Entrepreneurship Episodes

What does it take to build a vacation rental company that can grow, evolve, and remain successful for nearly seven decades? In this episode, Alex & Annie sit down with Rick Elliott and Brandon Cox of Elliott Realty to explore the people, systems, leadership decisions, and business fundamentals behind the company’s longevity. Elliott Realty has been part of the Myrtle Beach vacation rental industry since 1959. Over those 67 years, the company has navigated new technology, changing traveler ...

Send us a message! In this episode, Alex & Annie sit down with Tim Hubbard, CEO of Corzly, to break down how a virtual property management model actually works and what it takes to make it successful. Tim started in long-term rental investing before shifting into short-term rentals more than a decade ago. As his portfolio grew across multiple states, and eventually internationally, he built the systems needed to manage properties remotely. That operational backbone became Corzly, a virtual ma...

Send us a message! In this episode, Alex & Annie sit down with Krista Goodrich and Kymberlee Nguyen, the duo behind Salty Dog Vacations, to talk about what it really takes to build a vacation rental company that guests remember and a team that is proud to be part of it. They share how Salty Dog grew from early investing decisions in Daytona Beach into a full-scale operation, and how their approach to branding goes beyond design choices. It shows up in the details, the guest experience, and th...

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! 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 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! 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...

Send us a message! Is your short-term rental business growing, or just getting harder to manage? In this episode, we sit down with Patrick Stewart, CEO of Grand Welcome, to explore how franchising offers property managers a scalable and sustainable path to success in today’s competitive STR market. Grand Welcome is one of the fastest-growing franchise-based vacation rental management companies in the U.S. The brand provides local operators with the tools, systems, and support they need to ...

Send us a message! In this week’s episode, Matt Landau returns to the show to share one of the most personal and transformational shifts of his career — a journey from building systems and scaling success to rediscovering the power of human connection. Long known as a community builder and founder of VRMB, Matt opens up about the moment everything changed. After years of being surrounded by the same ideas and doing the same routines, he stepped outside the norm and into a retreat that would f...

Send us a message! In this soul-stirring episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Brittany Blackman, former vacation rental business owner turned leadership coach and founder of Discover Freedom. Brittany gets real about what it took to walk away from the business she built and loved, after realizing that outward success came at the cost of her inner peace. She opens up about her battle with burnout, the pressure to be everything to everyone, and how learn...

In this week’s episode, Alex & Annie sit down with Fred Boothby, CEO of Enjoy Unique Stays, to explore how he’s breaking the mold in the vacation rental industry. What started as a small side business has grown into a thriving portfolio of 140+ properties across multiple states, redefining what it means to create experiential stays that go beyond the ordinary. Fred shares the bold strategies and innovations that have shaped his success, from crafting unique guest experiences to navigating the...

In this week’s episode, we sit down with Declan McGonigal, the dynamic owner-operator of My Beach Vacation Rentals, based in North Myrtle Beach. Declan’s story is one of grit, growth, and ingenuity, as he shares how he went from managing just two properties to overseeing a thriving portfolio of 70 vacation rentals in just a few years. Declan opens up about the lessons he’s learned along the way, from the early challenges of starting his business to the strategies that helped him scale success...

In this week’s episode, we welcome back Dennis Goedheid, founder and CEO of Casiola Vacation Homes. Dennis returns to share exciting updates on his company's growth, including the launch of a new franchise model. Since its inception, the franchise has rapidly expanded into key markets, including Aruba, where Casiola has seen tremendous success. Dennis also dives into the challenges and opportunities in the vacation rental space, from navigating property management in international markets to ...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Ian Carter, the former CEO of Hilton International and current Chair of the Board for Watches of Switzerland, Eataly, The Boston University School of Hospitality and Administration, and Boom. Ian shares his remarkable career journey, from his early days at General Electric to leading Hilton International through its historic merger with Hilton Hotels Corporation. We also dive into the vacation rental mark...

Exclusive offer for Alex & Annie listeners: Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit boomnow.com to claim this limited-time deal! In this week’s episode, we’re joined by Eric Moeller, the visionary founder and CEO of Freewyld, a brand creating nature-inspired cabin communities. Eric takes us on his entrepreneurial journey from real estate investment to building luxury short-term rental brands and developing Freewyld. ...

In this exciting episode, Alex and Annie sit down with Larry Hoffer, CEO of Rentalz, a company specializing in breakthrough growth solutions for vacation rental managers. Larry takes us on a journey through his two-decade career, starting from a personal double-booking mishap in Vail, Colorado, to becoming a key figure in the vacation rental industry. He shares how Rentalz, with its innovative services like OwnerPoint, ContactPoint, AnswerPoint and the recently launched TravelPoint, is dri...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex and Annie sit down with Heather Bayer, a veteran in the vacation rental industry. Heather shares her journey from running a management training company in England to becoming a prominent figure in the vacation rental space. She discusses her current role as the Director of Training for the Vacation Rental For...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are thrilled to welcome Rachel Alday, co-owner and co-founder of Abode Luxury Rentals. Rachel shares the fascinating journey of how she and her husband built a successful luxury vacation rental business that spans multiple high-end markets, including Park City, J...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Alexis Rivera Scott, the dynamic founder of Fairy Job Mom. Alexis shares her journey from a career in hospitality sales to becoming a powerhouse on LinkedIn with over 81,000 followers. She opens up about her transition from traditional employment to entrepreneurship, the challenges she faced along the way, and the importance of building a personal brand. Key Topics Discussed: 🔁 The Evolution of Alexis' Ca...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, we dive deep into the world of public relations with industry expert Jessica Gillingham, CEO and founder of Abode Worldwide. Jessica shares her unique journey into the vacation rental space, from her early days in Canadian tourism to launching her own booking platform, and eventually founding Abode Worldwide. She off...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: ⁠http://get.hostaway.com/alexandannie In this episode, we sit down with Zach Busekrus, Founder/CEO of StayWatch and host of the "Behind the Stays" podcast. Zach shares his unique journey into the short-term rental industry, from living exclusively in Airbnbs during the pandemic to founding a company that's revolutionizing how travelers find and book vacation rentals. ...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex & Annie are joined by Linny and Kyle Jones, the dynamic duo behind Dwell Luxury Rentals. Tune in to hear how they have transformed the vacation rental landscape in their small mountain town, Flagstaff, by bringing big-city luxury standards to the area. Linny and Kyle share their journey from working in five-s...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: ⁠http://get.hostaway.com/alexandannie In this insightful episode of Alex & Annie: The Real Women of Vacation Rentals, we are thrilled to welcome Mark Lumpkin, Director of Sales for STR Cribs. Mark shares his journey from a Florida local with a passion for real estate to leading a company that transforms vacant properties into stunning, resort-style short-term rentals ac...

Get your Scale Italia 2024 tickets here: https://www.tickettailor.com/events/scalerentalsitalia/1074426 Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this week’s episode, Alex & Annie welcome the team behind the Scale Italia - Gianpaolo Vairo, Damian Sheridan, and Cristiana Carpini - to discuss their rapidly growing conference series for professional vacation rental manage...