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that had potential if you could make it work for everybody, including the record industry. Barry wanted to try right away to sell a deal to the labels. But he didn’t plan on being too generous, because he was in the minority that truly believed Napster would win in court. When it did, he reasoned, it could drive a much harder bargain. If it lost the case before a deal was reached—well, that would be that. The assumption was that if Napster lost the case, there wouldn’t be any business.

Hummer Winblad naturally deferred on the legal question to Barry, its in-house expert. For Barry, the investment was a serious break from his past representing copyright holders. And it was a slap in the face to one technology client in particular, Silicon Valley firm Liquid Audio, which made software for streaming authorized music to listeners. At Wilson Sonsini, Barry had helped Liquid Audio go public. And the venture firm that had backed it was none other than Hummer Winblad. Before Barry made the final decision on Napster, he called Liquid Audio chief Gerry Kearby as a courtesy. What happened in that call is a matter of dispute. “I said, ‘I think it’s a really bad idea,’” Kearby recalled. “It screwed the musicians. He didn’t care. He was fully erect.” Asked if Kearby had indeed advised him against Napster, Barry first said he didn’t recall that. Then, in ascending order, he said Kearby’s version was counterfactual, made up, and a lie.

Whatever the reasons, Barry decided to take a huge gamble on Napster as the investment’s leader, a company director, and the next interim CEO, a job that he told his wife would last six weeks. Most of his previous colleagues, while impressed with his legal acumen and work habits, didn’t see him as well-suited for a job as the visionary leader of a chaotic revolution. But Barry didn’t mind making a splash. “He thought the current laws shouldn’t apply to new technologies, and that maybe an adjustment should be made,” a former colleague said. “When he believes in something, he would go all out. A lot of things Hank does, he does in a big way.”

The rest of Hummer Winblad had another motivation for approving Barry’s decision on Napster. Whether one viewed the risks as insurmountable or merely enormous, it was clear that if Napster won in court,

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