Beginner's Luck

By the time her two children awoke, Zornosa had already braced herself for a day very different from the one that she had envisioned. "I went from being extremely happy to fretting about how we were going to spin our employees on a less-than-positive opening," says Zornosa, who practiced her reassurance spiel on her daughter.

Such emotional twists are hardly unique these days, with highs and lows turning on the luck of the draw, on the time of day, on a Greenspan phrase. You work hard to pick the right company, the right CEO, and the right team. You scrutinize the market, the competitors, the financial backers, and the board of directors. You take every diligent step that you can to ensure a winning outcome -- and you still risk falling victim to the vagaries of a casino economy, where bad luck and bad odds can humble even the most deserving determination or the most impressive smarts. "When I started with the Internet, I thought, 'I'll do this for two years, and then I'll cash out and perhaps never have to work again,' " Zornosa recalls of her earlier stint at PointCast Inc., one of the Web's first shooting stars. "But the truth is that no matter how good things look, you never really know how they're going to turn out."

That's not to say that you can't tilt the odds in your favor. At a time when job hopping is increasingly losing much of its stigma and developing a reputation as a shrewd career strategy, switching your Internet bets in the middle of the game may be the only way to boost the probability of a big-time payout. There is no honor -- and very little money -- in staying at a table where the cards have gone cold. The new economy's casino favors the bold and the lucky. But mostly, it favors those players who do the math to find the best odds of striking it rich. By going with the favorite instead of with the long shot, Zornosa's decision to leave an early-stage startup and sign on with the already-established Women.com bolstered her chance of cashing in a winning IPO ticket. And while, as employee number 200-something, she held a smaller stake in this new company than she did at the previous two startups she worked at, neither of those companies had come anywhere near achieving Women.com's IPO.

Zornosa had hedged her bet in another important way: She had chosen a company that she knew she could feel good about regardless of how the market received the current offering. "Of course, I want the upside," she says. "But ultimately, I chose this team because I believe in what it's doing."

As it turns out, her faith was rewarded. For although the stock market continued its slump that ominous October day, shares of Women.com soon opened 30% above the offering price. "Everyone let out a huge sigh of relief," says Zornosa. Workers at the company's Foster City, California headquarters watched as the WOMN symbol sped across the stock-market ticker -- from $13 a share to $17, and then to $23! She'd picked a million-dollar horse after all.

By all accounts, Zornosa should have made the millionaire's list years ago. After a meteoric rise to editor at CMP Publishing Inc. and then to associate publisher at Ziff-Davis's PC Magazine, the savvy marketer took a gamble on the future of Internet publishing after being wowed by a demonstration of a new software product called PointCast. She joined PointCast in 1995, just before "push" technology news services became red hot. Venture-capital backers were lining up to invest, as were such suitors as Rupert Murdoch's News Corp., which offered to acquire the company for nearly $400 million. Yet PointCast's board of directors had set its sights on the ultimate payoff: an IPO.

Zornosa, one of PointCast's first 50 employees, played a key role in its early success. As head of sales and affiliate development, she hired scores of workers to help her oversee the service's expanding content, while using her connections in print journalism to recruit partners like Ziff-Davis, Wired magazine, and the Washington Post. When she first joined the company, she had taken a $100,000 pay cut, but the stock options that she eventually accumulated all but assured her that she was in for a jackpot-size payoff.

That is, if it all worked out -- the big "if" of life in the IPO world. Primping the company for the upcoming IPO, the board of directors began searching for a marquee name to fill the CEO spot -- which prompted PointCast's mercurial founder to quit in anger, an act that demoralized the staff and left Zornosa one of three executives in charge of keeping the company afloat in the interim. Meanwhile, PointCast's bulky technology had bogged down customers' computers and corporate networks, leading to a backlash in the market: A growing number of PointCast users were removing the application from their systems.