NEW YORK (TheStreet) -- Retirement for a serial entrepreneur doesn’t come easily. For Tim and Tracey Kerin, it means taking 27 years of business experience and starting yet another business: a taxi service -- in Costa Rica.
"As owners of five businesses in the Washington, D.C., metro, we discussed 'When is enough, enough?'" Tim Kerin tells TheStreet. "'When can we start living and enjoying life together? How much money can we survive on and maintain our businesses -- or sell them?' As entrepreneurs, most of our life savings went into the businesses. Our customers are based on our relationships, so it is difficult to proactively look at retiring unless you make a plan and act on it now."
And the Kerins are doing just that: mapping out their retirement plan and launching a "retirement" business a few years before they actually call it quits. The couple have purchased a villa in Playa Hermosa, Costa Rica that they will rent out for the next four years "in order to pay it off." Plus, they are launching an upscale taxi service catering to the booming tourist trade in the country.
"Once an entrepreneur, always an entrepreneur!" Kerin says. "This is exciting and challenging. It will also give us something to do while in retirement. It was very interesting to learn about how to do business in a different country and how to navigate your way to building relationships and opportunities. We are financing the business with one vehicle [to start] and [we’re] projecting three more by winter -- their high season."
Meanwhile, David and Leesa Thompson are trading the snow and two-hour commutes of Chicago for the sun and sailing lifestyle of Punta Gorda, Fla. The couple just launched a nautical time-share business, renting out their new 33-foot Hunter sailboat, as well as offering sailing lessons on the Gulf Coast.
"Several years ago, we were thinking about potential places where we’d want to retire, but we didn’t want to just step out of the work life altogether," David told Florida Weekly. The Thompsons are taking their 11 years of sailing experience to a sunnier and more profitable climate, catering to southwest Florida’s sailing enthusiasts. It could be the perfect example of a passion turned into a profit.
For journalists Pat and John Curry of Augusta, Ga., coffee was something they knew well -- and loved. They began grinding their own beans, and ultimately roasting them at home, in an effort to brew the perfect cup. Their "second act" business began five years ago, not so much as the result of a plan as unemployment.
"We hadn't planned on it, but after three layoffs in two and a half years -- one for me as a senior editor at a national trade magazine, two for him as a newspaper photo editor -- we decided we'd had enough," Pat Curry tells MainStreet. "We had started a little nights-and-weekends side business roasting coffee. It had started taking off, so he started roasting full time. We opened a coffee bar about two years ago and besides us, we [now] have four employees."
But for retirees looking to start a business, one roadblock is often overlooked: health issues.
"John was treated for stage three colorectal cancer," Pat says. Soon, John also suffered congestive heart failure as a result of chemotherapy. Meanwhile, their coffee bar, Buona Caffe, continued to thrive.
"Fortunately, he has responded well to treatment for both," she says. "The business is doing well. We have been named the 'best coffee in Augusta' for three years. We roast coffee for about 20 local restaurants and the Georgia Governor's Mansion."
Starting and maintaining a successful business is a challenge at any stage of life, particularly in retirement. But future resort transportation entrepreneur Tim Kerin puts the task in perspective. "There are only so many sunsets you can watch," he says.