CHAPTER 11

Wanderlust

Cyberspace—its early-’90s name—was a secret galaxy. Only those in a few bubble worlds were privy to its mysteries. To gain access, you had to be an academic or a scientist. Or someone in the military or the government. Or a computer hobbyist or a hacker. The early Net, like the tech world in general, was insular, elitist, geekcult.

Then, in a flash, in swept the multitudes. With the creation of the World Wide Web and the first Web browser, any fool civilian with dial-up and some cheap software could suddenly teleport to that stratosphere. And a traveler, once hurtled into that vaporous new realm, had to deal inexorably with the old in-out.

For all the pitfalls of an online existence (Handicap #1: massive time suck) and for all its upsides (the unhindered wanderlust, the personal empowerment, the ease of entry for those in search of information and connectivity), the medium would also plunge its users, if they so desired, into a raging ocean of sex. And not just good old garden-variety sex, but sex of such crazy category and range that it made Bosch and de Sade seem tame.

It might be called Tech’s First Law of Sex (borrowing from Sir Isaac Newton—and the Book of Genesis). With each novel technology in communications or entertainment, the first app to fall from the tree is the Sex App. And porn, one of the basest expressions of human desire, is often the crowd-pleaser, offering the cheapest thrill and the quickest kick. According to Gerard Van der Leun in Wired magazine, it was none other than William Burroughs, the Beat writer and proud subversive, who considered sex to be “a virus that is always on the hunt for a new host—a virus that almost always infects new technology first.”

Examples abound. After Gutenberg turned out the first printed Bible in the 1450s, virtually the second title off the movable-type press was a sampling of erotic prose.1 With the advent of photography in the 1820s and ’30s, it took only a few years before Paris photo studios would make a tidy sum selling erotic “art studies.” Once Thomas Edison and the Lumière brothers created the earliest “moving” pictures, customers in the late 1800s were soon peering through peepholes at female dancers, nude bathers, and strippers teasing the eye. A century later, when videotape caught on, the VHS format (so legend had it) triumphed over Betamax because the latter neglected—or refused—to accommodate what was then called “porno.” (This turned out to be a suburban strip-mall myth. JVC’s VHS stole the market from Sony’s Betamax not because of porn but primarily because Beta tapes ran for an hour, max, while VHS put out two-hour tapes—long enough to record an entire movie, porno or no.)²

Says Jane Metcalfe, cofounder of Wired, which was launched in the early ’90s, “You see it with Hi8 [the early camcorder] or cable TV or BBS [the computer bulletin board system]. There were all of these virtual worlds evolving, and the anonymity that went along with that freed up a lot of libido.… It’s worked for one technology after another, whether it was Betamax or the Minitel” (the French home-terminal service that in the 1980s became an electronic portal for erotic engagement, right in users’ living rooms).

In this grand tradition, it would be hard to overstate the importance of sexual commerce as a crucial come-on in attracting the masses to the fledgling Web.

Among digital age savants, Michael Wolff is both a historian and an oracle. Now a well-known media columnist, he spent a long stretch of the 1990s putting out NetGuide, a printed road map to the Web. (It sounds utterly antiquated today—a paper atlas for an electronic universe, updated every couple of weeks!—and yet NetGuide was a useful crib sheet for Internet newbies.) In his book Burn Rate, Wolff would chronicle his years in this digital dawn. “I remember when there was no porn on the Internet,” he now says. “I wondered why. And then suddenly it was everywhere—as if everyone was thinking the same thought. With the Internet, you had people leading fantasy lives at a new velocity. It was no longer the spirit of the ’60s and we’re all liberated. Instead, it’s private. It’s all furtive… and it’s everywhere.”

Over a long lunch, he lays out a back-of-the-napkin history of the Net’s erotic explosion in the ’90s. Michael Wolff is an imposing presence, known for his contrarian, categorical pronouncements on media issues, as well as his withering critiques of the grandees of the infotainment industry. With his shaved head, severe brows, and long, coiled frame, which he cloaks in impeccably tailored suits, he conveys the menace and tenacity of a raptor. Wolff’s contention is that “dirty talk” (often referred to at the time as “hot chat”) is really what kicked it all off. “AOL was an entire business founded on sex,” he insists. “Companies in the early to mid-’90s all knew this and said, ‘Our real revenues and Net traffic are about sex. Interactivity is really about sex.’”

Wolff speaks in a present tense that adds a volt of urgency. “In 1992,” he says, “the Internet has become this academic network that had been built on the military’s ARPANET. If you’re on a campus, you have access. It’s just text. It has no interface. There are a few specialty, clubby [platforms] like the WELL, ECHO, and MindVox. At the same time, you have these other systems that are consumer-driven: CompuServe and Prodigy… and AOL. These are closed systems—online bulletin boards. You cannot access them through the Internet.

