Alex and Annie: The Real Women of Vacation Rentals

Direct booking has been part of the vacation rental conversation for years, but one challenge remains hard to solve. Travelers are not always searching that way. In this episode, Alex & Annie sit down with Eric Goldreyer, CEO and founder of Savvy, to talk about why direct booking has struggled to become a consumer habit and what needs to change for travelers to find, trust, and use it more eas...

Revenue strategy always starts with a plan, but the market does not always follow it. A major event may not pace the way it did last year, certain property types may start falling behind, owners may get nervous about open dates, and new channel updates can quickly add more complexity to an already busy season. In this episode of Revenue Reality Check , presented by Beyond , Alex & Annie are jo...

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 Destinations. His career has taken him from building a local vacation rental comp...

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 The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in L...

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. This conversation is all about “vacation brain” and the strange, messy, and s...

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 way he looks at vacation rental management today. For him, the industry has al...

The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet. In this episode, we are joined by John Suzuki , Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental technology, the pace of innovation, and what this next chapter could mean for property managers. Joh...

In this second episode of First of the Month Wrangle, presented by Lasoh , Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh , to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered. This time, the conversation focuses on a simple but important question: can we stop marketing prop...

In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations. James shares how InvitedHome evolved from a broader multi-market vacation rental company into a luxury brand focused on ski markets. After operating across different types of d...

In this episode, we are joined by Paul Wohlford and Amanda Szubert of Call Center Solutions to talk about staffing, guest services, AI, and the growing need for reliable support in vacation rental operations. Paul and Amanda share how Call Center Solutions grew out of a real hospitality staffing challenge and how their nearshore team in Montego Bay, Jamaica now supports vacation rental and hotel c...

Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there. In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools. Chris shares what he has learned from nearly two decades in property management an...

In this episode, we welcome back Mike Flaskey , President and Chief Operating Officer of Marriott Vacations Worldwide. Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value. The conversation looks at the timeshare and vacation club model through a hospi...

Revenue strategy does not happen on autopilot. Markets shift, booking windows move, owners ask harder questions, and guests become more price sensitive. For vacation rental managers, the strategy that worked last month may need a second look today. That is the focus of Revenue Reality Check , a 6-part bimonthly series brought to you by Beyond . Each episode takes a closer look at the pricing decis...

In this episode, Alex & Annie sit down with Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about the evolution of vacation rental software and why adoption across the industry still has so much room to grow. Pierre-Camille shares how his own experience as an Airbnb host in Brussels led to the creation of Smartbnb, which later became Hospitable. What started as a solution for rep...

In this special episode, Alex and Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo’s Vacation Rentals of the Year program and what it takes to earn that recognition. Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year’s winning properties, the episode offers both a platform perspective...

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 end up telling for years. That is the idea behind Pour Decisions: When Stays Go Sideways , a special series presented by Safely .  In this series, Alex & Annie sit down with the Safely team and industry guests to unpack the kinds of g...

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, shared support, and strong operational foundations. Instead of forcing every market into the same mold, Awayday supports gr...

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 Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to...

In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie to talk 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 seasonality to its mix of inventory and long-standing operating norms. Tom also shares what it takes...

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 human trafficking through awareness, education, and part...

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 surrounding it. Leo and Sarah will be serving as emcees for this year’s event, and they share...

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 BookingPal, to talk about how distribution is evolving and what i...

Growth in short-term rentals often gets framed as a numbers game. More properties, more markets, more tech, and more scale. But what if growth isn’t about doing more but choosing better? In this 1st of the Month Bonus episode, Alex & Annie sit down with Carly Traub, Co-Founder and CEO of Lazy Sunday Rentals, to talk about what it really looks like to build a business intentionally in a fast-mo...

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 his portfolio grew across multiple states, and eventually internationally, he built the systems needed to...

In this episode, Alex & Annie sit down with Krista Goodrich and Kymberlee Nguyen, the duo behind Salty Dog Vacations, to talk about what it really takes to build a vacation rental company that guests remember and a team that is proud to be part of it. They share how Salty Dog grew from early investing decisions in Daytona Beach into a full-scale operation, and how their approach to branding go...