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process of moving its offices to Santa Monica. Citron should have taken it as a sign.

Glaser was brimming with confidence in November, when he divulged a little of his game plan at a digital-music conference in Los Angeles. By then, RealPlayer had 88 million registered users, and Glaser said there was no reason that more content wouldn't be coming to Real's format from the big labels. Acknowledging that the intellectual-property rights and payment issues were tricky, Glaser nonetheless proclaimed: “We've been making real progress.” Tieless in a gray shirt and glasses, Glaser waved his hands as he painted a future with music streaming and purchases of digital downloads, as soon as the security issues could be worked out. “Imagine a record store open twenty-four hours, with every album ever made, no checkout stand, with instant delivery, that's never out of stock,” Glaser said. “You would think that everyone would be excited about what it would do for the industry.”

Not exactly everyone was, however. Citron made the rounds of the labels in Los Angeles and flew to New York every few weeks, telling record executives that Real was working on a new system—how could they make it worth the labels' while to participate? “Real was on top of the world, and people wanted to learn what we were up to, so they took the meetings,” Citron said. “But there was no urgency to do anything.” In one office or another, Citron would run through the options. “I'd say, ‘What if we charge 50 cents a song?' and they'd say that would undercut the physical product. So I'd say, ‘Well, how about a dollar?' and they'd say there would be piracy if it cost that much. Every time you answered a concern, they would come up with another one.”

Citron was used to dealing with irascible entertainment executives, but he was still unprepared for the hostility he encountered on some of his trips. Al Smith, a top Sony executive he dealt with in New York, often came across as sweet and grandfatherly. But he was also a husky six-foot-three and a buddy of Sony's U.S. music chairman Tommy Mottola, an old-school record executive from Brooklyn who had once been on the brink of co-owning a label with Network independent promoter Fred DiSipio. That deal had been scotched in 1986, after NBC reported that DiSipio and a close associate, promoter Joe Isgro, had just met with John Gotti and other top mobsters at a New York hotel. Smith had his hard