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Michael Wolf thought his career would be in government. He spent every summer in Washington, DC, and wanted the FBI. Then Bain came to campus, and he took a detour that turned into 15 years of startups.

Today he is the CEO of ResortPass, the world's largest marketplace focused on getting hotels more revenue from day guests. The idea starts with perishable inventory: hotels have mastered revenue management for the room, but an empty pool, fitness center or spa today is revenue that never comes back. ResortPass now works with nearly 3,000 hotels, sent a million people to hotels this past summer, and about 40 percent of its hotel partners are independents. More than 95 percent had never offered day access before.

In this episode, Michael explains why the day guest is the same guest who books an overnight room, just for a different part of the stay. We talk about why ResortPass often performs best when a hotel is at high occupancy, how the company built its own system of record because a PMS has no place for a day guest, and why ancillary revenue feels like a win here and a penalty in the airline world.

He also shares how premium hotels use ResortPass to test new products, why the biggest results come from hotels with an internal champion, and his contrarian view on how little innovation there is in an industry this size.

If you run a property with a pool, a spa or a gym that sits quiet some days, this one is for you.

This Week’s Guest:

Michael Wolf - CEO of ResortPass LinkedIn: https://www.linkedin.com/in/wolfm/

Your Host:

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

This Week’s Guest:

Dina Belon-Sayre - President, Staypineapple Hotels LinkedIn: https://www.linkedin.com/in/dinabelon/ Explore Staypineapple Hotels: https://www.staypineapple.com/

Your Host:

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

Dina Belon-Sayre, President of Staypineapple Hotels, opens with a story from a Portland snowstorm when she waited tables herself, fed a stranded hotel and received a thank-you check from a guest. Her point: any Staypineapple employee is empowered to make the same call. She traces her unusual path from theater, psychology and criminal justice studies through hotel design, construction and a decade in sustainability consulting, to spotting a five-story painted pineapple from her Seattle office window and joining the company ten years ago. She rose from director of real estate to president. Dina explains the upside of a playful, edgy brand (the "Naked Experience," no navy blazers or scripts) and the occasional offended guest, and why it's fine not to be for everyone. She describes hiring for emotional intelligence, critical thinking and a willingness to be authentic. On growth, she notes owners are risk-averse, Staypineapple hasn't franchised without management because service is the brand's through-line, and the company may package tools for other independents. Her soapbox: AI and LLM booking could run over independents within 18 months, and collections may need to become their AI intermediary at a fair cost.

Scott is in Sicily, so Zach, Ben Wolff and Edwin Kramer take the docket. Edwin checks in from a new boutique hotel on Spain's Costa Blanca, and Ben is fresh from the glamping show.

The first story: Hilton's CIO says AI assistants have put online travel agencies under real threat, yet he expects personal AI agents to become commissionable channels too. The crew asks what "direct" even means when an agent that never sleeps keeps rate-shopping after the booking is made. Edwin says post-booking shopping could be a bigger disruption than the booking itself. Then Booking.com tightens how much guest data, including phone numbers, it passes to hotels.

Next, Lola, the new AI travel assistant from Kayak's co-founders, wholly owned by Booking Holdings. It has a free tier, a $5 a month membership and a $25 a month VIP plan, and both paid plans need a 12-month commitment. Edwin thinks it could make the OTA stronger. Ben is highly skeptical that anyone will pay up front for perks.

Then Choice Hotels buys RV club Harvest Hosts for a reported $130 million. The crew talks about farm hospitality, RVers who eventually want a real bed, and what IHG and Wyndham do next.

The closer: Europe's new anti-greenwashing rules took effect September 27. Edwin explains why they are hard to police and why hotels may go quiet about sustainability instead.

Plus spice of the week: a hot September in southern Europe, and why this is the moment to experiment.

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/