This Week in Hospitality: Airbnb’s Next Big Bet, the AI OTA Showdown, and Lessons from Jamaica

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The episode opens with a “ground truth” dispatch from Jason Henzell of Jake’s Hotel in Treasure Beach, Jamaica, laying out how community tourism, agritourism, and repeat-guest loyalty can anchor a destination—then how two major hurricanes force an operator to turn resilience into strategy.

From there, the hosts dissect Airbnb’s widening blast radius: airport transfers, grocery delivery tests, revived experiences, a bigger hotel push, and (again) a non-points loyalty experiment. Ben argues the ambition is coherent but execution has historically lagged—so the question is what Airbnb actually nails in the next 6–12 months.

Then the episode turns to the bigger tectonic shift: agentic AI and whether it breaks the OTA model. Scott calls it noise until it works; Ben and Edwin push that consumers will prefer conversational planning to endless deal-scrolling, pressuring commissions and “propping up mediocrity” less and less.

Spice of the Week closes on the coming job title nobody’s staffed for yet: the people who manage fleets of agents—and the businesses that still win because humans show up.

This Week in Hospitality is presented to you by Journey.

Journey is a loyalty platform built specifically for independent boutique hotels and high-touch hospitality brands. Our mission is to give operators the same powerful rewards engine, data intelligence, and guest insights that major chains rely on — without asking them to give up the individuality, soul, or story that makes their property extraordinary.

If you’re an owner or operator of an extraordinary, independently owned and operated hotel or residence — and you want to see whether your property is a fit for the Journey Alliance — you can learn more and apply at https://www.journey.com/alliance

Key Topics & Timestamps

00:00 — Intro

01:44 — Ground Truth from the Owner: Jake’s Hotel & Treasure Beach rebuild

24:57 — Story #1: Airbnb’s “super app” push: transfers, hotels, loyalty

38:05 — Story #2: Agentic AI vs OTAs: Marriott/Wyndham integrations and Booking fears

53:01 — Story #3: Choice Hotels trims low-performing U.S. economy inventory

1:00:11 — Spice of the Week

Your Hosts:

Zach Busekrus — Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/

Scott Eddy — Global Travel & Hospitality Expert @MrScottEddy
LinkedIn: https://www.linkedin.com/in/mrscotteddy/
Instagram: https://www.instagram.com/mrscotteddy/

Ben Wolff — Founder of Onera & Oasi
LinkedIn: https://www.linkedin.com/in/ben-wolff/
Instagram: https://www.instagram.com/iambenwolff/

Edwin Kramer — Luxury Hotelier Consultant & Former GM
LinkedIn: https://www.linkedin.com/in/edwinckramer/
Instagram: https://www.instagram.com/edwinkramer/