This week Airbnb shipped the biggest AI update in its history, and in the same days its CEO admitted that his own app barely works inside the AI agents people are downloading.
Brian Chesky tried booking an Airbnb through Instinct and through Meta’s Muse. Both struggled, with hotels and even more with homes.
That is a strange thing to say in a week like this one:
Instinct raised $1B at a $10B valuation, four times its price in August
Muse has millions of downloads and sits at the top of the app stores
Airbnb launched its own AI search, built without a chatbot
The problem?
A consumer agent is an assistant that acts for you: it books, buys, pays bills and cancels subscriptions. That works when the task is a single transaction. A trip on Airbnb means browsing, comparing homes, messaging a host and deciding with friends, and that is where today’s agents get lost.
📚 In this newsletter, I break down what Chesky is building at Airbnb, why he thinks the agents of the moment break on real consumer products, and where he expects consumer AI to go next. With clips from the interview!
High-signal analysis on markets, capital and the companies shaping the next decade
Inside you will find:
Why Chatbots Fail at Shopping and Travel Why Chesky still refuses to put Airbnb inside a chat box, and the interface he expects instead.
Why Airbnb’s Whole App Is Becoming an Agent How Chesky defines an agent, and what Airbnb’s fall release says about where apps are going.
Why Airbnb Still Breaks Inside Instinct and Muse Where today’s agents fail, and the four conditions Chesky says consumer AI needs.
Why Agents Need Their Own Operating System What Chesky told Sam Altman about the ChatGPT app store, and why he thinks Apple and Google will decide what comes next.
What Instinct’s $10B Backlash Says About the Race to Be the Main Agent Why the main-agent seat is fragile, and where the infrastructure money is going.
How Airbnb Ships 80% More Features With AI Why Chesky thinks token leaderboards were a mistake, and why AI is widening the gap inside teams.
Where Chesky Would Build If He Were 26 Again The categories and interfaces he would bet on today, and why he expects 50 to 100 more Anthropics.
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Let’s begin!
1. Why Chatbots Fail at Shopping and Travel
Chesky has been saying the same thing for years, long before Instinct existed: a chatbot is the wrong interface for e-commerce. When ChatGPT took off, Airbnb was one of the few large consumer companies that refused to rebuild its app around a chat box, and for a while that looked like being slow.
