They Just Can't Stop Themselves

Once exotic, serial entrepreneurs are everywhere these days. From their tolerance for failure to their creative use of resources to their sense of when to leave, they have a lot to teach more traditional company owners.

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Ron Berger lives by routine. Every morning at 5:30, he climbs on his Stairmaster for 45 minutes and reads business magazines through rimless glasses. Then he dons a dark suit and patterned tie, eats low-carb cereal with blueberries (or splurges on an Egg McMuffin without the muffin), and drives his midpriced Mercedes to the office by 7:30. He leaves 11 hours later, eats a South Beach-approved dinner, and watches CNN until his 11 o'clock bedtime.

Thus it's a surprise to discover this mild Oregonian is a consummate risk taker, a serial entrepreneur who's started five companies, one after another. The businesses have ranged from a camera retailer that grew to 54 stores but then went bankrupt to a company that managed the system by which video stores pay fees to movie studios. He took that company public. Another one of his businesses was acquired. His current venture, Figaro's, which Berger calls a "take-and-bake pizza" concept, had systemwide revenue of $24 million last year.

So this measured man with his measured days flirts with failure and financial exposure about as often as most people buy a new car. And he's not alone. Once a novelty, serial entrepreneurs are moving into the mainstream. Venture capitalists report that a growing number of the people pitching them refer to themselves as serial entrepreneurs, and if you attend an event at a chamber of commerce or a business school these days, chances are good that many of the speakers will tout their serial bona fides. "In the 1970s and '80s, only 10% of our entrepreneurs were serial," says venture capitalist Gary Morgenthaler, of Morgenthaler Ventures, which manages $2 billion in investments. Today, Morgenthaler says that number is closer to 25% -- and he expects it to grow to 30% or even 50% in a few years. Forty-one percent of this year's Inc. 500 CEOs say that they plan to start another company, and 69% of the alumni of Springboard Enterprises, a top women's business incubator, describe themselves as serial entrepreneurs.

Of course, the serial life is not for everyone. Many business owners find fulfillment running a single enterprise. But for those who are considering starting multiple companies, the current generation of serial entrepreneurs can offer a blueprint. And the strategies they employ often have relevance for anyone who owns his or her own business.

• What You Learn From Company No. 1: When and How to Leave
• What You Learn From Owning More Than One Company: Don't Fall in Love With the Product
• What You Learn by the Third Company: How to Leverage Your Resources Creatively
• What You Learn by the Fourth or Fifth Company: It's Okay to Fail
• What You Learn by the Sixth or Seventh Company: Don't Hire People Like Yourself
• What You Finally Learn: It Does Get Easier
• What You Never Learn: When to Stop

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