Podcast Episodes

Send us a message! Condo-hotels and resort-style properties sit in a tricky middle ground. They are not traditional hotels, but they are not quite vacation rentals either. Many still run on hotel tech stacks, charge hotel-style commissions, and operate with hotel mindsets. Meanwhile, guests are increasingly searching on vacation rental channels, homeowners are asking why they cannot find their units online, and off-site managers charging half the commission are pulling inventory away. In ou...

Send us a message! In this episode, we are joined by Deepak Mehrotra, founder and CEO of California Design Den, for a practical discussion on how linen decisions affect short-term rental operations over time. Drawing from more than 20 years in textile manufacturing, Deepak shares how California Design Den evolved from supplying major retailers to working directly with short-term rental operators. The conversation focuses on how linen choices shift as portfolios grow, and why decisions that se...

Send us a message! Last week with Moriya Rockman, we explored luxury through the lens of growth, relationships, and what it takes to scale a high-end portfolio without losing the hospitality at the center. This week, Nir Maimon brings the conversation to the definition itself, what “luxury” should mean, how it should be verified, and why the category loses trust when the label gets used too loosely. “Luxury” has become one of the most overused words in vacation rentals, and that is exactly th...

Send us a message! In this episode, we sit down with Moriya Rockman, founder of Smiling House Luxury, to explore how a single personal vacation home in the Swiss Alps became the starting point for a global luxury vacation rental portfolio. Moriya shares her journey from accidental host to global founder, including why she and her husband chose to stay hands-on operators while scaling internationally. She explains how staying close to hospitality standards shaped every stage of growth, from pr...

Send us a message! In this episode, Alex & Annie sit down with Frank Bosi, Senior Director of Partnerships at Hostfully, to unpack what it really takes to build a tech company that people trust. Frank’s journey began in luxury hotels long before short-term rentals became a professionalized industry. That hospitality foundation now shapes how he approaches partnerships, leadership, and growth inside one of the most culture-driven PMS brands in the space. This conversation explores why cultu...

Send us a message! Welcome to the 1st of the year special episode. Alex and Annie are kicking off 2026 by looking back at the moments that shaped 2025, the lessons they’re carrying forward, and the intentions guiding the year ahead. They share how the podcast evolved over the past year, including more on site recordings and conference conversations than ever, plus why storytelling is becoming a bigger advantage for vacation rental brands right now. You’ll also hear Alex’s personal announcemen...

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! DARM week is almost here, and we’re kicking things off with the person behind it all — Amy Hinote, Founder of VRM Intel and creator of the industry’s most conversation-packed event. In this episode, Amy gives a behind-the-scenes look at what’s coming to DARM Conference 2025, from the surge of AI-driven innovation to the sessions, speakers, and tech reveals everyone will be talking about. The industry is moving fast, and Amy walks us through why this year’s conference is sha...

Send us a message! VRMA International 2025 is in the books and if you were there, you probably felt it too: this year hit differently. More people, deeper conversations, and a sense that the vacation rental industry is entering a new chapter. But what actually stuck after the applause faded? In this episode, Alex & Annie sit down with Tim Rosolio, Ela Mezhiborsky, and Jessica Gillingham to reflect on what stood out most, not just from the sessions, but from the conversations around the show. ...

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! Big news to kick off the month! 🚀 In this first-of-the-month bonus episode, Alex & Annie sit down with the Boom founders, Moran, Shahar, and Alon Goldboim, to talk about Boom’s recent $12.7 million funding round and what it means for the future of the short-term rental (STR) industry. The Goldboim brothers share how they built Boom, the world’s first AI-powered Property Management System (AiPMS), and how their newest innovation, BAM (Business Agentic Manager), is redefining...

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! This year marks 40 years of the Vacation Rental Management Association (VRMA), a milestone that comes at a pivotal time for the industry. In this episode, Alex & Annie sit down with Anne Gardner, Executive Director of VRMA, to explore how the association is entering a new chapter of growth, engagement, and industry leadership. Anne reflects on her first year as Executive Director and shares how listening to members, strengthening communication, and re-energizing voluntee...

Send us a message! When Airbnb changes its policies, the ripple effect can shake operators everywhere. For many, the problem is deeper than one policy update. Relying too heavily on a single platform leaves businesses vulnerable, and the cracks are starting to show. In this episode, Mark Simpson, CEO and founder of Boostly, shares why now is the time for vacation rental operators to double down on direct bookings. Drawing from more than a decade of helping hosts grow beyond OTAs, Mark brings ...

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...