Property Management Episodes

Send us a message! In this episode, Alex & Annie sit down with Arlen Busenitz to talk about his unconventional path from a Kansas farm to pastoring a small-town church, volunteering as an EMT, working with NASA through a defense contractor, and ultimately becoming CEO of Destin Dreamers. Before he was running a luxury vacation rental company on Florida's Emerald Coast, Arlen was hauling 500-pound rocks in a 1976 Jeep pickup to pay for college. It's an unlikely origin story but one that laid t...

Send us a message! In this unfiltered conversation, Sarah Bradford joins us once again to break down the most common and costly mistakes she sees vacation rental operators still making today. Drawing from more than two decades in the industry and her experience building, scaling, and ultimately selling two successful vacation rental companies, Sarah revisits pivotal moments that shaped her leadership, operations, and decision-making. This episode is practical, direct, and rooted in real si...

Send us a message! This episode was recorded live at DARM 2025, right in the middle of the event, while the conversations were still unfolding and the energy was still fresh. Alex & Annie sit down for two fireside chats with Alex Cisneros (StayTerra) and Dennis Goedheid (Casiola) to talk through what’s showing up in the industry right now, and what operators are being asked to decide even when the path forward is not perfectly clear. If you were at DARM, this conversation will likely put w...

Send us a message! In this episode, we are joined by Jim DeVos, industry veteran, former co-owner of Best Beach Getaways, for the first public reveal of VR Works — the backend system he spent years building to fix the operational pain points he couldn’t ignore. Jim breaks down how VR Works evolved from an internal solution into a fully integrated platform, how it nearly doubled their profit, and why an operator-first mindset shaped every design decision. He also explains the onboarding and pr...

Send us a message! In this episode, we sit down with Brandon Hall, Founder and CEO of Hallson Hospitality, to explore how a guest-first philosophy can become a true engine for growth in the vacation rental industry. Brandon’s journey into hospitality began long before he managed homes. After co-founding OneHope Wine and spending 15 years growing a nationally recognized brand, he developed a deep understanding of customer experience, brand building, and emotional connection. Those principles s...

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! When everything you’ve built disappears overnight, how do you begin again? In this episode, we sit down with Angela “Angie” Leone, founder of Coconut Condos in Maui, to share a story of loss, faith, and rebirth after the devastating Lahaina wildfires. Just days after finding a buyer for her thriving vacation rental company, Angie’s world changed forever. The wildfires destroyed her office, her vehicles, and 45 of the 50 homes she managed — a lifetime of work gone in an i...

Send us a message! In this episode, we’re joined by Kerri Gibson, CEO and Co-Founder of Chalets Hygge, a hospitality brand inspired by the Scandinavian idea of hygge — finding joy and contentment in life’s quieter moments. After years in the corporate tech world, Kerri took a much-needed step back to rediscover what truly mattered. That pause led her to create a business grounded in balance, creativity, and genuine human connection. What began as a single renovation project has grown into ...

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! In this episode, Alex & Annie are joined by Marissa Galle, founder of Click Media, to explore the real impact of photography, video, and social content on brand perception and booking behavior. Marissa shares how vacation rental operators can move beyond generic listings and start using visual storytelling to connect with guests, stand out on OTAs, and bring more personality into their marketing. From FPV drone shots to content repurposing strategies, she breaks down what w...

Send us a message! As the vacation rental industry matures, growth has become the holy grail for many property management companies. But what happens when scaling too fast starts doing more harm than good? In this episode, Ashley Ching, Founder & CEO of Inhaven, joins us to unpack her in-depth research on why many large property management companies fail and what separates the ones that last. Drawing insights from over 100 executive interviews across the hotel, restaurant, and vacation ren...

