Guest Experience Episodes

Advocacy often stays on the back burner until a regulation directly threatens the business. For Tyann Marcink Hammond, that moment came when vacation rentals in parts of Missouri were reclassified from residential to commercial properties, causing some tax bills to rise dramatically. In this episode, Tyann returns to share how that experience pulled her deeper into vacation rental advocacy and showed her why operators need to get involved before policy decisions are finalized. She expla...

Send us a message! 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 easily. Eric shares how Savvy evolved from BNB Finder into a book-direct market...

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 sometimes costly decisions guests make when they are out of their normal routine. From poolsid...

Send us a message! 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 properties and start marketing to people? For many vacation rental operators, marketing ...

Send us a message! 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 companies with reservations, outbound calls, after-hours support, back-office w...

Send us a message! 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 hospitality lens, including how major brands build trust, keep owners engaged, an...

Send us a message! 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 and a firsthand look at the kind of hospitality Vrbo is celebrating. Tim sh...

Send us a message! 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 help operators drive more direct bookings and increase profit through deeper relati...

Send us a message! 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 goes beyond design choices. It shows up in the details, the guest experience, and th...

Send us a message! In this episode, Alex & Annie head to Florida’s scenic 30A to sit down with Dylan Bozarth, General Manager of 30A Escapes, for a real conversation about leadership, culture, and what it takes to build a team that truly lasts in the fast-paced vacation rental world. Dylan shares how his decade-long journey at 30A Escapes has shaped a people-first approach to property management. One that values work-life balance, communication, and genuine hospitality as the keys to long-ter...

Send us a message! As hospitality companies race to scale, many face a difficult trade-off: grow fast or stay personal. But Zzzing, a leading hospitality brand based in Malta, is proving you can do both. In this episode, we’re joined by Sab Mulligan, Head of Teams at Zzzing, to explore how they’ve scaled rapidly by using AI not to replace the human touch, but to protect and enhance it. Through a thoughtful blend of technology, team culture, and brand consistency, Zzzing is setting a new...

Send us a message! This week, Alex & Annie sit down with Valerie Gangas, Founder & CEO of Juniper Holiday + Homes, for a conversation that blends business, design, and deep personal transformation. Valerie shares how Juniper began with a personal real estate portfolio and evolved into a thriving multi-market vacation rental management company operating in Michigan, Wisconsin, Florida, and Utah. From navigating the early days of property management without industry experience to creating beaut...

Send us a message! In this episode, we’re joined by Simon Seroussi, Co-Founder of SuiteOp, a guest experience and operations platform built by operators, for operators. With a background in both hospitality tech and short-term rental management, Simon shares how SuiteOp was born from firsthand experience growing a 400-unit portfolio and the operational chaos that came with it. From automating smart locks to unifying guest portals, task management, and upsells, SuiteOp is designed to simplify ev...

Send us a message! In this episode, we’re joined by Lorraine Woodward, CEO of Becoming rentABLE, to explore how property managers and hosts can make their vacation rentals more accessible without needing a full renovation or massive investment. Drawing from her lived experience navigating life with muscular dystrophy and raising two sons with the same condition, Lorraine shares practical, real-world advice for designing spaces that serve a broader range of guests. From small, low-cost additions...

Send us a message! What happens when one of the world’s most trusted hotel brands steps into the vacation rental space? In this episode, we’re joined by Jane Gavin (Senior Director of Brand Marketing & Guest Experience) and Keven Wishard (Senior Director of Global & Continent Operations) from Homes & Villas by Marriott Bonvoy. With decades of hospitality experience between them, Jane and Keven take us inside Homes & Villas by Marriott Bonvoy’s bold approach to short-term rentals. One built...

Send us a message! As the hospitality industry evolves, guest screening and verification have become essential components of a safe and seamless guest experience. In this episode, we sit down with Ela Mezhiborsky, President and Co-Founder of AutoHost, to explore how cutting-edge technology is reshaping the way hotels and short-term rental operators manage risk, prevent fraud, and enhance security. Ela shares her insights on the growing role of AI and cybersecurity in guest verification, the cha...

In this week’s episode, we are thrilled to welcome back Terry Whyte, owner of Anna Maria Island Beach Rentals and a renowned expert in vacation rental technology and operations. As one of the leading voices in the vacation rental industry, Terry dives into the evolving landscape of vacation rental software, sharing his predictions and practical insights on what’s driving innovation in the field. From the rise of "all-in-one" solutions to the growing dominance of CRM platforms, this episode sh...

In this week’s episode, we’re thrilled to welcome back Tom Goodwin, CEO of Mountain Laurel Chalets and host of "For the Love of Gatlinburg" Podcast. Tom shares insights into his family-run vacation rental business in Gatlinburg, which has been a beloved destination for over 50 years. We dive into his journey of preserving the essence of Gatlinburg through his podcast and discuss how it celebrates the community's rich heritage and unique stories. Tom also gives an update on Mountain Laurel ...

In this episode, we sit down with Steve Turk, founder of Tangy Management, a vacation rental management company known for its unique hotel-inspired approach to hospitality. With over 24 years of experience in luxury hotels, Steve brings a fresh perspective to the vacation rental industry, blending high standards from the hotel world with the flexibility of short-term rentals. Steve shares the story of how he shifted from a career in luxury hotels to founding Tangy Management, and the unique valu...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Ian Carter, the former CEO of Hilton International and current Chair of the Board for Watches of Switzerland, Eataly, The Boston University School of Hospitality and Administration, and Boom. Ian shares his remarkable career journey, from his early days at General Electric to leading Hilton International through its historic merger with Hilton Hotels Corporation. We also dive into the vacation rental mark...

Exclusive offer for Alex & Annie listeners: Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit boomnow.com to claim this limited-time deal! In this week’s episode, we’re joined by Eric Moeller, the visionary founder and CEO of Freewyld, a brand creating nature-inspired cabin communities. Eric takes us on his entrepreneurial journey from real estate investment to building luxury short-term rental brands and developing Freewyld. ...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex & Annie are joined by Linny and Kyle Jones, the dynamic duo behind Dwell Luxury Rentals. Tune in to hear how they have transformed the vacation rental landscape in their small mountain town, Flagstaff, by bringing big-city luxury standards to the area. Linny and Kyle share their journey from working in five-s...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex and Annie are joined by Eric Goldreyer, the CEO and owner of BnBFinder. Eric shares his journey in the bed and breakfast and vacation rental industry, discussing his previous ventures and how they led to the creation and success of BnBFinder. He also talks about the challenges and opportunities within the ind...

In this episode of "Alex & Annie: The Real Women of Vacation Rentals," hosts Alex & Annie welcome special guest Meaghan Moylan, host of the "Workflows and Espressos" podcast and Executive Director of Outpost - a Vacation Rental and Property Management company located in the Jackson Hole, Wyoming. Meaghan shares her inspiring journey of embracing new opportunities in the dynamic vacation rental industry. The Year of Yes Mentality Meaghan highlights how adopting a "year of yes" mindset opened d...