Bill Morrissey’s commute comes with a view from several thousand feet up. Each week for the past 35 years (weather permitting) he has boarded the cockpit of his plane and taken off on a short flight from San Juan Island to Mount Vernon, Washington.

The trip between his two offices would take around two-and-a-half hours by car and ferry, but where’s the fun in that? Morrissey, who runs Sound Financial Planning with his partner Tammy Prouty, counts whales among his neighbors and enjoys views of the Olympic Mountains.

Ask him if he has any plans to leave the region behind and he’ll tell you: “I’m going to die here with my boots on.”

Scattered among America’s resort towns are financial advisory firms, mostly small shops, that have found a way to thrive in areas with small populations and a seasonal economy. Building a practice in these conditions isn’t easy, but those who have put in the extra effort say it’s well worth the sacrifice.

The view for advisors who decide to open a practice in Vail Valley
The view for advisors who decide to open a practice in Vail Valley James Thorne

So where would you work, if you could work anywhere? And what would you be willing to give up to get there? If you’re considering a move to the town of your dreams, here are some things you should know from advisors who have made it work.

Digital tools are opening doors: The first lesson for advisors who want to start a practice in a resort town: either bring a book of business with you or practice patience. The good news is, technology has made managing clients from afar an easier task.

While it’s sometimes compared to Martha’s Vineyard, San Juan Island lacks the population of an East Coast resort. Only around 7,000 people live on the island year-round. And while those residents tend to be wealthy, most of Morrissey’s business still comes from his office in Mount Vernon, on the mainland.

Luckily, Morrissey is finding that being physically isolated no longer has much effect on his ability to run a business. “What we’re finding is it doesn’t really matter where you’re located anymore,” he says.

An advisor who opens a practice in Friday Harbor, Washington, counts whales among their neighbors and enjoy views of the Olympic Mountains.
An advisor who opens a practice in Friday Harbor, Washington, counts whales among their neighbors and enjoy views of the Olympic Mountains.
James Thorne

Operating as a one-man band from his office in the town of Friday Harbor, Morrissey depends on cloud-based account management systems as well as physical support from his team in Mount Vernon.

If you’re considering a move, take a realistic account of the kinds of resources you’ll have available in the new locale. Look into opportunities to contract out or automate roles where possible.

You can’t rush trust. Stuart Green can trace his family’s financial roots back to his great grandfather, who started a stock brokerage in Kansas City. But when Green first came to Colorado’s Vail Valley, he knew the young community wasn’t ready for a financial advisory practice.

Instead, he started a commercial laundry business to support the hotel industry. Over the years, the ski town’s population exploded, and Green decided to get his CFP. More than a decade later, he and his partner Tracy Tutag have built Aprisent Financial Group into a local institution based in Edwards, Colorado.

Being a long-term local made things easier, since residents often don’t trust outsiders who come into town to start a business. “When people come up here, they can come across as a carpetbagger,” Green says. "I’ve seen people come into the area thinking that this would be a relatively easy place to establish a business, and they had trouble.”

Green’s reputation as a family man and his philanthropic efforts with Habitat for Humanity also helped to cement his reputation. “This is a business very much based on trust, and people want to believe that you are trustworthy,” he says.

The smaller community also meant that Green didn’t have the luxury of catering to specific segments. He has clients outside the valley, who tend to have more assets than locals. But the area also attracts a number of successful professionals. “A lot of these people ran significant companies or were high level execs with big companies,” he says. “It’s a very sophisticated community for a small town.”

Green cautions that advisors should make sure they’re interested in sticking around for the long haul. In small towns, the key to success is often more about perseverance than rapid growth.

Know your market: Marlo DeMoss’ circuitous path to financial advisor began under the sea. Her passion for diving in the Bahamas led her into insurance, which later morphed into financial advice. The ocean is still her passion, but now she runs DeMoss Financial out of Tavernier, Florida, and services clients from Key Largo to Key West.

DeMoss is still a diver and an avid fisherwoman. When she wants a vacation from the seaside life, she goes skiing in Idaho.

Advisor Marlo DeMoss is also a diver and fisherwoman.
Advisor Marlo DeMoss is also a diver and fisherwoman.

DeMoss has never done traditional advertising, and grew her business slowly through word of mouth. Also, she rarely turns down a client. “If you say no to one person in a small town, it may hurt your business,” she says. Instead, she does a lot of work that isn’t profitable, knowing that it will help her reputation. Her clientele range from people just starting out to those will multimillion-dollar stock portfolios.

“People say specialize, set account minimums. Neither of those would work in this kind of environment,” DeMoss says.

Her region is driven by tourism, but it’s still a small town. And success in a small town often means being a jack of all trades. “You want to be the financial quarterback for your client,” DeMoss says.

Every town is different, so do your homework. The Census Business Builder, an online tool from the U.S. Census Bureau, is a helpful starting point for assessing the local market in towns throughout the country.

Bill Morrissey of Sound Financial Planning says he never plans to leave the Olympic Mountain region.
Bill Morrissey of Sound Financial Planning says he never plans to leave the Olympic Mountain region.

Different regions bring different risks. DeMoss knows that each year will bring, like clockwork, the threat of destructive hurricanes. And while nobody can predict the scale or timing of such events, DeMoss does what she can to prepare her clients financially. That means having standing ACH instructions on all non-qualified accounts. In the event of an emergency, clients can get money when they need it.

For Bill Morrissey, the advisor in the San Juan Islands, even remote threats deserve an appropriate plan. Wildfires from the mainland seem to be getting closer every year, bringing smoke and haze to the otherwise crystal-clear islands.

Less immediate, but much more concerning, is the looming danger of earthquakes from the Cascadia subduction zone. “We’re long overdue for quake,” Morrissey says. “We emphasise to our clients the importance to prepare for it.”

Despite the many quirks and obstacles to operating in a resort town, DeMoss and others claim they wouldn’t live anywhere else. “I think the positives of where I live and the business far outweigh any negatives,” says DeMoss, adding that a tightknit community is more important than one that’s ideal for business. “All of my clients are friends.”

James Thorne

James Thorne

James Thorne is a contributing writer for Financial Planning. Follow him on Twitter @jamescthorne.