Send us a message! What does it take to scale luxury vacation rentals while protecting the legacy of the brands that built them? In this episode, Alex & Annie welcome back Scott Wiseman, CEO of Nocturne Luxury Villas, for an inside look at how Nocturne approaches acquisitions in the luxury vacation rental space. Instead of treating acquisitions as one-size-fits-all deals, Scott explains how his team works with founders to create personalized exit plans that honor their legacy, protect employee...

Send us a message! Flexible cancellation policies are no longer optional in today’s vacation rental market. Guests expect them, OTAs prioritize them, and competitors are already adapting. But for property managers, relaxed policies often feel like a direct threat to revenue and owner trust. In this episode, we talk with Sasha Lawler, CEO and Founder of Roam, about how her company is eliminating that trade-off. Roam’s embedded insurance model allows managers to offer flexible bookings that att...

Send us a message! In this week’s episode, we’re joined by Adrienne Clark (President & COO) and Caleb Yaryan (Chief Product Officer) of Xplorie, a trusted partner for vacation rental operators looking to enhance guest satisfaction while gaining a competitive edge. For nearly 30 years, Xplorie has been connecting lodging providers with local attractions in more than 70 destinations across the U.S., creating seamless, curated activity experiences that guests value. But more than just a perks pr...

Send us a message! In this special first-of-the-month bonus episode, Alex & Annie sit down with longtime friend and industry leader Tyann Marcink Hammond to talk about a timely and much-needed initiative to support host education. Tyann shares how she’s leading an effort to prepare short-term rental operators ahead of the 2026 FIFA World Cup, starting in Kansas City and expanding to other host cities across North America. Annie also shares a major personal announcement. After a successful ...

Send us a message! Airbnb’s evolving policies have become one of the most pressing conversations in vacation rentals today - sparking questions, frustrations, and new realities for property managers across the industry. In this episode, Alex & Annie welcome Dennis Schaal, Founding Editor at Skift, to unpack what these changes really mean for property managers, and the broader short-term rental ecosystem. With more than 25 years of experience covering online travel, Dennis brings a sharp journ...

Send us a message! What if imposter syndrome wasn’t a weakness, but a sign you’re growing? In this episode, Alex and Annie are joined by Michelle Marquis, founder of The Marquis Effect and now author of The Bossy Girl’s Guide to Leadership, which has just been released. Written for women navigating leadership and self-doubt, the book is part memoir, part guidebook, and 100% Michelle’s authentic voice. Michelle reveals the mindset shifts that shaped her journey, including: Earn It While...

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 of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Paul Kromidas, Founder & CEO of Summer, to talk about the growing need for asset intelligence in short-term rental investing, and why gut feel is no longer enough when deciding which properties to buy. Paul shares his journey from building products at Airbnb to launching Summer, a powerful underwriting and asset management platform designed specifically for STR operators. Originally built as...

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! This week, we’re joined by Deborah Labi, a seasoned hospitality professional and the founder of Have You Got, a verified global guest referral network designed to help independent property managers expand their reach and maximize revenue without sacrificing the personal touch that sets them apart. With two decades of experience in the industry, Deborah understands the frustration of turning away great guests, whether due to lack of availability or location. That challenge led...

Send us a message! Many short-term rental operators think that getting listed on Airbnb or Vrbo is enough. But in today’s competitive landscape, basic distribution is no longer enough to stand out or to sustain growth. In this episode, we’re joined by Lennart Kok, VP of Distribution and Marketing at NextPax, to explore what smarter vacation rental distribution really looks like. With a background at Hilton, Booking.com, and now NextPax, Lennart brings rare insight into where distribution ofte...

Send us a message! In our first of the month bonus episode, we’re joined by two well-known names in the vacation rental industry: Lino Maldonado and Brady Stump, co-founders of the newly launched StakeholdersVR. You’ve probably heard early buzz about this exciting new venture, and today, Lino and Brady are here to tell us what it’s really all about. From how the idea came together to why it’s gaining traction, they give us a full look behind the scenes. StakeholdersVR offers a new model th...