlighted the growing importance of voice. With new dictation tools on the rise, Airbnb plans to roll out voice agents for search and customer service this fall.
On a personal level, Chesky has found AI invaluable, using it to retrieve information quickly and reduce the number of meetings required to stay informed.
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