About four years ago, Jim Kucher and his wife and business partner Cindy Leahy sat in a darkened Baltimore bar, drowning their sorrows. The couple's 10-month-old startup, Wickford Technologies, had fallen victim to the tech sector's implosion, and their lawyer had a message for them.
"This has either cured you forever of a horrible disease or given you a taste for something you'll never be able to get rid of," Kucher recalled his lawyer saying.
For Kucher, it was definitely the latter. He went on to start a consulting company and later became executive director of the University of Baltimore's entrepreneurship program - an effort he still heads. Now, Kucher knows all too well the plight of the serial entrepreneur. "It is something that you just really really develop a passion for, and you have to, because it's insanity," Kucher said.
In Maryland and around the country, these entrepreneurs help fuel the economy, with ventures from retail to restaurants to technology companies. More than 80 percent of new jobs are created by entrepreneurs, said Michael Morris, chairman of the department of entrepreneurship and emerging enterprises at Syracuse University's Whitman School of Management.
Here's the picture some experts paint of habitual entrepreneurs. Generally they're a breed apart from those who want the security of a steady paycheck and benefits as well as a good night's sleep. They embody innovation, enthusiasm and perseverance.
The need for achievement is key, as is their sense of self-efficacy. They're driven and they believe they control their own destiny. They're willing to take risks, but they aren't foolish. They're more than willing to trade the securities of a steady paycheck and benefits for the excitement and uncertainties of building their own business.
While their businesses may be different, there are similarities in what drives them and keeps them coming back for more, despite the uncertainties and struggles. Many are willing to pour their life's savings into a dream, or borrow to the hilt to do it. They're not too shy to look for funding. Some work night and day for months - even years - without a salary. And they have a knack for spotting a need and identifying opportunities, experts say.
Once they get a taste for running their own business, whether that first one was a failure or a success, they can't help themselves from doing it all over again. Chocolate king Milton S. Hershey, for instance, had three candy-making ventures fail, was snubbed by his family and nearly went under again before he scored with a caramel company. Not content, he sold it for $1 million in 1900 to focus on developing what was then a luxury product - chocolate - for the mass market.
'Antennas are out'
"I think their antennas are out a little bit more," said Ven Sriram, a professor of marketing at the University of Baltimore who is working on a study about urban entrepreneurship in the United States and in emerging markets.
Take Kehar Singh, 38. Singh said he had already owned two Baltimore restaurants and a nightclub with his brother, Binda Singh, 31, when he toured the Ambassador in Baltimore's Canterbury-Tuscany neighborhood in 1997.
Even though the restaurant was hidden inside a 1930s apartment house, Singh said he knew instantly it would work because of its location near the Johns Hopkins University's Homewood campus and some of Baltimore's most affluent areas, its architectural detail and its extensive garden that, in warm weather, becomes an outdoor dining area.
"The minute I walked in the room, I looked out of the back doors, over the garden and I told them: 'I will take this place,' " Kehar Singh recalled.
Singh's journey from rural India to restaurant mogul began in 1985 when he emigrated to America. He worked 16 hours a day, six days a week as a waiter until he saved up enough money to buy his first restaurant, Banjara in Federal Hill, in 1992. Despite the long days, the work seemed easy compared with his life on a farm in his homeland where he had to care for livestock around the clock. His brother arrived from India the day Banjara opened.
A dozen years after Kehar came to Baltimore, he and his brother opened the Carlyle Club restaurant just a few blocks away from the Ambassador - an opportunity they seized partly, Kehar Singh said, because there were no other fine-dining Middle Eastern restaurants in Baltimore. The brothers, who also invest in real estate, added a third restaurant in the neighborhood four months ago, taking over the Spice Company in the nearby Colonnade.
Is there another restaurant in their future?
"Every time I open one, I always say, 'never again.' But perhaps," Kehar Singh said.
Edward L. Dopkin can relate. He, too, has built up something of a restaurant mini-empire - his along a stretch of Cold Spring Lane in North Baltimore. He recently opened his fourth restaurant there, saying it would be his last. "But who knows? I've said it before," Dopkin confessed in an interview at his newly remodeled Miss Shirley's restaurant on the border between Baltimore's Keswick and Roland Park neighborhoods.
The Baltimore native, who grew up in the food business, can't stop starting over. His craving for the industry dates back to 1969, when his parents opened The Classic Catering People. Then a restaurant, the family business grew into a major catering company that Dopkin now owns with two sisters and a cousin. Since then, he has opened and then sold The Bagel Place, which he grew into a chain of 15 stores, including shops in New York and Washington, and Nate's and Leon's, a downtown Baltimore deli.
But it was in the early 1990s that Dopkin began building his current venture, buying a struggling restaurant called Roland Park Cafe and turning it into Loco Hombre, a popular Mexican restaurant on Cold Spring Lane. Almost a decade later, he bought the neighborhood landmark next door, Alonso's. And in 2004, Dopkin leased a vacant building and parking lot across the street from his adjoining restaurants to gain more parking for his customers.
