Faces of the Lowcountry – Mike Overton

How a summer job turned into a lifelong passion.

In 1979, Mike Overton, now founder and president of Outside Brands, crossed the drawbridge to Hilton Head, then passed through the only traffic light on the Island to teach windsurfing for the summer. 

Mike’s first windsurfing customer had a terrible day and wanted his money back and while Mike complied, he was not deterred. In fact, he was able to eke out a living for his first five years and decided to stay for a while longer. Forty years later, he still owns and operates Outside Hilton Head, the little company he founded that grew to one of the largest outdoor, leisure and recreation companies in the South. 

“I didn’t start out with an end-state in mind for my company,” Overton said. “I have always been driven by my passion for the outdoors, for sports and for people and it has been that passion that fuels me. Throughout our company’s journey, it has been certain milestones that lead to our next phase of growth, milestones that could not have been predicted.” 

While Hilton Head must have been a perfect location for an outdoor enthusiast, Mike’s first business lesson (location, location, location) was critical for success. In his case, that included calm water conditions and no alligators, which wasn’t as easy as it sounds to find. Remember, this was the pre-internet days, so commissioning aerial photos was the only way to do it.

2016, at Page Island, with Rowlie Busch. 

Mike knew that even the perfect location would not be enough to ensure success, so he sought out advice and mentorship and in doing so, asked for just 10 minutes of Charles Fraser’s time. That 10 minutes turned into an eight-hour meeting that included a tour of Sea Pines and a boat trip around the Island and ended with Mike setting up a card table at South Beach to start his windsurfing school. Let’s call that milestone No. 1.

Milestone No. 2 was one of those serendipitous moments that makes you wonder “what if that didn’t happen?” In the ‘80s, one of Mike’s employees attended a dinner hosted by Phil Lader, then Sea Pines president, and she was fortuitously seated next to Bill Masters, a world champion kayaker. The next day, Bill called Mike and Mike added kayaking to his service offering. 

The purchase of a series of islands off Daufuskie Island in the ‘90s was another milestone that lead to Outside’s expansion into the B2B space where the islands are still used as the base for the corporate team building and leadership training division. Strategically, this expansion helped to offset what was a highly seasonal business and is a division that continues to thrive 20 years later. 

The most recent milestone happened in 2014 when Mike was inspired by a talk he heard by Sally Jewell, Secretary of the Interior, who spoke about the crisis of digitally obsessed youth. Mike, who knows all too well the importance of disconnecting and living an experience-enriched life, found a new passion — getting kids outside and protecting the environment. The Outside Foundation was founded.

Many milestones, mentors, a strong team and what Mike calls his “entrepreneurial disease” have fueled Outside’s continued growth. If you are wondering what could possibly be next for the company and Mike Overton, it’s Savannah. As different as Savannah is from Hilton Head, it shares water, nature and history, not to mention, provides a new target market and storefront in the highly anticipated Plant Riverside District on the Savannah River.

1985, Windsurfing Hilton Head staff photo. Front row, from left: Michael Meyer, Peter Ruhlin, David Vernon, Mike Overton, Steffan Hutter, Ken Kendrick. Back row: Robert O’Donnell, Friend, Colin Kappler, Nevile Cork, John Treadaway. 

Lessons Learned

Here are three lessons Mike Overton learned in 2020 and plans to bring to 2021. 

1. Expect the unexpected. Live every day as if it’s your last, or your first. 

2. Be nimble. Be prepared to shift or even reinvent how you do business. Cross-train employees to enable shifting of resources. 

3. Silver linings. Try to find opportunities that a negative situation can open up. 

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