"So, what inspired you to write 'Sexyback'?"
That's how Jimmy Fallon began his interview with Sean Parker at the NExTWORK conference. Played by Justin Timberlake in the film The Social Network, the real Sean Parker has seen some incredible highs and some dismal lows during his life. But throughout, he's been balanced on the cutting edge of the Internet, not only as the first president of Facebook, but also as an early employee at controversial peer-to-peer file-sharing network Napster and as a co-founder of up-and-coming streaming music service Spotify.
"I sort of failed systematically at least in terms of my own goals," Parker told Fallon of his history in the industry, "but somehow failure has transformed into a weird kind of success."
Parker, who was busted by the F.B.I. for running successful corporate hacks as a teenager, spoke of his early days, classifying himself as a "grey hat" hacker. While white hats are "computer security professionals," Parker said that grey hat and black hat hackers are a more troublesome bunch.
"Grey hats are mischief makers who think they're really doing good but they're not," he said. "You learn that when the F.B.I. shows up on your doorstep. Black hats, they're the ones you watch out for, they're the ones who are out to destroy. I knew some of those guys; they were sociopaths."
Work at Napster soon followed, but seemingly led to a dead end when the company became the bane of the music industry and resulted in huge lawsuits for everyone involved.
"Napster was not a commercial success," he said. "There was a time I was quite afraid if I made any money it'd be an incentive for record labels to resume litigation against me, so I lived under this dark cloud."
After Napster, Parker said that he could "easily have been a one hit wonder and drifted off into obscurity," but instead forged on, trying to build a consumer product. But the industry at the time was not interested in what Parker had to offer. Until the PayPal IPO in 2002, Parker was forced to live a vagrant sort of life, "sleeping on couches," and setting up rules "about how long I'd freeload off of any one individual."
His big project today is Spotify, a music streaming service that has had huge success in Europe, but has been held up in the U.S. because of licensing deals. Parker, who spoke lovingly about the service, believes that Spotify will make it to America. He touted Spotify's ability to let you see friends' music collections via Facebook, and to see what they're playing in real-time.
"It's really, really, really cool," he said, calling it, "the realization of the dream we had with Napster."
He was not, however, impressed with Apple's upcoming iCloud service, which will let users access their iTunes music collections (among other files) from compatible portable devices and PCs.
"iCloud is like a feature, just not that significant," he said. "All you do is upload music to the cloud and then it's there. I don't know why anyone would do that. I don't get it."
To Parker, "different mediums should be monetized in different ways," because "consumption patterns are completely different."
"With music," he went on to say, "you're listening to the same songs over and over you're building playlists, you're constantly exploring and then going back and revisiting your old favorites," he said. "It's a whole different consumption pattern."
Despite Facebook's huge dominance today, Parker does not believe that it will be the last word in social networking.
"Facebook is definitely not the endgame," he said. "It would be incredibly presumptuous and self serving to think Facebook was the end of history. The only way it could be the end of history is if it becomes an artificial super intelligence that takes over the world."
Facebook's success, he believes, has a great deal to do with the decision to begin the social network for college students.
"We entered the market through college because college kids were not Myspace users, Friendster users," he said. "No one actually believed outside of us that you could enter the market through this niche market and gradually through this carefully calculated war against other networks become the one network to rule them all."
Fallon brought up Myspace, one example of a powerful social network that has since fallen into major decline. Parker blamed Myspace's troubles on their failure to develop new products quickly enough, calling them a "junkheap of bad design that persisted for many, many years."
Then again, Parker said he himself has spent time "trolling on Myspace all day long for girls, trying to get laid."
Facebook and Myspace, though "very similar" in the early days, differed in one key aspect of their visions. Parker called Myspace "fraudulent in a sense that all these users were not representing themselves honestly" while instead "putting their best foot forward and living in a fantasy world of their own construction." Facebook, Parker said, gave people a way to make a real identity, a practice that has not always met with acclaim.
"There was no verifiable, accountable, persistent identity that could follow you from place to place, that you maintained and curated in an accurate way," he said. "Until you establish that identity layer for the Internet a lot of things aren't possible. Myspace wasn't providing that."
Though Parker is far wealthier than the broke entrepreneur he was back when Facebook was first coming together, he says that he "doesn't really care about money," despite the infamous billion dollar quote in The Social Network. But not everyone feels the same way. According to Parker, plenty of new billionaires get "trapped in an endless cycle where they don't think they're succeeding quickly enough," worrying over their place on the Forbes list, and holding private, explicit conversations about their net worths.
For himself, Parker has chosen to eschew an obsession with wealth for other pursuits. Some things, however, he can't go near. For example, he admitted, he was once a serious gamer. "I had a huge problem with gaming to the point where it was taking over my life," he said, though he hasn't played a game in at least 14 years. "I have an extremely addictive personality. I had to replace it with boozing and whoring."
These days, he blends his own tea for fun instead.