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Launch Sell (Repeat)

When building a business is a serial thrill

Jeremy Jaech is now on his third start-up, Trumba Corp. He also founded, developed and eventually sold two previous start-ups, Aldus Corp. and Vista Corp., but found he didn?t enjoy retirement as much as a new venture.

Want to know a surefire way to get investors to fund your new technology start-up? Jeremy Jaech's got the secret: Have another successful tech start-up on your résumé and go back to your previous investors. Jaech grins behind his wire-rimmed glasses. "That's not," the serial entrepreneur concedes, "generally useful advice."

But managers of angel and venture capital funds say they like to see proposals that involve executives with proven ability to both start up and start over ? and over, and over. "It does make a difference," says Greg Gottesman, a managing partner with Seattle's Madrona Venture Group, who says five of the last 10 deals his fund has done involved entrepreneurs they've been successful with before. "If you've done it before," he says, "the chances that you can do it again are higher."

Researchers at Clemson University have examined "serial entrepreneurs," a category of businesspeople they defined as those who have launched three or more businesses. They found that such people have three things in common: a willingness to accept risk; a penchant ? even a preference ? for innovation; and a strong desire both to achieve and to be recognized for that achievement.

The study also found that such serial entrepreneurs are a rare breed. Only slightly more than 12 percent of the 664 entrepreneurs the Clemson study surveyed fit the definition. The vast majority of entrepreneurs, 76 percent, are satisfied launching just one company.

The Clemson study, however, excluded the Pacific Northwest, and there's ample anecdotal evidence that the culture of entrepreneurship here is different, just like our preference for strong coffee and Gore-Tex.

"This is a very entrepreneurial place," says Gottesman. "If you're not from here, you don't understand. It's OK here to be working at a start-up. It's cool. You say that in other parts of the country, they say, 'Why would you do that?'"

By that criterion, Jeremy Jaech is one cool guy. He's started and sold two technology companies, both times making enough money to allow him to retire very comfortably. He launched his third business in 2004.

He says he tried to retire. He really did. The first time was when he and his partners sold Aldus Corp., the creator of the groundbreaking PageMaker desktop publishing program, to Adobe Systems Inc. in 1994. "I made a nice chunk of change," he says, "and I could have not worked, and I tried it for a year."

He recalls leaving that April for an extended golf vacation in Portugal, then spending the summer hanging out with friends. "I played a lot of golf," he says. "It was fun." But by September, his friends had gone back to work, leaving him alone on the links. Jaech says he remembers vividly being out on the first hole at a course east of Lake Washington, trying to hit a wedge shot out of a mud puddle and getting soaked in the process. "Why," he recalls asking himself, "am I doing this? I've really gotta get back to work. This is going to kill me."

So Jaech joined with some colleagues to found Visio Corp., the business drawing and diagramming software company. That project went well, and in 2000 they sold the company to Microsoft Corp. Jaech stayed on for six months, then left Microsoft and decided to try a different approach to this retirement thing. "I did a lot of charity, nonprofit," he says. He even launched his own angel investment fund, with its own office and a small staff. It broke even, Jaech says. "We made a lot of pre-bubble-burst investments. One of them paid for all the others."

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© Washington CEO Magazine 2008