Will AI Replace Hospitality Teams?
Podcast Summary
AI is transforming guest communication in short-term rentals and hospitality. In this episode of STR Global Unlocked, I speak with industry leaders Aarlo Stone Fish, Anthony Vancauwenberghe, Jay Ullrich and Cole Rubin about AI agents, automation, guest experience, operations, reviews, upsells, and the future of hospitality.
We discuss what operators often get wrong about automation, why guest communication is no longer just a support function, how AI can improve response times and guest satisfaction, and where the human touch still matters. The conversation also explores the future of STR operations, revenue opportunities through upsells, and whether guests will still talk to humans in an AI-powered hospitality world.
We Say What Others Won’t
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Resources mentioned in the show:
Connect with Aarlo Stone Fish, Anthony Vancauwenberghe, Jay Ullrich and Cole Rubin on LinkedIn and learn more about how AI, automation, and next-generation guest communication tools are reshaping the future of short-term rentals and hospitality.
Guest Appearing in this Episode
Aarlo Stone Fish, Anthony Vancauwenberghe, Jay Ullrich and Cole Rubin
Aarlo Stone Fish
Aarlo Stone Fish is the Co-Founder of Besty AI, an AI-powered property management platform built for short-term rentals. With a background in technology, AI, and entrepreneurship, he focuses on helping operators automate guest communication, improve efficiency, and scale hospitality businesses through smarter systems.
Anthony Vancauwenberghe
Anthony Vancauwenberghe is the Co-Founder of STAY-C, a Belgian hospitality and real estate company operating across short-term rentals, hotels, expat housing, and student housing. Since launching STAY-C in 2020, he has helped expand the company into multiple property types and cities across Belgium.
Jay Ullrich
Jay Ullrich is the CEO and Co-Founder of HostBuddy AI, a platform designed to automate guest communication for short-term rental hosts and property managers. Before building HostBuddy AI, he co-founded a short-term rental management company in San Diego and scaled it to more than 40 units, giving him firsthand experience with the operational challenges hosts face.
Cole Rubin
Cole Rubin is the Co-Founder of Conduit, formerly known as HostAI, an AI platform focused on automating operations and guest communication for short-term rental and hospitality businesses. Before building software for the industry, he managed a large residential and short-term rental portfolio, which gave him deep practical insight into the inefficiencies of property management.
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