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Welcome to The Vacation Rental Show where we dive into the latest hot topics, technology and strategies, to help you take the vacation rental world by storm. Hosted by industry veteran, Lynell Gordon.
142 Episodes
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Tiffany Moldovan, Director of Property Management at Beach Realty in the Outer Banks of North Carolina, joins Lynell Gordon to discuss one of the most dramatic market shifts in vacation rental history. The traditionally stable Outer Banks market, known for generational Saturday-to-Saturday seven-night stays, saw 10,000 additional three-to-six-night reservations in 2025 while seven-night bookings dropped by 9,000. Tiffany reveals how Beach Realty adapted to this revolution by implementing flex stay pricing strategies that yield 120 percent of weekly rates through strategic combinations of shorter stays. She shares the data-driven approach that convinced resistant owners to embrace change, including quarterly stats updates and year-end profit analysis. Tiffany also discusses managing 450 properties with dedicated rental managers, converting OTA guests to direct bookings through SMS marketing and urgency-based tactics, and why booking windows have compressed from 180 days to just 60-90 days. This episode is brought to you by LSI Tools, with 22 customized tools designed to supplement your vacation rental software and transform how you manage guest information.
This episode is sponsored by LSI Tools.
Michael Steinkirchener, founder of Uncharted Vacations, joins Lynell Gordon on The Vacation Rental Show to share his unconventional approach to building a vacation rental management company. Unlike competitors chasing unlimited growth, Michael deliberately caps his portfolio at 100 properties to maintain personal relationships with every owner and guest. He reveals his innovative "Redesign on Our Dime" program that finances property updates for cash-strapped owners while boosting retention and revenue. Michael discusses critical startup advice including choosing the right tech stack from day one, the importance of negotiating with vendors, and why cleaners deserve far more recognition than they receive. He shares insights on ancillary revenue streams, the surprising low uptake of travel insurance (currently 10-15% when it should be 30-40%), and how showing owners the monetary value of included services strengthens partnerships.
This episode is sponsored by Streamline.
What happens when you build a property management company with the vision to operate in places you love while helping your closest friends achieve financial freedom? Christian Gissing, founder of True North Property Management, shares his 11-year journey from bootstrapping in Traverse City, Michigan, to managing properties across four countries including Jamaica, the UK, Bali, and Mexico.
In this episode, Christian reveals his innovative branch manager program that functions like a franchise but with more extensive support, allowing partners to leverage all back-end systems while focusing on local operations and owner relationships. He discusses the hard lessons learned about firing quickly when core values are violated, building a business designed for exit whether you plan to sell or not, and why the first hour of your day determines your energy and leadership impact.
Christian's philosophy centers on creating a life he doesn't need a vacation from and making his business bigger than himself by transforming team members' lives. His transparent approach to failure, growth, and multi-country expansion offers actionable insights for property managers ready to scale beyond their comfort zones.
This episode is sponsored by RevMax.
When booking windows collapse from a year to just two weeks and hurricanes strike repeatedly, how do luxury property managers not just survive but thrive? Casey Alderman, property manager at Parsley-Baldwin Realty in Boca Grande, Florida, shares her proven strategies for navigating unprecedented market disruption.
In this episode, Casey reveals how she transformed disaster preparation into a trust-building advantage, maintained premium pricing without racing to the bottom, and created guest loyalty that transcends property amenities. Operating on a boutique seven-mile island where competitors are close friends and celebrity guests expect white-glove service, Casey has mastered the art of adapting while staying true to core values.
From proactive hurricane checklists to creative length-of-stay pricing, Casey offers actionable insights for property managers facing their own market challenges. Her philosophy is clear: relationships matter more than revenue, complacency kills growth, and there's always something more you can do to enhance your operation.
This episode is sponsored by Lynnbrook Group.
What makes a technology partnership truly sustainable? Mike Norde, Director of Third-Party Partnerships at Inhabit, reveals the strategy behind one of the industry's most powerful ecosystems. With deep expertise from his leadership roles at Streamline, Mike shares how welcoming competitors actually drives innovation, why treating partners like guests creates lasting relationships, and how to identify vendors who deliver real value versus those peddling empty promises.
In this episode, Mike discusses Inhabit's approach to API access, the importance of collaborative problem-solving over blame games, and why happy employees translate to happy guests. He offers practical advice for property managers building their tech stacks and vendors looking to integrate with major platforms. Mike also predicts significant consolidation in property management technology over the next three years, which could reduce costs and headaches for operators.
