We recently ran an excerpt from Cole Stryker’s new book, Hacking the Future about the importance of anonymity. Here’s the second excerpt from this book, our latest book club selection. This time it’s about navigating parts of the web that not everyone knows about… We’ll be hosting a chat with Stryker in the near future, to be announced soon.

I first heard whispers of the deep Web on 4chan. It was often positioned by active users as a place where even the most hardened /b/tard (a nickname for heavy users who hang out on 4chan’s “random” board a lot) can find things to shock the system. The deep Web is depicted there as the submerged portion of an iceberg. The Web that we know is the tip, and the massive portion underwater is the deep Web.

“I’ve just come back from the deep Web,” they say, “and look what I found.” They share ghastly images and stories, perpetuating the legend of this vast underbelly among underbellies. In these conversations I was led to believe that the deep Web—also called the invisible Web, the darknet, undernet, and several other sinister-sounding names—was home to the sort of content that would get you thrown in jail if it were ever traced back to you. This is true, to an extent, but technically the deep Web comprises anything that isn’t crawlable by major search engines like Google. This can mean dynamic URLs that have a long string of parameters that might confuse spiders (the software that “crawls” Web sites to index them for search). Any content that’s behind a pay wall or other password authentication is technically included in the deep Web. This would include your e-mail or a pay-to-view newspaper Web site. Any content that lies behind a form, like a survey or poll, often can’t be crawled. Some sites purposefully exclude spiders using robots.txt, a file that tells spiders to steer clear of certain Web pages for various legitimate, legal reasons. Pages that are made up of flash content obviously can’t be crawled because there’s no raw text on the page. So to say that the deep Web is the seedy back alley of the Internet is not entirely accurate.

However, there are parts of the deep Web, accessible only with the use of certain anonymizing software, where baddies sometimes hang out. The deep Web is rife with readily available child pornography, terrorist rhetoric, drug and sex trade—all manner of taboo and hateful communication.

One such piece of anonymizing software is called the Onion Router, or Tor, briefly mentioned earlier. Tor reroutes communications coming from your computer around the world across a distributed network of volunteer-run nodes that make up the Tor Network. Tor passes users’ traffic through three servers before sending it along to its destination. The network was originally sponsored by the U.S. Office of Naval Research to help military agents abroad bypass firewalls and other “censorware” in countries like China. For this reason, some speculate that the service is routinely monitored by the U.S. government and cannot be trusted.

Technically, Tor is not an anonymizing service so much as an obfuscating one. Tor alone can’t keep anyone anonymous; it’s merely one item in the smart anon’s tool belt. Tor works to anonymize your Internet connection, but can also be applied to specific programs. The most popular program used in tandem with Tor is the Internet browser. The Tor team has built a Firefox extension that applies several “onion-like” layers of obfuscation to data communicated through Firefox. Because Tor routes your traffic around the world, it’s not very fast. The more people volunteer to contribute their machines as nodes, the faster Tor will get.

I thought I’d check it out for myself. I downloaded the Tor software, ran the executable file, and installed the software. When I ran the program, within seconds a browser window opened saying, “Congratulations. Your browser is configured to use Tor. Please refer to the Tor Web site for further information about using Tor safely. You are now free to browse the Internet anonymously.” I typed in a URL I found on 4chan for an underground deep Web portal called Hidden Wiki, waited about thirty seconds (an eternity in the era of Wideband and FIOS), and a blank page popped up, reading “Looking for Hidden Wiki?” The last two words were blue, indicating a hyperlink, so I clicked it, and up popped a page that looked just like Wikipedia. A sidebar listed the categories that are available to browse: blogs, books, political advocacy, but also drugs and underage erotica. I clicked on a link called “Killer for Hire.”

This can’t possibly be for real, can it?

You can call me Slate. All you need to know is that I am well trained and can perform what you need done. I do not need to know your situation with the hit and prefer not to. I’m hired when you want to make sure that the hit doesn’t get traced back to you.

• Minimum age for hit is 18.
• I do not care of the gender of the hit.
• I do not kill pregnant women.
• I do not torture the target.
• If hit is a political figure, or is in law enforcement (judges, policemen) there will be an additional fee.
• For an additional fee, I can set it up as a “suicide” or an “accident”
• Hit will take place within 4 weeks.
• Hits outside of the continental US will require an additional 2 weeks of logistics and $5000 in travel fees.
• Once the hit has been made I will message you with a picture or a video and the remaining balance must be paid in full.

