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Sean Parker…With a Little Help From His Friends

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At 19, Sean Parker helped create Napster. At 24, he was founding president of Facebook. At 30, he’s the hard-partying, press-shy genius of social networking, a budding billionaire, and about to be famous—played by Justin Timberlake in David Fincher’s new film, The Social Network.

Sean Parker was sitting in World Civilization class at his Virginia high school when someone brought him a note. His father, it read, was waiting to take him to an orthodontist appointment. A chill ran down Parker’s spine. He didn’t have an orthodontist. When he got outside, his father angrily whisked him into the family minivan. When they arrived at their modest suburban house, a team of F.B.I. agents was toting papers and a desktop computer out of Sean’s room.

Within a few short years, Parker went from apprehended 16-year-old hacker—he had managed to break into the computer networks of numerous multi-national corporations and even military databases—to world-class Internet entrepreneur. In 1999 he became rather notorious, at 19, for helping an even younger teenager named Shawn Fanning create Napster. That free song-sharing service upended the music industry. More recently, Parker played an indispensable role as the founding president of Facebook, the mammoth social-networking site where 500 million people now spend 700 billion minutes a month. Had he not joined founder Mark Zuckerberg in Palo Alto in the summer of 2004, when the fledgling Facebook was just five months old, the service almost certainly would not be the colossus it is today.

Parker is widely considered a Web oracle; more than a few acquaintances and colleagues use the word “genius” to describe him. He understands not only computers and Web networks but also how people want to incorporate them into their lives. As a result, he’s been stunningly successful. That said, he has a libertine side. Parker has a knack for missing deadlines and appointments, for disappearing for weeks on end, for avoiding the press. (His decision to cooperate with a Vanity Fair profile is unprecedented and rather out of character.) He was pushed out of Facebook after an arrest for cocaine possession in 2005. (No charges were filed.) Even among his many supporters, he has a reputation for being an erratic party animal.

Now he is about to achieve a new level of fame, as one of the main subjects of the highly anticipated film The Social Network. In theaters this month, the movie purports to tell the story of Facebook’s first year, partly by focusing on a darker side of Parker’s persona. Justin Timberlake plays a suave, conniving Parker, who both in the movie and in reality was Zuckerberg’s main mentor during Facebook’s crucial early days. But as crafted by screenwriter Aaron Sorkin, Parker comes across as a pushy, greedy—and, yes, visionary—schemer. “A million dollars isn’t cool,” Parker says at one point in the movie. “You know what’s cool? A billion dollars.” Zuckerberg, played by Jesse Eisenberg (see page 189), comes across as cocky, angry, and somewhat sex-obsessed.

The real Parker is both more complex and more interesting, despite the considerable skills of Sorkin and director David Fincher. In fact, Parker, a svelte, wavy-maned clotheshorse, is a uniquely quirky figure in the annals of 21st-century business. At age 30, he is already worth close to a billion dollars, thanks mostly to the cache of Facebook stock he still owns. An autodidact who barely finished high school, he is nonetheless almost painfully cerebral. A sickly child whose asthma sometimes landed him in the hospital, he devoured books from a very young age; his father, a U.S.-government oceanographer, began teaching him programming at age seven. There is hardly a topic—literary, political, medical, or technological—about which he cannot offer an informed and nuanced opinion in his rapid-fire patter. (Don’t get him started on Ben Franklin’s role as a media pioneer.)

Most of all, he turns his knowledge and instincts toward Internet business strategy as a way, he says, of “re-architecting society. It’s technology, not business or government, that’s the real driving force behind large-scale societal shifts.” Indeed, Parker has such a superb track record for predicting where technology is headed (and which type of product and service will appeal to consumers) that companies often invite him to invest simply to tap his brain. “Few people are as smart as he is,” says Facebook’s Zuckerberg, aged 26, who still consults quite frequently with his former partner.

But, for all his Web-world savvy, Parker at times seems just as drawn to recreational indulgence. His is the life of programmer-as-rock-star—often spent among real-life rock stars—with the lifestyle that that implies. He routinely stays up very, very late, talking intensely about subjects he cares about and/or partying—and sleeps in much of the following day. Says San Francisco tech investor Ron Conway, a longtime friend, “The fact that Sean is so scattered yet so brilliant is something you just don’t see often. He’ll probably start another five really significant life-changing companies before he’s through.”

Parker’s high-school hacking bust seems itself cinematic: a down-home version of a Matthew Broderick scene from WarGames. The teenager had been sitting in the family den, all night, drilling deeply into the bowels of a Fortune 500 company, which he refuses to name. Back then he had a hobby, he says, of hacking into different sorts of organizations, keeping a file of .com, .edu, .mil, and .gov Internet domains he had penetrated in various countries around the world. His goal was to break into one of each type in a laundry list of countries. He claims that once inside he usually alerted the system administrator—from his or her own e-mail—to vulnerabilities he had discovered.

Unfortunately, after this particular night, his father came downstairs at five A.M. Parker had been performing erratically in high school—sometimes pulling A’s but just as often simply refusing to work, and nearly failing. It was all deliberate, he claims. “I had a desire to prove to myself that I was actually in control—that I wasn’t a puppet,” he says. “I didn’t want to kowtow to the system.” Seeing his son hunched over his terminal, Parker’s father, outraged, apparently had a vision of yet another lost day at school. “So,” recalls Parker, “he grabbed the keyboard from my hands, ripped it out of the computer, and took it upstairs. I started crying and saying, ‘Dad! You don’t know what you’re doing! I have to log out!’ But he didn’t let me.” Unable to cover his tracks, Sean Parker’s dalliances were exposed, his location identified by tracking him through his Internet-service provider. In the end, as a minor, he was sentenced only to community service.

But one aspect of this story may help elucidate Parker’s subsequent attitudes toward rebellion. He performed his court-ordered duties at a library with other teenage offenders. There he met a girl whom he describes as a “punk-rock princess.” One day she wrote her phone number on Parker’s hand—in ballpoint pen, he remembers fondly—and a few months later, he says, “I lost my virginity to her.” He explains: “I thought it was an incredible cosmic irony. This was the most romantic experience of my life and I met her because I’d been raided by the F.B.I.”

Around the same time, Parker made the online acquaintance of 15-year-old Shawn Fanning, another talented hacker. Fanning recalls their first conversation. “Right away we were talking about things like theoretical physics. We realized we had a lot in common.” Along with a couple of buddies, the pair soon launched an Internet-security firm called Crosswalk, offering to advise companies that might otherwise have been their targets. It didn’t succeed. Parker, meanwhile, began working as a programmer at a major Internet company near his Virginia home, receiving academic credit during his senior year.

Against his parents’ wishes, Parker decided not to apply to college, and when Fanning told him about his plan to create Napster, he immediately asked to get involved, becoming a co-founder and contributing key ideas. He picked up and moved to San Francisco, having never before spent any time away from home, says his mother, Diane, a TV-advertising broker.

In its first year, the music file-sharing network gained tens of millions of enthusiasts. Parker soon became a habitué of nightclubs and raves. But in the process Napster drew the wrath of record companies, which launched an all-out legal assault. Within 14 months, a federal judge would order Napster to stop allowing users to download copyrighted material. E-mails that Parker had written, blithely discussing the likelihood that users were breaking the law, were enlarged and displayed in open court by industry attorneys. Though an appeals judge let the service keep operating, it was the beginning of Napster’s long, slow death. Parker himself was pushed out by Fanning’s more elderly partners. Thus began a cycle of vertiginous triumph followed by humiliating failure.

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