'This is crazy'
It wasn't long, though, before he started feeling, "This is crazy. We have this building, let's put something in there."
And so in 2005 he opened Miss Shirley's, a breakfast and lunch joint that wouldn't compete with his existing dinner restaurants across the road. Business was so booming there that he recently moved Miss Shirley's to a bigger space across the street and opened S'Getti Eddie's, a pizza, pasta and grinder place, in the once-empty building.
Dopkin, 54, knows that if he hadn't started Miss Shirley's, he likely could have retired in five years. But for someone like him, who has to keep busy all the time, what fun would that be?
"This is fun to me," Dopkin said. "This is my social life, and you have to sort of be crazy to do that."
For entrepreneurs like Dopkin, the stress and worry of starting a new business is part of the excitement, said J. Robert Baum, an associate professor of entrepreneurship at the University of Maryland's Robert H. Smith School of Business and editor of The Psychology of Entrepreneurship.
"They love to start companies and put things together and see how far they can go, but when it starts to be that they have to spend a lot of their time managing it - in other words, hiring people, motivating people ... they lose interest," Baum said. "And then they start all over again with something else."
Ethan D. Leder has done it over and over again, too. He sold his first company more than a decade ago for about $2 million. He sold his second company several years later for about $500 million. Then Leder went on to start a third company and sell that one in 2003 for about $180 million.
Today, as a founder and chief executive officer of the 700-employee Bethesda-based United BioSource Corp., 44-year-old Leder says he now has the financial flexibility to take risks he thinks will pay off and make business decisions without worrying about stability.
"For me there was a drive, a real desire, to make sure I had financial security at an early age," Leder said, "and once you accomplish that, it's freeing."
Indeed, from the conference room of United BioSource's offices, Leder said that with that freedom he can now turn this latest venture into the leading company in its field.
Leder was on his way to becoming an "absolutely mediocre lawyer," he said, when he realized he would be better suited for something else. He found that law requires discipline, rigor, focus and attention to detail, but that his mind works like more of a whirlwind of ideas.
As he practiced law, Leder began a health care newsletter that never sold. Then he and a partner started American Home Therapies, which delivered intravenous medications to patients in their homes. They began the company virtually, keeping their day jobs as lawyers. But within months the pair quit their law jobs, pooled $15,000 in savings, moved in with their respective girlfriends to save money, and sublet a small office in Washington.
When Leder told his parents he was quitting law to pursue his health care business full time, they thought he was crazy, he recalled. They assumed he would fail in his first year and go back to practicing law, Leder said.
But American Home Therapies sold in 1992 for about $2 million, and Leder knew he would never go back to law. He went on to begin and then sell two other companies, and he could have easily retired at age 36. Instead, Leder took a few months off, ran a few marathons, spent time with his family and then geared up for his current project - United BioSource.
While many would shy away from the worry of starting their own company, experts say entrepreneurs thrive on it. Once they've successfully started one company, the serial entrepreneur often forgets the pain of the startup and remembers only the excitement of what they've done, making them more than willing to do it all over again.
Karen Axelton, executive editor of Entrepreneur magazine, believes that most entrepreneurs are serial ones. Even those who start one company and run it until retirement tend to get restless when it's time to stop working, and they get involved in a new project, she said.
"Anyone who is an entrepreneur, they like to keep their hand in the game," Axelton said.
Entrepreneurs who have had one successful business and made a name for themselves in the community are more likely to be approached by other people with ideas. Someone may ask them to invest, be partners or join a board, and they get lured back into yet another entrepreneurial endeavor, Axelton said.
That's what happened to Mark Wesker, who founded Sequoia Software 14 years ago, then sold it in May 2001 for about $185 million. When Sequoia was starting, Wesker didn't draw a salary for two and a half years. He lived on a tight budget and the salary of his wife, a lawyer. Stressful days and sleepless nights were commonplace. And there were weeks, Wesker recalled, when he didn't have enough money to pay his employees.
After the company sold, Wesker, then 39, promised his wife that after staying on full-time through August to help with the transition, he'd take the rest of the year off - a promise it took him less than a month to break.
"I was getting ready to pull my hair out," he recalled.
So when former colleagues approached him about a new project, Wesker quickly agreed to come on board as a co-founder of Artifact Software. They began plans in September 2001 for the new Baltimore company, which now has about a dozen local employees and more overseas, and incorporated in early 2002.
Even the second time around, there were still weeks in the beginning when Wesker couldn't pay employees. There are still sleepless nights. And even though Wesker learned from his mistakes at Sequoia, there were new mistakes to be made with the new business.
"It's amazing how quickly you forget the bad stuff," Wesker said during an interview at Artifact's Inner Harbor East office. Wesker did, however, learn at least one lesson from his business endeavors: He'll never retire.