Alex and Annie: The Real Women of Vacation Rentals

• 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 Rosolio2️⃣ Trust, verification, and real-world AI risks with Ela Mezhiborsky3️⃣ Marketing visibility and the future of discoverability with Jessica GillinghamWhether 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 [email protected] #vacationrentals #shorttermrentals #vrma2025

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• 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 corridor2️⃣ How leadership and team structure can prevent burnout3️⃣ Creative ways to engage and communicate with homeowners4️⃣ Why defining core values transforms company culture5️⃣ The importance of collaboration among local property managers6️⃣ Insights on market shifts post-2021 and preparing for sustainable growthThis 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 [email protected] #vacationrentals #shorttermrentals #culture

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• 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 together2️⃣ The “5 Fs” that became her foundation for resilience: Faith, Family, Fitness, Friends, and Focus3️⃣ The healing power of cold plunges, saunas, and daily routines4️⃣ Building the Lahaina Dreamers Cohort:  a community helping women rediscover purpose after tragedy5️⃣The power of faith, perseverance, and post-traumatic growthConnect 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 [email protected] #vacationrentals #shorttermrentals #hospitality

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• 1st of the Month Bonus: Boom Founders Announce $12.7M Funding Raise, Plus Agentic AI for STR

  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 what true AI automation looks like for property managers.From their vision of “business-as-a-software” to the story behind their investor partnerships, this conversation dives deep into the future of AI-driven STR operations, profitability, and guest experience — and why Boom’s approach to AI is fundamentally different from every other PMS on the market.We cover:1️⃣ The story behind Boom’s $12.7M funding raise and what it enables next2️⃣ How the Goldboim brothers combined real estate, tech, and AI expertise to build Boom3️⃣ What Agentic AI means and how BAM helps operators move from reacting to predicting4️⃣ Why Boom’s all-in-one design gives AI a true advantage over bolt-on solutions5️⃣ The future of “business as a software” and how AI will power every part of STR operationsLearn more about Boom:LinkedIn: https://www.linkedin.com/company/boom-now/ Website: https://www.boomnow.com/ Connect with the Boom Brothers:Moran Goldboim: https://www.linkedin.com/in/moran-goldboim-9bb9b118/ Shahar Goldboim: https://www.linkedin.com/in/shahar-goldboim-80820b95/v Alon Goldboim: https://www.linkedin.com/in/alon-goldboim-56821880/ 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: https://www.lodgify.com/ Offer valid until December 31, 2025.Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.👉 https://hubs.ly/Q03B9lmX0Considering an exit strategy? Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.👉 Contact [email protected] #vacationrentals #shorttermrentals #AIinhospitality

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• Turning Connection into Conversions: How Chalets Hygge Achieved 70% Direct Bookings with Kerri Gibson

  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 a collection of cozy retreats and a thriving brand where 70% of bookings come directly from guests. With Lodgify at the core of her tech stack, Kerri has built systems that simplify operations while keeping guest relationships personal and meaningful.We discuss:1️⃣ How a personal sabbatical evolved into a purpose-led hospitality brand2️⃣ Building trust through authenticity and storytelling3️⃣ Why repeat guests are the strongest driver of direct bookings4️⃣ How Lodgify helps her maintain genuine connection at scale5️⃣ Lessons from expanding into a boutique motel guided by the same valuesConnect with Kerri:LinkedIn: https://www.linkedin.com/in/kerri-gibson-cpa/ Website: https://chaletshygge.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.Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.👉 https://hubs.ly/Q03B9lmX0Considering an exit strategy? Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.👉 Contact [email protected] #vacationrentals #shorttermrentals #directbookings

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