Steve Jobs

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 work with 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 after a deal was done. It was. But by then the other labels were happy about how the iTunes Store was working and went along, so Sony was forced to capitulate.

Jobs announced the launch of iTunes for Windows in October 2003. “Here’s a feature that people thought we’d never add until this happened,” he said, waving his hand at the giant screen behind him. “Hell froze over,” proclaimed the slide. The show included iChat appearances and videos from Mick Jagger, Dr. Dre, and Bono. “It’s a very cool thing for musicians and music,” Bono said of the iPod and iTunes. “That’s why I’m here to kiss the corporate ass. I don’t kiss everybody’s.”

Jobs was never prone to understatement. To the cheers of the crowd, he declared, “iTunes for Windows is probably the best Windows app ever written.”

Microsoft was not grateful. “They’re pursuing the same strategy that they pursued in the PC business, controlling both the hardware and software,” Bill Gates told Business Week. “We’ve always done things a little bit differently than Apple in terms of giving people choice.” It was not until three years later, in November 2006, that Microsoft was finally able to release its own answer to the iPod. It was called the Zune, and it looked like an iPod, though a bit clunkier. Two years later it had achieved a market share of less than 5%. Jobs was brutal about the cause of the Zune’s uninspired design and market weakness:

The older I get, the more I see how much motivations matter. The Zune was crappy because the people at Microsoft don’t really love music or art the way we do. We won because we personally love music. We made the iPod for ourselves, and when you’re doing something for yourself, or your best friend or family, you’re not going to cheese out. If you don’t love something, you’re not going to go the extra mile, work the extra weekend, challenge the status quo as much.

Mr. Tambourine Man

Andy Lack’s first annual meeting at Sony was in April 2003, the same week that Apple launched the iTunes Store. He had been made head of the music division four months earlier, and had spent much of that time negotiating with Jobs. In fact he arrived in Tokyo directly from Cupertino, carrying the latest version of the iPod and a description of the iTunes Store. In front of the two hundred managers gathered, he pulled the iPod out of his pocket. “Here it is,” he said as CEO Nobuyuki Idei and Sony’s North America head Howard Stringer looked on. “Here’s the Walkman killer. There’s no mystery meat. The reason you bought a music company is so that you could be the one to make a device like this. You can do better.”

But Sony couldn’t. It had pioneered portable music with the Walkman, it had a great record company, and it had a long history of making beautiful consumer devices. It had all of the assets to compete with Jobs’s strategy of integration of hardware, software, devices, and content sales. Why did it fail? Partly because it was a company, like AOL Time Warner, that was organized into divisions (that word itself was ominous) with their own bottom lines; the goal of achieving synergy in such companies by prodding the divisions to work together was usually elusive.

Jobs did not organize Apple into semiautonomous divisions; he closely controlled all of his teams and pushed them to work as one cohesive and flexible company, with one profit-and-loss bottom line. “We don’t have ‘divisions’ with their own P&L,” said Tim Cook. “We run one P&L for the company.”

In addition, like many companies, Sony worried about cannibalization. If it built a music player and service that made it easy for people to share digital songs, that might hurt sales of its record division. One of Jobs’s business rules was to never be afraid of cannibalizing yourself. “If you don’t cannibalize yourself, someone else will,” he said. So even though an iPhone might cannibalize sales of an iPod, or an iPad might cannibalize sales of a laptop, that did not deter him.

That July, Sony appointed a veteran of the music industry, Jay Samit, to create its own iTunes-like service, called Sony Connect, which would sell songs online and allow them to play on Sony’s portable music devices. “The move was immediately understood as a way to unite the sometimes conflicting electronics and content divisions,” the New York Times reported. “That internal battle was seen by many as the reason Sony, the inventor of the Walkman and the biggest player in the portable audio market, was being trounced by Apple.” Sony Connect launched in May 2004. It lasted just over three years before Sony shut it down.