This episode is sponsored by Streamline.
What if you could offer hotel-level concierge service to your vacation rental guests without adding any workload to your team? Milad Ghods, co-founder of Bellhopt, joins Lynell Gordon on The Vacation Rental Show to share how his company is solving a problem 87% of guests experience: making that first-day grocery run. After countless trips where he and his co-founder arrived exhausted at rentals only to find empty refrigerators, they created a pre-arrival grocery service that operates entirely on autopilot for property managers.
In this episode, Milad reveals how Bellhopt's ordering platform with 20,000 SKUs creates magazine-perfect refrigerator presentations across 20 states. He discusses the white-label approach that makes property managers the heroes, the integration capabilities that eliminate operational burden, and the results-driven business model with no subscriptions, no contracts, and automatic commission payouts. Most remarkably, Bellhopt has achieved 100% property manager retention over 4.5 years. Discover how concierge services are becoming the secret weapon for differentiation in an increasingly competitive market.
This episode is sponsored by Streamline.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Lino Maldonado (CEO) and Brady Stump (Co-founder) of Stakeholders VR to explore a revolutionary new model for property management consolidation. Unlike traditional acquisitions that strip away local brands and force tech stack changes, or franchise models, Stakeholders VR has created what they call "the third lane"—a supergroup model that allows top-tier property managers to diversify their portfolios, maintain their brands, keep their tech stacks, and participate in something larger without losing their entrepreneurial fire. This conversation reveals how generational family businesses can derisk personal net worth, access servant leadership support, and build long-term wealth while keeping the heart and soul of what made them successful in the first place.
This episode is sponsored by Rental Guardian.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Angie Leone, CEO and founder of Coconut Condos in Maui, to explore one of the most heart-wrenching yet inspiring stories in vacation rental history. From managing 60 properties with a staff of 13 and being named SBA Women-Owned Business of the Year in May 2023, to losing 45 properties, her office, and warehouse in the Lahaina fire just three months later—two days before her planned business sale closed—Angie's journey embodies resilience, faith, and the power of non-negotiables. This conversation provides a roadmap for property managers on setting boundaries from day one, navigating catastrophic loss, knowing when to rebuild versus reinvent, and finding hope through unimaginable adversity.
This episode is sponsored by Streamline.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Matthew Gurley, Director of Sales and Partner Integrations at Lynnbrook, to explore the revolution happening in vacation rental payment processing. With over a decade of experience in vacation rental fintech, including roles at BookingPal and now Lynnbrook, Matthew reveals how payment technologies are fundamentally transforming the industry. From the shift toward digital wallets capturing 68% of transactions by 2026 to automation that saves two full accounting salaries annually, this conversation provides a roadmap for property managers navigating the transition from traditional credit card processing to integrated fintech solutions while eliminating fraud and streamlining operations.
This episode is sponsored by Lynnbrook.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Grace Souter, Director of Digital Marketing at Inhabit, to explore the evolution of vacation rental marketing strategies from small-scale storytelling to enterprise-level automation. With over 15 years of experience including roles at BlueTent, Vacasa, and various Outer Banks property management companies, Grace reveals how marketing approaches must fundamentally shift as companies grow from under 100 units to over 1,000 properties. From handwritten welcome notes and local coffee bags to AI-powered email segmentation and automated insights, this conversation provides a roadmap for property managers navigating the transition from personalized hospitality to scalable systems while maintaining authentic guest experiences.
This episode is sponsored by Bluetent.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with three industry leaders who are launching a revolutionary nonprofit initiative. Rachele Hobbs (CEO of Hobbs Realty), Sue Jones (founder of HR4VR), and April Burns (ICND Senior Account Executive) introduce Hospitality Heroes, a 501(c)(3) organization born from Hurricane Helene's devastating impact on Western North Carolina. Their mission centers on one powerful truth: "The people behind the places deserve a plan." From pre-disaster education and employee preparedness to real-time crisis communication and recovery support, these women are building the first comprehensive disaster response network specifically for hospitality workers and property management teams.
This episode is sponsored by Streamline Summit 2025: Soar.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Anne Gardner, Executive Director of VRMA, to explore how the largest global community for vacation rental professionals has transformed through member-driven feedback and strategic listening. Anne reveals how VRMA evolved from traditional conference programming to a member-led approach featuring over 50 volunteer planners, personalized learning paths, and actionable Monday-morning solutions. From emergency preparedness partnerships to M&A education, this conversation showcases how VRMA is positioning property managers for success in an accelerating industry landscape while maintaining the foundational community spirit that has defined the organization for 40 years.
