Welcome to the first edition of the Alex & Annie Real Talk Roundtable. Every operator wants 5-star reviews, but the path to earning them is not always about the flashiest parts of the stay. In this conversation, Alex & Annie are joined by Koryn Okey of Breezeway, Miles Hobson of…
AI can make it feel like everyone else is moving faster. Every day, there’s a new tool, a new workflow, a new opinion, and another conversation that makes it seem like you should already have a complete AI strategy in place. But the reality is that many vacation rental operators…
The vacation rental industry has been through a lot of growth, change, and recalibration over the last few years. Companies have scaled quickly, larger players consolidated, AI entered the scene, distribution became more complex, and for many operators, the business itself became harder to navigate. But for Bob Milne, President…
In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations. Bob has spent decades in the vacation rental industry, with leadership experience across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair…
In this episode, Richard Vaughton shares his perspective on what it really takes for vacation rental operators to build long-term value. His view is that the operators who are willing to invest more intentionally in their business may be better positioned as the industry continues to change. That includes areas…
AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building? In this episode, Alex and Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for…
AI is changing the way vacation rental operators work. And for companies willing to approach it thoughtfully, that shift can create more space for what hospitality has always been about. In this episode, we discuss how vacation rental companies can use AI to take the energy they have spent managing…
Welcome to the second episode of Pour Decisions: When Stays Go Sideways, presented by Safely. In this episode, Alex and Annie are joined again by Amanda Martins, VP of Business Development at Safely, for another round of real guest stories, summer stay surprises, and practical takeaways for short-term rental operators.…
Welcome to the second episode of Pour Decisions: When Stays Go Sideways, presented by Safely. In this episode, Alex and Annie are joined again by Amanda Martins, VP of Business Development at Safely, for another round of real guest stories, summer stay surprises, and practical takeaways for short-term rental operators.…
AI conversations in vacation rentals can get big very quickly. In this clip, Ed Ulmer of Barefoot talks about something much more practical. How can AI help a team understand what needs their attention today? For property managers, that is where the opportunity gets interesting. The daily work is full…
A flashy interface can get attention. But in vacation rental technology, the real test is whether the company behind the software understands the people using it. In this episode, Ed Ulmer, CEO of Barefoot, shares why service and customer connection matter so much in this industry. Vacation rental companies are…
⭐ We’re excited to welcome Call Center Solutions as one of our sponsors! Call Center Solutions helps businesses improve customer engagement, streamline operations, and provide reliable support through customizable contact center services. Their team supports customer care, administrative services, and sales operations, helping companies create better customer experiences while giving…
⭐ We’re excited to welcome Monarch Collective as one of our sponsors! Monarch Collective is a national vacation rental management platform built for local brands that want to grow without losing what made them successful in the first place. They acquire and operate established vacation rental companies across the U.S.,…
⭐ We’re excited to welcome Barefoot as one of our sponsors! Barefoot is a property management software platform built for vacation rental companies that need strong operational tools, reliable trust accounting, and the flexibility to manage growth with confidence. From reservations and owner management to accounting, reporting, and guest services,…
⭐ We’re excited to welcome BookingPal as one of our sponsors! BookingPal is a channel management platform that helps vacation rental property managers distribute listings across top channels like Airbnb, Booking.com, Vrbo, and more. Through one connection, operators can expand visibility, manage listings, rates, and reservations more efficiently, and access…
⭐ We’re excited to welcome Lasoh as one of our sponsors! Lasoh is the industry’s only AI-native guest marketing platform, built to help vacation rental operators increase revenue per stay, stays per guest, and booking conversion rates. Through its SMART Marketing and Guest Portal products, Lasoh helps operators turn guest…
⭐ We’re excited to welcome Direct Booking Tools as one of our sponsors! Direct Booking Tools is a premium conversion and intelligence platform designed specifically for professional vacation rental operators. Their platform helps improve the guest journey, increase direct revenue, and give management teams clearer booking insights to make more…
⭐ We’re excited to welcome Hospitable as one of our sponsors! Hospitable helps short-term rental operators automate guest communication, streamline workflows, and stay on top of daily operations with less manual work. Built to help operators run their rentals on autopilot, Hospitable supports everything from messaging and task management to…
⭐ We’re excited to welcome Hospitable as one of our sponsors! Hospitable helps short-term rental operators automate guest communication, streamline workflows, and stay on top of daily operations with less manual work. Built to help operators run their rentals on autopilot, Hospitable supports everything from messaging and task management to…
⭐ We’re excited to welcome BookingPal as one of our sponsors! BookingPal is a channel management platform that helps vacation rental property managers distribute listings across top channels like Airbnb, Booking.com, Vrbo, and more. Through one connection, operators can expand visibility, manage listings, rates, and reservations more efficiently, and access…
Trust accounting may not be the flashiest part of vacation rental management, but it is one of the most important. In this episode, we’re joined by Ed Ulmer, CEO of Barefoot, for a conversation about why trust accounting should not be treated as a back-office function. Ed shares how his…
In this episode, we are joined by Ed Ulmer, CEO of Barefoot, for a conversation about trust accounting, vacation rental technology, and what operators need from their systems as their businesses become more complex. Ed shares how his background in tourism, destination marketing, real estate, and software all shaped the…
In our latest First of the Month Wrangle, Orlie Benjamin talks about why Lasoh is opening its Founding Member Program to a small group of vacation rental operators. The idea is to build Lasoh with the people who are actually going to use it. Orlie shares how founding members can…
Launching new tech features can feel a little like pressing a mystery button and hoping the whole house does not start blinking. Every system touches another system, and when they do not talk to each other, even a small update can turn into a much bigger operational headache. In this…
