Sean Parker is late. He was due at Gramercy Tavern at 1pm and at 1.15pm his assistant calls to say he is on his way. By 1.25pm, there is still no sign of him and I sit wondering if he is going to arrive. He has cancelled lunch once already, complaining of a knee injury and he has a reputation in Silicon Valley for being unreliable and flaky.
Parker is indulged because he has been a driving force in several pioneering internet companies, including Napster and Facebook (although he was ejected as president of Facebook for alleged bad behaviour) and has others up his sleeve. He is portrayed in The Social Network, the Facebook film, as a gifted but amoral playboy who charms his way to the side of Mark Zuckerberg, Facebook’s founder, and brutally ejects a rival.
The devil has the best line in the Aaron Sorkin-scripted film. When Parker, played by Justin Timberlake, meets Zuckerberg at a New York restaurant, he floats across the room, orders food for everyone, spins enticing tales and leaves with the come-on aphorism: “A million dollars isn’t cool. You know what’s cool? A billion dollars.” In real life, Parker’s Facebook stake is now worth $2bn.
So it is hard, waiting for him at a “very private banquette” (as Parker’s office has specified on the booking) at the Danny Meyer restaurant in lower Manhattan, to disentangle fact from fiction. Parker is having trouble with it himself since some parts of the script, for which Sorkin won an Oscar this week, ring true. He is indeed a bon viveur who wears designer suits and at the age of 31 has just spent $20m on a carriage house in nearby Greenwich Village.
At 1.30pm, the real-life figure turns up, shaking my hand apologetically. True to form, he is dressed immaculately in a dark suit, grey and white checked shirt and a black tie secured with a silver tie-pin. He says he has flown to New York from San Francisco for our lunch because he felt guilty about cancelling last time, and is staying at a hotel – the heating in his house is being repaired.
“The lateness thing is part of my branding almost but, in this case, I’d planned on getting here on time,” he says. “I had to go by the house to pick up some things. I was trying to find a belt to come over here and it’s like a nightmare. I’m crawling through this ET-like maze of plastic sheeting.” He waves his arms around to portray the scene and gives a wide-eyed, high-pitched laugh, somewhere between a giggle and a whinny.
Those who know Parker say he is kinder and more sensitive than the Sorkin portrayal. Indeed, the man now perched on the banquette before me is friendly and solicitous and is working to offset his new reputation as, as he puts it, “an asshole”. Yet he is also more like a Sorkin character than anyone I’ve ever met – if not the anti-hero of The Social Network.
He is pale-faced and intense, with a mop of reddish-brown hair and a beard, and talks as fast and rhetorically as a West Wing wonk. An auto-didact who did not attend university, he will happily extemporise about any topic from Italian wine to network engineering, and has the self-confidence-cum-arrogance of the Silicon Valley elite. I mention his knee and he gives a long, precise explanation of his cartilage problem, with hand gestures. “The meniscus is this piece of cartilage. It’s like there’s a bone here and a bone here and they fit together. Ordinarily bones have a ball and groove, that’s the typical joint structure. The knee is different. It’s flat bone to flat bone and this thing in the middle is the meniscus.” His own meniscus, “instead of being shaped like a [ring] doughnut, is shaped like a Boston eclair.”
The anatomical details done, we turn to the menu. Parker says Gramercy Tavern is his favourite restaurant but, as a night owl who often does not rise before noon, he tends to have dinner. “I don’t think of it as a lunch place so I have no idea if it’s going to be any good,” he says, before diverting into an explanation of the importance of table placement in gaining a third Michelin star (Gramercy Tavern has one star).
“Have you had the smoked trout?” he asks. “I’m not normally one for smoked fish but this is not like any smoked fish you’ve ever tasted. It’s amazing. Even if you’re not into fish, we could get one and you could just taste it. It’s really, really good. It’s like the best thing on the menu.” He pauses. “I might have hyped it now so if you don’t like it, you’ll blame me. It’s awful.” He laughs uproariously.
We both order the trout with cipollini purée and pickled onions. After quizzing the waitress about the snapper, Parker takes the rack and belly of lamb but decides not to have the belly (“I’m not super-hungry”), while I opt for sea bass with Swiss chard, capers, pine nuts and sweet onion sauce. We both have water and also order an Arnold Palmer (a mixture of lemonade and iced tea).
While we wait for our food, he describes the house he has bought, which he has rented for the past year. It was built in 1820 to serve a nearby mansion. “I can only imagine what the mansions of Fifth Avenue must have been like. I’m living where they kept the horses,” he says. His former landlord, the Italian drinks heir Enrico Cinzano, owned it for 20 years and had distinctive taste.
