Claim OwnershipThe Vacation Rental Show, Hosted by Lynell Gordon
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Welcome to The Vacation Rental Show hosted by Lynell Gordon where we dive into the latest hot topics, technology and strategies, to help you take the vacation rental world by storm.
154 Episodes
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🎙️ Quick message from Lynell Gordon, host of The Vacation Rental Show:
If these weekly conversations with industry operators, innovators, and leaders are helping you grow your business — here's how you can help us reach more vacation rental professionals like you:
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Your follow and review help us understand what's working so we can bring you more of the content you actually need. Whether you're managing properties, growing your portfolio, or serving this industry — this show exists to help you succeed.
Take a quick minute today. Your support makes all the difference.
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Sébastien Grosjean has built 14 businesses over two decades, including launching the industry's first channel manager. With a family legacy spanning four decades in vacation rentals, he brings hard-earned wisdom on what actually drives business growth.
In this episode, Sébastien breaks down the ego paradox every entrepreneur faces, explains why 90 percent of listings lose 10 to 20 percent of revenue unnecessarily, and shares the difference between working in your business versus on your business. He reveals why cross-pollinating with other industries creates breakthrough innovations, how to navigate the two critical delegation challenges, and why your best executor often makes your worst manager.
From his personal journey through mental health challenges to building multiple successful companies, Sébastien offers a holistic perspective on business that goes beyond tactics to address the fundamental principles of entrepreneurship, learning, and purpose.
This episode is sponsored by Bluetent.
Ann Marie O'Rourke transformed Sandpiper Management from the ground up by focusing on what matters most: cleanliness, communication, and customized service. As owner of this boutique property management company serving Kiawah Island and Seabrook Island near Charleston, Ann Marie has built a business model that balances exceptional guest experiences with unwavering owner loyalty.
In this episode of The Vacation Rental Show, hosted by Lynell Gordon, Ann Marie reveals the bold decision that changed everything: replacing her entire cleaning team and paying staff more to ensure five-star cleanliness standards. She shares how handwritten notes, local recommendations, and personal touches create repeat guests who eventually become property owners themselves. Ann Marie discusses the challenges of balancing owner and guest needs, the importance of transparent communication, and why treating each property as a unique investment rather than a one-size-fits-all approach has become her competitive advantage.
This episode is sponsored by Lynbrook Group.
Sofia Rossato, Executive Vice President at Inhabit, joins The Vacation Rental Show to share strategic insights on capturing event-driven revenue and implementing AI tools that actually work. With experience managing billion-dollar divisions in fintech and proptech, Sofia brings a unique perspective to property management challenges.
Sofia reveals how property managers can prepare for the 2026 World Cup and other major events to capture 55% average rate increases and up to 90% for premium located units. She breaks down the 300 mile zone strategy for attracting tournament attendees and shares the tactical steps for implementing AI in your business starting today.
Sofia also discusses 2026 market trends showing RevPAR 16% higher for operators using Inhabit products and Streamline, the importance of strategic thinking time versus tactical firefighting, and her leadership framework using IDS to bring teams along in problem solving.
This episode is sponsored by Streamline.
Most property managers chase growth by signing every property they can find and treating bookings as transactional revenue opportunities. Shervin Jamshidpour built RestNest differently - starting with one friend's house in Kelowna, British Columbia, leveraging guest inquiries he couldn't accommodate to onboard new properties, and growing to 26 ultra-high-end vacation rentals by prioritizing relationships over rapid expansion.
His first booking was $40,000 direct. Four years later, 99% of bookings still come direct with average nightly rates around $4,000. He doesn't chase mid-range properties or rely on OTAs. He actively caps growth between 30-50 homes because anything beyond would compromise the personalized service defining RestNest's competitive advantage.
Shervin maintains year-round relationships with guests who text him for real estate advice - not just vacation bookings. He showed up at foreclosure court to pitch property management to auction winners. And he discovered luxury guests are actually easier to serve than budget travelers because they own high-end homes themselves and understand that expensive systems sometimes break.
This episode is sponsored by Streamline.
Creating memorable vacation rental experiences goes far beyond clean properties and smooth check-ins. The small branded details you leave in guests' hands become lasting impressions that keep your name top-of-mind long after checkout, and drive rebookings year after year.
Steve Zimmerman, CEO and owner of Beach House Logos, has spent 25 years helping vacation rental managers create these strategic brand touchpoints. From custom spices that travel home to guests' kitchens to hand-drawn destination map tote bags that spark conversations, Steve reveals how functional, beautiful branded items build emotional connections that generic marketing can't replicate.
He shares strategies for homeowner acquisition gifts that actually get attention in crowded markets, the "oops gift" approach that turns service failures into loyalty wins, and why a property manager in Oregon built a 200-home portfolio focusing exclusively on pet-friendly branding. Steve also discusses working with marketing teams, choosing products with lasting impact, and why consistency matters more than flash when building vacation rental brand recognition.
