What's Next? Ever wonder what you'd do if you sold your business? These six entrepreneurs have some surprising answers.
By Anne Fisher

(FORTUNE Small Business) – Michael Romano, 54, sold the family business, a 120-year-old wine and spirits distributor, two years ago for what he says was a "seven-figure number I couldn't refuse." Now he does what he's wanted to do since he was 6: play-by-play sportscasting for a local hockey team, the Chicago Steel. Jack Kahl, 63, sold Manco, the leading U.S. maker of duct tape, to German conglomerate Henkel in 1997 for $116 million. He stayed on to run it until 2000, and is now retired--but, he says, "I'm busier than I've ever been." Kahl consults for entrepreneurs on "everything from financing an earthworm farm to selling golf equipment to Wal-Mart." His pet project: leading a $550 million fundraising campaign for the nonprofit Cleveland Clinic. Jan King, 47, after selling her Los Angeles publishing company in 1998 for around $10 million, wrote a book, Business Plans to Game Plans: A Practical System for Turning Strategies Into Action, and is now negotiating with her publisher, John Wiley & Sons, on a series of books for women business owners.

Doesn't anybody retire anymore? You know, retirement, as in gone fishing or golfing? As in kicking back and watching the world go by? We're not talking about those unlucky wage earners who let their 401(k)s stay too long at the tech-stock party and will have to work into their 70s. The entrepreneurs mentioned here can easily afford to do whatever they want, including nothing. Yet especially among this group, it seems that the word "retirement" itself needs to go find a rocking chair someplace. There are no statistics on what small-business owners do after they sell their companies--no one is counting, for example, how many launch another startup. But among boomer entrepreneurs, now in their early 40s to late 50s, who built thriving businesses and then sold them or took them public, the idea of idling away the hours is anathema. Instead, most start or buy another business or set out to save the world (or just a small corner of it) through nonprofit work. Or they pursue some combination of the two--often with time left over for that morning tennis match and Tuesday night Hold 'Em.

Why are today's entrepreneurs so antsy? Now that the U.S. economy is getting stronger, the trend to start that second act should only accelerate. During the last recession many small-business owners postponed selling out, not wanting to give their baby away at fire-sale prices. That has changed. Says Verne Harnish, CEO of Gazelles, an executive-development firm for small to midsized companies: "With the mergers-and-acquisitions market sizzling and big companies trying to buy innovation, right now is the perfect moment to sell a business and go and do something else."

Powerful demographic forces are at work too. "The wild '90s made many more people rich at a relatively young age than has ever happened before," says Rick Eigenbrod, a psychologist in San Mateo, Calif. "That has raised a whole new set of issues. After all, who wants to 'retire' at 36 or 46 or even 56? So the question becomes, What do you do after you get everything you've always wanted--and still have decades of life ahead of you?" Harnish calls this a "classic midlife crisis on a massive scale. The whole country's gone crazy. Just look at the bestseller lists, where you'll find books like The Purpose-Driven Life [by Rick Warren] and [Po Bronson's] What Should I Do With My Life?"

The answer for most of those type-A personalities is not whiling away time on the beach. (For an exception, see the profile of the retired management-training entrepreneur who, after some difficulty and with practice, has adapted to a life that includes skiing at least 80 days a year.) Jim Warner sold his $80-million-a-year computer graphics company in 1992 and started a firm called OnCourse International in Boulder that counsels CEOs who are wrestling with midlife uncertainties. "Entrepreneurs are addicts. They get hooked on activity and achievement," he says. "And they have a huge fear of losing their edge--of having people look at them and say, 'Oh, he used to be somebody.' "

If you're faced with the happy dilemma of having the money and time to start a new life, the six characters in the following profiles may spark a few ideas. Some, like Tom Clements, who sold his software business and is now building a Catholic university near Atlanta, are searching for spiritual nourishment. "I used to read almost nothing but computer magazines," he muses. "Now I'm reading the Confessions of St. Augustine." Others, such as serial entrepreneur Harry Gruber, want to help the disadvantaged. He has launched a for-profit business to help nonprofits raise money over the web. And then there's Sabrina Kay, a Korean immigrant who sold her fashion business and has gone back to school to get (go figure) an MBA.