A second hit-man site sounds like a Hollywood Russian mafioso wrote it. “It is mutual interest to make everything anonymously,” he warns, insisting, “it is not a joke.” He gives careful instructions on how to pay through Bitcoins (more on this soon) and reiterates the need for total anonymity on both sides of the transaction. “I don’t know you and you don’t know me.” If these sites are jokes, they are convincingly conceived. Moving on from the hit men, there are firearm salesmen, hackers for hire (“destroy your enemies!”), an extensive list of Bitcoin traders, illegal gambling sites, white supremacist blogs, whistle-blowing blogs, new world order conspiracy chat rooms, transnational activists, Anonymous operation forums, hacker/phreaker communities, and porn. Oh, the porn. Genital mutilation, necrophilia, zoophilia, watersports, etc. Anything you can imagine is at your fingertips. Which brings us to child pornography. I don’t have the guts or inclination to click through to any of these sites, but they’re there. And according to people hanging out on 4chan, the stuff available from the Hidden Wiki is only a shallow fraction of what’s out there were one prone to dig deeper.

Perhaps the most notorious site available through Tor is the Silk Road, a black market where users can find 340 different illegal drugs: weed, cocaine, heroin—a digital bazaar of pills, tabs, and powders. If I wanted, I could easily order up a smorgasbord of illicit substances and have it delivered within a few days. You have to pay a Bitcoin just to browse the site—its inaccessibility keeps out most looky-loos. The site doesn’t have everything, of course. You won’t find any chemicals that are easily weaponized. Sellers promote their wares through a reputation system that isn’t much different from the one popularized by eBay. The site only accepts Bitcoins, which, along with mandatory Tor usage, help to ensure the anonymity of buyers and sellers. The Silk Road is one of many hubs for black-market drug trade on the deep Web. It’s difficult to tell if the DEA (Drug Enforcement Administration) is going to crack down on this sort of thing, or if we’re peering into the future. Anonymizing applications and efforts to pierce such software seem to be progressing apace.

Freenet is another piece of software used to mask identity online. It’s been downloaded over 2 million times. Freenet’s creator, Ian Clarke, is concerned about the freedom to communicate. He grew up in the south of Ireland in the ‘80s in a family of Protestants, whom he says are fastidious about staying out of Irish politics. From a young age he was interested in understanding people who held different views.

I remember reading [Sinn F?in’ leader] Gerry Adams’s autobiography at a time when most people considered him a terrorist. I can remember that if he was interviewed on TV they had to use an actor to do a voiceover, because it was illegal to broadcast his actual voice. It wasn’t that I agreed with Gerry Adams’ beliefs or actions, but I did feel that it was far more productive to understand where people are coming from, to try to step into their shoes, rather than simply demonizing them, which was official government policy at that time. It left me with a strong sense of the futility of censorship, and the value of free communication.

My experience with Freenet’s “Linkageddon,” one of several directories, is similar to that of Tor’s Hidden Wiki. Some of it is innocuous (Bob Chapman’s Financial Analysis), some of it funny (Anti–Harry Potter fundamentalists), and some of it horrific (ubiquitous underage porn). Everything looks like an old Geocities page.

Clarke describes Freenet like a decentralized postal system, where people carry each other’s mail. For instance, you need to get a letter to your friend Bob in Boston, and your friend Diane is going to Boston for a business trip. You give Diane your letter and have her hand off the letter to James, who happens to live in Bob’s neighborhood. The system is decentralized and doesn’t rely on any one person more than the others. If Bob can’t deliver your letter, you might ask Cheryl, who will be passing through Boston as well. The advantages to this system are such that James doesn’t have to know who’s sending the letter, and there’s no central postal hub that can restrict the delivery of mail through censorship or incapacity. According to research by Freedom House, Freenet is one of the most popular anonymity systems used in China. This was no accident. Clarke says that he intended for the software to be used by activists.

Next Wednesdy, at 11am PT/2pm ET, we’ll be hosting our talk with Chris Sprigman and Kal Raustiala about their book, The Knockoff Economy, which was our September book of the month (excerpt one and excerpt two). We also wanted to get moving on October’s book of the month, Hacking the Future: Privacy, Identity, and Anonymity on the Web, by Cole Stryker. Here’s the first excerpt we’ll be running, from the intro of the book.