Parker has kept the entrance hall, which Cinzano lined with the sides of an old New York subway train, complete with taped subway noises. “I love the subway cars,” he enthuses. “Enrico said to me [Parker adopts a slightly menacing Italian accent], ‘Sean, you know, at some point I’m going to have to take back the subway cars.’ ” Long rhetorical pause. “‘But Sean, I’ll find you new subway cars.”
I have been laughing along with Parker’s stories since he turned up, feeling as enjoyably caught in his wake as the characters in The Social Network. So it seems a good time to mention the film. When I do, Parker turns serious for the first time. “Mmmm,” he says ruminatively, pointing at my tape recorder on the table. “That thing’s on, right?”
He thinks for a while. “There is no simple answer to what I think. It is a long conversation and you can easily take one quote out of context and frame it in one way or the other, so I have to trust you.” I nod, wondering what his definition of “a long conversation” might be, given the length and detail into which he has gone about his knee, his house and the trout.
He warms up with an anecdote. “Sony screened the film for me and a couple of friends, which was nice of them, given that they knew I’d hate it. My friends were up in arms at the end. They were screaming and one of them got drunk and started yelling at the woman from Sony, ‘He’s going to sue you! He’s going to sue you!’ and I’m like, ‘Shut the f**k up! Be quiet please. Let’s be dignified here.’ ” He imitates his frantic efforts to keep the peace.
While he is talking, the trout arrives. “It’s like a whole other ball game. It’s not even like fish, it’s like butter,” he says. I taste the trout as he watches me intensely. The taste is dense and creamy. “It’s amazing, isn’t it? You like it?” I agree that it is delicious and he makes a two-fisted punch of delight. “Yes!” he cries. “I’ve done something right today.”
Parker asks if I would like a glass of wine and the waitress suggests a pairing of Cantalupo Il Mimo, an Italian rosé made with the Nebbiolo grape. The news sends Parker off at a tangent. “The Nebbiolo grape is the most underrated grape,” he enthuses. “The Barolos and Barbarescos, all the great Italian wines, are based on the Nebbiolo grape. It is versatile. You get these really spicy minerally wines, you get earthy tones and leather and then you get these fruity wines.”
He returns to his reflections about the film. “I’m watching it and thinking this is really interesting. This character is definitely not me. It is a plot device created by Aaron Sorkin to tell the story that Aaron Sorkin wants to tell. At the same time I’m looking at David Fincher’s work [the film’s director] and saying this is brilliant and this guy has an obsessive devotion to accuracy.”
Parker and Sorkin clearly did not get on. “My interactions with Sorkin were agonisingly weird. He is by far the weirdest person I have ever met. I had dinner with him and a few hours before I got an e-mail from his assistant saying, ‘Sean, this does not need to be a long conversation. Aaron is only going to use it to win your trust.’ ” He laughs loudly. “I went, ‘What? What is this guy thinking?’ ”
The dinner turned out to be “like the most phony, stilted conversation ... It was as if he had scripted our conversation and when I deviated from the script, he came back to it.” I am laughing too much to eat as Parker builds up to his story’s punchline. “He was also twitching through the entire meal. Like uncontrollably twitching. Shaking in fact ... I don’t think he won my trust.”
The film did make him famous, I point out. Surely that has its uses? Parker contests that. “If you Google me, every five minutes someone will talk about me and they will say, ‘That guy is a jerk’, or ‘He’s an asshole’ and then strangely every once in a while someone will say, ‘That guy’s so awesome’. I’m, like, Uuuggh. I was perfectly capable of doing what I wanted in my life without this.”
The main course arrives and Parker, who is allergic to nuts and must carry an EpiPen, asks our waitress about the hazelnuts that were supposed to come with his lamb – he is allergic to nuts. It turns out that, although he had forgotten to mention it before, she has told the kitchen not to put them in. He is obviously, as he said, a regular.
Since he disputes his portrayal in the film, I ask him about what drives him and how he defines his job. “Solving specific problems is what drives me. I am not interested in having a career. I never have been,” he says. “This in no way resembles a career. I think a career is something your father brings home in a briefcase every night, looking kind of tired.”
It is an arresting image and I ask him if he is thinking of his own father, who was until recently chief scientist of the US National Ocean Service. “Yes, I think that’s accurate,” he says soberly. “He wanted to be entrepreneurial but he had a family and he didn’t feel able to take the risk of putting everything aside. He actually told me, ‘If you are going to take risks, take them early before you have a family.’ ”
Parker took those words to heart, building on his early hobby as a hacker in Virginia, to link up with other teenagers who had become fascinated by the potential of the internet. These included Shawn Fanning, the founder of Napster. Parker decided not to apply for college (a decision that “seemed totally insane” to his mother) and to develop Napster instead.
