Christopher Poole is 22 years old, and as is often true for men his age, his mental life has been punctuated by a series of passing enthusiasms: video games, online chat rooms, Japanese animation. Currently he seems to be going through a Robert Moses phase. On the nightstand in his New York City apartment is a copy of The Power Broker: Robert Moses and the Fall of New York, a 1,300-page biography of the mid-20th-century urban planner who, in pursuing his vision of a modernized New York, destroyed one neighborhood after another. A book of photos on Poole’s coffee table documents the Moses-era demolition of midtown Manhattan’s vast and graceful old Penn Station. (“Gut-wrenching,” says Poole.) And on a recent Thursday afternoon, as he walked to work past Washington Square Park and observed the sweeping renovations under way there–a controversial relandscaping imposed by current city planners in the face of heavy local opposition–he saw parallels with the old autocrat’s imperious approach to such projects. “Robert Moses is probably smiling,” he said. “Like, ‘Fuck the people–what do they know!’ ”

Like many people, Poole thinks there are better ways than Moses’s to manage the tangled social, cultural, and infrastructural needs of a community of millions. But unlike most people–let alone most 22-year-olds–he actually has some experience doing just that. Seven years ago, Poole created the website 4chan, an online community that now has nearly 11 million monthly users and is, in some respects, as unruly as any metropolis. The site is what’s known as an image board, a type of online message forum that encourages users to post both images and text, and its users now contribute more than a million messages a day, their content tending in the aggregate toward a unique mix of humor, pornography, offensiveness, and, at times, borderline legality. It has long been one of the largest message forums in the world, but Poole, the only owner 4chan has ever had, continues to run it as he has always done: in his spare time, with a little help from online volunteers and just enough advertising revenue to cover bandwidth costs.

Visited mostly by young men in their late teens and early 20s, 4chan is loosely organized by topics of interest–music, games, TV, animation (Japanese and otherwise). But nearly half its messages are posted in a single random-topics section known as /b/, and /b/’s anarchy sets the tone for the site in general. It’s out of /b/ that swarms of gleeful online troublemakers–trolls, in Internet parlance–occasionally issue forth to prank, hack, harass, and otherwise digitally provoke other online communities and users. From /b/, as well, the Internet at large absorbs a steady stream of catchphrases and sight gags–LOLcats, rickrolling, and other ubiquitous Internet memes that seep up from the endless, dizzying churn of /b/’s vast reservoir of inside jokes. Often intended to shock, shot through with racism, misogyny, and other qualities deliberately chosen from beyond the contemporary pale, the words and images of /b/ have become an online spectacle: “Lunatic, juvenile … brilliant, ridiculous and alarming,” the Guardian newspaper’s website once called it. “The id of the Internet,” it has been called more than once.

By no coincidence, 4chan stands out not only for the content its users generate but for the way they generate it: with a degree of anonymity almost unheard-of in the online world. Though Poole himself is known to the site’s users by the cryptic pseudonym “moot,” on 4chan even using a pseudonym is rare. The site has no log-in function, so each message can be posted under whatever name its author chooses, but users are strongly encouraged to post with no identifying name at all. Roughly 90 percent of all messages on 4chan are posted under the site’s default identity, “Anonymous.” And those messages are not only anonymous but ephemeral, because 4chan has no long-term archives: old message threads are automatically deleted when new ones need the room. This mechanism was originally meant to save storage costs, but as Poole notes, “it’s both practical and philosophical.” Among other things, it challenges the idea that digital identity should follow you across time, linking what you say when you’re a teenager to the middle-aged business owner you might become. In 4chan’s heavy traffic, a message can vanish within hours or even minutes of its posting.

As approaches to community management go, this is pretty much the opposite of what the mainstream Internet seems headed toward. Anonymity, once thought to be a defining attribute of online interaction, is nowadays widely approached as a bug to be fixed. Managers of newspapers’ online comment sections in particular have grown wary of it, blaming the irresponsible mentality of anonymous commenters for bitter flame wars and rambling digressions. Several newspaper sites have lately closed their comment sections to anonymous posting altogether, and at least one now requires commenters to post under their own verified credit-card billing names. But the clearest demonstration of the Internet’s move away from anonymity has been the rise of social-networking sites like Facebook, whose appeal to both users and marketers rests on a closing of the gap between online and offline identities. Facebook’s 26-year-old CEO, Mark Zuckerberg, seems to be an unusually fervent believer in the virtues of “radical transparency” in online dealings–he famously once told an interviewer that “having two identities for yourself is an example of a lack of integrity”–but he is not alone among the Silicon Valley elite in linking the decline of anonymity to the promise of a more tolerant, peaceful, and profitable digital world.

