Alex and Annie: The Real Women of Vacation Rentals

Your property management system says one thing. Your revenue management platform says another. Your accounting reports tell a different story. So which numbers can you actually trust? As AI becomes more integrated into vacation rental operations, inconsistent data across systems presents a growing challenge for property managers. In this episode, Alex & Annie sit down with John An, Founder and CEO of TechTape, to explore why disconnected systems and conflicting data can lead to misleading...

A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests. And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache. In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Alexandra “Ali” Chaney of 30A Beach Stays & Vacations, alongside Amanda Martins and Zach Grimes of Safely, for a candid conversation about the unpredictable side of vacation...

A guest books a beautiful vacation rental, has an incredible stay, and leaves with memories worth sharing. But when they tell others about their experience, whose brand do they remember? In this episode, Alex & Annie sit down with Michelle Gilliland, VP of Sales at Savvy, to explore what it takes to build a recognizable brand in a market where OTAs dominate traveler attention. Drawing from nearly 15 years of experience in the vacation rental industry, Michelle brings a unique perspective ...

The way travelers discover vacation rentals is changing. Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent. In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years ...

In this fourth episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Eric Goldreyer, Founder and CEO of Savvy, to unpack one of the latest conversations surrounding Airbnb and direct booking. Airbnb has been testing a program that allows some hosts and co-hosts to drive their own demand to an Airbnb listing in exchange for a reduced platform fee. The company may be calling it direct booking, but Orlie and Eric argue that the ...