Podcast Episodes

In this special re-air of one of our most popular episodes, Alex & Annie brings together a powerhouse panel of industry experts, known as the OGs of the Panhandle. Our guests—James Olin, Steve Caron, Lino Maldonado, and Paul Wohlford—share invaluable insights from their decades-long journeys in the vacation rental industry, reflecting on where it all started, where it is now, and where it’s headed. Episode Highlights: The Early Days: Travel back with our panel as they recount the challenges a...

In this special re-air of one of our most popular episodes, Alex & Annie revisit our insightful conversation with Tom Goodwin, CEO of Mountain Laurel Chalets. Tom’s remarkable journey in the vacation rental industry, from unexpected beginnings to building a brand rooted in community, continues to inspire. Tom's Journey: Discover how Tom's unexpected entry into the vacation rental world, through his wife's family-run business in Gatlinburg, evolved into a thriving venture. His initial 18-month...

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 offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & Annie listeners also receive free Jini for Property Managers. Claim this offer here: ⁠https://www.ownerpoint.io/alex-and-annie⁠ - Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit ⁠⁠https://www.boomnow.com/⁠ to ...

Exclusive offers for Alex & Annie Listeners: - Get a FREE OwnerPoint Analyst with a demo ($1200 value). Enjoy 10% off OwnerPoint Pro or OwnerPoint Connect services, plus over 50% off additional markets and zip codes. Alex & Annie listeners also receive free Jini for Property Managers. Claim this offer here: https://www.ownerpoint.io/alex-and-annie - Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit ⁠https://www.boomnow.com/ to clai...

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...

In this week’s episode, we sit down with Shahar Goldboim, CEO of Boom, to discuss the world’s first AI-driven Property Management System (AiPMS). Shahar shares the story behind Boom’s inception and how his passion for innovation in real estate led to the creation of a cutting-edge solution for property managers. By blending AI with the complexities of property management, Boom is revolutionizing the way companies scale, optimize operations, and enhance the guest experience. Shahar also giv...

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...

In this special first-of-the-month episode, Alex and Annie bring back one of their most impactful discussions from June 2022, perfect for the peak of hurricane season. This re-airing of Episode 36 features Pete DiMaio from TravelBoom, who shares vital strategies for preparing vacation rental managers and hoteliers for potential disasters, particularly hurricanes. Pete walks through his comprehensive "Six P’s of Disaster Planning," a methodical approach to ensure that vacation rental businesse...

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 Welcome to our August 1st of the month bonus episode! Today, we welcome back Simon Lehmann, a seasoned expert in the vacation rental industry and the co-founder and CEO of AJL Atelier. With over two decades of experience, Simon has been at the forefront of innovation and strategy, guiding countless property management companies throu...

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...

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 Join Alex & Annie as they dive into an enlightening conversation with Margenett Moore-Roberts and Gia Sharp, key figures in the short-term rental advocacy scene in New York City. This episode explores their personal journeys, the challenges posed by current rental regulations, and their relentless efforts through RHOAR (Restore Ho...

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...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by Scott Wiseman, CEO of Nocturne Luxury Villas. Scott brings a wealth of experience from his journey through the hospitality industry, from hotels to luxury tour operators, and now leading the charge in high-end vacation rentals. Scott's journey in hospitality began at 15 after a transformative family vacation to Acapulco. His career has spanned from hotels to luxury tour operators, including leadership roles a...

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 are joined by Eric Goldreyer, the CEO and owner of BnBFinder. Eric shares his journey in the bed and breakfast and vacation rental industry, discussing his previous ventures and how they led to the creation and success of BnBFinder. He also talks about the challenges and opportunities within the ind...

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 of Alex & Annie: The Real Women of Vacation Rentals, we're joined by two powerhouse guests in the vacation rental space - Jason Sprenkle, CEO of Keydata, and Jacobie Olin, President of C2G Advisors. Jason has over 20 years of experience in vacation rentals, previously running 360 Blue in the Panhandle area. ...

In this episode, Alex & Annie are joined, for the third time, by Marcus Rader, CEO and co-founder of Hostaway - the largest all-in-one solution for vacation rental property managers. Regulatory Challenges & Unique Perspectives Marcus shares candid insights from his recent travels, including staying in an "illegal" rental in New York City. He dives into the growing pains of regulation across different markets and the underlying psychology behind it. The Quest for Quality at Scale The discus...