This episode is sponsored by Streamline Summit 2025: Soar.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Sue Jones, founder and owner of HR4VR, the vacation rental industry's first and only dedicated human resources support services provider. With over 30 years of experience in HR, Sue reveals the critical mistakes property managers make when scaling their businesses and shares her proven strategies for building teams that can grow with your company. From the revolutionary 20% rule for management time allocation to the hidden costs of well-intentioned policies, this conversation provides actionable insights for property managers looking to move from firefighting culture to strategic leadership while reducing HR liability and maximizing team engagement.
This episode is sponsored by RevMax.
Want to grow your vacation rental business but not sure where to start? This is the place to be.
Welcome to The Vacation Rental Show, where we teach you how to grow and scale your vacation rental business, hosted by Lynell Gordon.
Tune in every week as she sits down with the best in the biz to unlock the latest hot topics, technologies, and trends in the industry.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Derreck Kayongo, upcoming keynote speaker at Streamline Summit 2025: Soar and Executive Director of Clean Production Action. As an internationally recognized corporate social entrepreneur with over seventeen years of experience in human rights and environmental sustainability, Derreck reveals the shocking truth about chemical footprints in vacation rental properties and how property managers can lead the hospitality industry toward safer, more sustainable practices. From his journey as a refugee who founded the Global Soap Project to his current work revolutionizing chemical safety, this conversation provides actionable insights for property managers looking to reduce environmental liability while creating competitive advantages through eco-conscious hospitality.
This episode is sponsored by Streamline Summit 2025: Soar.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Karla Saladino, Managing Partner of Mirador Real Estate, to explore the complex dynamics of New York City's rental market and the unintended consequences of well-intentioned housing policies. With over twenty years of experience and 10,000+ transactions under her belt, Karla provides insider insights into how regulatory changes are creating a housing crisis, forcing 80,000-100,000 units to sit vacant, and driving developers away from the nation's largest rental market. From building successful real estate teams to navigating rent stabilization laws, this conversation reveals the hidden realities behind New York's housing shortage and offers lessons for real estate professionals operating in regulated markets.
This episode is sponsored by iTrip.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Ashley Ching, Founder and CEO of Inhaven, to explore a comprehensive case study that reveals why national hospitality management companies consistently fail—and what property managers can learn from these patterns. Through extensive research and interviews with executives across vacation rental, hotel, and restaurant industries, Ashley has identified five key principles that separate successful property management operations from those destined for failure. From Vacasa's recent struggles to Resort Quest's historical challenges, this analysis provides actionable insights for property managers seeking sustainable growth without repeating the mistakes of their predecessors.
This episode is sponsored by Streamline.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Annie Holcombe, Director of Technical Supply Partnerships at NextPax and co-host of one of the industry's most popular podcasts, Alex & Annie: Vacation Rental Podcast. With deep roots in hospitality spanning both hotel management and vacation rentals, Annie brings unique insights into the business development strategies and mindful distribution approaches that separate successful property managers from those struggling to grow. From creating company-wide sales cultures to navigating the overwhelming technology landscape, Annie demonstrates why authentic leadership and strategic thinking drive sustainable success in today's competitive market.
This episode is sponsored by Bluetent.
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Mark Lumpkin, Sales Director at STR Cribs, to explore how strategic property improvements and quality amenities drive success in today's competitive vacation rental market. With over a decade in the industry as a licensed general contractor, Mark reveals his "heads and beds" strategy for maximizing revenue through legal space conversions, why investing in quality amenities saves money long-term, and how themed properties eliminate competition by creating unique guest experiences. From transforming garages into profitable bedrooms to building Dallas Cowboys-themed retreats with original stadium seating, Mark demonstrates that understanding your guest avatar and focusing on exceptional properties, rather than managing hundreds of mediocre ones, is what separates successful STR investors from those experiencing declining revenues.
This episode is sponsored by Bluetent.
In this compilation episode of The Vacation Rental Show, host Lynell Gordon explores the hard-won wisdom of industry veterans who share their most expensive early mistakes. Jonathan Fonvielle reveals why being selective with homeowners matters more than chasing revenue, Scott Leggat emphasizes that advocacy must be proactive rather than reactive, and Adam Knight discusses the dangers of scaling too quickly without focus. From the wrong homeowner costing more than lost revenue to regulatory battles being won before they start, these leaders share the hindsight lessons that could save new operators years of struggle and significant financial loss.
This episode is sponsored by Bluetent.
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