Josh Harris' Sunday Styles Treatment: The Ultimate Tech Cautionary Tale

Josh Harris—the Silicon Valley O.G. who washed up when the 1.0 tech bubble burst—had his second life profiled by the Sunday Styles. Harris is the ultimate Where Are They Now? of the tech scene. And where is he?

Living in a pool house in L.A., playing poker at a race track. Allen Salkin—the Seymour Hersh of the Styles section—files this weekend on Harris, who's doing some kind of strange press round for Ondi Timoner's documentary about him, We Live In Public. The last guy to file on Harris? Jayson Blair.

Harris was maybe the first chronic oversharer. The guy who founded Jupiter Communications and Pseudo Programs once webcammed his entire life and broadcast it for web-savvy voyeurs to see. He could be considered a pioneer in a culture that gave rise to Julia Allison—who, of course, appears in the doc—as well as Twitter, Tumblr, Facebook, and pretty much any other form of communication that shoves someone's life down your throat.

Maybe suspiciously, Salkin's plugged Harris before, when writing about a group of New York writers who abstain from oversharing at their salons (but still tell their story to the New York Times). He's dipping back into the same well for his profile on Harris. Commence quoting of tech luminary Jason Calicanis, whose pool house Harris is now possibly housed in:

"He is one of the 10 most important people in the history of the Internet," said Jason Calacanis, an entrepreneur of digital media who once chronicled New York's tech scene in his publication, The Silicon Alley Reporter. "He may not be the most famous."

But Salkin eventually gets to the good stuff, chronicling how far Harris, who once threw parties at his SoHo loft in which there was "sushi served off naked women, boxing, hip-hop artists including Eminem, and Mr. Harris sometimes dressed as his alter ego, a shrieky clown in smeared makeup named Luvvy, based on the wife of Thurston J. Howell III, a character from "Gilligan's Island."

You know someone's has both made it and simultaneously sealed their fate once they start dressing up as Pennywise impersonating Lovey. And so it was. Harris:

  • Had only $741 to his name when Salkin interviewed him.

  • Sold the apple farm he tried to escape to from Manhattan in 2006.

  • Had to ensure part of the buyout deal for his second company, the marginally successful Operator 11, involved a provision that'd pay off his $150K AmEx bill.

  • Went to Ethiopia to start another entertainment channel (which was well documented). Instead, he ended up smoking lots of weed (which wasn't).

  • Just this year, when Timoner won a Grand Jury Prize at Sundance, she had Harris fly out for the festival Q & A's. He only came pending oatmeal and the promise of a visit to a dentist. He never came back from Park City with Timoner.

  • Is also delusional. Salkin experienced Harris' insanity first hand when Harris explained that he thinks the F.B.I. went after him for being connected to 9/11.

The denouement is that Harris is trying to start a new startup, and Jason Calacanis wants to help. The startup is called The Wired City. Any New York Times sentence that begins with the word "basically" should prepare readers for a concept that, if not boiled down to less than a sentence, is otherwise absurd. And it is:

Basically, it would have a large group of people living in a sort of three-dimensional real-world Facebook, where "friends" could participate in one another's every move.

He explained that if two people were Wired City participants having lunch at a restaurant talking about clowns, friends watching remotely could send video that would, perhaps, be broadcast on the table showing a clip from "Shakes the Clown" followed by menu recommendations. The cleverest friends would be rewarded.

Josh Harris' Sunday Styles Treatment: The Ultimate Tech Cautionary TaleS

It's hard to be completely cynical about an idea like The Wired City—as history's proven, crazier ideas have taken off—but Harris' manic self-destruction is ultimately going to be the large roadblock here. Salkin—who could've made a great trend piece out of this, too—lets a few salient points escape him, as he's wont to do.

Timoner's last documentary, Dig!, which detailed the almost-rise and tragic fall of The Brian Jonestown Massacre (a band led by a singer with another really, really bad Icarus complex), basically tells the same story. Guy reaches apex of fame and decides to throw it all away in a fit of self-indulgence. The Brian Jonestown Massacre isn't the band it could be, but they still play shows and make money, boosted by the spectacle put on display in Dig!, which lead singer Anton Newcomb quietly, smartly capitalized on. If Harris is smart, and can reign in the crazy, he might be able to hose some angel investors into doing the same, thereby giving him a second chance.

The fates of Mark Zuckerburg - the Facebook Boy Wonder whose life is getting the Aaron Sorkin treatment - Twitter's Evan Stone and Biz Williams, Tumblr's David Karp, and a bunch of other young, hot tech entrepreneurs have yet to be completely written. If they've got any sense about them, they're gonna pay close attention to Harris, whose tragic genius now amounts to insane, conspiratorial Styles Section kickers:

Walking past his old Pseudo offices at Houston and Broadway, Mr. Harris, who said he has never been in love, adjusted his dark sunglasses.

"It's a funny thing being in fear for your life," he said. "It's kind of addictive."