Beginner's Luck

So she declined a spate of job offers from early-stage startups and instead set her sights on finding a more-established venture. "I was looking for a company that was already in place," recalls Zornosa. "I wanted a big play, something with financial assets that hadn't yet been exploited in an IPO." She approached the task methodically, almost mathematically, paring down a list of 30 companies to the 3 best bets.

Women.com seemed the perfect choice. Formed in 1992, the women's content portal was one of the Internet's 30 most trafficked Web sites. It was the only one among the 30 that hadn't yet gone public or been acquired. The company's chairman and CEO, Marleen McDaniel, got along famously with the company's young founder and had the board of directors' full support. And while the company's strategy was in place and the IPO within sight, there was still room for a senior executive such as Zornosa to play an important role. "She's had a major impact," says McDaniel, noting Zornosa's responsibility for executing a merger that brought 11 Hearst magazines and 80 employees into the fold. "And I've since given her even more responsibility."

Of course, the Women.com job did have a downside: Zornosa's $175,000-a-year salary was only about half of what she could probably have earned in a conventional publishing job. Meanwhile, her relatively small stake in the company would never yield the kind of mind-boggling riches that increasingly define success in Silicon Valley. "And there's no guarantee that I'll cash in," says Zornosa, who notes that her 135,000 stock options require the standard four years to become fully vested.

Yet, even in the wake of the October 15 IPO, Zornosa feels satisfied with -- and rewarded by -- her decision. "The reward fantasy came about when I first started working in the Internet field," she says. "But I've done a lot of growing up since then. Maybe I'll end up with a new house or a new car. And that will be great. But what's important is that I made this decision with my list of priorities still intact."

Matt Rothman: Smaller Bets on More Numbers

Call it the billion-dollar button.

Matt Rothman knew that placing GetMedia Inc.'s electronic "buy" button on Microsoft's Windows Media Player and Internet Explorer 5 could put the fledgling Internet startup on the map. That one button could trigger a stream of revenue from music fans craving to own the CDs that they would hear via the browser's radio toolbar and Windows Media Player. And it would all but guarantee the venture capital needed to launch the four-month-old e-commerce company into orbit.

So when Rothman, 41, a former Sony Corp. of America executive turned strategic consultant, received a phone call from a Microsoft executive last May, he quickly moved to turn an opportunity into a deal. He'd already helped GetMedia's founder and chairman, Robert Goldman, to retool his promotional slide show into a slick investor pitch highlighting the huge market for impulse music buying via the Web. He had scheduled meetings with a dozen VCs; convinced two huge radio networks to install the San Jose, California company's buy button on hundreds of their stations' Web sites; and brought in a big-name public-relations agency and an executive recruiter to help carry out his "get big fast" plan to push the company toward an IPO and a billion-dollar market cap.

But the Microsoft deal would be the linchpin. Rothman worked the contacts that he'd made while leading Sony's online effort and set up a face-to-face meeting with executives from Microsoft. Then he and Goldman got on a plane and flew to Redmond, Washington. Five intense hours after entering a windowless conference room on the Microsoft campus, the two men emerged with a term sheet that ensured that GetMedia's buy button would lie within a finger's reach of tens of millions of Microsoft users. "It was really amazing," Goldman says of Rothman's deal-making prowess. "He should become a multimillionaire because of what he's done."

He just might. Although Rothman's consulting rate is more than $2,000 a day, it isn't his day rate that he's taking to the Internet casino. It's his system of placing a handful of smaller bets on a variety of different numbers, knowing that at least one of those numbers will hit. In a shrewd business deal with Goldman, Rothman had gotten himself not only cash but also a slice of the soon-to-go-public company. "My stake won't necessarily make me a millionaire," Rothman says of his small piece in GetMedia. "But, for four months' worth of work, it'll be a pretty good payoff." And that payoff is just one of seven that he will get: Rothman acts as a consultant to six other companies -- and has a stake in each of them.