This episode is sponsored by Bluetent.
Scaling a vacation rental business beyond your first market requires more than ambition—it demands strategy, systems, and the right partnerships. In this episode recorded at Streamline Summit, Lynell sits down with three industry leaders who reveal what it really takes to grow successfully.
Koen Roelens scaled from a hotel industry side hustle to 600 properties across Florida by admitting he's terrible at operations and hiring accordingly. Larry Hoffer from Z-Point helps property managers use data to target the right properties before competitors do, with access to all 125 million residential properties in the United States. And Mishan Andre runs luxury properties in Cabo using Streamline's automation to free up time for actual growth.
Together, they share hard-won insights on when to invest in operational infrastructure, how to enter new markets strategically, why communication is the foundation of everything, and how to choose technology partners who actually show up when you need them.
This episode is sponsored by Streamline.
Jason Gann, Account Executive at RevMax, shares his surprising discovery after transitioning from competing revenue management platforms to Inhabit's comprehensive solution. With a decade of industry experience, Jason reveals why RevMax goes far beyond basic dynamic pricing—offering length-of-stay pricing automation, comp set analysis, maximum yield optimization, and professional revenue manager support. The conversation explores how property managers can capture hidden revenue through premium lift strategies, maintain compliance while maximizing bookings, and access fractional CRO expertise for a fraction of traditional hiring costs.
This episode is sponsored by RevMax.
Jay Sudowski brought an unconventional background to vacation rental management: running critical IT infrastructure for Denver's transportation system and school districts. In 2022, he bought Beachside HHI in Hilton Head, South Carolina with just thirteen properties while simultaneously selling his tech company and training for a half Ironman. Three years later, he's nearly doubled the portfolio to thirty properties while maintaining an ultra-lean team of three full-time staff.
In this episode of The Vacation Rental Show hosted by Lynell Gordon, Jay shares why managing vacation rentals feels easier than keeping payment processing systems running for hundreds of thousands of transit users, how his three-bedroom property 0.6 miles from the beach grosses one hundred ninety thousand dollars annually, and the hard lesson he learned about firing homeowners who don't align with brand standards regardless of their revenue potential.
Jay discusses achieving forty-five percent direct bookings in Hilton Head's traditionally Saturday-to-Saturday market, why inland properties dramatically outperform oceanfront homes on ROI, and his systematic approach to growing slowly enough to maintain quality with current tools and team.
This episode is sponsored by Streamline.
Taylor Moore and Danielle Giancola built Nomadic Vacays from zero to 57 properties in Naples, Florida in just over four years, starting during the COVID-19 pandemic after relocating their entire family from New Jersey. Their unconventional approach prioritized infrastructure over gradual scaling, building systems designed for 100 properties from day one.
In this episode of The Vacation Rental Show, Taylor and Danielle share why they insisted on implementing Streamline, how their 22-step onboarding process with video tutorials makes operations plug-and-play for any team member, and the immersive 18-month strategy where they worked 16-hour days learning every aspect of the business from the ground up.
They discuss the brother-sister partnership dynamics that make their collaboration work, how they help family members create service businesses within their business ecosystem, and the hard lesson they learned about partnership alignment when their initial third partner's vision didn't match theirs.
This episode is sponsored by Rental Guardian.
Amanda Look built Salt Air Properties from one house in 2009 to 100 properties with a fully employed staff of 30 people in Bar Harbor, Maine. Her journey started while working full-time at a bank, and when her first vacation rental booked solid within three days of going online, she knew she was onto something special.
In this episode of The Vacation Rental Show hosted by Lynell Gordon, Amanda shares why she chose to hire all cleaners as employees rather than subcontractors, how she maintains team culture through daily appreciation programs, and the creative ways she keeps seasonal workers engaged and supported. She discusses her rule about never onboarding properties after June 1st, why she broke that rule this year, and the consequences that validated her original instinct.
Amanda also reveals how she's transitioning from operator to owner through leadership training programs, why she still picks up trash occasionally to stay grounded, and how she built proprietary service programs when national vendors wouldn't service her rural market.
This episode is sponsored by Streamline.
Jennifer Mucha built Arrived from one home in Sunriver, Oregon to 350 units across multiple states over 21 years. Her growth strategy combined organic expansion with strategic acquisitions, teaching her invaluable lessons about what works and what creates unexpected challenges when scaling a vacation rental business.
In this episode of The Vacation Rental Show hosted by Lynell Gordon, Jennifer shares why geography is the hardest factor to control when growing, how remote employee culture differs dramatically from local teams, and why she transitioned from in-house to fractional marketing teams. She discusses the complexities of acquiring existing businesses, the importance of employee alignment with company culture, and her philosophy of building a business around activities that bring you joy.
Jennifer also explains how she outperformed every competitor in her first market through pricing optimization and search visibility, why she's used Streamline for over a decade, and what advice she'd give property managers just starting their growth journey.
This episode is sponsored by Lynnbrook Group.
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.
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