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new company she might be interested in. “It’s called Napster,” he said. “Go check it out.” When she went home, Richardson logged on to Napster’s site. “This is the most unbelievable thing I’ve ever seen,” she said aloud. If a company had been designed from inception to press all of Richardson’s buttons, it would have been Napster. An intense music fan, she had attended house-music shows and other concert festivals overseas and had been depressed to find little she liked as much when she returned to American record stores and radio. A single mother of two children, she couldn’t go out to smoky clubs every night looking for new acts. And much of her career had been spent in musical backwaters where she couldn’t have found what she wanted to hear even if she had stuck the kids with a sitter. Then, as a venture capitalist in Boston, Richardson had supported Firefly, which recommended new music to listeners based on what they and others with similar tastes liked already. The firm was later sold to Microsoft, and while it was not the biggest financial win of Richardson’s career, it was still the one she felt most passionate about.

If Firefly was a Zagat guide to music, Napster was Waiters on Wheels. It would bring nearly any dish you wanted from anywhere to your home, and it was free. Suddenly, just by downloading one program, Richardson could find thousands of songs to sample. She told Amram she wanted in, and he hired her for a six-month term. She was the first and only candidate he interviewed. Asked later why he picked Richardson for the job, Amram gave his familiar refrain: “I didn’t have a lot of time.” But he added that Richardson had “a lot of enthusiasm and passion for the business.” Besides, he said, “the first task was building a management team and raising money. She had done that, and she was plugged into the VC community.”

Richardson was a good choice for a more esoteric reason as well. With her warm and engaging personal style, she came across as far younger than her thirty-eight years. Yet she was fluent in the financial language of the Valley. The combination made her a near-perfect safari guide to bring the wide-eyed teenagers toward the billionaire VCs they would soon need to approach. “Eileen was a good person to have as a first CEO,” Shawn said. “We got along really well. She was easy to interact with, kind of energetic, and kind of experienced in areas we were not. She seemed to enjoy the time as much as we did.”

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