Even the most carefully managed luxury properties can fall victim to guests who make some very questionable decisions. And when the damage is done, who actually pays for it? In Episode 4 of **Pour Decisions: When Stays Go Sideways**, presented by Safely, we are joined by **Alexandra “Ali” Chaney of…
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…
Every five-star stay has a main character. But who gets the spotlight? 👀 When travelers book through OTAs, the platform often becomes the name they remember. So where does that leave the property manager behind the experience? In our latest episode, Michelle Gilliland, VP of Sales at Savvy, joins Alex…
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…
How well does AI understand your vacation rental business? 🔎 As AI search becomes part of the travel planning journey, the way property managers present information about their properties, reviews, and local expertise is becoming increasingly important. In this clip, Gil Chan, Founder and CEO of CraftedStays, explains why structured…
Could Airbnb’s “direct booking” experiment actually introduce more hosts to true direct booking? That’s the unexpected upside Orlie Benjamin sees in Airbnb’s new program. For hosts who have never built a direct booking strategy, simply being introduced to the concept could open the door to learning how to drive their…
What actually helps a vacation rental website show up in AI search? 🔎 To find out, Gil Chan and the CraftedStays team ran 24,000 queries across four AI chat engines, examining which property managers appeared in the results and what their websites had in common. Some of the findings challenged…
Lost keys and repeated locksmith calls can quickly turn guest access into a daily operational headache. For properties still relying on traditional keys, these challenges can create unnecessary work for property managers and frustration for guests. In this clip, Matt Seyed of Secure Lodging Systems shares what he continues to…
In this episode, we are joined by Gil Chan, Founder and CEO of CraftedStays, for a timely conversation about how AI is reshaping the way travelers discover and book vacation rentals. From direct booking websites to AI-driven search, Gil shares what operators should be paying attention to as the search…
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…
In this clip from our recent episode, Dawn Keathley of dormakaba explains why reliable access plays such an important role in the arrival experience. By the time guests reach the property, they should be able to get inside, settle in, and start their vacation without hesitation. For property managers, that…
In this clip from episode 4 of the First of the Month Wrangle, presented by Lasoh, Eric Goldreyer, Founder & CEO of Savvy, talks about why vacation rental discovery will continue to happen across multiple channels. For property managers, the bigger question is where to focus limited time and marketing…
What happens when the tools running your vacation rental business each define your data a little differently? That is part of the problem John An is tackling with Tidewell by TechTape. In this clip, John gives us a first look at what Tidewell is and why TechTape is bringing it…
What happens when Airbnb starts calling something “direct booking” but the booking, the data, and the guest relationship still live on Airbnb? That question opens up a much bigger conversation about what direct booking actually means and what operators are really building when they invest in their own marketing. In…
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…
A guest can spend months planning a vacation, travel all day, arrive with tired kids and luggage in tow, and then have the entire experience unravel at one very important moment: the front door. In this episode, we are joined by Dawn Keathly of dormakaba and Matt Seyed of Secure…
A guest can spend months planning a vacation, travel all day, arrive with tired kids and luggage in tow, and then have the entire experience unravel at one very important moment: the front door. In this episode, Alex is joined by Dawn Keathly of Dormakaba and Matt Seyed of Secure…
What does it look like when a vacation rental company decides its brand should better reflect the business it has become? Alex & Annie went on site at 30A Escapes for its brand reveal party to find out. In this YouTube-exclusive episode, we talk with the team behind the company…
In this YouTube-exclusive episode, Alex & Annie go on site at 30A Escapes for the company’s brand reveal party and get a firsthand look at the next chapter of the business. What started as a new website eventually became something much bigger: an opportunity for the team to rethink how…
Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica. This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the team behind it, and get a closer look at how CCS supports vacation rental businesses from…
Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica. This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the people behind it, and get a closer look at what it takes to build a hospitality…
Growth can create pressure to keep chasing the next milestone, even when that growth starts pulling attention away from what matters most. In this clip, Josh Parry, Managing Partner & CPO of Ciirus, explains how being independently financed has allowed Ciirus to stay focused on customer satisfaction, product investment, and…
The full replay of our 3rd Real Talk Roundtable is now available on our YouTube channel. 💡 In this edition, Chris Walker of Direct Booking Tools, Vanessa Humes of ICND, and Tim Johnson of Seaside Vacations and Sales joined us to talk about what really drives direct bookings. The conversation…
