Shawn spent twenty-five years in hospitality watching properties pour money into marketing that did nothing. Ross spent nine years in big tech moving numbers by a tenth of a percent, then fixed a sixteen-room hotel's website before lunch and never went back.

In the first episode of The Underbooked, they take apart the searches guests actually type — and why the biggest travel sites in the world are structurally unable to answer them. It isn't that the OTAs are stupid. It's that the cost of being specific is higher for them than it is for you.

In this episode:
• Why "nestled in the heart of the historic district" has never been searched by a human being
• The photograph you should be taking instead of the one you paid four thousand dollars for
• What OTA commission actually costs once you count the discount, the loyalty credit and the staff time
• Why one amenity checkbox creates a refund, a bad review and a front-desk argument on someone's anniversary
• The three things to stop doing tomorrow — and the one page to write instead

Shawn and Ross disagree three times, and none of it gets tidied up.

Brought to you by Hotel Hot Tubs — which is also Ross's company, so take the endorsement accordingly.