Entrepreneur: Mike Overton and the winds of fortune

How Outside Hilton Head rose from humble beginnings to a five-part success — with its own island.

Mike OvertonEven with all his creative might, Mike Overton could have never imagined that the little part-time windsurfinginstruction business he started on the south end of Hilton Head Island would one day become the sprawling, multifaceted company known as Outside Hilton Head.

The 52-year-old Washington, D.C., native was a long-haired college student at the University of Vermont in 1979 when a dinner conversation with a Hilton Head resident planted the idea for a company that taught tourists how to windsurf. That conversation turned into a partnership, and Overton and his then-partner named their fledgling business Sailin’ Shoes, after a song by Little Feat. The partner soon changed course and moved to Vermont, but not before convincing Overton to give the beach idea a shot.

“He said, ‘The economy’s booming on Hilton Head.’ I thought, ‘I know how to windsurf,’ so I packed up, stopped for breakfast at Mom’s, and drove to Hilton Head,” Overton said at his notably unpretentious headquarters at the Plaza at Shelter Cove. And just like that, the forestry student who had never been south of the Mason-Dixon line (he eventually earned his degree in resource economics) found himself using a small bit of inheritance money to buy six windsurf boards.

At the time, he says, the appeal of an island adventure trumped most of his trepidation. But even a powerful drive and ambition can’t change nature, and Overton quickly learned that teaching windsurfing in the ocean was almost impossible — the job required calm, safe waters and consistent winds. So he began poring over aerial photos, and eventually discovered that South Beach at low tide was a suitable replacement. By the end of his first summer, he had schooled about 500 people in the fine art of windsurfing. “I managed to sell a few T-shirts too,” he says.

The following summer Overton returned to Hilton Head and doubled his number of students. He merged his company with another and became Island Watersports. He branched out into powerboat rentals and opened a store selling windsurfers, accessories and T-shirts. Things were booming, but he tired of getting his hands greasy on outboard motors and sold his interest in the company in 1984 to return to his roots.

“When I went back to just windsurfing and retail, I was the largest windsurfing instruction business in the country,” he said.


Still, the seeds for what has become a dramatic reshaping of the company were beginning to fall into place.

First, Overton joined forces with Patagonia, an eco-conscious company specializing in outdoor wear, and was introduced to the concept of kayaking and ecotours. Before long, Outside Hilton Head began specializing in both. “Kayaking is easier to pick up (for beginners) and better suited for tours and sightseeing,” Overton said.

Then, in 1999, a friend introduced him Page Island, a chain of islands tucked behind Daufuskie Island, which has become a base camp for the company’s burgeoning teambuilding arm. “We got back into powerboats, too, so we could take people over to Page Island for corporate team-building programs,” he said. Aside from a few kayak shelters and bathrooms, the island has barely been touched. “It’s the perfect place to eliminate all distractions,” he says. “You can get a real appreciation of just being there.”

He also began what he calls “full-destination management” for corporate clients, groups and family gatherings. “We take care of the A-to-Z of activities, events, meetings and tours.” Outside Hilton Head has also expanded into recreation management for several local residential communities, including Palmetto Bluff, Berkeley Hall, Hampton Hall and Hampton Lake.

With five distinct enterprises under the Outside Hilton Head umbrella, Overton — still the sole proprietor, president and CEO — employs 40 people full-time and about 70 at the height of the tourist season.

“I’ve never worked for anyone after high school, but I think I’m a good boss,” he said. “I read a lot about what it takes to own a company, and I learn something new all the time from our corporate clients. For example, when we have a corporate client — a lot of them are Fortune 500 and Fortune 100 companies — come in for a team-building retreat, I research what they want to emphasize, and I get a lot out of that.”

And when he needs to get away from his 60-hour-a-week schedule, he returns to activities himself, such as snow-skiing, often with his 18- and 21-year-old daughters.

“When I started this business, I thought it would be cool to teach windsurfing for a summer,” he says. “And then it was another summer, and another summer. I never dreamed it would turn into a career. It’s always changing, and that keeps it fun.”

The company has five distinct branches: recreation management for private communities, leisure and recreational tours, corporate teambuilding, destination management, and retail.
Details: 843-686-6996, outsidehiltonhead.com