Name: Alan Rothenberg
Companies started so far: 6
Weight: 161 lbs.
Hair color/eye color: brown/brown
Distinguishing characteristics: Always wears black, doesn't wear socks, and is often seen with a cell phone and yo-yo
Last seen: Traveling by airplane
Rothenberg's first company was unlikely to ever offer shareholding options: He started a carpooling service in high school, driving 11 kids to and from school, charging parents $10 per child, per week. Sixteen months later, he had enough money to buy a new car. You'll find that common among serial entrepreneurs, suggests Rothenberg, who explains: "Usually we find a need of our own, and we try to fill it."
Rothenberg himself is a sparkling example. By the time he reached college, he was keenly interested in stereos. So he sold cassette tapes and stereo equipment to his fellow students, ultimately becoming the second-largest distributor of Maxell tapes in Massachusetts. "They were the hottest tapes at the time but not anymore," laments Rothenberg, who had five employees and earned $6,000 per week by the time he closed shop.
Before finishing college, he was importing exotic cars from Europe at a20 percent savings and then selling them to U.S. buyers. "Again, no inventory," he reveals wryly. Rothenberg's business only lasted six months but garnered $120,000 and needed two extra workers. But soon another venture caught his eye: a contemporary art gallery.
After graduating college, Rothenberg opened his gallery in Boston in 1986. By the time he closed it to move on to other things in 1993, he had 10 employees and was earning $4 million a year.
While the art gallery was thriving, Rothenberg dabbled in a technology research and development company, Light Age Technology, circa 1989. Based in Waitsfield, Vermont, the company had taken in less than $1 million when he sold most of it (he still owns 10 percent).
Later, in 1995, Rothenbergco-founded KinderActive, a CD-ROM publishing company that generated several million dollars a year in sales. At the same time, he was tooling around with JuniorNet, a firm in Boston that opened to the public almost a year ago. The success of this venture remains to be seen, but one of the major partners is Highlights for Children magazine, and Rothenberg wants this advertising-free children's service-content provider (http://www.juniornet.com) to be on par with the Walt Disney Co.
And if JuniorNet reaches Disney's heights, would you expect Rothenberg to hand over the reins to somebody else? Of course. "I don't see myself just managing a large corporation," he says.
But wait a second, kids--don't rush to try this at home. Rothenberg warns that the career of serial entrepreneur is a risky one--which is part of the appeal. "There is the rush and danger at the same time," he notes, "and each time I start a new entity, I take a substantial amount of my cash reserves, or net worth, and put it into something completely untested and unproven. For some families, that can tear them apart."
Then in the next breath, Rothenberg, who is married and has three young children, offers this dare: "For some individuals, the loss of sleep at night and thinking about things--well, living and breathing this environment--can be pretty scary. But the true entrepreneur really looks forward to it . . . and excels during those times."
Geoff Williams has written for numerous publications, including Entrepreneur, Consumer Reports, LIFE and Entertainment Weekly. He also is the author of Living Well with Bad Credit.