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Richardson had weaknesses, though they were less pronounced than Fanning’s style of blustery confrontation and Amram’s attempts to catch up with the speed of light. One obvious shortcoming was her lack of management experience. She also had a habit of failing to focus methodically on the task at hand. And she could get overinvolved emotionally with the firms she invested in and those that worked there. “Either you love her or you hate her,” said her sometime adviser, sometime employer, sometime backer and sometime boyfriend, John Lee.

Besides her immediate and intense attraction to Napster’s technology and her own career ambitions, Richardson had a personal reason for wanting to take on her first CEO job. That reason was Lee, her on-again, off-again romantic partner. Lee was the CEO of the purported coffee company, which would soon emerge under its real name, Xtime. Even though the two were in an off period in their romance, they remained close, and Richardson had agreed to help Lee by serving as a vice president at Xtime Inc. Lee loved being an Internet CEO, which at the time struck many as the most desirable job in the world. Richardson, though, thought Lee was getting a little full of himself. She didn’t feel she had much left to prove, having been a successful VC for years, but she was tempted to show him up close that she could run her own company, then have it run circles around his.

A lot of their mutual friends thought Richardson and Lee would one day get hitched. It was her most serious relationship since her marriage, which had ended in the late 1980s. No matter how many times the stormy duet had broken up, they always returned to one another. The problem, as Richardson saw it, was that they were too much alike. “We were both used to being the dominant person in a relationship,” she said. Other friends questioned the wisdom of her getting involved at Xtime, thinking it was poor judgment to work for her ex. Their relationship had hurt her professionally once before, and in time it would prove a distraction at Napster. But Richardson had never done things the conventional way.

SILICON VALLEY VENTURE CAPITALISTS come from an extraordinary array of backgrounds. Before the industry was nearly taken over by amateurs in

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