Alex and Annie: The Real Women of Vacation Rentals

Midterm rentals are moving from a side option to a real strategy. In this episode, Alex & Annie sit down with Jeff Hurst, CEO of Furnished Finder and former HomeAway and Expedia Group leader, to explain why 30+ day stays are gaining traction as many STR markets move into a more mature phase. Jeff breaks down what makes midterm rentals different from short-term rentals, what demand is actually...

Destination marketing is in a pressure test. Short-term rentals have become a major part of how people travel, yet many DMOs still struggle with how (or whether) to include them. At the same time, AI is speeding up the research-to-booking journey and forcing destinations to rethink what “relevance” even means. In this episode, Alex and Annie sit down with Stuart Butler (President of Visit Myrtle B...

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-...

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 fo...

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 bec...

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 ho...

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...

Welcome to the 1st of the year special episode. Alex & 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 fo...

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...

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, an...

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...

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-fi...

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 c...

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 indu...

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 stoo...

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 value...

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 veh...

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 (...

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 genuin...

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...

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 marke...

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...

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 h...

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. D...

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...