called Harmony. He had attempted to convince Jobs to license Apple’s FairPlay format to Harmony, but when that didn’t happen, Glaser just reverse-engineered it and used it with the songs that Harmony sold. Glaser’s strategy was that the songs sold by Harmony would play on any device, including an iPod or a Zune or a Rio, and he launched a marketing campaign with the slogan “Freedom of Choice.” Jobs was furious and issued a release saying that Apple was “stunned that RealNetworks has adopted the tactics and ethics of a hacker to break into the iPod.” RealNetworks responded by launching an Internet petition that demanded “Hey Apple! Don’t break my iPod.” Jobs kept quiet for a few months, but in October he released a new version of the iPod software that caused songs bought through Harmony to become inoperable. “Steve is a one-of-a-kind guy,” Glaser said. “You know that about him when you do business with him.”

In the meantime Jobs and his team—Rubinstein, Fadell, Robbin, Ive—were able to keep coming up with new versions of the iPod that extended Apple’s lead. The first major revision, announced in January 2004, was the iPod Mini. Far smaller than the original iPod—just the size of a business card—it had less capacity and was about the same price. At one point Jobs decided to kill it, not seeing why anyone would want to pay the same for less. “He doesn’t do sports, so he didn’t relate to how it would be great on a run or in the gym,” said Fadell. In fact the Mini was what truly launched the iPod to market dominance, by eliminating the competition from smaller flash-drive players. In the eighteen months after it was introduced, Apple’s market share in the portable music player market shot from 31% to 74%.

The iPod Shuffle, introduced in January 2005, was even more revolutionary. Jobs learned that the shuffle feature on the iPod, which played songs in random order, had become very popular. People liked to be surprised, and they were also too lazy to keep setting up and revising their playlists. Some users even became obsessed with figuring out whether the song selection was truly random, and if so, why their iPod kept coming back to, say, the Neville Brothers. That feature led to the iPod Shuffle. As Rubinstein and Fadell were working on creating a flash player that was small and inexpensive, they kept doing things like making the screen tinier. At one point Jobs came in with a crazy suggestion: Get rid of the screen altogether. “What?!?” Fadell responded. “Just get rid of it,” Jobs insisted. Fadell asked how users would navigate the songs. Jobs’s insight was that you wouldn’t need to navigate; the songs would play randomly. After all, they were songs you had chosen. All that was needed was a button to skip over a song if you weren’t in the mood for it. “Embrace uncertainty,” the ads read.

As competitors stumbled and Apple continued to innovate, music became a larger part of Apple’s business. In January 2007 iPod sales were half of Apple’s revenues. The device also added luster to the Apple brand. But an even bigger success was the iTunes Store. Having sold one million songs in the first six days after it was introduced in April 2003, the store went on to sell seventy million songs in its first year. In February 2006 the store sold its one billionth song when Alex Ostrovsky, sixteen, of West Bloomfield, Michigan, bought Coldplay’s “Speed of Sound” and got a congratulatory call from Jobs, bestowing upon him ten iPods, an iMac, and a $10,000 music gift certificate.

The success of the iTunes Store also had a more subtle benefit. By 2011 an important new business had emerged: being the service that people trusted with their online identity and payment information. Along with Amazon, Visa, PayPal, American Express, and a few other services, Apple had built up databases of people who trusted them with their email address and credit card information to facilitate safe and easy shopping. This allowed Apple to sell, for example, a magazine subscription through its online store; when that happened, Apple, not the magazine publisher, would have a direct relationship with the subscriber. As the iTunes Store sold videos, apps, and subscriptions, it built up a database of 225 million active users by June 2011, which positioned Apple for the next age of digital commerce.

