Steve Jobs

Perhaps the oddest meeting was when Dr. Dre came to visit Jobs at Apple headquarters. Jobs loved the Beatles and Dylan, but he admitted that the appeal of rap eluded him. Now Jobs needed Eminem and other rappers to agree to be sold in the iTunes Store, so he huddled with Dr. Dre, who was Eminem’s mentor. After Jobs showed him the seamless way the iTunes Store would work with the iPod, Dr. Dre proclaimed, “Man, somebody finally got it right.”

On the other end of the musical taste spectrum was the trumpeter Wynton Marsalis. He was on a West Coast fund-raising tour for Jazz at Lincoln Center and was meeting with Jobs’s wife, Laurene. Jobs insisted that he come over to the house in Palo Alto, and he proceeded to show off iTunes. “What do you want to search for?” he asked Marsalis. Beethoven, the trumpeter replied. “Watch what it can do!” Jobs kept insisting when Marsalis’s attention would wander. “See how the interface works.” Marsalis later recalled, “I don’t care much about computers, and kept telling him so, but he goes on for two hours. He was a man possessed. After a while, I started looking at him and not the computer, because I was so fascinated with his passion.”

Jobs unveiled the iTunes Store on April 28, 2003, at San Francisco’s Moscone Center. With hair now closely cropped and receding, and a studied unshaven look, Jobs paced the stage and described how Napster “demonstrated that the Internet was made for music delivery.” Its offspring, such as Kazaa, he said, offered songs for free. How do you compete with that? To answer that question, he began by describing the downsides of using these free services. The downloads were unreliable and the quality was often bad. “A lot of these songs are encoded by seven-year-olds, and they don’t do a great job.” In addition, there were no previews or album art. Then he added, “Worst of all it’s stealing. It’s best not to mess with karma.”

Why had these piracy sites proliferated, then? Because, Jobs said, there was no alternative. The subscription services, such as Pressplay and MusicNet, “treat you like a criminal,” he said, showing a slide of an inmate in striped prison garb. Then a slide of Bob Dylan came on the screen. “People want to own the music they love.”

After a lot of negotiating with the record companies, he said, “they were willing to do something with us to change the world.” The iTunes Store would start with 200,000 tracks, and it would grow each day. By using the store, he said, you can own your songs, burn them on CDs, be assured of the download quality, get a preview of a song before you download it, and use it with your iMovies and iDVDs to “make the soundtrack of your life.” The price? Just 99 cents, he said, less than a third of what a Starbucks latte cost. Why was it worth it? Because to get the right song from Kazaa took about fifteen minutes, rather than a minute. By spending an hour of your time to save about four dollars, he calculated, “you’re working for under the minimum wage!” And one more thing . . . “With iTunes, it’s not stealing anymore. It’s good karma.”

Clapping the loudest for that line were the heads of the record labels in the front row, including Doug Morris sitting next to Jimmy Iovine, in his usual baseball cap, and the whole crowd from Warner Music. Eddy Cue, who was in charge of the store, predicted that Apple would sell a million songs in six months. Instead the iTunes Store sold a million songs in six days. “This will go down in history as a turning point for the music industry,” Jobs declared.

Microsoft

“We were smoked.”

That was the blunt email sent to four colleagues by Jim Allchin, the Microsoft executive in charge of Windows development, at 5 p.m. the day he saw the iTunes Store. It had only one other line: “How did they get the music companies to go along?”

Later that evening a reply came from David Cole, who was running Microsoft’s online business group. “When Apple brings this to Windows (I assume they won’t make the mistake of not bringing it to Windows), we will really be smoked.” He said that the Windows team needed “to bring this kind of solution to market,” adding, “That will require focus and goal alignment around an end-to-end service which delivers direct user value, something we don’t have today.” Even though Microsoft had its own Internet service (MSN), it was not used to providing end-to-end service the way Apple was.

Bill Gates himself weighed in at 10:46 that night. His subject line, “Apple’s Jobs again,” indicated his frustration. “Steve Jobs’s ability to focus in on a few things that count, get people who get user interface right, and market things as revolutionary are amazing things,” he said. He too expressed surprise that Jobs had been able to convince the music companies to go along with his store. “This is very strange to me. The music companies’ own operations offer a service that is truly unfriendly to the user. Somehow they decide to give Apple the ability to do something pretty good.”

Gates also found it strange that no one else had created a service that allowed people to buy songs rather than subscribe on a monthly basis. “I am not saying this strangeness means we messed up—at least if we did, so 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.