I think anonymity on the Internet has to go away. People behave a lot better when they have their real names down… I think people hide behind anonymity and they feel like they can say whatever they want behind closed doors.

In July 2011, Randi Zuckerberg, then marketing director of Facebook, uttered the words above during a panel discussion hosted by Marie Claire magazine. She couldn’t have anticipated the firestorm those few words would generate among those already uncomfortable with the direction the Web had taken in the preceding year.

Two years prior, Google CEO Eric Schmidt, in an interview with CNBC’s Maria Bartiromo, gave the downright schoolmarmish advice, “If you have something that you don’t want anyone to know, maybe you shouldn’t be doing it in the first place.” Schmidt, who once led an antitrust crusade against Microsoft, has claimed that Google will avoid Microsoft’s missteps because the search giant faces compelling incentives to please a customer base that will seek services elsewhere the moment Google does anything shady. But what if Google’s been tracking your search results for your entire life? Google, just one of dozens of companies that mines user data, knows your favorite foods, your sexual proclivities, and your medical history, to say nothing of the personal information they host in the form of e-mails and other documents. Would it be as simple as just walking away?

Before the Internet Age, computers were perceived by the public as unfeeling, literally calculating metal boxes that just might help bring about a nuclear apocalypse. As machines go, they were just as cold as their industrial-era forebears, if not more so–at least you can watch the parts move on a steam engine. At least you knew it wasn’t somehow plotting against you. It wasn’t so long ago that computers were seen as a dehumanizing tool of a dystopic new technocracy, imbued with the fear and existential despair brought by the Cold War’s lingering sense of impending doom.

But then something changed. Today we see computers (we don’t even really call them that anymore, they’re mobiles or laptops or something that sounds friendlier) as being vital, almost countercultural gadgets that bring empowered individualism, collaborative communities, and, depending on whom you ask, an almost spiritual enlightenment. They’re sleek and sexy. They’re our salvation from a world of physical limitations and disparities. Computers help us learn, work, and connect–Facebook now claims 850 million members, a figure that eclipses the number of people who were online in 2004. Pop stars interface with tween girls on devices with names like “Razr Maxx.” How did we get here? How did these calculators, manipulated by flat-topped military brainiacs in austere labs, become something so integral to the human experience that to call them an extension of the self hardly seems like an overstatement?

Surely part of the answer is technological. We all know the first computers filled entire rooms in order to accomplish the computational tasks that you can now do (gee whiz!) in the palm of your hand. Another part of the transformation has to do with design evolution of machines. An iPad is certainly much sexier than bland, beige computers that existed even a decade ago.

But more than style, cost, and convenience, more than any other factor, the simple act of linking one computer to another brought about a new stage of human social evolution, the most rapid and far-reaching in human history with the possible exception of the printing press. And it happened because a bunch of geeks in California, Massachusetts, and elsewhere in the country picked up where the military-industrial complex left off after the Cold War.

The Internet could have never been born of state decree. It’s too dangerous. It’s too difficult to monitor and control. It’s far too unwieldy. No, something so decentralized, open, and free could only have been conceived in an environment embodying those characteristics. The military had designed a decentralized computer network equipped with routing and packet switching because they wanted the system to survive if one of its nodes was located in a city that was nuked. This open platform enabled geeks to tinker in their basements and surreptitiously fiddle with pay phones while they made fascinating new discoveries about how communications systems worked, and how they could overcome the restrictions around those systems.

Throughout the ’80s we saw something truly magical, the formation of the first ad hoc virtual communities–Bulletin Board Systems. It wasn’t cheap, but with the right tools and know-how, anyone could set up a BBS and start up a little nation-state that played by his rules, and if the members of the BBS didn’t like it, they could go somewhere else, or start their own. It was an opportunity for people to become “as gods,” in the words of Web pioneer Stewart Brand, in control of their own identities, and thus their destinies, like never before. You could be gay on the Internet and nobody could do a thing about it. You could pretend you were a cat. You could be a prince online, whether rich or poor in reality. Now we’re getting to the crux of it.

