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…
Distribution in vacation rentals may look simple from the outside, but behind the scenes it’s far more complex. Channels are constantly evolving, new features are introduced, every PMS works differently, and every property manager operates their business in their own way. That means getting everything mapped correctly across systems is…
AI in hospitality is starting to shift from fear to opportunity. In this clip, Alex talks about how automation can help operators deliver a better guest experience. When tasks like routine communication are handled by systems, teams can focus on the conversations that truly need a human touch. The moments…
Distribution in the vacation rental industry is getting more complex. Property managers today are balancing major OTAs, niche platforms, luxury channels, and an expanding tech stack, all while trying to deliver great guest experiences. In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down…
Distribution in the vacation rental industry has never been more complex. Property managers today are balancing major OTAs, niche platforms, emerging luxury channels, and an increasingly layered tech stack, all while trying to deliver exceptional guest experiences. In this episode, Alex & Annie sit down with Blake Warner, CEO of…
Midterm rentals and short-term rentals can both be great businesses, but they’re built for different goals. In this episode, Jeff Hurst, CEO of Furnished Finder, shares a simple way to think about the difference: A truly great STR can be a world-class investment, but it’s hard to find. A great…
In this episode, Tim Hubbard shares how virtual property management works behind the scenes. Instead of opening local offices in every market, his team operates as a centralized hub, supporting property managers across dozens of cities while local teams stay focused on boots-on-the-ground execution. No matter the location or property…
What does short-term rental management look like when you remove geography from the equation? In this week’s episode, we sit down with Tim Hubbard, CEO of Corzly, to break down the virtual property management model and how it works in practice. Tim started as a real estate investor managing his…
In this episode, Alex & Annie sit down with Tim Hubbard, CEO of Corzly, to break down how a virtual property management model actually works and what it takes to make it successful. Tim started in long-term rental investing before shifting into short-term rentals more than a decade ago. As…
In this episode, Krista shared the inspiration behind her Becoming a Boss Lady Real Estate Investor books, and it starts with something a lot of people relate to. She did not have a mentor in the investing space, so she created the resource she wished existed. As her portfolio grew,…
Boss Lady Energy is having clear standards and the spine to enforce them. At some point, you stop negotiating with the same patterns. You get clearer about what you will tolerate in business and in life, and you stop calling it “being flexible” when it’s really just you absorbing things…