Yet many, even among that same Silicon Valley elite, have found reasons to regret the loss of anonymity online. Poole’s selection as a speaker at the technology world’s invitation-only TED conference last February provided him with an opportunity to express those reservations. Standing in sneakers and a zippered hoodie on the expensively designed TED stage (the same one Bill Gates would be speaking from the next day), Poole gave a brief talk that was as thoughtful and polite as 4chan can be rude and unhinged, and he made a compelling case for the anonymity that helps make 4chan what it is. Support for anonymous communication often comes down to a standard set of arguments: people should have a place where they can speak truth to power (blow a whistle on corruption, assess whether an emperor has clothes) without fear of reprisal; they should also have a place where they can be true to themselves (explore an unconventional sexuality, seek treatment for a stigmatized disease) without risking ostracism and worse. But while Poole embraces these arguments, what he says in defense of the anonymity on 4chan is at once less high-minded and (in ways he is only slowly coming to understand) more far-reaching:

“People deserve a place to be wrong.”

Poole didn’t particularly want 4chan to be anonymous when he started it. He was 15, an only child of divorced parents, living with his mother in a Westchester County suburb of New York City and gripped by a midadolescent fascination with Japanese animation, or anime. That had led him to a good place to find anime images: the Futaba Channel, a popular Japanese image board also known to its English-speaking fans by its Web address, 2chan.net.

One of the things that struck Poole was that the site let people post in its discussion forums exceptionally quickly. It didn’t especially register with him that Japan also happened to be a place where cultural distinctions between public and private life matter deeply–where, in a sense, having two identities isn’t so much a failure of integrity as a working definition of it. Nor did the related facts that Japan’s Internet users tend to have a particularly deep-rooted attachment to online pseudonyms and other alternate identities (as Facebook, still struggling to crack the Japanese market, has learned the hard way) or that the Futaba Channel, like most Japanese image boards, has always offered fully anonymous posting with no log-in required. None of this was what compelled him to grab a copy of the Futaba Channel’s source code, rewrite the site’s text in English (guessing at some of the Japanese words’ meanings, running the rest through the translation engine Babel Fish), and start operating it as 4chan in October 2003. Poole recalls how Babel Fish translated the kanji signifying Futaba’s default username: “Nameless.” He changed it to “Anonymous,” and that, more or less, was that.

“It wasn’t a principled decision,” says Poole. Not at first. “It became one, as I grew from 15 to 18 to now 22…. But as a 15-year-old, I wasn’t too concerned with a lot of the things I really stand for now. I kind of grew into that.”

4chan kind of grew into it, too. In the beginning, the site had only two topic sections: /a/ for anime-related posts, and /b/ for everything else. In subsequent years Poole gradually added topics, and there are now nearly 50 of them, including /v/ for video games,​ /fa/ for fashion, /po/ for paper craft and origami, and at least three for specialized varieties of Japanese cartoon erotica and porn. But /b/ has grown more steadily than any of the others, and it long ago surpassed anime as 4chan’s principal reason for being. As the one section without any explicit rules about what can and can’t be posted (other than certain sitewide prohibitions against child pornography and other violations of U.S. law), /b/ is where 4chan makes good on what its anonymity promises: the freedom to say anything without the obligation to suffer consequences.

To a first-time visitor, /b/ may not seem very promising at all. Aside from the sheer quantity of tastelessness that courses through its message threads, they present a wall of endlessly recycled inside references, catchphrases, and fragmentary punch lines, the briefest sampling of which will baffle: “herp derp,” “newfag,” “over 9000!,” “So I herd u liek Mudkips,” “serious business,” “The Game (you just lost it),” “an hero,” “Candleja–.” Much harder to convey, though, is the improbable awesomeness of what /b/ reveals to those who come to know it better: the flashes of inspiration and deranged wit that flicker continually as /b/’s anonymous millions–the /b/tards, as they call themselves–work and rework variations on the esoteric routines. As this compost heap of in-jokes ripens, sometimes one of them will vault into popularity as a broader Internet meme (the most visible recent example, perhaps, is Pedobear, a creepy, vacant-eyed cartoon teddy bear whose picture is used to ridicule seekers of child pornography).

4channers have a word for all this: lulz, which in its strictest sense means laughs, jest, cheap amusement, but in a broader sense encompasses both the furious creativity that generates /b/’s vast repertoire of memes and the rollicking subcultural intensity they inspire. And if 4chan’s anonymity is good for anything, it turns out, it’s good for lulz. Consider, Poole explains, how the fixed identities in other online communities can stifle creativity: where usernames are required (whether real or pseudonymous), a new user who posts a few failed attempts at humor will soon find other users associating that name with failure. “Even if you’re posting gold by day eight,” says Poole, “they’ll be like, ‘Oh, this guy sucks.’ ” Names, in other words, make failure costly, thus discouraging even the attempt to succeed. By the same token, namelessness makes failure cheap–nearly costless, reputation-wise, in a setting like 4chan, where the Anonymous who posted a lame joke five minutes ago might well be the same Anonymous who’s mocking it hilariously right now. And as the social-media theorist Clay Shirky has suggested in another context (explaining how the plummeting costs of networked collaboration encourage, say, a thousand open-source software projects to launch for every one that gets anywhere), the closer a community gets to “failure for free,” the better its chances of generating success.

