Podcast Episodes

Send us a message! In this week’s episode, we're joined by Matt Gurley, Director of Sales and Partner Integrations at the Lynnbrook Group, for a deep dive into the payment side of vacation rentals that most property managers overlook until it’s too late. From fraud prevention to faster checkouts to smarter cash flow tools, Matt breaks down how Lynnbrook is simplifying payment processing and helping operators keep more of what they earn. With a career that started in the OTA integration trench...

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! Is the short-term rental industry on the edge of a travel recession, or just entering a new phase of normalization? In this episode of Alex & Annie: The Real Women of Vacation Rentals, AirDNA’s Chief Economist Jamie Lane joins us to explain what the data is revealing about the 2025 market. With demand softening among budget travelers, international bookings pulling back, and economic uncertainty on the rise, Jamie helps make sense of the mixed signals facing STR professionals...

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episode of Alex & Annie: The Real Women of Vacation Rentals, Shelley Brown joins us to talk about how breaking outdated expectations and embracing your weird can lead to more authentic leadership and a deeper sense of belonging.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! Alex & Annie bring you behind the scenes at VRNation 2025 to explore direct booking strategies, industry growth, tech innovation, and the evolving role of associations in vacation rentals. Recorded live in Austin, Texas, this special bonus episode captures real-time insights from the conference floor. Alex & Annie had on-the-spot conversations with some of the industry’s most influential voices and rising innovators to unpack the real story behind what’s shaping the vacatio...

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, Alex & Annie sit down with Jason Gann, a well-established figure in vacation rentals who has carved out a unique path as both a sales executive and an emerging comedic talent. Jason takes us through his fascinating career journey - from selling hair-cutting shears to stepping into the world of vacation rental technology, navigating the fast-changing landscape of property management software, and now leading conversations around revenue management at Beyond Pri...

Send us a message! As the hospitality industry evolves, guest screening and verification have become essential components of a safe and seamless guest experience. In this episode, we sit down with Ela Mezhiborsky, President and Co-Founder of AutoHost, to explore how cutting-edge technology is reshaping the way hotels and short-term rental operators manage risk, prevent fraud, and enhance security. Ela shares her insights on the growing role of AI and cybersecurity in guest verification, the cha...

Send us a message! We’ve got BIG news to share! In this special bonus episode, we welcome back industry powerhouse Amy Hinote to reveal all the exciting details about the 2025 Women’s Summit! What better time to celebrate this announcement than during International Women’s Day on March 8, 2025? This global day of recognition honors the achievements of women in every industry—including the incredible women shaping the vacation rental space. And what better way to continue that celebration than b...

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 special episode, Alex & Annie take you to the heart of the Track NEXT25 Conference, TravelNet Solutions' premier annual conference, held in the vibrant city of Nashville. This annual user conference brings together company representatives, executives, vendors, and customers for a blend of fun, fellowship, and educational sessions designed to maximize the value of Track software. Alex teamed up with Justin Panzer, VP of Marketing for TravelNet Solutions, to delve into what made this ye...

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...