Podcast Episodes

In this week’s episode, we sit down with two of the most influential voices in the short-term rental (STR) advocacy space - David Krauss, CEO & Founder of Rent Responsibly, and Alexa Nota, COO & Co-Founder. With regulations and housing discussions at the forefront of industry challenges, Rent Responsibly is leading the charge in empowering hosts, owners, and managers to unite, educate, and advocate for fair policies. From community-building to data-driven insights, David and Alexa share how t...

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 episode of Alex & Annie: The Real Women of Vacation Rentals, we’re thrilled to welcome back Alex Shapiro, CEO and co-founder of CanMonkey. Alex joins us to share exciting updates on how his company has continued to revolutionize trash management for vacation rentals and beyond. CanMonkey, which started as a bootstrap idea in 2018, now operates in 28 states and services over 5,000 properties across 350 cities. With innovative solutions, a gig-based workforce, and a deep understanding o...

It's a milestone moment for Alex & Annie: The Real Women of Vacation Rentals as we celebrate our 200th episode together with some of the most brilliant and influential podcasters in the vacation rental industry. To make this occasion extra special, Amber Hurdle and Travis Wilburn take over hosting duties, flipping the script by putting Alex & Annie in the guest seats. This episode is a tribute to the journey of not just Alex & Annie but the entire podcasting community that amplifies the voice...

In this week’s episode, we are thrilled to welcome back Terry Whyte, owner of Anna Maria Island Beach Rentals and a renowned expert in vacation rental technology and operations. As one of the leading voices in the vacation rental industry, Terry dives into the evolving landscape of vacation rental software, sharing his predictions and practical insights on what’s driving innovation in the field. From the rise of "all-in-one" solutions to the growing dominance of CRM platforms, this episode sh...

Welcome to the first episode of the year! What better way to kick off 2025 than with our tradition of reflecting on the past year’s highlights and setting an inspiring tone for the year ahead. In this episode, Alex and Annie revisit the most listened-to episodes of 2024, unveil their “Words of the Year” for 2025, and outline their bold goals and exciting plans for the months to come. Whether you’re looking to reflect on your own journey, draw inspiration for the year ahead, or stay updated...

In this week’s episode, we’re thrilled to welcome back Tom Goodwin, CEO of Mountain Laurel Chalets and host of "For the Love of Gatlinburg" Podcast. Tom shares insights into his family-run vacation rental business in Gatlinburg, which has been a beloved destination for over 50 years. We dive into his journey of preserving the essence of Gatlinburg through his podcast and discuss how it celebrates the community's rich heritage and unique stories. Tom also gives an update on Mountain Laurel ...

In this special throwback episode, we revisit a powerful conversation with Amber Hurdle, CEO and founder of Employer Brand Central. Originally aired around this time last year, this episode marks a pivotal moment for Alex & Annie as they navigated career transitions and personal growth. Amber’s wisdom, energy, and insights set the tone for what was to come, not just for the hosts, but for countless listeners. Amber reflects on the importance of building strong personal and employer brands, ov...

This week, we’re thrilled to welcome back John Hildebrand, founder of Hilde Homes and a leading advocate in the short-term rental industry. From his early days as a property manager to becoming a leading voice in vacation rental advocacy and education, John shares his inspiring journey with authenticity, humor, and valuable insights. With firsthand experience navigating the challenges of hosting, John highlights the vital role of advocacy in driving positive change for operators, guests, and ...

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...

Register at ⁠https://vrdarm.com/registration/⁠ and get $200 off when you use the promo code AlexAnnieVIP In this exciting episode, we are joined by the dynamic Amy Hinote, founder of the Vacation Rental Data and Revenue Management Conference (DARM). Amy shares her vision for DARM 2024, revealing exciting details about the venue, agenda, and the groundbreaking educational sessions planned for property managers and industry professionals. Tune in to learn about innovative strategies for revenue...

In this episode, we sit down with Steve Turk, founder of Tangy Management, a vacation rental management company known for its unique hotel-inspired approach to hospitality. With over 24 years of experience in luxury hotels, Steve brings a fresh perspective to the vacation rental industry, blending high standards from the hotel world with the flexibility of short-term rentals. Steve shares the story of how he shifted from a career in luxury hotels to founding Tangy Management, and the unique valu...

This week, we’re coming to you live from the heart of Florence, Italy, where Alex & Annie attended Scale Italia 2024! In this special on-the-ground episode, we bring you a dynamic mash-up of conversations with some of the most influential figures in the vacation rental and property management industries. Hear firsthand perspectives from Italy’s vibrant conference floor, where the future of global property management, tech trends, and regulatory changes in the short-term rental space were top of ...

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...