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FortuneCity had gone public at a time when investors didn't care about profit. Even though the company was losing money, it had raised nearly $100 million in an IPO. Like TheGlobe.com, FortuneCity offered users free homepages on the Web. It had added other services as well, including places for users to store digital music in private or public libraries. So there was some logic behind Macnee considering putting the company's money, or its high-flying stock, into Napster. In late 1999, Macnee fielded separate calls from both Fanning and Bales. Fanning "was being very coy," Macnee said. "He said everyone and their brother wanted to invest, and he was going to be very choosy." Bales was more persistent, calling repeatedly and coming to meet Macnee in New York. Bales went over Napster's prospects and confidently predicted that the company would win in court. "Bales struck me to be, for his times, a very shrewd entrepreneur," Macnee said later, "but sort of made for the time: a wheeler and dealer made for the up market." Bales never offered Macnee a job, "but I sensed him recruiting me. It was clear he had no love for Eileen," he said.

Macnee was interested enough to fly out to San Mateo, where he met Richardson, technology chief Eddie Kessler, and, briefly, Shawn, who was wearing a black Napster baseball cap. Macnee wasn't impressed by Richardson, who was "all over the map," he said. Later, Macnee checked with his firm's lawyers and a former RIAA executive to get their take on the lawsuit. He came away thinking there was a much greater risk of Napster losing than its executives let on. He asked if the company would indemnify FortuneCity if the firm invested and Napster lost in court, and they told him no. That turned out to be the deal breaker. "For us to take on a legal battle like that would have been nuts. We just said, 'Let's stick to what we know about,'" Macnee said.

Another CEO candidate, Ernst & Young technology strategist Yobie Benjamin, wasn't deterred by Bales, Richardson, or even the legal dilemma. He was gung ho through all the interviews until he spoke by phone with John Fanning. When Benjamin asked Fanning about the financial might of Napster's enemies, Fanning told him: "I'm going to buy Universal. I'm going to buy Disney." Benjamin came to his senses and dropped out of contention for the job. "It was a total megalomaniac view of the world," Benjamin said. "This will be the ultimate business school