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Airbnb’s CEO said his company is using “faster and cheaper models” than OpenAI’s. Also, Vinod Khosla has a fix for enterprise AI failures.͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­
Oct 23, 2025

Applied AI

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Welcome back! 

At its developer conference earlier this month, OpenAI showed a forthcoming feature that lets ChatGPT users access services from Expedia, Uber and Spotify directly in the chatbot. Some consumer apps might view such a feature as a threat because it bypasses their sites, preventing them from showcasing other products.

For his part, Airbnb CEO Brian Chesky told Bloomberg Wednesday he won’t let people use his company’s travel booking service in ChatGPT because he “didn’t think [the OpenAI product] was quite ready.” Chesky said the decision was based on technical considerations—Airbnb’s requirement that people take several steps to verify their identities—as opposed to competitive concerns. 

As for whether Airbnb will eventually integrate its app with ChatGPT, he said, “I think so” and that he has advised OpenAI about the feature and that his app would need to operate in an “almost self-contained” manner within the chat app.

Fair enough. But while Chesky said ChatGPT could become an alternative to Google for people who are planning trips, he said he also envisions Airbnb becoming a “one-stop shop for travel.” 

Chesky also said Airbnb is “relying a lot” on Alibaba’s Qwen open-weight model to power an AI customer service agent, launched in May. While Airbnb also uses OpenAI’s newest models for the same agent, Chesky said “there are faster and cheaper models” that are a better fit for handling many queries. Airbnb also uses models from several other providers, he said. 

The Qwen name-check shouldn’t be a huge surprise. My colleagues have covered the rise of the Alibaba-made model alongside another Chinese entrant, DeepSeek. Qwen has exceeded Meta Platforms’ open-weight Llama models on several technical benchmarks and is a top challenger to DeepSeek’s R1.

Still, mentioning an open-source AI competitor in the same breath as OpenAI could be gamesmanship on Chesky’s part as he talks to OpenAI about how they might work together.

There are signs that the shade might be going both ways. OpenAI, in the launch video for its Atlas web browser this week, prominently featured VRBO, one of Airbnb’s biggest rivals.

Whatever competitive friction may exist between Airbnb and OpenAI probably wouldn’t affect the relationship between the two companies’ CEOs. Chesky is close with Sam Altman, as he reiterated in the Bloomberg interview, and he advised Altman after the OpenAI board briefly fired him in late 2023. 

Khosla: Some Enterprises Are Doing AI The Wrong Way

It’s well-known that many large companies have had a tough time getting value from their initial investments in AI. Vinod Khosla, co-founder of Sun Microsystems and Khosla Ventures, says that’s because they’re following an outdated playbook for adopting new technology. 

“Most enterprises [that] are executing AI are doing it with people who are not qualified to execute,” Khosla said yesterday during an appearance on The Information’s TITV. “It‘s like saying, ‘Hey, we have a race car and Joe Blow can go drive it, but he’s not going to get the most of that race car.’” 

In contrast, Khosla said AI projects generally go “swimmingly well” when companies do them with startups like Distyl AI, a three-year-old Khosla Ventures portfolio company whose software automates business processes such as analyzing customer data or managing HR functions. (My colleagues recently scooped Distyl’s latest funding round)

Khosla seems to be referring to the practice of using technical staff known as forward-deployed engineers, pioneered by Palantir, that work with customers to incorporate AI into business systems and remain available afterwards to ensure they’re seeing value from it. Distyl uses FDEs, as does OpenAI (in an initiative you can read about here) and Sierra, an AI customer service startup led by former Salesforce co-CEO Bret Taylor.

One drawback with buying AI with FDEs is it can be expensive. But for firms that prefer to go it alone, Khosla said he thinks that, eventually, in-house technical staff will gain the expertise to make more AI projects successful.

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