With all of his savings and a bank loan, he purchased his first boat and founded Peconic Water Sports in Southold, New York. He planned to offer wakeboarding lessons and private charters. In the months before his first summer, Flotteron built a website and tried to publicize his new venture. He enlisted his younger brother and a friend to help out, both of whom got their captain's licenses.
From Memorial Day to Labor Day, Flotteron and his employees work seven days a week to take full advantage of the short season. To keep costs low, Peconic eschews some traditional business expenses. Instead of a brick-and-mortar office, he uses a boat. Payments are accepted via a Square reader on an iPhone and waivers are signed on an iPad.
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During the winter months, Flotteron lives "on almost nothing" to make money available for the business. The off-season is spent updating the website, upgrading boats and equipment, and expanding the menu of offerings.
Last winter, Flotteron spent six months in the Dominican Republic, learning to teach kite boarding. An instructor he met on that trip now teaches at Peconic.
The story of Joey Flotteron's career-change is part of CNBC's series "Escaping The Cube."
—By CNBC's Karen Stern