The dot-com shuffle –

Gordon Shephard may not consider himself a gambler, but he has gambled more than once over the past four years, leaving huge stakes on the table by exiting several Internet start-ups before he's pocketed the payoffs. And he's not alone. In Silicon Valley, where it seems everyone dreams of becoming a millionaire, that certainly doesn't seem like a strategy to strike it rich -- or does it?

"A lot of people are on their third and fourth start-ups, and nothing has really panned out," says Chetta Crowley, a recruiter with FileMaker in Santa Clara, Calif. "It's really like 'they're' waiting for that big one to go through."

Ten months ago, Shephard, the IT director at, an e-business solution provider in Sunnyvale, Calif., left his job at, a similar company in Cupertino, Calif., just 60 days before being fully vested. And it wasn't the first time. Shephard left even more money in stock options when he resigned from Netscape prior to his move to Oblix.

Leaving Oblix before he had worked there for 10 months, Shephard didn't receive a penny, but he found it a surprisingly easy decision. "The way you have to look at it is, would two months at Loudcloud make up for ten months at Oblix?" says Shephard. And his answer was yes. "The financial decision was easy to make," he says, but "the relationships that you leave behind make it more difficult."

Engineers aren't looking only for big money. They also want to work with innovative technology, and they want the opportunity to deploy it in a new business venture. Shephard says people like him simply want "to be the best at what you do and build great things," adding that "you work because you are driven."

Jeffrey Whitehead, an engineer at, a customer review Website in Mountain View, Calif., tells a similar story. Whitehead spent three years at Netscape when it was still a small company with about 300 people. He then moved to Knowledge Universe, a Web-based training company in Menlo Park, Calif., working there for nine months before jumping ship to Epinions. He left stock options behind with each move. "I moved to Epinions because I was excited about the team and vision, and I got excited about Epinions' prospects," says Whitehead. But the prospects of a big payoff are only part of the reason for changing jobs, according to these IT professionals.

"I found that the grass is always greener. Jumping between jobs, you always had a better chance at promotion," says Josh Jacobs, the CTO at, an e-business service provider in San Francisco. Jacobs is an experienced job hopper, having worked at more than six companies in ten years before becoming a founding member of Bigstep. People leave jobs -- and their stock options -- for a number of reasons. "They are going to a more attractive opportunity or believe in the business more," Jacobs says. "People are not motivated by the money thing. They can get stock options at any company."

So where is the payoff in all this job hopping? Ron Some, an executive search consultant for Tech Search in Sausalito, Calif., says there is a "class of people who are serial entrepreneurs." Once a company goes public, there is a mass exodus of workers who don't want to work in a bureaucratic environment in which they have to talk to stake holders to gain consensus. It's more compelling to leave and ride that same wave in another start-up. "The culture shift is what makes these people feel like fish out of water," Some says.

And yet these same employees often ask for more stock options when accepting a job at another start-up. And with each new start-up, IT workers addicted to the start-up energy are a long ways from settling down. "It's not about the money," Some says. "But people are primed: Candidates are becoming more savvy about getting the basics plus everything else."

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