What's the success of serial entrepreneurs?

Five years ago, Tom Scott and Tom First realized they would never have to work again. Friends from college, the pair had launched a juice brand called Nantucket Nectars from the back of their island boat and catapulted themselves -- the self-dubbed "juice guys" -- into the stuff of entrepreneurial legend as their beverage took off nationwide.

They sold a majority of their company to Ocean Spray Cranberries Inc., and when Cadbury Schweppes PLC later bought the entire business for an estimated $100 million in March of 2002, both men were set for retirement -- and they were only in their mid-30s.

But there was no retiring in their futures. Today Messrs. Scott and First are both deep into new ventures that, for now at least, appear headed for success. Mr. Scott leads Plum TV, a New York-based company that operates local television channels in historic, affluent markets such as Aspen, Nantucket and Martha's Vineyard, and has had notable investors including Starwood Capital Group CEO Barry Sternlicht, singer Jimmy Buffett and former Viacom CEO Tom Freston.

Mr. First is in the midst of a new start-up: O Beverages LLC, in Cambridge, Mass., which markets a line of naturally flavored waters already sold in nearly 20 states through Safeway, Balducci's and Bristol Farms, among other stores. In between Nantucket Nectars and their current ventures, the two men started a beverage-distribution-software company that was sold to a publicly traded technology company.

"I'm a crazy competitive person, so there's no way I'm stopping," Mr. First says. "I like being in the trenches."


WSJ's Raymund Flandez speaks to New York entrepreneur Ari Meisel, 24, who has founded four companies -- including three before he was out of high school.

Voices of Experience: Perspectives on starting multiple companies from people who have been there as founders or co-founders.
Call them serial-preneurs. While some entrepreneurs struggle their whole lives to bring one idea or product to market, there's another breed: those who do it once, twice or three times more, disproving the notion of beginner's luck. In some cases, the brands and people are household names, such as Steve Jobs with Apple, Pixar and NeXT. But the ranks also are populated with lesser-known entrepreneurs who fly under the radar, hitting one start-up home run after the other.

"I really believe that some people are kind of entrepreneurial adrenaline freaks," says Wayne Stewart, a management professor at Clemson University in Clemson, S.C. "They really get their kicks by starting businesses."

In 2000, Mr. Stewart published a study with two other researchers looking for common traits among serial entrepreneurs -- which he defined as those who had owned and operated three or more businesses. Of the 664 entrepreneurs studied, only 12% fit the bill. But those who did scored higher in all three categories examined: They had a higher propensity for risk, innovation and achievement. They were less scared of failure. And they were more able to recover when they did fail.

Beyond that, many serial-preneurs bring tactical advantages from their first venture to apply the second and third time around. For instance, they recruit top talent from their original companies to subsequent ventures. They double-dip financially, getting money -- and connections -- from people who backed their earlier brainstorms. Several lean heavily on a trusted partner for financial, professional and emotional support in whatever endeavor they undertake.

More than anything, however, the greatest, and more crucial, challenge among repeat entrepreneurs is figuring out how to rekindle for future ventures the innocence, love and hunger that fueled their first enterprise. Despite hitting it big early with Nantucket Nectars, Messrs. First and Scott both struggled after the sale to find a business that inspired them as much as being the juice guys.

"A lot of the drive early on was the drive to not have to leave Nantucket, or write the resume, or go do anything else. We were hustlers," says Mr. First. Adds Mr. Scott: "What happened was that while approaching the things we love -- boats, water, weather -- we stumbled on juice. I've learned from this that it doesn't matter what I'm good at. It matters what I like."

What's the Motivation?

So why do some entrepreneurs who strike gold once continue to start over? A general contractor might launch a business because he has certain skills, and then stick with it until retirement. Or a banker will work her way up the corporate ladder, happy with the security of a paycheck and benefits, and retire once she has saved enough. By contrast, serial entrepreneurs' main job is the act of creation -- and thus they keep creating new businesses, often after they no longer need the paycheck.