CHAPTER THIRTY-TWO

MUSIC MAN The Sound Track of His Life Jimmy Iovine, Bono, Jobs, and The Edge, 2004

On His iPod

As the iPod phenomenon grew, it spawned a question that was asked of presidential candidates, B-list celebrities, first dates, the queen of England, and just about anyone else with white earbuds: “What’s on your iPod?” The parlor game took off when Elisabeth Bumiller wrote a piece in the New York Times in early 2005 dissecting the answer that President George W. Bush gave when she asked him that question. “Bush’s iPod is heavy on traditional country singers,” she reported. “He has selections by Van Morrison, whose ‘Brown Eyed Girl’ is a Bush favorite, and by John Fogerty, most predictably ‘Centerfield.’” She got a Rolling Stone editor, Joe Levy, to analyze the selection, and he commented, “One thing that’s interesting is that the president likes artists who don’t like him.”

“Simply handing over your iPod to a friend, your blind date, or the total stranger sitting next to you on the plane opens you up like a book,” Steven Levy wrote in The Perfect Thing. “All somebody needs to do is scroll through your library on that click wheel, and, musically speaking, you’re naked. It’s not just what you like—it’s who you are.” So one day, when we were sitting in his living room listening to music, I asked Jobs to let me see his. As we sat there, he flicked through his favorite songs.

Not surprisingly, there were all six volumes of Dylan’s bootleg series, including the tracks Jobs had first started worshipping when he and Wozniak were able to score them on reel-to-reel tapes years before the series was officially released. In addition, there were fifteen other Dylan albums, starting with his first, Bob Dylan (1962), but going only up to Oh Mercy (1989). Jobs had spent a lot of time arguing with Andy Hertzfeld and others that Dylan’s subsequent albums, indeed any of his albums after Blood on the Tracks (1975), were not as powerful as his early performances. The one exception he made was Dylan’s track “Things Have Changed” from the 2000 movie Wonder Boys. Notably his iPod did not include Empire Burlesque (1985), the album that Hertzfeld had brought him the weekend he was ousted from Apple.

The other great trove on his iPod was the Beatles. He included songs from seven of their albums: A Hard Day’s Night, Abbey Road, Help!, Let It Be, Magical Mystery Tour, Meet the Beatles! and Sgt. Pepper’s Lonely Hearts Club Band. The solo albums missed the cut. The Rolling Stones clocked in next, with six albums: Emotional Rescue, Flashpoint, Jump Back, Some Girls, Sticky Fingers, and Tattoo You. In the case of the Dylan and the Beatles albums, most were included in their entirety. But true to his belief that albums can and should be disaggregated, those of the Stones and most other artists on his iPod included only three or four cuts. His onetime girlfriend Joan Baez was amply represented by selections from four albums, including two different versions of “Love Is Just a Four-Letter Word.”

His iPod selections were those of a kid from the seventies with his heart in the sixties. There were Aretha, B. B. King, Buddy Holly, Buffalo Springfield, Don McLean, Donovan, the Doors, Janis Joplin, Jefferson Airplane, Jimi Hendrix, Johnny Cash, John Mellencamp, Simon and Garfunkel, and even The Monkees (“I’m a Believer”) and Sam the Sham (“Wooly Bully”). Only about a quarter of the songs were from more contemporary artists, such as 10,000 Maniacs, Alicia Keys, Black Eyed Peas, Coldplay, Dido, Green Day, John Mayer (a friend of both his and Apple), Moby (likewise), U2, Seal, and Talking Heads. As for classical music, there were a few recordings of Bach, including the Brandenburg Concertos, and three albums by Yo-Yo Ma.

Jobs told Sheryl Crow in May 2003 that he was downloading some Eminem tracks, admitting, “He’s starting to grow on me.” James Vincent subsequently took him to an Eminem concert. Even so, the rapper missed making it onto Jobs’s iPod. As Jobs said to Vincent after the concert, “I don’t know . . .” He later told me, “I respect Eminem as an artist, but I just don’t want to listen to his music, and I can’t relate to his values the way I can to Dylan’s.”

His favorites did not change over the years. When the iPad 2 came out in March 2011, he transferred his favorite music to it. One afternoon we sat in his living room as he scrolled through the songs on his new iPad and,

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