Alex and Annie: The Real Women of Vacation Rentals

Alex and Annie

With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.

  1. Sarah Bradford Unfiltered: Fix These Vacation Rental Mistakes Before 2026

    6D AGO

    Sarah Bradford Unfiltered: Fix These Vacation Rental Mistakes Before 2026

    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 situations. From financial missteps and weak owner communication to outdated technology, unhealthy competition mindsets, and tolerating the wrong homeowners, Sarah shares what she would fix immediately if she were starting again today. As the industry heads into 2026, this conversation offers a timely reality check on what needs to change and what operators can no longer afford to ignore. We cover: 1️⃣ The financial habits that quietly put operators at risk 2️⃣ Why trust accounting, budgeting, and clean books are non-negotiable 3️⃣ Common owner relationship mistakes that lead to unnecessary churn 4️⃣ How silence from homeowners can signal problems long before complaints 5️⃣ Why competing on commission is rarely the right move 6️⃣ The danger of delaying technology and PMS upgrades 7️⃣ How weak company culture shows up in performance and retention 8️⃣ When to say no to homeowners 9️⃣ Why outdated homes hurt your brand more than you think 🔟 What operators should fix now to stay competitive heading into 2026 Connect with Sarah: LinkedIn: https://www.linkedin.com/in/sarah-bradford-032129b1/  Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. #vacationrentals #shorttermrentals #propertymanagement

    59 min
  2. DARM 2025 Fireside Chats: What the Industry Is Finally Saying Out Loud

    DEC 17

    DARM 2025 Fireside Chats: What the Industry Is Finally Saying Out Loud

    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 words to what you were feeling. And if you weren’t, it offers a clear window into the discussions that mattered most this year. What you’ll hear in this episode: 1️⃣ Why StayTerra targets reputable, community‑rooted operators 2️⃣ Where centralization helps, and where local teams must stay empowered. 3️⃣ Why multi-brand scale starts with getting data into one place 4️⃣ Why loyalty is still tough to crack in vacation rentals. 5️⃣ A more grounded take on luxury: less formality, more ease. 6️⃣ How Casiola is building growth through partnerships and ambassadors. 7️⃣ AI guest service that anticipates needs and raises expectations fast. 8️⃣ The next challenge: being discovered when AI gives only a few options.  Connect with Alex Cisneros: LinkedIn: https://www.linkedin.com/in/alexjcisneros/ Website: https://stayterravaca.com/  Connect with Dennis Goedheid: LinkedIn: https://www.linkedin.com/in/dennisgoedheid/ Website: https://www.casiola.com/  Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. #vacationrentals #shorttermrentals #DARM2025

    44 min
  3. Reinventing the Backend: Jim Devos Debuts VRWorks

    DEC 10

    Reinventing the Backend: Jim Devos Debuts VRWorks

    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 pricing philosophy behind VR Works, and why he believes now is the right moment to introduce it to the wider industry. If you’re curious how seasoned operators who have lived every operational pain point design systems that make teams faster, owners happier, and scaling far less chaotic, this conversation is a must listen. We Discuss: 1️⃣ The operational challenges that sparked VR Works 2️⃣ How building internally led to faster, clearer workflows 3️⃣ The specific efficiencies that nearly doubled their net profit 4️⃣ Why an operator-first mindset shaped every design choice 5️⃣ Reducing migration pain through smarter data import and onboarding 6️⃣ Why he’s introducing VR Works now 7️⃣  Updates on Swanky Vacay and his continued operator journey Connect with Jim: LinkedIn: https://www.linkedin.com/in/jim-devos-35254912/  VRWorks: https://www.linkedin.com/company/vrworks-llc/  Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. Considering an exit strategy? Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities. 👉 Contact anthonybarrera@nocturneluxuryvillas.com  #vacationrentals #shorttermrentals #hospitalitytech

    37 min
  4. The Guest-First Strategy: How Brandon Hall Built a Scalable Vacation Rental Brand

    DEC 3

    The Guest-First Strategy: How Brandon Hall Built a Scalable Vacation Rental Brand

    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 shaped the DNA of Hallson Hospitality and helped him grow from three homes to eighty while keeping hospitality at the center. That approach earned Hallson Hospitality national recognition, including being named 2024 Vacation Rental Management Company of the Year by VRMA - a clear testament to the power of guest-first thinking at scale. Across this conversation, Brandon shares the mindset, touchpoints, systems, and leadership decisions that allowed him to scale without losing the heart of his brand. We cover: 1️⃣ How a guest-first philosophy creates long-term scalability 2️⃣ The role of brand standards in building a portfolio that performs 3️⃣ Why he turns away owners who don’t align with the guest-first model 4️⃣ Small touches that create big loyalty 5️⃣ How team culture supports hospitality at scale 6️⃣ The tech stack behind the scenes 7️⃣ His approach to responsible scaling in 2026 Connect with Brandon: LinkedIn: https://www.linkedin.com/in/brandonhall/ Website: https://hallson.co/ Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. Considering an exit strategy? Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities. 👉 Contact anthonybarrera@nocturneluxuryvillas.com  #vacationrentals #shorttermrentals #guestexperience