"Most people can't understand why someone who made $10 million would do it again," says Seth Godin, who founded Yoyodyne, an interactive direct-marketing company bought by Yahoo in late 1998. He's now running a new online venture called Squidoo, a free tool that lets users build Web pages about any topic within a searchable community. "That's because most people don't like working, and they think it's irrational to keep working," he says. "But most entrepreneurs don't care about money; it's a tool."

For instance, Scott Jones was a multimillionaire by age 30, having co-founded the company Boston Technology, maker of a voice-mail system now used by many telephone companies world-wide. He retired, and learned how to fly planes and perform aerobatics, but was quickly bored. So he went back to work and has since co-founded Gracenote Inc., an Internet-accessible music database used by iTunes, as well as a robotic-lawn-mower company and a search engine that uses human guides in real time. Those years not creating, he says, were "the most unhappy years of my life."

Moreover, serial entrepreneurs harbor an unusual appetite for risk -- something they can inherit from their parents. Dan Bricklin, 56, has started four companies in his lifetime; his first Software Arts, was sold to Lotus Development Corp. in the mid-1980s. Mr. Bricklin's father was a small-business owner who ran a printing business, as did his grandfather.

Mr. Bricklin, who now runs Software Garden Inc. in Newton Highlands, Mass., says he feeds on the thrill of starting something new and untested. "It's like that sense of walking across a stream on the rocks -- sort of knowing where you're going, but sort of not." As for risk? "If you actually seen the ups and downs of a business, and your family isn't terrified, that makes it a lot easier to do yourself."

Likewise, Tim Miller caught the entrepreneurial bug at age 18 when he received about $500,000 after his father sold a company. Mr. Miller stashed that money away, planning to invest in his own company one day. Fifteen years later, he dipped into the fund to start a software firm called Avitek Inc. based on an idea his then-employer didn't want to explore. Mr. Miller recalls how family members fretted about the danger of going it alone, with his brother specifically questioning his judgment after he hired his fourth employee: How could he possibly put other people's livelihoods on the line?

"But it never truly occurred to me that I would potentially need to let any of them go at any point," Mr. Miller says, adding that he believes successful entrepreneurs "see opportunities where other see risk." He sold Avitek in 1999 for about $13.5 million, without layoffs, and is now running a venture called Rally Software Development Corp., based in Boulder, Colo.

The Value of Teamwork

Mr. Miller didn't succeed alone; he had a partner, Ryan Martens, who now works with him at Rally Software. Their compatibility is an asset whose value Mr. Miller finds hard to quantify. While Mr. Martens as the chief technology officer is deeply invested in software development, Mr. Miller is the business guy. "I think great leaders build teams," Mr. Miller says, "and those teams have some glue and they tend to stick together."

Whether by design or not, on second and third ventures, serials often surround themselves with familiar faces. Partly it's about familiarity and trust. Messrs. Scott and First both tapped ex-Nantucket Nectar employees for their newest ventures. They typically talk to each other several times a week, and Mr. Scott is an investor in O Beverages. "We've never doubted the other's total respect and having the other person's good interest at heart," Mr. First says.

Repeat relationships are also about expediency. Elizabeth Cogswell Baskin has run four companies, including two advertising agencies and a book-packaging operation. Now 46, she's the CEO of Tribe Inc., a $3 million Atlanta advertising agency that works with brands including Porsche, Home Depot and UPS, and peppered throughout Tribe's ranks are faces from her previous companies. "I think it is a huge shortcut to hire someone you already have a relationship with," Ms. Baskin says.

At age 77, Jack Goeken lays claim to having helped start a string of well-known enterprises: MCI, InFlight Phone, Airfone and several others. Now, he's deeply involved in a new start-up, Polybrite International Inc., a Naperville, Ill., company that produces a screw-in LED light bulb that will fit in normal lamps. His daughter Sandra, 49, has worked with him on every venture since MCI, and says one of her father's greatest strengths is "herding tigers" -- that is, finding entrepreneurial, and sometimes difficult to manage, individuals who can make a project happen, but then making sure they don't stick around too long.
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