The Vacation Rental Show

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.