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On Tuesday, OpenAI quietly picked up an AI travel agent. On Wednesday, United Airlines slammed the door on AI agents booking flights. You couldn’t script a better standoff if you tried.

Meanwhile, Anthropic told investors its AI is now speeding up its own research, a week before it goes public. Totally normal week.

This week, we’ll deep dive into OpenAI’s play to become your travel agent, and why the travel industry isn’t rolling out the red carpet.

In today’s edition:

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Most people pick the biggest model and never change it. That’s like taking an Uber Black to grab a coffee. Anthropic just published a guide to choosing the right Claude model, and the price gaps are huge: Haiku 5.5 starts at $0.10 per million input tokens, while Fable 5.2 costs $8.

Here’s how to get the right one:

💡 Pro Tip: Keep your context lean. A turn carrying 150K tokens of context costs about $0.03 in cache reads, vs. roughly $0.004 at 20K. Summarize or /compact at natural breaks and watch the bill shrink.

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✈️ United Airlines is blocking AI agents from booking flights and touching customer accounts, citing security risks and FAA rules, just in time for holiday travel.

🏪 OpenAI launched Businesses in ChatGPT, which lets companies claim their profile, upload product feeds, and run sponsored Business Agents in front of 1.2 billion weekly users. Any business that has ever begged customers for a Google review now has another profile to maintain. Google Business Profile, you have a new rival, and it has 1.2 billion weekly users.

🚨 Anthropic’s IPO filing says its AI now does enough of its research to roughly double its pace of progress, crossing a key safety threshold days before a listing that could value it at $1.4 trillion.

📞 Swatters are using AI voices with fake “ums” and background gunfire to fool 911 dispatchers, apparently because filler words are the real Turing test. About 14% of dispatchers say they’ve already been targeted with AI tools.

OpenAI has acquired Odessia, a year-old AI travel agent startup, and brought its founder in to work on OpenAI’s travel plans. The kicker? OpenAI hasn’t announced a thing. The news came from founder Francis Davidson himself on X, and TechCrunch says it looks a lot like an acqui-hire.

Here’s what you need to know:

Now, about Davidson. He founded Sonder in 2014 while still in college. It leased upscale apartments in cities worldwide, became a unicorn, and hit $143 million in revenue. Then came the pandemic. A SPAC raised less than the company needed, he stepped down as CEO in June 2025, a key Marriott partnership fell apart, and Sonder went bankrupt.

So OpenAI just hired a founder whose last travel company went under to work on a product it hasn’t announced, through a startup that no longer exists. On paper, that’s weird. In practice, it makes total sense. Davidson knows travel inside out; travel is one of the top things people use personal AI assistants for, and OpenAI already counts Booking.com, Expedia, and KAYAK as partners. When it launched ChatGPT agent back in July 2025, travel was one of the headline use cases.

Now add that OpenAI also launched Businesses in ChatGPT the same day, letting brands claim profiles and run their own agents inside ChatGPT. The direction is obvious. ChatGPT doesn’t want to recommend your trip. It wants to book it.

Here’s the uncomfortable part.

Less than 24 hours later, United Airlines moved to block third-party AI agents from booking flights and accessing customer accounts, including through travel agencies and aggregators. United’s reasons: shared logins can expose sensitive data, agents can trigger unintended purchases or burn MileagePlus miles, and automated bookings could break FAA and DOT rules.

Your AI can still show you United’s fares. It just can’t hit “buy.”

United also said it doesn’t want another middleman between it and its customers. That’s the real story. The security concerns are fair, but airlines have spent years pushing travelers to book direct. An AI agent sitting on top of every airline, hotel, and aggregator is the ultimate middleman.

🔮 Prediction:

United won’t be the last. I expect at least one more major U.S. carrier to formalize a similar policy before the holiday rush ends, because no airline wants to explain to a customer why their AI spent 80,000 miles on a middle seat to Cleveland.

But blocking won’t hold forever, and here’s why. Leverage goes to whoever owns the customer. Right now, airlines own the booking and the loyalty program, so they can say no. If ChatGPT becomes the place where 1.2 billion weekly users start planning trips, saying no starts costing real money. That’s the bet OpenAI is making: hire people who know travel, work with the companies that already want the traffic (Expedia, Booking, KAYAK), and let the holdouts feel the pressure.

So the endgame isn’t open access. It’s licensed access. Airlines will approve “official” agent channels with their own rules, verified identities, and almost certainly a fee. It’s the same pattern we saw with online travel agencies: fight them first, then sign distribution deals.

What I’m watching: whether OpenAI ships a dedicated travel product with airline partners baked in, and whether United’s new “written permission” clause for AI agents turns into a paid partner program. My bet is both, within 18 months.

For travelers, the short term is messy. Your AI can plan the trip, but you’ll still be clicking “confirm” yourself for a while. For founders building agents, the lesson is clear: the hard part isn’t the AI anymore. It’s getting permission to act.

💬 Would you let ChatGPT book your next flight, miles and all? Hit reply and tell me. I read every one.

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Until our next AI rendezvous,

Anthony | Founder of Uncover AI