iBooked Online

When you decide to grow a business, there are only really a handful of ways to do it. Go deeper where you are. Add services to the clients you’ve got. Buy someone. Franchise it. Or expand geographically.

Most of those are deliberate decisions. Geographic expansion in this industry almost never is. It happens because someone asks.

You know the version. A friend, a cousin, someone who’s heard you’re good at this. They’ve got a place three hours up the coast and they’d rather it was you managing it.

The question underneath that is whether you can actually do it from where you are.

This week I sat down with Fred Cercena from Getaway VR, who has been answering that for over a decade. From his base in New York, he runs roughly 70 properties across Vermont and Maine.

The fantasy is laptop freedom. No office, no footprint, a property three hours away quietly paying for itself. The reality is tighter. Managing from a distance works fine. Operating from a distance fails the second something breaks at 9pm and your part-time cleaner doesn’t answer the phone.

Fred’s point is that distance costs you more infrastructure, not less. He has offices in both markets and almost nobody visits them. They exist so there’s somewhere to hold supplies and keys, and somewhere a maintenance guy can grab what he needs at short notice. Skippable overhead, until you picture a guest in the house with a problem and a cleaner who was never going to be a maintenance team.

The people side is what makes it work. He’s out of daily operations entirely now, with an area manager in each market and a GM overseeing both. And the ladder is internal. In Maine they promoted a housekeeper to area manager, and an area manager to GM, which means the person running both markets has actually cleaned the houses.

He earned his own way out the same way. Ten or twelve properties in, he was driving up every Monday, meeting cleaners, doing hot tub drain-and-fills, installing locks himself. He calls it the learning process, and it’s the part people try to skip.

Two other things stuck. Getaway VR joins the Chamber of Commerce in every town they operate in, because when you’re never on the main street, being known is the substitute for being seen. And he’s blunt that staffing is the thing to research before you commit, not after. Resort towns are expensive to live in and sometimes you need a metro area close enough to bring labour in from.

On tools he’s more disciplined than most of us. Streamline, SendSquared pulling calls and messages into one inbox, PriceLabs with a full-time revenue manager running it. His line on that last one: PriceLabs is like driving a Ferrari, and there’s a difference between owning one and knowing how to drive it. I admitted we run about ninety tools across our businesses. He does not.

What you’ll learn in this episode:

🗺️ Why remote management needs more local infrastructure, not less

🧰 The lean tech stack running two markets across 70+ unit

👥 How to build an internal career path from housekeeper to GM

🏘️ Why joining the local Chamber of Commerce matters when you live in another state

📋 The three things to research before committing to a remote market

Fred owns Getaway VR, managing short-term rentals across Vermont and Maine from New York. Bought his first property in 2008, started managing for others in 2011, went full-time in 2012. getawayvr.com.

So if that friend with the place three hours away calls this week, the answer isn’t no. It’s just that the yes costs more than you think, and most of that cost sits on the ground rather than on your laptop.

📺Watch the episode here