Leadership Episodes

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 our first-of-the-month bonus episode, we are joined by Orlie Benjamin, founder and CEO of Lasoh, a marketing technology platform designed to help vacation rental operators own their guest relationships and drive direct revenue. Lasoh provides a branded digital guest portal and integrated CRM that allows operators to engage with guests from the moment of booking, offer upsells, and run smart, automated campaigns. Orlie shares how her background in corporate marketing and ...

Send us a message! In this episode, we sit down with two industry powerhouses: Dennis Goedheid , CEO of Casiola, and Shahar Goldboim , CEO of Boom and founder of DesignedVR, to unpack the story behind their groundbreaking new partnership. As the vacation rental industry continues to mature, operators are finding new ways to grow that prioritize sustainability, clarity, and control. This conversation explores the revenue-sharing agreement between DesignedVR and Casiola, a creative alternative ...

Send us a message! In this empowering episode of Alex & Annie: The Real Women of Vacation Rentals, Shelley Brown joins us to talk about how breaking outdated expectations and embracing your weird can lead to more authentic leadership and a deeper sense of belonging. As the original "Rebel in a Gown," Shelley brings her signature blend of authenticity, artistry, and humor to a conversation that challenges the status quo on leadership, burnout, and belonging. Shelley shares how an unexpected...

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we’re joined by Ian Ackland, Managing Director of the Americas at Booking.com, for a candid look at how one of the world's largest travel platforms is evolving its approach to better serve property managers. With more than 30 years in the travel industry and over a decade at Booking.com, Ian shares how the company is shifting from being just a distribution channel to becoming a true partner for vacation rent...

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 episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Boogie Wittenburg, the new CEO of TravelNet Solutions, makers of Track PMS. With a background in mission-critical technology powering global brands, Boogie brings a fresh, people-first perspective to the vacation rental tech space. We dive into Boogie's leadership philosophy, the cultural shift happening at TravelNet, and the strategic vision shaping Track PMS’s next chapter. From enhancing ...

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Julie Brinkman, CEO of Beyond, to explore how the company is transforming the way property managers approach pricing and profitability. From dynamic pricing to market intelligence, Beyond has become a vital tool for short-term rental professionals looking to scale sustainably and outperform their competition. Julie shares how the company empowers property managers with smarter data, automa...

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...

Send us a message! In this special episode, Alex & Annie sit down with the original queens of vacation rentals: three powerhouse women who helped shape the industry from the ground up. Meet Jeanne Dailey (Founder & CEO, Newman-Dailey Resort Properties), Valerie Hawkins (Co-Owner & CEO, Perdido Key Realty), and Audrey Miller (Co-Founder & CFO, Cottage Connection of Maine) - each with a story full of grit, heart, and game-changing innovation. From starting with whiteboards and spiral notebooks to...

Send us a message! In this episode, we are joined by some of the most influential leaders in the vacation rental industry. From VRMA (Vacation Rental Management Association), we welcome Executive Director Anne Gardner and Chair of the Board of Directors Jodi Refosco. Representing VR Nation, we have President Matt Tesdall and Executive Director Heidie Henriksen. Together, we dive into the exciting evolution of both organizations, their upcoming conferences, and the importance of collaboration in ...

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Expedia Group, to discuss VRBO’s vision for 2025 and beyond. Tim shares insights on VRBO’s evolving strategy, including how the platform has transformed since its transition from HomeAway, its commitment to professional property managers, and its focus on delivering exceptional guest experiences. He also provides an inside look...

In this episode, we sit down with Wil Slickers - an industry legend who transformed a single podcast into Hospitality.FM, a full-fledged media company. Wil shares how he scaled his brand from a passion project into a thriving network of nearly 40 hospitality-focused podcasts. Wil discusses the challenges and breakthroughs in building a media empire, from securing sponsorships to expanding into new content formats like video, book publishing, and event management. He also shares his insights o...

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’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...

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 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...

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 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...

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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...