Computer technology has changed many things, but the most profound has been the ability to empower individuals to redefine themselves in a social environment, to hack into their personhood, their identity, and truly become who they want to be. It doesn’t matter if you’re ugly or physically disabled–no one needs to know. And that freedom is contingent on the ability of Web users to take control of their identities–to be as anonymous or pseudonymous as they want to be.

At least, that was how it was supposed to work.

As the Web has developed since the ’80s, it’s become more lucrative for people who want to sell you things. And it follows that it’s become more lucrative to become the kind of politician who pushes for regulation of the Internet so that people who want to sell you things can do so more efficiently. Meanwhile, the rise of social networks has been accompanied by an unsettling accumulation of private information, given over to corporations willingly by those who wish to seamlessly engage with the Web.

At the same time, a global network of pranksters, activists, and bullies, drawing from two decades of privacy and free-speech activism, have taken on the anti-persona of “Anonymous,” donning masks and causing havoc ranging from picking on classmates to bringing down the Web sites of multinational corporations. These (mostly) smart, well-connected people from a seemingly infinite range of backgrounds and an equally diverse set of motivations see anonymity as a source of power, perhaps the most integral human liberty that can be provided in a free society. They’re loosely organized, and they often clash within the group. But their amateurish disorganization mirrors the early Internet in that there’s no primary control center, no head to decapitate. Similarly, the folks behind WikiLeaks have taken up the fight against control of the Web from a different angle. They’re less chaotic, and thus more approachable to the media. They at least operate under the pretense of working within the law, but the threat they pose to the establishment is equally grave. Where their fathers hacked machines, these freedom-loving network natives are hacking the media, politics, and, most important, the self, in dynamic and unpredictable ways.

It made sense that the Internet would become a battleground between the haves and have- nots, with information as the currency involved, whether personal or political. What we’ve seen in 2010 and 2011 is that the Internet isn’t quite as locked-down as power brokers thought, and people weren’t going to give up control of the open Internet without a fight.

That the Internet evolved the way it did almost seems like an accident. It spilled throughout the globe. In many ways it upends traditional power structures, encourages unlikely alliances, and spreads knowledge and hope for a better world. Governments and corporations may be able to sway the gavel, the sword, the coin, but the individual controls the wires, wrangling technology to conduct asymmetrical warfare, continuously evolving new ways to wrest control from the historically powerful.

The Web will continue to see warfare in the coming decade. Its primary battleground will be the identity space. Your ability to define who you are as a human, to be as open or as private with your personal information as you want to be, to speak out against injustices anonymously, or to role-play as someone you wish you were–these are the freedoms we will fight to keep. Will you decide who you are or will you be defined by the identity brokers?

On the face of it, we recognize cyber bullying, faceless slander, and data theft to be universally recognized evils, and we should therefore do what we can to mitigate them. The simple, obvious solution is to force everyone to wear a name tag in cyberspace, so that everyone is responsible for their actions online, just like in the real world. Evildoers use anonymity as both a shield and a weapon. If we rob them of both, we’ll have less evil.

My position: It’s just not that simple. Throughout Hacking the Future I trace the rich heritage of anonymous speech in a free society and examine its most popular current manifestations. I explore the bits and bytes behind the argument. I use the technology and come face-to- face with unspeakable evils in dark places I’d prefer never to return to. I consult the men who shaped the Internet and the soldiers toiling in the trenches of network security who intimately recognize the terrifying potential of the Wild Wild Web daily. I talk to code breakers, whistle- blowers, researchers, hacktivists, and mothers.

This book is essentially a 137-page rebuttal to Ms. Zuckerberg’s comments. Her attitude is shared by many within the tech industry, and even more outside that universe. I wanted to figure out if it’s worth living with anonymity on the Internet because I believe, without a doubt, that the Internet is the most important tool we have for promoting liberty. The identity issue may be the most crucial decision we face in the coming decade.

The Web is being pulled in two directions. In the worst fears of free-speech advocates, the Internet becomes tightly regulated and real-name identities are enforced, such that everything you say can be traced back to you. The reverse dystopia is a lawless frontier, where cyber terrorists, pedophiles, and information thieves run free. The decisions that lawmakers and CEOs make today regarding the privacy of Internet users will determine the way the Web looks in the future. As the “real world” and cyberspace become increasingly intertwined, society has yet to determine if it wants the Web to be an electronic extension of one’s off-line life or something entirely different.