040: How to Turn STR Guests Into Loyal Customers | Matthew Orley

040: How to Turn STR Guests Into Loyal Customers | Matthew Orley

Most short-term rental operators focus on adding more units, entering new markets, and automating their operations. But what if the strongest competitive advantage is not the size of your portfolio, but the relationship you build with your guests? In this episode of STR Global Unlocked, I speak with Matthew Orley, CEO of Red Cottage, about how STR operators can build a memorable brand that drives guest loyalty, repeat stays, and direct bookings. Matthew explains why many property managers do not truly own their guest relationships, how Red Cottage built a successful membership program, and why loyalty needs to offer more than simple discounts. He also shares how a clearly defined target guest, a consistent portfolio, and proactive communication can turn one-time bookings into long-term customer relationships. Which questions are answered in this episode? - How can STR operators build a brand guests actively return to? - Why do many property managers still not truly own their guest relationships? - What makes a membership and loyalty program work in short-term rentals? - How can STR brands increase repeat stays and direct bookings without relying on discounts? - Why are brand consistency, guest communication, and a clearly defined target audience so important? - How should operators balance AI and automation with high-touch human service? - And why could the human relationship become the strongest competitive advantage in an increasingly automated STR industry? Resources * AJL Atelier – Global STR Consulting [https://www.ajlatelier.com [https://www.ajlatelier.com]]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. * Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/ [https://www.linkedin.com/in/simon-lehmann-8375753b/]]  Stay connected: * Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 [https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960]  * Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO [https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO]  * Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O [https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O]  * Website: https://www.ajlatelier.com/podcasts [https://www.ajlatelier.com/podcasts]  * Newsletter: https://str-global-unlocked.beehiiv.com/ [https://str-global-unlocked.beehiiv.com/]

039: Hospitality Isn’t Ready for the Future Guest | Jamie Lane

AI is changing hospitality, but I believe the bigger question is not just how AI will change our tools, our operations, or our businesses. The bigger question is: what happens when AI starts changing the customer? In this episode of STR Global Unlocked, I’m joined by Jamie Lane, Chief Economist at AirDNA and one of the leading voices on travel demand, market trends, and the future of short-term rentals. Together, we talk about how AI-driven productivity, job shifts, income distribution, and changes in disposable income could reshape travel demand in the years ahead. Because while many operators are focused on how AI can improve pricing, guest communication, automation, and efficiency, I think we also need to understand what AI could do to the wider economy around our guests. Which questions are answered in this episode? 1. What happens when AI starts changing the customer, not just hospitality businesses?  2. How could AI-driven productivity, job shifts, and income distribution affect travel demand?  3. Why should short-term rental operators pay attention to macroeconomic trends?  4. Could changes in disposable income reshape who travels, how often they travel, and where they stay?  5. And what can hospitality leaders do today to prepare for the future guest? Resources * AJL Atelier – Global STR Consulting [https://www.ajlatelier.com [https://www.ajlatelier.com]]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. * Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/ [https://www.linkedin.com/in/simon-lehmann-8375753b/]]  Stay connected: * Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 [https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960]  * Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO [https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO]  * Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O [https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O]  * Website: https://www.ajlatelier.com/podcasts [https://www.ajlatelier.com/podcasts]  * Newsletter: https://str-global-unlocked.beehiiv.com/ [https://str-global-unlocked.beehiiv.com/]

038: Short-Term Rentals Are Entering Their Most Dangerous Era | Shaun Shirazian

In this episode of STR Global Unlocked, I speak with Shaun Shirazian, CEO of Lodgify, about one of the biggest shifts happening in short-term rentals and hospitality: the rise of AI search, direct bookings, and the future of guest experience. Shaun shares what Lodgify is seeing across more than 30,000 hosts and 100,000 listings, why the short-term rental market has become more competitive, and why the old price advantage over hotels is disappearing. He explains why direct bookings are becoming more important, how hosts can reduce dependency on OTAs like Airbnb, Booking.com and Expedia, and why some operators are already seeing bookings come directly from ChatGPT. Which questions are answered in this episode? 1. How is AI changing the way travelers search for short-term rentals? 2. Why are hosts already getting bookings from ChatGPT? 3. Are direct bookings becoming more important for STR operators? 4. What percentage of direct bookings is realistic for hosts today? 5. Why is the short-term rental price advantage over hotels disappearing? 6. What do the best operators understand that average hosts still miss? 7. How can hosts reduce their dependency on Airbnb, Booking.com and Expedia? 8. Why is guest experience becoming the real competitive advantage? 9. What role will technology play in professionalizing short-term rental operations? Resources * AJL Atelier – Global STR Consulting [https://www.ajlatelier.com [https://www.ajlatelier.com]]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. * Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/ [https://www.linkedin.com/in/simon-lehmann-8375753b/]]  Stay connected: * Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 [https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960]  * Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO [https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO]  * Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O [https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O]  * Website: https://www.ajlatelier.com/podcasts [https://www.ajlatelier.com/podcasts]  * Newsletter: https://str-global-unlocked.beehiiv.com/ [https://str-global-unlocked.beehiiv.com/]

037: Will AI Replace Hospitality Teams? | Stone Fish, Vancauwenberghe, Ullrich, Rubin

Book a strategic consultation with me now: https://bit.ly/simon-consultation 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. Which questions are answered in this episode? *  How is AI changing guest communication in hospitality and short-term rentals?  *  What do operators often get wrong when implementing AI agents?  *  Should AI fully replace human guest communication teams?  *  Where is the line between automation and human hospitality?  *  How can AI improve response times, reviews, and guest satisfaction?  *  What is the real ROI of AI automation for property managers?  *  Can AI reduce headcount and increase company value?  *  How can AI identify upsell opportunities like early check-in, late checkout, and add-on services?  *  Why is guest communication connected to operations, cleaning, locks, PMS, and workflows?  *  Will guests still talk to humans in the future of hospitality? Resources * AJL Atelier – Global STR Consulting [https://www.ajlatelier.com [https://www.ajlatelier.com]]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. * Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/ [https://www.linkedin.com/in/simon-lehmann-8375753b/]]  Stay connected: * Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 [https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960]  * Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO [https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO]  * Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O [https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O]  * Website: https://www.ajlatelier.com/podcasts [https://www.ajlatelier.com/podcasts]  * Newsletter: https://str-global-unlocked.beehiiv.com/ [https://str-global-unlocked.beehiiv.com/]

The Margin Mistake Killing Most STR Companies!

Book a strategic consultation with me now: https://bit.ly/simon-consultation Profit margins can make or break a short-term rental business - but most operators are looking at the wrong numbers. In this video, I break down the real profit benchmarks for STR operators across different business models, including property management companies, aparthotels, hybrid models, urban portfolios, and resort/vacation rentals. You’ll learn what healthy gross and net margins look like, why revenue alone can be misleading, and which KPI reveals whether your business is truly profitable or just looks good on paper: contribution margin per unit per year. Resources * AJL Atelier – Global STR Consulting [https://www.ajlatelier.com [https://www.ajlatelier.com]]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. * Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/ [https://www.linkedin.com/in/simon-lehmann-8375753b/]]  Stay connected: * Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 [https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960]  * Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO [https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO]  * Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O [https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O]  * Website: https://www.ajlatelier.com/podcasts [https://www.ajlatelier.com/podcasts]  * Newsletter: https://str-global-unlocked.beehiiv.com/ [https://str-global-unlocked.beehiiv.com/]