Lifestyle Entrepreneurs: Making a Life, Not Just A Living

By Mark Henricks

Ron Kipp’s colleagues thought he was crazy. He was making good money, with prospects for a long career at one of the world’s top companies. And yet he was quitting his $100,000-a-year job at IBM to move to the Grand Cayman islands to become an entrepreneur. And not just any entrepreneur -- the owner of a scuba diving tour company.

“A giant stride into madness,” Kipp says. “That’s what people said I was doing when I left IBM to go into diving.” The first few years, he paid himself an annual salary of $12,000, about what Big Blue paid him monthly. Instead of a $180,000 house in Cleveland, he slept in a converted harborside warehouse with no stove or bathroom. Rather than overseeing a white-collar workforce, he was the workforce, filling air tanks, guiding tours and sweeping floors for long hours daily.  

 “I loved it,” Kipp says. “I looked at the boats outside and they were mine. When I swept the floors, they were mine.” And when winter snow covered Ohio, Kipp basked in tropical balm. When his ex-colleagues were trapped in endless meetings, Kipp floated free in crystalline Caribbean water on one of his more than 5,500 scuba dives.

“I’m never going to retire,” Kipp says over coffee one recent Sunday morning in his residence in the capital city of Georgetown. “How could I? Ninety-nine percent of the poor slobs in the world wish they could do this.”

Indeed. Today the term most likely to be applied to Kipp is not “crazy," it’s “lifestyle  entrepreneur.” A lifestyle entrepreneur is somebody who goes into business not primarily for financial rewards, but for lifestyle reasons. The lifestyle payoff may be living on the beach, in the mountains or near a resort. It may be working fewer or more flexible hours, staying home to care for young children or aging parents, escaping the tyranny of corporate supervision, doing the kind of work you love, or any combination of the above. Lifestyle entrepreneurs don’t want to be the next Bill Gates so much as the next Ron Kipp.

And they're anything but rare. As many as 90 percent of the roughly 20 million American small business owners appear to be motivated by lifestyle more than money, according to John Warrillow, president of a Toronto market research company specializing in the small business market. Warrillow & Co.’s studies of what motivates small business owners identify three types.

“Mountain climbers” are driven to increase sales and achieve business success. That’s the traditional concept of the entrepreneur, Warrillow notes, yet these go-getters represent just 10 percent of small business owners. Thirty percent are “Freedom Fighters” seeking mainly independence and the opportunity to call their own shots and work when they want, where they want and for whom they want. The rest, some 60 percent, are “Craftspeople” motivated by the desire to do a particular type of work and do it well. “Craftspeople don’t even think of themselves as entrepreneurs,” says Warrillow. “They think of themselves as plumbers, photographers or whatever.”

But these people are, unquestionably, in business, and other studies support Warrillow’s findings of their lifestyle motivations. A 1999 Lou Harris survey, cited by author Dan Pink in his paean to self-employment, “Free Agent Nation” (Warner), found money was the main driver for very few small entrepreneurs and self-employed people. Fully nine of 10 said a desire for  independence prompted them to become entrepreneurs.

Lifestyle entrepreneurship isn’t getting any rarer either. “It’s a trend,” says Don  Bradley, executive director of the Small  Business Advancement National Center at the University of Central Arkansas. “I’m seeing it more and more.” Bradley says lifestyle entrepreneurs who come to him for help striking out on their own tend to be burned-out mid-careerists. Many are corporate executives, while some are refugees from dot-com startups that went bust. And instead of working 100 hours a week trying to surf the next new thing to an IPO, they're starting distinctly more laid-back businesses restoring log cabins, building one-of-a-kind furniture and running Ozark bed-and-breakfasts.

Part of the push into lifestyle entrepreneurialism stems from the fact that jobs aren't as plentiful as they were. “As the economy tanks, the percentage of Craftspeople increases,” Warrillow explains.  “There’s a very strong correlation.” In other words, unless the general economy rebounds sooner than most people foresee, there are likely to be more lifestyle entrepreneurs in the near future.

That won't necessarily be all bad. Just ask Ron Kipp. Today Bob Soto’s Diving Ltd., the nearly moribund outfit Kipp took over 20 years ago, is one of biggest businesses in Grand Cayman, with seven boats, five locations and 45 employees. Kipp is now a bona fide millionaire entrepreneur, but he’s already been living the lifestyle many a would-be millionaire dreams of for the last two decades. “It all worked out," Kipp says, looking back on his giant stride into lifestyle entrepreneurship. “It wasn't just a lark."

