Steve Jobs

did Real and Pressplay and MusicNet and basically everyone else,” he wrote. “Now that Jobs has done it we need to move fast to get something where the user interface and Rights are as good. . . . I think we need some plan to prove that, even though Jobs has us a bit flat footed again, we can move quick and both match and do stuff better.” It was an astonishing private admission: Microsoft had again been caught flat-footed, and it would again try to catch up by copying Apple. But like Sony, Microsoft could never make it happen, even after Jobs showed the way.
    Instead Apple continued to smoke Microsoft in the way that Cole had predicted: It ported the iTunes software and store to Windows. But that took some internal agonizing. First, Jobs and his team had to decide whether they wanted the iPod to work with Windows computers. Jobs was initially opposed. “By keeping the iPod for Mac only, it was driving the sales of Macs even more than we expected,” he recalled.But lined up against him were all four of his top executives: Schiller, Rubinstein, Robbin, and Fadell. It was an argument about what the future of Apple should be. “We felt we should be in the music player business, not just in the Mac business,” said Schiller.
    Jobs always wanted Apple to create its own unified utopia, a magical walled garden where hardware and software and peripheral devices worked well together to create a great experience, and where the success of one product drove sales of all the companions. Now he was facing pressure to have his hottest new product work with Windows machines, and it went against his nature. “It was a really big argument for months,” Jobs recalled, “me against everyone else.” At one point he declared that Windows users would get to use iPods “over my dead body.” But still his team kept pushing. “This
needs
to get to the PC,” said Fadell.
    Finally Jobs declared, “Until you can prove to me that it will make business sense, I’m not going to do it.” That was actually his way of backing down. If you put aside emotion and dogma, it was easy to prove that it made business sense to allow Windows users to buy iPods. Experts were called in, sales scenarios developed, and everyone concluded this would bring in more profits. “We developed a spreadsheet,” said Schiller. “Under all scenarios, there was no amount of cannibalization of Mac sales that would outweigh the sales of iPods.” Jobs was sometimes willing to surrender, despite his reputation, but he never won any awards for gracious concession speeches. “Screw it,” he said at one meeting where they showed him the analysis. “I’m sick of listening to you assholes. Go do whatever the hell you want.”
    That left another question: When Apple allowed the iPod to be compatible with Windows machines, should it also create a version of iTunes to serve as the music-management software for those Windows users? As usual, Jobs believed the hardware and software should go together: The user experience depended on the iPod working in complete sync (so to speak) with iTunes software on the computer. Schiller was opposed. “I thought that was crazy, since we don’t make Windows software,” Schiller recalled. “But Steve kept arguing, ‘If we’re going to do it, we should do it right.’”
    Schiller prevailed at first. Apple decided to allow the iPod to workwith Windows by using software from MusicMatch, an outside company. But the software was so clunky that it proved Jobs’s point, and Apple embarked on a fast-track effort to produce iTunes for Windows. Jobs recalled:
To make the iPod work on PCs, we initially partnered with another company that had a jukebox, gave them the secret sauce to connect to the iPod, and they did a crappy job. That was the worst of all worlds, because this other company was controlling a big piece of the user experience. So we lived with this crappy outside jukebox for about six months, and then we finally got iTunes written for Windows. In the end, you just don’t want someone else to control a big part of the user experience. People may disagree with me, but I am pretty consistent about that.
     
    Porting iTunes to Windows meant going back to all of the music companies—which had made deals to be in iTunes based on the assurance that it would be for only the small universe of Macintosh users—and negotiate again. Sony was especially resistant. Andy Lack thought it another example of Jobs changing the terms