The desire to create a portable digital music player arose directly from the development of iTunes: as more and more Apple execs and engineers started listening to MP3s on their computers, it was only a matter of time before they wanted to take their digital music with them in some sort of portable digital version of the old Sony Walkman. The few pocket-sized MP3 players on the market were poorly designed and clumsy to use. It wasn’t so much that the sound was bad, but instead that the procedures for loading them with music and then finding what you wanted to hear were hopelessly opaque. Steve was proud of iTunes, and especially of how easy it made it for someone to organize and manage large libraries of recorded music. Not one of the existing devices could make the most of his nifty piece of software.

The only solution, the team decided, would be for Apple itself to make something better. It was a gambit that would push the company further out of its comfort zone: the only mass-market consumer electronics product it had ever manufactured was a long-forgotten Apple-branded digital still camera from the Sculley years. Steve himself had been involved in nothing like this since the illegal “blue box” long-distance telephone dialer he and Woz built and sold back in the 1970s. Computers were Apple’s focus and raison d’être. But this group was starting to function at such a high level that they welcomed the challenge of making a new kind of device. And none of them thought a portable music player alone would be transformative, so it seemed like a low-risk gamble. The terminology they used suggested the limits of their ambitions: many of them saw a music player primarily as a “computer peripheral,” like a printer or a Wi-Fi router.

As the head of hardware engineering, Jon Rubinstein always kept his eyes open for new electronic components—processors, disk drives, memory chips, graphics technologies—that might pique Steve’s interest or give Apple a competitive edge. In late 2000, during a trip to Japan, Ruby stopped by Toshiba, the electronic giant that, among other things, made hard drives for personal computers. The Toshiba engineers told Ruby that they wanted to show him the next “big” thing in laptop hard drives—the prototype of a miniature, 5-gigabyte disk drive that wasn’t even two inches in diameter. It could fit into a cigarette pack with plenty of room to spare, and yet was capacious enough to hold thousands of digital files, whether these were images, documents, or, say, songs. Ruby couldn’t believe his eyes. This was the first thing he’d seen that had enough capacity at a small enough size to form the heart of an Apple music player. Unlike the tapes or CDs that you played in Sony’s Walkman or Discman, this hard drive would have enough disk storage to hold copies of perhaps a thousand tracks, rather than just a dozen. And its “random access” capabilities distanced it even more from the likes of a Discman, since it gave you the potential to find a particular song out of that enormous trove almost instantly.

In January 2001, Ruby asked some former Newton engineers to begin work in earnest on some sort of portable audio device around the Toshiba micro-drive. In March he put an engineer he’d hired from Philips NV, Tony Fadell, in charge of the group. Fadell, an energetic entrepreneur with the build of a college wrestler and the intensity of a high school football coach, had worked at General Magic back in the early 1990s, with Bill Atkinson, Andy Hertzfeld, and Susan Kare, veterans of the original Macintosh team, who had told him horror stories about Steve in his early days. “I expected an overbearing tyrant,” he says, “but he wasn’t like that at all. He didn’t resemble the guy from their stories at all. On the things he cared about he could be very intense, but in general, he was much softer, much more considerate. He wasn’t a crazy micromanager. He trusted his guys.”

No one had any idea what the end product would look like, or how users would control it, or how much it would have to function like a tiny computer itself, or how exactly it would interact with iTunes song libraries on the iMac, or even when it possibly could be shipped. All they knew were the basic requirements: that it would somehow pack the tiny hard drive, an audio amplifier powerful enough to drive headphones, a small screen to display and navigate through the music it contained, a microprocessor or microcontroller to give it enough smarts, software to make it programmable and to help it interact directly with iTunes, and a high-speed FireWire port to let it mate via a cable with a Macintosh, in the space of something that you could easily slip into a front pocket of your Levi’s. Of course it had to look cool and of course Steve wanted it as soon as possible.

In this way, Steve had not changed at all: he still presented his team with outrageous goals that seemed impossibly out of reach. But there were two things that had changed, things that improved the odds that his team could live up to his stretch targets. Steve himself was more willing to reshape his goals as the development process revealed either limitations or new opportunities. And the group he had assembled was the most talented collection of people he had ever worked with, a naturally ambitious crew that knew that Steve encouraged their spirit of constant inquisitiveness and willingness to push boundaries. “What I loved about working for Steve,” says Cue, “is that you learned that you could accomplish the impossible. Again and again.”

Another reason that Steve felt confident that Apple could create a great consumer device was that a successful music player could only be the result of a holistic mix of great hardware and software. The iPod was truly a “whole widget” challenge, as Steve described it. With a crash schedule in hand, Fadell led the group building the iPod, but contributions came from everyone on the executive team, as well as from engineers who worked elsewhere in the company. Turning Ruby’s Toshiba microdrive into the heart of a pocket-sized piece of functioning hardware was not, by any means, the biggest challenge. The hard part was creating a usable device, one that would make those thousand tracks accessible with a click or two of a switch, and that would pair simply and directly with a Mac so its owner could import copies of his iTunes digital music files, along with his custom playlists. It also would be nice to be able to display some information about each track and to take full advantage of iTunes’ ability to sort them by artist, album title, and even genre. To make all that happen, the music player would need enough smarts to host a rudimentary computer database program. The iPod, in other words, would actually be a tiny, specialpurpose computer.

But that was just the beginning. Out of all the various aspects of computing, Steve was always most fascinated with the contact point between a person and a computer. It was the user interface that had made the Macintosh seem the epitome of a personal computer in its time. There were good reasons that Steve found this point of interaction so critical. If the point at which a person interacted with a machine was complicated, he or she would likely never unlock its secrets. Most people don’t care about the innards of their computer—they care only about what’s on the screen, and what they can get to through that screen. Steve understood the profound importance of this from the very beginning of his career. It was part of what distinguished him from so many other computer makers, most of whom were engineers who believed that a rational customer would of course care deeply about the insides of his or her computer. This bias held true nearly two decades after the introduction of Mac. So if Apple could make its portable music device a cinch to interact with, users would revel in portable, programmable music in a way they’d never imagined possible. If Apple couldn’t do so, its machine would be a clunker like all the rest.