From high school teacher to his own private island

From high school teacher to his own private island

By Sid Lipsey

With his recent home purchase, one Florida man not only made it into the record books, he became an inspirational figure to teachers everywhere.

High school math teacher turned entrepreneur Mark Pentecost just bought Little Bokeelia Island off the southwest coast of Florida. The purchase price was $14.5 million, reportedly a record for a residential sale in southwestern Florida. The 104-acre private island comes with a 6,486-square-foot Spanish-style villa with 4 bedrooms and 5 baths, a mini-village with bungalows for guests, numerous ports and beaches, a tennis court, and a pool with lagoon. (Click here or on a photo for a slideshow.)


For many a teacher who daydreams during class about running away to a private island someday, Pentecost and his wife, Cindy, are living the dream. And they know it. "We high-five each other a lot and say, 'I don't know how we got here, but we're not giving it back!'" says Pentecost, founder and CEO of a company called It Works. "We've been really blessed."

His rags-to-riches story began with a modest goal when he was teaching math in the 1990s: He just wanted to make an extra couple hundred bucks a month. But after a couple of years of wild success in direct sales, he left teaching and eventually launched It Works in 2001 to sell slimming body wraps that people can wear under their clothes. Since then, It Works has expanded to skincare and nutrition products. It moved to Florida four years ago, and last year racked up $456 million in sales.

Still, "who would have thought that we could own an island?" The idea never entered his mind until he saw Little Bokeelia on an episode of AWE TV's "Private Islands."

When the home hit the market in 2012, he looked into it but was scared off by the $29.5 million asking price. "At the time, I thought it was a little more than we could jump into," he says.


A few years and price reductions later, he now owns an island where explorer Ponce de Leon is said to have stepped foot.

"We're proof that the American dream is still alive," Pentecost says.

He isn't the island's first entrepreneur, though. Charles Burgess, inventor of the dry cell battery, bought it in the 1920s and built the villa. Among the friends Burgess entertained on Little Bokeelia: Thomas Edison.

Pentecost hopes some of Edison and Burgess' old-school entrepreneurial mojo will rub off on him while he's on the island. "You're sitting where Edison and Burgess invented different things and you're thinking how to be creative yourself," he says.

Life on Little Bokeelia Island won't be all work. "I like making money like Warren Buffett, but I'm more Jimmy Buffett. I like to be laid back but do things different."

His intentions for the island are an example of that. Although he plans to use it as an occasional weekend getaway for his wife and three kids, its primary use won't be as a home; it will be as an off-site corporate retreat for his employees and business partners.

"We know it's important to work hard," he says. "But at the same time you gotta take time to unplug and to energize. And we think the island is going to be our way to do that and help us innovate even more."

Click here or on a photo of Little Bokeelia Island, just purchased by a former high school math teacher for a record $14.5 million.

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If buying a private island like Pentecost's is out of the question, you could always rent one: