Through changing platforms, new technology, AI agents, and automation, one thing about hospitality hasn’t changed: people still want to connect with people.

In this episode, Jason Muth and Rory Gill sit down with Annie Holcomb, founder of Annie & Co., co-host of the Alex & Annie Podcast, VRMA board member, and longtime vacation rental industry leader. Annie takes us through more than 30 years in hospitality—from working a hotel front desk to vacation rental management, Expedia, Marriott Homes & Villas, channel management technology, and eventually launching her own company.

We also dig into Jason’s experience expanding onto Booking.com, why the platform can open the door to international and business travelers, what operators should understand about distribution, and how OTAs can help build a recognizable brand. Then we look at VRMA, the changing relationship between traditional vacation rentals and STRs, podcasting, AI, and where automation should—and shouldn’t—replace human interaction.

Things we discussed in this episode:

1. Annie’s 30-year hospitality career spanning hotels, vacation rentals, technology, OTAs, consulting, and entrepreneurship.
2. Why great guest service and strong owner relationships remain essential despite massive changes in technology.
3. How Booking.com can connect smaller operators with international travelers, business guests, and new audiences.
4. Why Jason’s Booking.com launch quickly generated more than ten percent of his company’s total bookings.
5. What operators should understand about Booking.com payments, monthly invoices, taxes, fees, and account setup.
6. How OTA exposure can strengthen brand recognition and ultimately support a successful direct-booking strategy.
7. Why building a company brand requires different decisions than building everything around one individual personality.
8. How VRMA is bringing traditional vacation rental managers and newer short-term rental operators together.
9. Why podcasting creates powerful relationships by letting operators share authentic experiences, lessons, and personal stories.
10. How AI should eliminate repetitive work while creating more time for meaningful human hospitality and relationships.

Get in touch with ANNIE:

Podcast - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.alexandanniepodcast.com/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://anniecosolutions.com/

#SmartStayShow #ShortTermRentals #VacationRentals #Hospitality #PropertyManagement #Bookingcom #DirectBooking #VRMA #HospitalityTechnology #ArtificialIntelligence #AI #GuestExperience #PropertyManagers #VacationRentalManagement #STR #Automation

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