For nearly five decades, Outside Brands has been helping residents and visitors experience the Lowcountry from a different perspective – one paddle stroke, boat ride, team-building exercise, and outdoor adventure at a time.
What began in 1979 as a fledgling windsurfing school has grown into one of the Southeast’s largest outdoor recreation and destination management companies. Today, the organization encompasses five distinct divisions; serves clients throughout Hilton Head Island, Bluffton, Savannah, and Palmetto Bluff; and employs a team of approximately 140 people.
Many current leaders began as interns or seasonal employees before advancing into management and executive positions.
Yet despite its remarkable growth, the company’s mission remains rooted in the same principle that inspired its founder nearly half a century ago: connecting people to extraordinary places, products, and experiences.
As Outside Brands celebrates its 48th year in business, founder and CEO Mike Overton reflected on a journey that began with a chance conversation on a frigid winter night hundreds of miles away from the South Carolina coast, in Burlington, Vermont.
A team shot of the Outside Hilton Head crew in the earlier days of the brand’s time in the Lowcountry.
Overton was attending the University of Vermont when an unexpected dinner conversation changed the course of his life. One of his roommates had visitors in town, and among them was a young man who talked enthusiastically about Hilton Head Island and his plans to launch a windsurfing school.
“He said he was going to start a windsurfing school, and I said, ‘Well, I know how to windsurf,’” Overton said. “He goes, ‘Really? I really need somebody who knows how to windsurf.’ About midnight that night, we decided to go into business together.”
Mike Overton began his career on Hilton Head Island with a windsurfing school in Sea Pines at South Beach Marina.
Fate soon provided the means to make the dream possible. After his grandfather passed away, Overton inherited enough money to purchase six windsurfers. When school ended that spring, he loaded them into a small Toyota pickup truck and headed south. At the time, he had never traveled farther south than Washington, D.C.
By the time he crossed the drawbridge onto Hilton Head Island, it was dark. The island was vastly different from the bustling destination it is today. There were few roads, little development, and only a fraction of the commercial activity residents and visitors now take for granted.
Outside Brands Destination Management has become the area’s go-to source for high-end corporate events, weddings, and special occasions .
His new business partner greeted him with an unexpected surprise. “He handed me a beer and said, ‘I’ve got to tell you something. I’ve decided to move to Vermont with my girlfriend.’”
Suddenly, Overton found himself alone in a place he barely knew, trying to launch a business with six windsurfers and a dream.
Learning the Hard Way
Like many entrepreneurs, Overton’s first lessons came through trial and error. His first customer had an experience that could generously be described as less than ideal.
“I took him to the Shipyard Beach Club to teach him how to windsurf,” Overton said. “He had a miserable time. I don’t think he ever stood up for more than five seconds. He cut his knee, got stung by a jellyfish, and wanted his money back.”
Recognizing that enthusiasm alone would not guarantee success, Overton enrolled in a professional windsurfing instructor certification program in Florida. There, he learned what would become a guiding principle throughout his career.
“They taught you the three most important things in business – at least pre-internet – which were location, location, location,” Overton said.
Armed with new knowledge, he began searching for the ideal place to build his business. That search eventually led him to one of Hilton Head Island’s most influential visionaries.
Visitors to Hilton Head Island take in the sights on the way to Daufuskie Island.
A Meeting with Charles Fraser
When Overton asked around for advice, several people pointed him toward Charles Fraser, the legendary developer whose vision helped shape modern Hilton Head Island. Overton managed to secure a brief appointment. What happened next exceeded all expectations.
Instead of a quick meeting, Fraser spent hours with the young entrepreneur, showing him around Sea Pines, introducing him to the island’s unique assets, and listening to his ideas.
“He said, ‘I think you have a really good idea,’” Overton said.
Fraser encouraged him to establish his operation at South Beach Marina and offered him a simple but invaluable opportunity: a card table inside the South Beach General Store. It was enough.
By the Fourth of July in 1979, Overton was teaching windsurfing lessons in Sea Pines. He taught a few hundred students that first summer. The following year, business expanded so quickly that he hired his first instructor.
The foundation had been laid.
A happy dolphin poses for the camera on an Outside Brands adventure.
That first summer also taught Overton something about Hilton Head itself. The island was still young as a destination, still shaping its identity, and still small enough that a good idea could find room to grow. The Lowcountry’s natural setting was not simply a backdrop for business. It was the business.
The marshes, creeks, beaches, tides, and wildlife offered something no manufactured attraction could replicate. Overton recognized early that people did not come to Hilton Head only to be entertained. They came to feel connected to a place.
That understanding would become one of the company’s most important advantages. Rather than building experiences that competed with the environment, Outside Brands built experiences that helped people enter it, understand it, and appreciate it.
