David Blech1992: $295 MLNIn 1990, he launched D Blech & Co. By 1994 it collapsed. He is now beginning to serve a four-year sentence in federal prison for manipulating stock prices.
Walter Alessandrini2000: $770 MLNHe joined fibre-optic equipment maker Avanex as CEO 11 months before it went public. Soon it was trading at nearly 200 times revenue.
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John Chambers2000: $1 BLNHe joined Cisco Systems in 1991 has been CEO since 1995. The year he made the 400, 80 percent of all internet traffic passed through Cisco routers. Michael Novogratz2007: $1.5 BLNHe was one of a group that took Fortress Investment Group public at $18.50 a share. As the stock hit $35 on its first day, the five of them became billionaires. Mark Pincus2011: $2 BLNIn 2011, his company, Zynga, completed the largest IPO in the tech sector since Google it suffered losses after that. He stepped down as CEO in July 2013.
Image: Blech: Robert Caplin / The New York Times / Redux Chambers, Novogratz, Pincus: Getty Images
