The dot-com shuffle

By Gael Core, |  Career

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.

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