Discovering what you yearn to do with the rest of your years takes some introspection, say those who've been there--often a year, or even three, of slowing down to heed those inner stirrings your business has probably kept you too busy to notice. Whatever you come up with, says wine-merchant-turned-sportscaster Romano, "don't let anyone talk you out of it. Don't play it safe at a point in your life when you don't have to. Dream big."

COLLEGE BUILDER Tom Clements, 48 Alpharetta, Ga.

FORMER LIFE: Created the nation's first online human resources firm CURRENT PURSUIT: Opening Georgia's first Catholic college

One day you're struggling with all the stuff business owners do--making payroll, keeping clients happy, developing new products--and the next day, or so it seems, you and your partners have $70 million and no more company to run. That was what happened to Tom Clements when he bowed out of his Atlanta-based business, Conduit Software, which was among the first Internet companies to sell online human-resources and employee-benefits administration to big corporate clients. It was 1999, the peak of the dot-com boom, and, as Clements says now, "The money offered to us was just too good to turn down." That's not to say that overnight riches weren't a little disorienting. "Suddenly I had all this money and freedom," says Clements, a devout Catholic. "I thought, 'God, why did You give me this?'"

The answer that came to mind over the months that followed: Build a Catholic college. There are 235 of them in the U.S. but none in Georgia. "I did some market research and found out that Catholic education was growing fast in Georgia. But the question was, How are students going to get a Catholic [college] education without moving out of state? Statistics show that 85% of college students choose a college that's within a four-hour drive of their homes," Clements says. "So putting a Catholic college near Atlanta would give many more students that choice."

Born and reared in Minnesota, Clements took premed courses, with a minor in computer science, at Notre Dame. "Going to a Catholic university really helped me keep my faith when I left home," he says. "How do we help kids keep their faith today in an increasingly secular society?" Slowly at first, he found enough Catholics with the same concern--including the 16 members of his board of trustees, five full-time employees, and 35 active volunteers--to have so far raised more than $14 million to start Southern Catholic College. It's been a staggering challenge. "This is five or six times more complicated than running my business ever was," Clements says. "At the beginning, I wrote a rough draft of bylaws that had nine major areas of unknowns, including fundraising--which is tough without alumni--and curriculum and accreditation and all kinds of other things I had never dealt with before." Today it's all coming together: Southern Catholic's doors are scheduled to open in the fall of 2005, with 150 students already enrolled and about 5,000 more requesting applications. Eventually, Clements hopes, the student body will number about 3,000. To keep in touch with what today's college kids want, Clements, who has four children, gets advice from his two oldest.

Clements's seed money has come almost entirely from private donations. "I've had inquiries from entrepreneurs who want to invest in this, but I have to explain that it's not for profit," says Clements. "I tell them the payoffs are eternal." In the here and now, of course, benefactors get a tax deduction.

FROM TECH TO TEXTS Jenny Lawton, 40 Greenwich, Conn.

FORMER LIFE: Started a web management firm CURRENT PURSUIT: Running two bookstores in Greenwich

It isn't every business that lets you rub elbows with Madeleine Albright, Barbara Bush, Rudy Giuliani, Henry Kissinger, and Toni Morrison, but Jenny Lawton's does. As owner of a store called Just Books, she has hosted meet-the-author breakfasts for these and other luminaries. Lawton's story exemplifies a path chosen by many entrepreneurs who've sold their first companies. Want to run a business but don't want to start another enterprise from scratch? Then buy one.

Nothing in Lawton's background suggests that she would end up as a bookseller. A mathematician by training, she couldn't find a job--"In the early '80s nobody was hiring female mathematicians"--so she signed on as an "administrative assistant to an administrative assistant" at a heating and air-conditioning company in Boston, where she became interested in computers. A few jobs later--including a stint at MIT's Lincoln Laboratory, where she managed computer systems and learned to write code--she started an Internet venture called Netdaemons Associates that did tech support and web management for big corporate clients. When she sold the firm for a sum in the high six figures in 1999, she was 35.