“And AOL’s first real competitive advantage is that it doesn’t censor. Everybody else is censoring in a fairly heavy-handed way. They have corporate owners; it never occurred to them not to censor [because] they don’t want dirty stuff. AOL starts to figure out: this sex chat is an incredible driver. And they find out that not only do people like sex chat, but once you start, you cannot stop. And over the course of ’92, ’93, ’94, AOL explodes on the basis of sex chat”—in which individuals flirt or share erotic fantasies or have suggestive conversations in the form of digital exchanges that they type on their keyboards. (“Some say [AOL] was the house that porn built,” one ex-AOL manager tells me, requesting anonymity. “At places like Yahoo and elsewhere, monitors were brought in to clear up the chat rooms and take down inappropriate content. Not at AOL. The stance was: these are private areas.”)

Wolff circles back again to describe those rudimentary networks. “There are parallel systems,” he says, that are “not actually [part of] the Internet, but Internet-accessible: the newsgroup hierarchies.… At its peak there are probably more than one hundred thousand of these. Then, at some point, the ‘alt’ hierarchy is created. And there grow hundreds and hundreds of essentially sex-related bulletin boards in every possible permutation.… The original ‘alt’ newsgroups were entirely about sex. It suddenly was ushering in the age of the fetish.

“Just to give you an idea of what these alt.sex groups were like, Ben Greenman, now an editor and writer at the New Yorker, was one of the guys writing these synopses”—for the NetGuide that Wolff was publishing. “At the time he was about twenty-two. He wrote this thing—I fell down laughing when I read it. This is twenty years ago and I remember it perfectly. The group was alt.sex.spanking. I remember Ben wrote to describe it, ‘If spankers had a nation, [this] would be their Congress.’ So for the first time in human history we are segmenting sexual practice into communities.3

“Functionally,” Wolff continues, “we have this thing going on on AOL as well as this thing going on on the Internet—still parallel cultures. But it’s contained. AOL is charging a lot. The Internet is accessible through arcane avenues—you jack in through a community college ID. You’ve got to be able to work UNIX code.” Next, he recalls, “two things happen to open the Internet. First was the invention of the browser, in 1993.” (The Web itself, created in the early 1990s, was a system of protocols spearheaded by physicist Tim Berners-Lee, who decided to offer them to users for free. Soon, software engineer Marc Andreessen and his colleagues would distribute Mosaic, the first popular Web browser. Shortly afterward came the first search engine and then, over time, the first modern laptop and the first weblog—later called a blog—among a string of other firsts.)

In the mid-’90s, says Wolff, “AOL abandons its hourly fees. This is the single largest development in the new mass appeal of the Internet and in the use of the Internet as a sexual tool: flat-fee pricing. Suddenly, you can spend as much time as you want on AOL pursuing your sexual obsession and it’s not going to cost you any money.” In short succession, AOL rolled out Instant Messenger. In a separate window on your screen, you could engage in a private conversation. Then came “a searchable database of fellow chatters,” as Wolff describes it, “that grew to vast proportions (any interest or kink was immediately searchable).” Buddy lists came along to help keep tabs on people in your personal network.

“At sort of the same time,” Wolff recalls, “the Internet goes graphic”—offering dirty pictures too—and soon “AOL links to the Internet and AOL becomes the way Main Street taps into the Internet. AOL sends those discs everywhere.” Wolff is referring to free-trial CDs that people would use to install AOL software on their home computers and that were distributed in every imaginable manner: packaged with popcorn boxes or Blockbuster video rentals; bundled as floppies—and flash frozen—along with Omaha Steaks; shrink-wrapped on the outside of magazines, neatly sheathed and almost Trojanesque.

In no time, the service took off, and digital media swiftly became mass media. The public’s growing attraction to the Web, according to Wolff, was in large part a product of two forces: “Sex chat on AOL—and porn pictures online. And it happens fast. People are generating their own content. The sex thing is the profound thing because it’s the accessible thing. It’s consumer-friendly. It’s this incredibly interesting, frightening form of entrapment. Pornography has always had this habituating aspect. But [historically] it was rate-limited by the fact that pornography had been fairly exclusive, expensive, and embarrassing. You’d get it in brown paper. Now it’s plentiful, free, easy to keep—and secret, so you don’t have to feel embarrassed about it.

