Mekki Jaidi, Charlotte Yordon and Annie Jackson of Outpost, a company that manages vacation rentals, cleans commercial and residential spaces, and offers real estate photography services.

Five years ago Mekki Jaidi was yearning to make Jackson Hole his full-time home but was hung up on how he could make a living in an isolated corner of the northern Rockies.

The New Yorker, who’d abandoned a career trading derivatives, had owned a short-term vacation rental near the base of Snow King as an investment property for about a year when he made the call to pack it up and wing it, basically hoping for the best.

“I was obsessed with this place,” Jaidi said. “Obsessed with every single little facet.”

An aha moment about how to carve out a life in Teton County came while reviewing the invoices from his short-term rental’s property manager (Jaidi declined to name the business). There would be 15 or 20 percent upcharges, with other unwelcome fees thrown in.

“I’d get statements and felt that I could do better,” he said, “performance-wise.”

So Jaidi created a competitor.

That business, Outpost, started out pocket-size its first winter, 2014-15, with just seven rentals in its fledgling basket of properties. It was a one-man show essentially, with only Jaidi’s girlfriend and now-wife, Jane, helping out.

Jaidi derived some income from those seven clients, took some real estate photos on the side to make ends meet and ran an Outpost blog focused on the outdoorsy mountain town lifestyle to set his new business apart.

The formula worked. By 2016 there were more than 20 properties and a few added employees to help manage them. Word kept spreading, and as of mid-December there were 118 rentals listed with Outpost and a 15-person workforce managing them. That real estate is spread all around the valley, with the majority falling along the Snake River’s west bank and about a third of the units located in the town of Jackson.

The selling point has been simple: It pays to go with Outpost.

“We’ve been able to double homeowners’ nets who have switched over to us,” Jaidi said, “while also keeping their costs down.”

An Outpost client will see proceeds from a place that’s typically booked some 250 days a year, he said, an occupancy rate that easily beats out those achieved by competitors in the valley.

Outpost’s “all-encompassing” way of billing has won over clients, said Annie Jackson, the company’s director and one of the first employees.

“It’s transparent,” Jackson said, “and that really gone a long way, because they don’t feel like they’re being nickeled and dimed.”

For the first few years, Jaidi, Jackson and the rest of the staff got the impression that Jackson Hole residents didn’t know what to make of Outpost. It seemed amorphous, perhaps because of its media arm and outdoor lifestyle-centric branding.

An expansion to include an in-house housekeeping business, O2 Cleaning, helped clear up the confusion. A fleet of seven charcoal vans and a truck seen rolling around town to service Outpost’s properties — and other residential and commercial buildings — have helped hammer home what exactly Outpost is: a property manager.

While that’s the first and foremost venture, side businesses do continue springing up. The latest, going by “Outfitted,” is a gear delivery service for clients that brings goods from bear spray to baby diapers to their doorstep with a few clicks of a mouse.

Outpost’s home base is also moving, and will soon be relocating from digs on East Pearl to 160 E. Broadway, next door to Kismet Fine Rugs.

There’s no end in sight, Jaidi said, to Outpost’s expansion.

“We want to continue to grow this thing,” he said. “The first few years, they weren’t easy.”

There were late-night runs of fans and noise machines during those upstart years, and also some true memory-makers: like the time Jaidi and his wife bought and delivered a new twin mattress on Christmas Eve to appease an uncomfortable guest.

“It was definitely paycheck to paycheck,” Jaidi said, “but we’re really starting to come into our own and put resources into it that are making this thing even better.”

Contact Mike Koshmrl at environmental@jhnewsandguide.com or 732-7067.

Jennifer Dorsey is chief copy editor and Business section coordinator. She worked in Washington, D.C., and Chicago before moving to the Tetons.

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