Sep 2, 2014 · 7 minutes

There was a healthy dose of surprise from both the literary and tech communities last year when it was announced that Thomas Pynchon was writing a novel about New York's Silicon Alley in the wake of the dotcom crash.

Pynchon, who is arguably America's greatest living fiction writer, is known for postmodern metafiction and absurd historical revisionism -- in other words, not exactly the cold, binary zeroes and ones that technologists and startups say they worship. He's more David Foster Wallace than Tim Berners-Lee. At the time of the announcement, I even wrote a stupid blog post offering up fake rejected Thomas Pynchon startup books -- I think something like a hundred people read that post, thus providing even more evidence that the overlap between Pynchon fans and startup/VC enthusiasts is a pretty thin subset of society.

Now, almost a year after Pynchon's New York tech tome "Bleeding Edge" was released to mixed reviews, I finally got around to reading it. (I know, as one of those few who loves Pynchon and writes about New York tech for a living I have no excuse for waiting so long). And while it may be "Pynchon Lite" as Michiko Kakutani says in her New York Times book review, for people working in or covering tech it's surely one of the best fictional accounts of technology and startup life ever written -- Not that it has a ton of competition in that regard.

While cinematographers and lighting aficionados found much to like about David Fincher's "Social Network," fans of factually accurate storytelling were less enthused. And while HBO's "Silicon Valley" found plenty of fans in its namesake region, others like myself felt that it could've taken some of the most important issues facing the tech scene, like sexism, a little more seriously (either that, or the show could've tried to be a lot funnier).

The bulk of "Bleeding Edge" is set in New York City during the months between the dotcom crash and the September 11 attacks. This imbues the novel with an eerie sense of dramatic irony -- people know things are bad, but they have no idea how bad things will get. So your startup failed? No big deal, get a job on Wall Street or even suffer at a cubicle farm until the investment climate improves. And even if you're unemployed it's not as if we're at war or anything... It's the same vibe struck by those early powerful episodes of "The Sopranos" which took place around the same time: "Things aren't great, but they'll get better. Right? RIGHT?"

The story centers on Maxine Tornow, an unlicensed fraud investigator and single-ish mother of two boys. Her character is derisively called "a walking New Yorker cartoon" by Rebecca Liao of The Los Angeles Book Review, but that's sort of the point. She represents an older notion of New York, one that doesn't exist anymore and maybe never did, where wisecracking detectives rub elbows with lovable dirtbags and deadbeats; a place before real estate developers or tech firms or Giuliani or whoever came in and turned the city into something that, while not objectively "better" or "worse," is at least unrecognizable to Maxine.

But the target of Maxine's latest fraud case is not your garden-variety dirtbag or deadbeat -- it's sociopathic boy genius Gabriel Ice who heads up hashslingrz, a giant security firm that's not at all hurting in the wake of the dotcom bust. In fact, it's doing better than ever, buying up all these failed husks of companies and allegedly (it's Maxine job to find out for sure) using them to secretly funnel cash to potentially nefarious accounts in the Middle East.

This thrusts her into a world of slimy VCs, morally-compromised programmers, paranoid techno-anarchists, and shifty government operatives whose interest in hashslingrz may or may not be related to an impending terrorist attack on the United States. She's taken to drug-addled startup parties, thrown with an extravagance reserved only for those who know the end is hear, which are like the tech equivalent to "American Psycho"'s Wall Street hedonism.

Looking back to this older, more primitive world of tech startup excess conveys a strong sense that, despite the fact that the Internet has come into its own over the past decade-and-a-half, not all that much has changed. The idealism of startup culture, which was supposed to act as some better, more principled version of American capitalism relative to the corporatism that dominated most of the 20th century, is just as corruptible by greed and governments as any other "free market" revolution. March Kelleher, a leftist blogger whose daughter in an act of rebellion marries Ice, writes, "Don't get me wrong. I love them nerds, in another life I would've been a nerd groupie, but even nerds can be bought and sold, almost as if times of great idealism carry equal chances of great corruptibility."

Pynchon captures the language and elitist geek mentality of tech scenes surprisingly well. But the book's most powerful themes relate to our desire to use the Internet and technology to escape from real life. When Maxine becomes too overwhelmed by the murderous and money-hungry real world, she finds exile in a virtual community called Deep Archer (pronounced "departure") which is a bit like Second Life meets the Deep Web, built by her friends Justin and Lucas. Heavily encrypted and as-yet unsullied by corporations or suburbanites, it starts out as a virtual mirror to the New York Maxine thinks she's lost, full of misfits and a little dangerous, but freer than anything she's found in the meatspace.

That is, until Justin and Lucas take Deep Archer open source. In a subversion of what's usually thought to be a force of good for the Internet, making the code available to everybody merely opens the floodgates for corporations and governments to turn the network's Deep Web experience into something as hackneyed as an AOL portal. Yes, avenues still exist to escape deep into the virtual world, but even there Maxine finds ghosts of old lovers, likely planted there by government agents to bring her psychological torment. The Internet, despite hopes that it would be a haven for free discourse and democratic thought, making the world smaller and safer, is really just another tool that can be exploited by the powers-that-be if we let them.

Late in the book, Maxine still believes that "nobody's in control of the Internet." Her father's not so convinced:

You serious? Believe that while you still can, Sunshine. You know where it all comes from, this online paradise of yours? It started back during the Cold War, when the think tanks were full of geniuses plotting nuclear scenarios. Attache cases and horn-rims, every appearance of scholarly sanity, going in to work every day to imagine all the ways the world was going to end. Your Internet, back then the Defense Department called it DARPAnet, the real original purpose was to assure survival of U.S. command and control after a nuclear exchange with the Soviets.
But, Maxine argues, the Internet has moved from the military into civilian hands. "The worst you can say is it's maybe getting a little commercialized," she argues. "And look how it's empowering all these billions of people, the promise, the freedom."

Her father is unmoved: "Call it freedom, it's based on control. Everybody connected together, impossible anybody should get lost, ever again. Take the next step, connect it to these cell phones, you've got a total Web of surveillance, inescapable."

Of course anyone who reads Pando regularly knows this -- just look at Yasha Levine's coverage of Tor, a supposed haven for techno-anarchists that was actually built by the US military-surveillance complex to cloak the online identity of government agents and informants. Or look at Google's deep connections to "former spooks, intelligence officials and revolving door military contractors."

So what can anybody do about it? Focus on busting small-timers like Maxine, while the big fish swim free hurting anyone they like? Blog about everything wrong with the world like March, just so people can call you a lunatic and discredit you? Or give into the Web, either to make a few bucks or find some solace. After all, if true freedom is so impossible to achieve, isn't the illusion of it the next best thing?

Like television's "Black Mirror," "Bleeding Edge" is a work of fiction that's unafraid to confront the darker side of all this technological innovation we spend so much money on and time obsessing over. Sure, the book is kind of a mess, running down rabbit holes that lead nowhere, but hey this is a detective story -- Raymond Chandler would be proud. And like the best detective stories, the answer to who shot whom or who got paid is a lot less important than the twisting journey, into deeper and deeper layers of corruption and the Web itself.

Maybe there's nothing we can do to the stop the relentless machine of power and corruption. If that's the case, perhaps it's best to focus, like Maxine does, on merely teaching our children to be kind -- that way, they at least don't end up like Gabriel Ice.

[image via VeryPhil]