“What’s more, pornography had been lonely. But it’s not lonely anymore. It’s interactive. So the fundamental nature of prurience is revolutionized. There’s only one thing missing in this revolution, which is speed. Pictures load slowly. Speed starts to come in ’97—you went from dial-up to Ethernet. And after ’97, you get moving pictures.… Fetishists become entrepreneurs.… Webcams catch on and they are essentially about voyeurism: a woman walking around naked or masturbating constantly.”4

In the meantime came the rise of search… and social. At first there were search engines such as Yahoo, AltaVista, Lycos, Excite, and Infoseek.⁵ “Then Google starts in ’98,” Wolff remembers. “Your ‘search’ is about sex. For a long time, the biggest search word was just ‘sex.’ Then people realized, ‘Oh, you could use this to get exactly what you want.’ So by the end of the decade”—with the advent of social media, popularized by the big online services like AOL, then segmented with focused networks such as Classmates.com and SixDegrees.com—“the Internet is about to become the greatest hookup medium in the history of the world.

“There is a point [to be made],” he concludes, “that the roots of the Internet are grounded in pornography, in a constant need for images and titillation and fetishized behavior. If you work out the implications of pornography, it’s always about a steady devaluation. And it devalues because there’s always more of it. The economic basis of media is scarcity: there are only so many minutes of airtime, for example, that one can buy [on a TV show—to place one’s commercials]. What happens, then, to the nature of media when there is no scarcity and there is an infinite amount? That’s what the Internet teaches us. It devalues all content.”6

The early Internet had sex appeal, quite literally.

During the mid-1990s, my friend Aidan Sullivan was the director of photography at the London Sunday Times Magazine. He was also a co-owner of image.net, an online licensing service that helped Hollywood studios digitize and distribute their film stills to European publications. Sullivan remembers his early 14K Hayes modem and its molasses-slow dial-up connection. “You’d hear this electronic pulsing—‘dindle-iddle-ing,’ then this under-the-ocean guttural crackle—then the pictures would build horizontally, line by line, like an old wire-service transmission. It took about three to five minutes.” And yet the first time he saw an Internet page build itself, he says, “I thought, ‘This is limitless. It’s enormous.’”

And so it was. Soon image.net’s business—and its Web traffic—soared. But their system often crashed, frustrating clients who had to endure significant “downtime” while waiting to access their images. So Sullivan and his colleagues went looking for larger, more reliable servers. “I went to visit the server site in Clerkenwell, in central London, in an open-floor warehouse,” Sullivan says. “The servers were big gray-black boxes with lots of cables coming out of them. And as we were walking by, there was one unit that was bigger than the others. It was going nuts. The lights were flashing. It sounded like it was alive—sort of buzzing, like it was steaming. And I said to the guy escorting me around, ‘Oh, I’ll bet that’s one of the banks.’ And he said, ‘No, actually, that’s the porn industry. And it goes 24/7.’ And I just thought, ‘Of course it is!’ They were serving porn clients and, like us, were guaranteeing uptime. Uptime, in this case, was a rather good phrase.”7

If Sullivan was a relative techno rube, Jane Metcalfe—the cofounder of Wired magazine—was something of an old soul.

I meet Metcalfe on the Embarcadero in San Francisco. We are soon walking through the headquarters of TCHO, the high-end chocolate manufacturer that she helped get off the ground in the mid-2000s with her partner, Louis Rossetto, and Timothy Childs, a computer-graphics innovator (and onetime NASA space shuttle contractor who would become an entrepreneur, sustainability expert, and chocolatier). The overpowering aroma of cocoa hangs in the air as we survey the factory, set on a waterfront pier the size of an airplane hangar.

Metcalfe and I go out for coffee. Engaging, candid, and full of youthful idealism, even in her fifties, she shares her perspective on the birth of Wired magazine—and wired culture. She and Rossetto had conceived and published Wired, which they rolled out in 1993, hoping it might someday become an indispensable handbook for understanding the impact of new technology on society and culture. It was an instant hit. (Now they’ve embarked on yet another business with intentions of caffeinating a nation, and the world beyond.)

Metcalfe’s compass back in those years was aligned not with New York or London but with the more free-spirited ethos that reigned in Amsterdam and San Francisco. In the ’80s she was living in the Netherlands with Rossetto when they began hammering out the template for the new tech magazine they wanted to launch in America. “Amsterdam was all about sex,” Metcalfe remembers. “It was an extremely permissive place. And I was forever arriving places and people’d say, ‘Boy you should’ve been here ten years ago.’ So to be in Amsterdam in the late ’80s and here [in San Francisco] in the ’90s was the right place at the right time.” Rossetto himself was an interesting case. A libertarian and onetime Young Republican leader as a Columbia undergrad, he became a novelist and journalist—ghostwriting a book called Ultimate Porno, documenting the experiences of a first assistant director in the 1970s working the Roman backlots while making the colossal orgiastic flop Caligula—before making his name as a writer and editor for tech-oriented publications.