    36 min
  5. It’s About DARM Time: Amy Hinote Sets the Stage for This Year’s DARM Conference

    NOV 26

    It’s About DARM Time: Amy Hinote Sets the Stage for This Year’s DARM Conference

    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 shaping up to be one of the most important gatherings for operators, tech leaders, and anyone keeping an eye on where short-term rentals are headed. If you’re gearing up for DARM or want to feel the buzz from afar, this episode sets the tone for an exciting week ahead. We discuss: 1️⃣ The excitement building going into DARM 2025 2️⃣ Why AI and agentic tools will take center stage across sessions 3️⃣ The tech battleground and the new products expected to debut 4️⃣ How operators are influencing roadmaps more directly than ever 5️⃣ Big themes shaping this year’s discussions: consolidation, agility, and industry evolution 6️⃣ The growing divide and opportunity between legacy operators and fast-moving emerging managers 7️⃣ Environmental and destination challenges that are becoming impossible to ignore 8️⃣ The trends and insights expected to define the next 12–18 months Connect with Amy: LinkedIn: https://www.linkedin.com/in/amymutual/  DARM Website: https://vrdarm.com/  Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. Considering an exit strategy? Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities. 👉 Contact anthonybarrera@nocturneluxuryvillas.com  #vacationrentals #shorttermrentals #DARM2025

    56 min
  6. After the Applause: Real Takeaways from VRMA 2025 with Tim Rosolio, Ela Mezhiborsky, and Jessica Gillingham

    NOV 19

    After the Applause: Real Takeaways from VRMA 2025 with Tim Rosolio, Ela Mezhiborsky, and Jessica Gillingham

    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.  From global distribution shifts and OTA quality standards to how AI is reshaping operations, trust, and discoverability, this is a candid look at what’s changing and what it means for property managers on the ground. We discuss: 1️⃣ The state of global distribution with Tim Rosolio 2️⃣ Trust, verification, and real-world AI risks with Ela Mezhiborsky 3️⃣ Marketing visibility and the future of discoverability with Jessica Gillingham Whether you joined the crowd in Vegas or followed along from afar, this conversation will catch you up on the bigger picture. Connect with Tim: LinkedIn: https://www.linkedin.com/in/tim-rosolio-434b2a98/ Connect with Ela: LinkedIn: https://www.linkedin.com/in/elamezhiborsky/  Connect with Jessica: LinkedIn: https://www.linkedin.com/in/jessicagillingham/  Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. Considering an exit strategy?  Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities. 👉 Contact anthonybarrera@nocturneluxuryvillas.com  #vacationrentals #shorttermrentals #vrma2025

    54 min
  7. Chillin' with Dylan: How to Build a People-First Culture in a Competitive Vacation Rental Market

    NOV 12

    Chillin' with Dylan: How to Build a People-First Culture in a Competitive Vacation Rental Market

    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-term success. We discuss: 1️⃣ The challenges of managing vacation rentals along the 30A corridor 2️⃣ How leadership and team structure can prevent burnout 3️⃣ Creative ways to engage and communicate with homeowners 4️⃣ Why defining core values transforms company culture 5️⃣ The importance of collaboration among local property managers 6️⃣ Insights on market shifts post-2021 and preparing for sustainable growth This episode is a reminder that growth starts with your people and that sustainable success in hospitality is built from the inside out. Connect with Dylan: LinkedIn: https://www.linkedin.com/in/dylan-bozarth-6225b8338/ Website: https://www.30aescapes.com/  Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. Considering an exit strategy?  Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities. 👉 Contact anthonybarrera@nocturneluxuryvillas.com  #vacationrentals #shorttermrentals #culture

    28 min
  8. Finding Strength in the Ashes: Angie Leone’s Story of Resilience after the Lahaina Wildfires

    NOV 5

    Finding Strength in the Ashes: Angie Leone’s Story of Resilience after the Lahaina Wildfires

    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 instant. But what followed wasn’t the end of her story. Through faith, family, and community, Angie found a way forward, creating new meaning, new strength, and a renewed sense of purpose in the ashes. She opens up about: 1️⃣ The day Lahaina burned  and how her family faced unimaginable loss together 2️⃣ The “5 Fs” that became her foundation for resilience: Faith, Family, Fitness, Friends, and Focus 3️⃣ The healing power of cold plunges, saunas, and daily routines 4️⃣ Building the Lahaina Dreamers Cohort:  a community helping women rediscover purpose after tragedy 5️⃣The power of faith, perseverance, and post-traumatic growth Connect with Angie: LinkedIn: https://www.linkedin.com/in/angela-leone-549295a4/  Website: https://www.coconutcondos.com/  Exclusive Offers for Alex & Annie Listeners: Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value). 👉 Use code AAA20 at checkout. Offer valid until December 31, 2025. Considering an exit strategy?  Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities. 👉 Contact anthonybarrera@nocturneluxuryvillas.com  #vacationrentals #shorttermrentals #hospitality

    56 min
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5
out of 5
34 Ratings

About

With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.

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