Not every guest stay ends with a five-star review. Some leave behind a mess. Some turn into a serious operational headache. And some become the kind of story you talk about for years. That’s exactly why we’re excited to launch Pour Decisions: When Stays Go Sideways, a new special series…
Have a story to share? We want to hear your worst guest stories. If you have a stay that went completely sideways and a lesson to go with it, submit it for a chance to be featured on a future episode of Pour Decisions. Bonus points if you bring your…
Growth is exciting, but not every new property is the right fit. In this episode, Jakob Dwyer, CEO of Awayday, shares why inventory selection plays such a critical role in long-term performance. Adding more homes may grow the portfolio, but adding the wrong ones can create operational strain, weaken brand…
In this episode, Jakob Dwyer, CEO of Awayday, shares why empowering local teams is essential to building a stronger vacation rental business. He explains why the people closest to the market are often the ones with the clearest view of what drives performance, from revenue opportunities and owner relationships to…
What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place? In this episode, we’re joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through local leadership, shared support, and strong operational…
What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place? In this episode, we are joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through a model built on local leadership,…
Collecting guest data is one thing. Knowing how to turn it into meaningful marketing is another. 🎯 In this episode, Orlie Benjamin shares how Lasoh’s newly launched Marketing Suite is built to help operators turn guest data into revenue-driving campaigns. Its AI-powered CRM is backed by hospitality marketing intelligence that…
“The property may be where the guest stays, but the real product is the experience.” ✨ This was one of our favorite moments from Episode 1 of our 6-part series with Orlie Benjamin of Lasoh. In vacation rentals, so much attention naturally goes to operations, pricing, and everything it takes…
We’re so excited to launch First of the Month Wrangle, a new 6-part series with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing. Throughout the series, Alex & Annie will be joined by…
We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing. Throughout the series, Alex & Annie will be joined by…
Success in vacation rental operations takes more than learning the technical side of the job. In this episode, Tom Stewart talks about why the people who grow in this industry are usually the ones who keep learning, see the bigger picture, and understand how different parts of the business connect.…
In this episode, we’re joined by Tom Stewart, COO of Resort Realty, to talk about the realities of operating in one of the most established vacation rental markets in the U.S. From seasonality and weather-related challenges to owner expectations, growth, and day-to-day operational complexity, this conversation offers a practical look…
In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie totalk about the realities of running a vacation rental business in the Outer Banks, one of the most established and distinctive markets in the industry. They get into what makes the market different, from its geography and…
Human trafficking is a global issue that often goes unnoticed. In many cases, it doesn’t look the way people expect, and the signs can be easy to miss. That’s what makes awareness and preparation critical, especially in environments like hospitality. In this episode, Betsy Steckler shares how Booking.com, in partnership…
Human trafficking can take many forms, and it can be much closer to everyday environments than most people expect. What makes this issue particularly challenging is not just its scale, but how often it goes unnoticed. It doesn’t always look the way people assume, and in many cases, the signs…
Human trafficking is a complex and often misunderstood issue, and one that can be present in hospitality environments. In our latest episode, we’re joined by Betsy Steckler and Jennifer Easterday from Booking.com, along with Philippa King from It’s A Penalty, to talk about how awareness, education, and practical action can…
Human trafficking is a complex and often misunderstood issue, and one that exists across communities, including within hospitality. In this episode, we’re joined by Betsy Steckler, Regional Director of Partner Services at Booking.com, and Jennifer Easterday, Head of Human Rights at Booking.com, to talk about how their teams are approaching…
Sarah Nan DuPre shares why the Short Stay Summit is one of her favorite conferences. From bringing policymakers into the conversation to creating space for more intentional connections, it’s an event that goes beyond the usual format and reflects the conversations happening across the short-term rental industry today. In this…
“If you’re not at the table, you’re on the menu.” In this episode, Leo Walton and Sarah Nan DuPre talk about what makes the Short Stay Summit such an important event for the industry. One of the most powerful aspects of the Summit is the opportunity for short-term rental operators…
The Short Stay Summit in London has become one of the most talked-about gatherings in the short-term rental industry. In this episode, we’re joined by Leo Walton, Co-founder of Truvi, and Sarah Nan DuPre, Strategic Partnerships Director at AirDNA, who will be emceeing this year’s event. Together, they share why…
In this episode, we’re joined by Leo Walton, Co-founder of Truvi, and Sarah Nan DuPre, Strategic Partnerships Director at AirDNA. Leo and Sarah are also the co-hosts of The Check-In Podcast, and they join us for a conversation about the upcoming Short Stay Summit in London and the industry conversations…
The vacation rental tech stack keeps evolving. Channel managers are expanding their capabilities, PMS platforms are adding new tools, and the lines between systems are starting to blur. In this episode, Blake Warner, CEO of BookingPal, shares how their team approaches product development by listening closely to the challenges operators…
⭐ We’re excited to welcome Hostfully as one of our premier brand sponsors! Hostfully is an award-winning property management platform built for short-term and vacation rental operators who want to run smarter, scale faster, and deliver better guest experiences. From unified inboxes and automation tools to beautiful digital guidebooks and…
⭐ We’re proud to have BookingPal as one of our premier brand sponsors! BookingPal helps vacation rental managers simplify and scale their distribution strategy. Their platform connects professionally managed inventory to leading travel marketplaces while providing the infrastructure needed to manage channels efficiently and reliably. With enterprise-grade connectivity, automation, and…