That may not be the only thing Poole meant when he talked at TED about 4chan’s importance as a place to be wrong. But it’s ultimately the reason he was on that stage, and it’s starting to look like the reason he’ll be in a spotlight for a while to come.

On May 13, 2010, just after the end of his sophomore year in college, Poole filed notice with the Securities and Exchange Commission about an extracurricular activity: raising $625,000 for a new online venture. The time had come, he felt, for something like a reboot. After seven years of administrative and technological tweaks to 4chan, he no longer sees it as a project much in need of his creative attention. Meanwhile, he notes, Web technology has evolved far beyond 4chan’s “decade-old code and decade-or-two-old paradigm”–that of the classic pre-Web bulletin board–and he is eager to reimagine what a modern discussion forum can be. The name of the new site is Canvas, and Poole hopes to launch it this fall. People will have the option of signing in, although Poole says he hopes to keep Canvas relatively free of “vanity and ego.” As on 4chan, users will be able to post comments anonymously and to switch fluidly between multiple identities.

It says something that investors in Canvas–who include Marc Andreessen (creator of the first graphical Web browser) and Ron Conway (an early Google backer)–would bet on a track record like Poole’s. For all of 4chan’s eye-popping traffic stats, it’s doomed to bare-subsistence revenue by the combination of its scandalous content (palatable only to low-rent advertisers like porn sites) and Poole’s profound discomfort with, as he puts it, the “tons of ways I could essentially rape the site for dollars” (including pop-ups, ads with sound, and other high-paying but obnoxious forms of advertising that would antagonize 4chan’s community). And whether it was the 2006 “dirty bomb” incident, in which 20-year-old Jake Brahm flooded /b/ with threats to detonate radioactive explosives at NFL games, or the harrowing of Jessi Slaughter this July, in which the troll hordes of /b/ rained death threats and other anonymous harassment on an 11-year-old Florida girl, the portrayal of 4chan in the national news has mainly reflected the image of a menace to be contained rather than an enterprise to watch.

And yet, many in the Internet business have been watching 4chan with interest. The steady growth of its traffic and the viral spread of its content, after all, represent the kind of social success that Web businesses require. “Getting engaged users is the tough part,” says David Lee, who invested in Canvas as a partner in Conway’s SV Angel firm. Profit or no profit, he explains, 4chan shows that Poole “is the rare entrepreneur who can get engaged users.” And given how firmly anonymity is held to be a recipe for social-media failure, it’s intriguing that the site works at all. 4chan “was a thing that challenged people’s assumptions in the Web industry,” says Jonah Peretti, CEO of the viral-media startup BuzzFeed and cofounder of the Huffington Post. “It was just so different from the way other people were thinking about community.”

This year Poole got an official invitation to speak to developers at Facebook’s headquarters in Palo Alto, CA. He was asked about his experiences running a site that Ruchi Sangvi, the Facebook product manager who proposed the visit, calls “the polar opposite” of their own. Roughly 80 Facebook employees attended, squeezing into a standing-room-only conference room, and though there was some trepidation at first–some Facebookers expected Poole to be an apologist for hackers and child porn–by all accounts the visit was cordial. “He’s a really, really smart guy with a great vision,” says Richard Cho, a Facebook recruiter who helped organize the event. In fact, Cho says Poole is “not dissimilar to Mark Zuckerberg,” in that both have “interesting viewpoints” about how people connect and share information. But there was also a simpler reason for Facebook’s sympathy for the man behind 4chan: “There are some of us that have frequented that site quite a bit,” Cho says. “ ’I can has cheezburger?’ is just a common part of our vernacular internally.”

After all, the radical transparency of Mark Zuckerberg and Facebook may not be mutually exclusive with what we might as well call the radical opacity of Christopher “moot” Poole and 4chan. Their uses may even be mutually necessary. Peretti puts it this way: if 4chan is the id of the Internet, then “Google is kind of like the ego, and Facebook is kind of like the superego.” If that’s so, then there’s only one way the trend toward radical transparency won’t end up killing the Internet’s soul: if we can leave the light of all that openness every now and then to spend some time in the shadows where the crazy lives.

Julian Dibbell is a freelance writer living in Chicago. His work has appeared in the Best Technology Writing series in 2007, 2008, and 2009, and he is the author of Play Money: Or, How I Quit My Day Job and Made Millions Trading Virtual Loot (Basic Books, 2006).