The Vacation Rental Show, Hosted by Lynell Gordon · 2026-03-17 · 26 min
What you'll learn: Why scaling your portfolio does not automatically increase your profit and how to structure deals that actually work The costly shiny object mistake Derek made and the simple rule that helps you avoid it Which operational area to systematize first to protect your guest experience as you grow Why speed is the single most consistent driver of five-star reviews at Sand Stays How to use AI strategically without replacing the human connection guests expect What an a la carte, technology support model for property management looks like in practice Derek DeCesere is the CEO of Sand Stays, a Maine-based vacation rental management company with more than 200 properties, 25,000 reservations, and over 10,000 five-star reviews. With more than a decade in short-term rentals, Derek has built a scalable operation grounded in strong systems, smart delegation, and a practical approach to technology that keeps guest experience at the center of everything.
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