Booking Holdings Is Running Ahead of Its Own Strategy

Every major travel company in 2026 is calling AI the most important shift in a generation. I’ve become obsessed with the capital allocation of these companies because it tells you whether they actually believe that, or whether they’re just saying it on earnings calls. 

Earlier this year, I examined where Airbnb is investing. Now it’s Booking Holdings’ turn. I used my Claude brain to pull apart Booking’s 10-Qs, 10-Ks, and earnings calls and stress-test the numbers. The story is different from Airbnb’s, and in some ways more interesting.

There is a legitimate version of the story that says Booking Holdings is the best-run company in online travel history. Revenues of $26.9 billion in 2025, up from $21.4 billion just two years earlier. Record room nights and merchant gross bookings representing 70% of the total, up from 22% in 2022. The loyalty program is gaining ground, and the 25-for-1 stock split makes the share price more accessible. It has a CEO, Glenn