"I really didn't know what I wanted to do next. I got a few offers to come in and turn around troubled dot-coms, but I was burned out on the whole Internet thing," she says. So she went to work for Mobius Venture Capital, charged with finding promising new businesses for the partners to invest in. "They didn't expect a bookstore," she says, "and they didn't invest in it." But Lawton saw potential there, so she bought it herself. "My husband and I had moved to Greenwich, Conn., and I read an article in the local paper that said this cool old store named Just Books was up for sale. The guy who had owned it for 30 years was retiring and moving to Oregon," Lawton recalls. "He had created a big events program and turned it into a sort of community center, and the way he ran the book business was very service-oriented. I thought, 'I could do that.' Besides, I was sick and tired of traveling so much that I never saw my two kids. I wanted something close to home--and here it was."

When Lawton bought Just Books in 2002, annual revenues stood at about $600,000. She's since opened a second store, Just Books, Too, in Old Greenwich, a few miles from the first one. Total sales have more than doubled, to $1.3 million. What does she read? "Fiction," she says. "Especially trashy mystery spy books. It's a hangover from all the time I used to spend on airplanes."

SERIAL ENTREPRENEUR Harry Gruber, 51 San Diego

FORMER LIFE: Started four companies that be sold for a total of $5 billion CURRENT PURSUIT: Launched a company to help nonprofits raise money online

"I tried to retire twice and failed both times. But I've never 'worked' a day in my life. I've always been so passionate about my work, it seemed more like a hobby." So says Harry Gruber, who can't seem to stop starting companies. Gruber began as a medical doctor, training in internal medicine, rheumatology, and biochemical genetics at the University of California at San Diego Medical School. Then he worked as a researcher, which led him in 1986 to his first business venture, a biotech firm called Gensia Pharmaceuticals that went public, reached a market capitalization of $1.7 billion, and today trades as Sicor. Two other biotech firms Gruber started, Aramed and Viagene, went public too, and were then snapped up by big drug companies for $750 million and $150 million, respectively. "At that point I was going to take some time off to spend with my kids," Gruber recalls. Instead, in the mid-1990s he started Intervu, a web video-streaming company that grew out of his fiddling with computers at home. In 2000 he sold that to Akamai Technologies for a little more than $3 billion. He was 47.

So once again Gruber thought about retiring, but there was a hitch: He had already started something else the year before. "I worked on John McCain's campaign, and I was fascinated by the amount of money and support that political candidates were able to raise over the Internet," he says. "So I thought, What if nonprofits could get that same kind of grass-roots emotional connection that politicians were getting, and boost their fundraising online? Wouldn't that be great?" At first, charities were chary: "There was an almost universal belief among nonprofits that the Internet wouldn't work for them. When we approached them, we got 100% turn-downs." Wasn't he discouraged? "Not at all. If you have an idea that everyone likes, think twice, because there must be something wrong with it."

With his medical training in rheumatology as a calling card, Gruber went to a local arthritis foundation chapter and offered to set up an Internet-based fundraising campaign free. "It worked so well, "we just built from there," he says now. His for-profit company, Kintera, runs thousands of simultaneous online fundraising efforts nationwide for clients such as the American Cancer Society, the American Red Cross, Big Brothers, and Special Olympics.

With 150 employees, Kintera charges a small percentage of donated funds and had $7.2 million in revenues last year. "For me, this is the best of both worlds--starting another business and 'saving the world,'" says Gruber. "One key is a mission that inspires employees. I always had one with the biotech companies and those exciting new gene therapies, and we've got one now too--giving back to the community."