In one long breath, he describes what happened in the following 18 months: “Founded the company, launched the product, moved to California, got on my hands and knees and installed all the servers for six weeks, got introduced to my first business people and hired them and fired them, and was sued by the record labels and suddenly I’m on MTV and now we’re sponsoring raves and going to crazy parties, and then bigger and bigger and bigger. And then the company’s dead and I’m in a beach house in North Carolina getting the call, ‘Sean it doesn’t look good. I don’t think you’ll have a job when you get back.’ And then it’s over. And one day Fanning and I woke up from this dream. It felt like we’d lived through an entire lifetime of experiences.”
We have talked for nearly two hours. I excuse myself for a break and when I return to the table Parker is talking on his BlackBerry. As he ends the call, he looks agitated and upset. Page Six, the gossip column of the tabloid New York Post, has a story that he undertipped a nightclub doorman by giving him only five dollars. “This is insane,” he mutters, “If I did it, it was an accident.”
We skip pudding. I have coffee while he takes an English breakfast tea and discusses the meteoric change in his fortunes. “You have got to be willing to be poor [as an entrepreneur],” he says. “There was a time when I was living out of a single suitcase. I had a rule that I wouldn’t stay on one person’s couch for more than two weeks because I didn’t want to become a bother.”
So is a billion dollars cool? He ponders the question carefully. “No, it’s not,” he says. “It’s not cool. I think being a wealthy member of the establishment is the antithesis of cool. Being a countercultural revolutionary is cool. So to the extent that you’ve made a billion dollars, you’ve probably become uncool.” He laughs at his retort to Aaron Sorkin.
It is nearly 3.45pm and his BlackBerry is flashing alarmingly as his assistants guide him towards his next appointment, at Spotify, an online music service in which he has invested. Still muttering about Page Six, he retrieves our coats and carefully tips the attendant. Outside, a driver awaits with a Cadillac Escalade. Parker offers me a ride but I do not want to delay him. He is late.
John Gapper is the FT’s chief business commentator
42 East 20th Street, New York
Bottle sparkling water $7.00
Arnold Palmer $4.00
Trout x2 $28.00
Sea bass $22.00
Rack of lamb $26.00
il Mimo x2 $18.00
Glass still water $3.00
English breakfast tea $5.00
Total (including tax) $127.39
Sean Parker’s ups and downs
As a teenage computer hacker in the Washington, DC, suburbs a decade and a half ago, Sean Parker had acceptable technology skills but none of the out-and-out wizardry of a Bill Gates or a Steve Jobs, writes Joseph Menn.
If one trait distinguished him, it was that he didn’t have the same tunnel vision as many of his peers. He thought the capabilities and flaws of computers and the internet were most interesting when they overlapped with the outside world.
He also had a precocious ability to spin business plans out of the ether. Napster, the song-sharing service, was fully Shawn Fanning’s creation and he would become its public face but Parker sprung to a natural role as business adviser and strategist, much as he would later with Facebook.
He was convincing enough, and the dotcom boom was so powerful, that even venture capitalists who might have concluded that Napster’s massive, directed file-sharing was illegal still wanted to put money in.
Napster itself was doomed in short order, though a record industry lawsuit first brought it headlines and millions more users. A lucrative settlement with the record industry – Parker’s secret goal from the start – foundered not because of his hubris but that of the hired professionals by then in charge of the start-up.
Parker himself was undone, at Napster and personally, by the wording in his e-mails to Fanning that were uncovered in the litigation. In one, he wrote that users “are exchanging pirated music”.
“I was incredibly depressed,” he said, after he took the hint and resigned in 2000. In 2001 he founded Plaxo, a system for keeping electronic address books up to date. Plaxo got top-tier venture funding amid a miserable climate but it again pushed the boundaries, nagging users with spam.
In Silicon Valley Parker is famed not only for his partying but for his difficulty finding operational roles inside companies. Venture investors forced him out at Plaxo and later stripped him of his post as Facebook president in 2005 after a drug arrest that didn’t result in charges.
He is now finding and managing investments for venture capital firm Founders Fund and playing a major part at Spotify, helping the music service try for licensing terms to play digitised songs from the big US record labels. If he clinches a deal, he will have come full circle and buried the Napster ghost.
Joseph Menn is an FT technology correspondent and author of ‘All the Rave: the Rise and Fall of Shawn Fanning’s Napster’