As Hilton Head Island grew, so did Overton’s business. When ownership changes at South Beach created new opportunities, he expanded beyond windsurfing. A sailing school, boat rentals, and retail operations soon followed. The company eventually became known as Island Water Sports, reflecting its growing range of services.
“We had a sailing school and a windsurfing school,” Overton said. “Upstairs, I put some T-shirts and windsurfers, and we changed the name of the company.”
By the mid-1980s, Windsurfing Hilton Head had become the largest windsurfing school in the United States. At the same time, the island itself was evolving. Commercial development expanded northward. Shelter Cove emerged as a major destination, and Overton recognized another opportunity. When the Shelter Cove Plaza was developed, the company opened a retail location there, establishing a presence that continues today.
Fishing expeditions are just one of the many offerings available with Outside Brands.
Seeing Opportunity Before Everyone Else
One theme runs consistently throughout Outside Brands’ history: identifying emerging trends before they become mainstream. In the early 1990s, the company became the first Rollerblade dealer east of the Mississippi River. Later in the decade, Overton turned his attention to another growing outdoor activity: kayaking.
Today, guided kayak tours are common throughout coastal communities. At the time, however, the concept was virtually unheard of. “I think we became the first company in the country to offer guided nature kayak tours,” Overton said.
Recognizing that success would require knowledgeable guides, the company developed a comprehensive naturalist training program. That commitment to education helped establish a reputation for excellence that extended well beyond Hilton Head Island. “It’s been internationally recognized on how we train our guides and naturalists,” Overton said.
The program transformed kayaking from a recreational activity into an educational experience, helping guests better understand the Lowcountry’s ecology, wildlife, and history.
That ability to evolve has helped Outside Brands stay relevant through changing travel trends, shifting economies, and the many reinventions of Hilton Head Island itself. Windsurfing gave way to kayaking. Kayaking expanded into naturalist-led tours. Outdoor adventures opened the door to corporate team building. Corporate relationships eventually supported destination management.
Kayakers get up close and personal with nature.
Each new step made sense because it grew from what the company already knew how to do well: manage logistics, build relationships, train people carefully, and deliver memorable experiences in exceptional settings.
Overton has never seen the company as being locked into one product or one era. Instead, Outside Brands has continued to follow the needs of its clients while staying rooted in its original love of the outdoors.
Perhaps no expansion illustrates Overton’s vision more clearly than Page Island.
In the late 1990s, the company acquired a chain of islands behind Daufuskie Island and began bringing visitors there for outdoor experiences.
Over time, Overton noticed something interesting. The remote environment naturally encouraged communication, trust, and collaboration. Those observations eventually led to the creation of the Page Island Growth Center, which focused on team development and leadership training. “We found it was a great place to grow teams and grow relationships,” Overton said.
The concept resonated with corporate clients. Within a decade, Outside Brands was conducting team-building and leadership programs for divisions of virtually every Fortune 100 company. What started as outdoor recreation had evolved into organizational development.
Adapting During Challenging Times
Long-term success rarely comes from standing still. When the economic downturn of 2008 disrupted the hospitality industry, two destination management companies (DMCs) serving Hilton Head Island ceased operations.
Rather than viewing the situation as a threat, Overton saw an opportunity. The company already had extensive relationships with corporate clients and sophisticated logistical systems. Expanding into destination management felt like a natural progression. Today, the destination management division is the largest part of Outside Brands’ business.
For many visitors, destination management is an unfamiliar term, but the role is essential to the success of corporate meetings, incentive trips, and conferences. “A DMC is really the best ambassador for a destination,” Overton said.
The division coordinates transportation, entertainment, décor, event production, activities, excursions, and countless behind-the-scenes details that create memorable experiences for visiting groups. Last year alone, the company hired more than 400 bands and entertainers for client events.
That expertise has helped establish Outside Brands as a trusted partner for organizations visiting Hilton Head Island, Bluffton, and Savannah.
Five Divisions, One Mission
Today, Outside Brands operates through five interconnected divisions. Its retail division includes stores in Shelter Cove and Palmetto Bluff. Its outdoor recreation division manages guided tours, kayak excursions, paddleboarding experiences, boating programs, and outdoor adventures across multiple markets. Its leadership and team-development division serves organizations throughout the country, helping teams strengthen relationships and improve performance. Its destination management division coordinates corporate experiences and events throughout the region. Finally, the Outside Foundation serves as the organization’s nonprofit arm, dedicated to getting children outdoors and promoting environmental stewardship.
Though each division serves a unique purpose, all support a common mission. “We’re really connecting people to how special it is here,” Overton said. “The nature, the history, and the culture.”
