Testing Everything and Scaling Smart with Derek DeCesere of Sand Stays

What does it actually take to grow a vacation rental business without losing your sanity or your profit margin? In this episode, Lynell Gordon sits down with Derek DeCesere, CEO of Sand Stays, a Maine-based property management company that has managed more than 200 properties, hosted over 25,000 reservations, and earned more than 10,000 five-star reviews. Derek shares the unfiltered truth about scaling, from the shiny object trap that cost him thousands per month, to why more units do not automatically mean more profit. He talks through the operational systems he built to protect guest experience, why speed is the single biggest driver of five-star reviews, and how he uses AI without losing the human touch that guests expect. He also pulls back the curtain on what is next for Sand Stays, including a flexible, a la carte service model built around technology support. This episode is sponsored by RentalGuardian.

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.

In this episode, Derek gets refreshingly honest about the mistakes he made growing Sand Stays, including overspending on services he never used, hiring too fast, and learning the hard way that more doors does not mean more profit. He walks through how he built out guest messaging as his first operational priority, why response speed is his number one five-star driver, and how he now balances AI-powered efficiency with genuine human hospitality.

Derek also shares his vision for the next chapter at Sand Stays, a flexible, a la carte model that positions the company as a technology support partner for small hotels, boutique motels, and individual property owners who need expert help without full-service management.

This episode is sponsored by Rental Guardian.

🎧 Listen on Apple Podcasts | Listen on Spotify 📺 Watch on YouTube | Follow The Vacation Rental Show for weekly insights

If you enjoyed this episode, make sure to:

Subscribe, rate, and review
Share this episode

👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show

The Vacation Rental Show is handcrafted by our friends over at: fame.so

Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.

Check out the three most downloaded episodes:

Got a question for The Vacation Rental Show?

Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.

Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.

Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.

👉 Submit your question here: https://lnkd.in/eFy_6ssW

Tune in to hear your answer featured on The Vacation Rental Show.

Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.

The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:

Scaling your vacation rental portfolio
Optimizing guest experiences
Revenue management strategies
Industry trends and market insights

Express your interest in being a guest →