THE STUDENT/PHILANTHROPIST Sabrina Kay, 36 Los Angeles

FORMER LIFE: Founder of a fashion design school CURRENT PURSUIT: Building a homeless shelter for women and children while getting an MBA

Ever wonder what it would be like to sell your business to a much larger company and then stay on as a fat-cat executive? Be warned: If Sabrina Kay's experience is any guide, you won't like it. In January 2003 she sold her fashion-design school, California Design College, to Pittsburgh's Education Management for an amount that was enough to set her up nicely for life. Part of what made the deal appealing to Kay was that EMC would give her the chance, she thought, to develop new educational ventures. She spent a year working for EMC, with the title CEO of Special Projects. It was not a good year. "Working in a billion-dollar corporation, there are a lot of politics and bureaucracy. When systems matter more than individual input, we entrepreneurs get flattened," she says. "I spent the last six months there twiddling my thumbs. So we parted ways."

Kay came to the U.S. with her parents as a 19-year-old who "didn't speak enough English to order lunch at McDonald's." She wanted to be a fashionista, and figured out how to apply CAD/CAM to designing at a time when few American designers even used computers. Her school started in 1991 with six students in her bedroom, and grew into the biggest nationally accredited school of its kind in the country, with a student body of about 800.

The business didn't leave time for Kay's own education. She's now a full-time student in the University of Southern California's executive MBA program. "It's challenging, because everyone else here has had far more business training," she says. "My background was really in the arts, and I just picked up the business stuff on the fly, so I have to work hard to keep up. But I love the intellectual stimulation."

At the same time, Kay has launched the Sabrina Kay Charitable Foundation, which has two main projects: building a homeless shelter, with educational programs, for women and children, and developing mentoring and internship programs for young people who want to enter fashion. "Right now Los Angeles has beds in shelters for 800 men but none for women. We have to fix that," she says. "And the mentoring programs are great. It's fun for me to help kids see their potential."

Will she start another company someday? Seems likely: Kay has already set up a venture capital firm called Fashion Umbrella that funds fledgling apparel companies. Still, she's in no rush to get back in the CEO seat. "The life I have now gives me a chance to be a normal human being. My company was a passionate love affair for 14 years, but I never had a social life. It would be nice to get married and have a family. That's something I just never got around to."

THE SKIER Jimmy Calano, 46 Boulder

FORMER LIFE: Founded a management training company CURRENT PURSUIT: Forces himself to ski at least 80 days a year

When Jimmy Calano sold his $82-million-a-year management training company, CareerTrack, in 1996, his friends formed a betting pool. The heaviest wagers were that his retirement would last less than six months. Ha! Eight years later he's still retired, although he admits to an occasional itch to start something. "The thing was, I was 38 when I sold CareerTrack, and I had been working ridiculous hours for so long that I felt I'd crammed a 40-year career into 20," he says. Calano had gotten married at 36, and even with a new baby, "I 'cut back' my hours to 70 a week. It was clear to me that I was constitutionally incapable of achieving work-life balance. If I wanted a family life, I'd have to sell." So he did.

Now he skis, mostly in Vail, Colo. "Skiing is my passion," he says. "It's almost a spiritual thing for me." He also reads about 100 books a year, has helped start an arts center in Boulder, and never misses his two kids' school plays.

"No one is more surprised than I am that I've managed to stay 'retired,'" Calano says. To test the waters, he first took a three-month sabbatical from his company, "just to see what it would be like to have time to go to museums and see my friends and travel--all those things I never could do when I was running the business. You might be surprised at how much you can find to do, if you force yourself to stay away from the office for a while." He adds, "I look at people like Jack Welch, Ted Turner, Sumner Redstone, and they're still doing deals in their 60s, 70s, and 80s. But is the next deal really more important than all the other great things in life? Don't they miss their families? I decided I'd rather have a million minutes than another million dollars."

Entrepreneurs often start new companies because they're uncomfortable with the loss of identity that comes from having left the old one, but that doesn't faze Calano. "When people ask what I do, my wife tells them I'm a private investor," he says. "I just say I'm unemployed--and getting more unemployable all the time." If he ever does start another company, what kind might it be? "I might like to run a ski resort."