That breadth gives Outside Brands a rare position in the local hospitality landscape. A guest might first encounter the brand through a kayak tour at Shelter Cove, a dolphin cruise, a paddleboard outing, or a retail purchase. A corporate planner might know the company for transportation, entertainment, themed events, or group excursions. A local family might connect through the Outside Foundation.
To Overton, those touchpoints are all connected. Whether the company is outfitting a visitor for a day on the water, coordinating a corporate event, or helping a child experience the salt marsh for the first time, the purpose is the same.
The company is not simply selling activities. It is interpreting the Lowcountry.
A Culture Built to Last
Businesses do not remain successful for nearly five decades without strong leadership and a dedicated team. For Overton, the company’s longevity comes down to people.
“I think any business at the end of the day grows based on two things: repeat business and referral business,” he said. “Both of those things are typically a result of relationships.”
Those relationships extend well beyond customers. The company boasts remarkable employee retention, with numerous team members spending decades with the organization.
“We have one employee aside from me who has been with us over 40 years,” Overton said. “We have quite a few that have been with us over 30 years and a lot that have been with us over 20 years.”
Many current leaders began as interns or seasonal employees before advancing into management and executive positions.
Overton attributes much of that success to the company’s culture and hiring philosophy. Several years ago, leadership worked to define the qualities that make an ideal team player. They ultimately identified three characteristics: “Humble, hungry, and smart,” Overton said.
While “humble” and “hungry” follow traditional definitions, the company’s interpretation of “smart” focuses less on intelligence and more on emotional awareness and interpersonal skills. “It’s more how they relate to other people,” he said.
Those qualities have helped create a workplace culture centered on collaboration, growth, and leadership development. That culture also gives employees room to grow. In a seasonal destination, where many hospitality businesses rely on short-term labor, Outside Brands has worked to create long-term career paths.
Team members are encouraged to take on responsibility, develop leadership skills, and understand the “why” behind the work. Overton believes that when employees are trusted to make good decisions, they are more invested in the outcome.
The result is a team that can handle complexity without losing the personal touch. Whether planning transportation for a large corporate group, leading a nature tour, or helping a family choose the right outdoor gear, the same expectation applies: Build the relationship first.
Creating a Legacy Through Conservation
One of the company’s most meaningful chapters began with a conversation about children and the outdoors. In the early 2010s, Overton attended a national outdoor industry conference where former REI CEO and future U.S. Secretary of the Interior Sally Jewell discussed a growing concern. The average child, she noted, was spending nearly all their free time in front of a screen.
The message resonated.
Back home, Overton and his team began discussing ways to make a greater impact. Those conversations led to the creation of the Outside Foundation. The nonprofit focuses on connecting children with nature while promoting environmental preservation throughout the Lowcountry.
The foundation’s roots can be traced to the company’s internal sustainability efforts, led by longtime team member and educator Genevieve “Gene” Gilmore, who helped develop the organization’s environmental initiatives before transitioning into nonprofit leadership.
Today, the foundation introduces thousands of children to outdoor experiences they might not otherwise have access to, helping inspire the next generation of environmental stewards.
Looking Ahead
As Outside Brands approaches its fifth decade, growth remains a priority. The company continues expanding in Savannah and Palmetto Bluff while exploring new opportunities throughout the region. Overton is particularly optimistic about Hilton Head Island’s future as a destination for high-end corporate groups and meetings. He also sees significant potential for continued growth in the company’s leadership and team-development programs.
Despite the scale of the company today, the company remains grounded in the same principles that launched it nearly 50 years ago: Relationships. Adventure. Education. Stewardship.
What started with six windsurfers and a card table has become one of the Lowcountry’s most enduring success stories. Along the way, Outside Brands has done far more than build a business. It has helped generations of visitors and residents discover the waterways, wildlife, history, and culture that make the Lowcountry unlike anywhere else.
For Overton, that connection remains the heart of everything the company does. “At the end of the day, our product is what’s indigenous to the Lowcountry – the nature, the history, and the culture,” he said.
In many ways, the Outside Brands story mirrors the story of Hilton Head Island itself. Both began with a bold belief in the power of place. Both grew through vision, adaptability, and careful stewardship. And both continue to thrive because people are drawn to something authentic here.
For Overton, the company’s success is not measured only in tours booked, events managed, or retail sales made. It is measured in moments: a child seeing a dolphin from a boat for the first time, a corporate team discovering new trust on Page Island, a visitor understanding the salt marsh in a deeper way, or an employee building a career around the outdoors.
That is the kind of staying power that cannot be manufactured. It has to be lived, season after season, tide after tide, relationship after relationship.
Nearly five decades later, that simple idea continues to carry Outside Brands forward.