That's because serial entrepreneurs are almost the opposite of their better-known colleagues, the traditional entrepreneurs who start businesses to make them successful and profitable over the long term. Serial entrepreneurs live for the start-up - cobbling together a new business, raising capital, and exploiting new markets. They start up and then sell out so they can do the whole thing all over again.

It's the difference between stick-with-it types like Bill Gates and Steve Jobs, and those who appreciate the atypical career path of Jesse Ventura, who went from the Navy to pro wrestling to Minnesota governor to talk-show host. The best serial entrepreneurs get out as soon as the business is a concern (sometimes waiting for the IPO, sometimes not) and lock in their profits. Others might not have an exit plan; just an exit.

"These people recognize what they do best, so they keep doing it," says start-up consultant Jack Derby of Derby Management. "They know their limits and know they don't want to work with mature companies."

Experts estimate that serial entrepreneurs are probably just a tiny percentage of the overall start-up universe, but get more attention - and more deals - because they have so much more experience with the successful business launch than the garden-variety entrepreneur does. After all, says Derby, they have proven track records, high-level contacts, and cash to invest from the proceeds of their previous efforts.

Serial entrepreneurs also have a different psychological makeup, and sometimes it's of a much darker cast, says author and clinical psychologist Dr. Steven Berglas, who has studied the subject extensively.

"They come to realize that success isn't enough by itself," he says. "They're forced to replicate their success, and they're only happy if they're doing it over and over and generating greater levels of success each time. That's how they get their self-esteem."

For the average businessperson, this kind of constant engine-revving sounds exhausting. But the serial entrepreneur wouldn't have it any other way.
- Jeff Siegel

Retiring Retirement


Each year, millions of retirement-age Americans chase a dream instead of a golf ball.