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Stuart Sheppard

Entrepreneurialism came early to Stuart Sheppard, founder and president of GWT Outdoors in Naples. In high school in Westchester County, New York, he and his buddies ran a house painting company. By college, they were renting out VCRs and VHS tapes. “We were always trying to do our own thing and find our own niche,” Sheppard says. 

After he graduated from college, Sheppard gave working for other people a shot, and spent 15 years in the financial industry employed by big-name firms such as Lehman Brothers. Eventually he admitted that working for other people wasn’t for him. “It started to wear thin,” he says, “so I fired myself out of that position.”

Back in business for himself, Sheppard launched a blinds-cleaning company where he “quickly became an all-star.” Soon he noticed a pattern: His clients would bring him worn-out shades asking him to work miracles, and he’d have to suggest they skip the cleaning and buy new shades instead. It didn’t take long for him to see the business opportunity. Soon he launched a Hunter Douglas window treatment business and sold off the blind cleaning company. The change sparked one of Sheppard’s favorite pieces of entrepreneurial advice: Adapt or die. “If you can adapt to changes quicker than your competitor, you’re going to do really well in life. But if you ignore circumstances that are changing, you’re going to go the way of the dinosaur.” 

That same adapt-or-die mentality got him into the outdoor pergola business, where he’s happily thriving today. GWT Outdoors specializes in custom adjustable pergola systems. 

Over the course of his career, through a variety of different businesses, Sheppard has been guided by the same entrepreneurial spirit that had him painting houses in high school. “I like being in control of my own destiny,” he says. “I like to know that every hour, every day, every year that I work I can control both the effort and the outcome. That keeps me motivated.”

Hot Tip: Keep it to yourself 

Sheppard has serious advice for new entrepreneurs: Stop shopping around your ideas. “If you have a great idea, just go do it,” he says. “Don’t talk about it too much with your friends. Almost everybody you talk to will try to talk you out of what you want to do.”

When Sheppard launched his Hunter Douglas business, his father told him he was crazy. “There are too many Hunter Douglas dealers in the world,” his father said. But Sheppard quickly took his company to No. 1 in the region, and it’s still a successful business today.

“It’s remarkable how many people will tell you not to do something,” Sheppard says. “Until you’re an entrepreneur, you don’t realize how many people will try to discourage you.” 

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