All About Dogs

Robin Knepp spent nine years in the Marine Corps, rising to the rank of captain with a specialty in logistics. "It's a very marketable skill," she says. But what lured the Woodbridge, Virginia, resident to leave the leathernecks wasn't a high-paying civilian job. Instead it was the opportunity to work full-time with dogs. Knepp, a lifelong canine-lover, took a six-week dog training course and began training pets on the side while still on active duty. The business grew to the point that when the inevitable transfer to a new post loomed, she opted to leave active duty and open All About Dogs. Originally a home-based training service, she has expanded it over eight years into a combination training and doggie daycare provider with 12 employees.

The $15,000 initial startup came from savings and credit cards. When she moved to a larger location, she obtained a government-guaranteed small business loan for $40,000. Knepp took just a 20 percent pay cut to become a lifestyle entrepreneur. "Part of that was because I started part-time time and didn't get off active duty until I knew I could make a decent living," she says. "It was a calculated risk." It paid off, she says, in the fun of working with dogs and dog owners. Entrepreneurship also allows her more time to vacation -- "anywhere in the mountains" -- and take her own two dogs to still more dog-training seminars.

Work-At-Home Dad

Jon Sidoli intended to get a job after selling his interest in the web consulting firm he co-founded. In the course of leading that business from zero to $600,000 a year in sales in only a year, he found that managing a fast-growing business was not his forte. He looked forward to being an employee again. But after his wife took a job requiring a two-hour commute, he decided to come up with another new venture instead. This one would be home-based so he could take care of the couple's elementary school-age daughter. "If I was working full-time, we'd have a daycare-and-dinner-at-eight-and-kiss-them-in-bed situation," says the 50-year-old resident of Irvine, California.  "I didn't think that was right."

That was four years ago and Sidoli's one-man enterprise advising school districts about skills required by new workers brings in less than half the $125,000 income he was used to. He relies on his wife's earnings from her high-level job and, when he has to, dips into the six-figure sum banked from the sale of his former venture. But the lifestyle benefit has been more than enough to keep him from looking back with regret. "If you enjoy your family and being there for your daughter and you can make a few bucks," he says, "then you're fine."

Egg Entrepreneur

Jane Pollak has been designing, decorating and selling hand-made egg designs from a studio added on to her Westport, Connecticut, home for so long, it's not clear where her lifestyle ends and her business begins, or vice versa. But the 30-year veteran lifestyle entrepreneur does have a clear vision of exactly what a lifestyle entrepreneur is. "It's somebody who does what they love, not necessarily for a jillion dollars," she states.

Pollak never had much of a career as an employee. For several years after she started selling her artwork in 1970, she focused on childrearing. But gradually, the elaborate geometrical creations she made from hen's eggs, melted wax and dye found a market. She incorporated in 1980, then added a toll-free number, a quirky slogan -- An Egg by Jane -- and a multi-threaded marketing effort that has her doing everything from appearing on the Today show to discuss Easter eggs to coming up with the idea of selling her eggs by the dozen -- for $3,000 a carton.

Her income of nearly $100,000 isn't much for a tony ZIP code in suburban New York, but Pollak loves the fringes, which include traveling to exotic locales such as Provence to take a photography class, and writing it off as a business expense. "I'm an artist," she explains. "And that's what my business supports -- what I love doing."

Golfing For Freedom

"I left corporate life because I hated the commute," says Cheryl Leonhardt. Fifty miles of creep-and-beep driving to the downtown Boston bank where she was a senior executive made almost anything look better, she recalls. That was especially true when the alternative she dreamed up was to earn money advising major corporations on how to help employees use golf as a business tool. Investing just "a couple of grand" to buy a computer and get business cards printed, she started in her home, first organizing and running a golfing association for women executives, then becoming a speaker, writer and business coach, all specializing in golf for business.

Today the Sudbury, Massachusetts, entrepreneur charges $8,000 per keynote speech, and more for corporate golf consulting sessions, but still hasn't caught up to her earnings as a corporate executive. "It still hurts," she says of the financial hickey. But when she wants to play golf instead of working, she notes, now that she's the boss she never has a problem getting the okay to leave work at 3 p.m. "I'm not driving a Bentley yet," she says. "But that isn't why I did this. I did this so I could be driving a Titleist. -- hey! You could use that!"

Copyright of Mark Henricks. Reprinted with permission.