As Metcalfe remembers their life in Amsterdam back then, she and Rossetto worked with a couple of the Oxford-schooled magazine editors who were plugged into “the cyberpunk-rave scene. Party kids would take the ferries over [from England] and continue all night… messaging each other about where the party was going to be. So the connection between the cyber scene and the rave scene—before the Web browser—was really interesting. It was being driven by the music—project[ing] imagery onto a sheet, timed to the beat. The culture was influenced by laser discs, by technological advances. It gave way to a time when people could manipulate art and information.” (The drugs, inevitably, helped grease the wheels as well.)

If Europe’s scene was dominated by ravers and cyberpunks, as Metcalfe tells it, out in California there was a comparable crowd (also influenced by music and the tech boom) that was tapping into the works of a passel of futurist-fantasist-noir writers deeply steeped in the counterculture.8 It was during this same period, Metcalfe notes, that sex would hijack the so-called MUDs and the MOOs, those virtual-reality multiplayer systems popular among early digital adopters. “These were online fantasy worlds,” she explains, in which people communicated via ASCII text, “but perhaps their very numeric limitations were what made it so erotic for people in the first place. It really unleashed your own individual imagination, sitting by yourself at your keyboard late at night, and just that thrill of connecting with another human, live, was so powerful that it really just drove this thing. These multiuser worlds became places where everything that would happen in real-life sexual circumstances played out. Only instead of it being between men and women and humans, it’s between, you know, a furry squirrel and a hairy ape, or a ten-foot-tall blue android or whatever else you can come up with. So that added this whole other, very playful dimension that actually started to manifest in the physical world at places like Burning Man”—the annual outdoor art happening and so-called fire party that was first hosted on a San Francisco beach in the mid-’80s and was later reconstituted as a festival-pilgrimage-and-portable-community for thousands in the Nevada desert—where, says Metcalfe, people would actually assume alternate identities. “The sexual fantasies of the online world,” she says, “became costumes and behaviors at places like Burning Man.”

During the ’80s and early ’90s, the Northwest Coast, from Santa Cruz up to Seattle, was all about tech erupting, venture capital spouting like a geyser, and hackers making headlines. Computer magazines—nerd journals jammed with gadgets, tips, and the scoop on the latest hardware and software—catered to the faithful. Wired, however, would be a new strain of publication entirely, a sort of next-level mash-up of the Whole Earth Review, MacWEEK, the cyberculture glossy Mondo 2000, and the many tech-biz mags then flooding the zone. Wired assembled a clued-in cabal of digerati: their mission was to enlighten readers about how the cyber revolution would upend the established order, empower nobodies everywhere, blur reality and fantasy, and feed everyone’s head. Wired had a jarring neon color scheme and radical-sleek layouts that did away with the literal and the linear. The look and feel of the magazine would make it plain that it was speaking in a new digital dialect that was decidedly outside the Frequency, Kenneth.

Metcalfe and Rossetto published their first issue in January 1993. And sex was not incidental to the content or to this new worldview. “One of the pull-quotes in the first issue,” Metcalfe recalls, stated that “‘Sex is the Killer App’ for new technology.” One story in that premiere edition focused on how online erotic networking had stepped up the real-world game of individuals’ sex lives (“This Is a Naked Lady,” by Gerard Van der Leun, the onetime director of Penthouse.com). Another was an interview with Camille Paglia, whom Wired called the “bad girl of feminism.” Paglia, in a conversation with Stewart Brand (father of the Whole Earth Catalog and The WELL, and formerly one of Ken Kesey’s Merry Pranksters), discussed, among other topics, Paglia’s recent book Sexual Personae; the “healthy” sexualization of American pop culture; and her encounters with Marshall McLuhan, the patron saint of Wired. “When you were sitting with McLuhan in the middle of the night,” Paglia remarked, “all you would see was the tip of his cigar glowing, and you would hear him making these huge juxtapositions.… [Divergent thoughts] ssssizzle when you bring them together.” Sometimes a cigar is more than a cigar.

Wired debuted at an auspicious juncture. “The magazine hit the newsstands the week Bill Clinton and Al Gore were inaugurated,” Metcalfe says. “Al Gore was talking about the information superhighway before anyone knew about it. It couldn’t have been better timed. It ushered in a whole new generation, colored by a different set of values and a different set of references. World War II was way over. Even [the] Vietnam [War] felt distant. We thought: this is a post-Vietnam world and if we have a different set of tools in our hands, we can change the world. It was a giddy time. And there’s that A. J. Liebling quote: ‘Freedom of the press is guaranteed only to those who own one.’ It made sense: suddenly everyone would have these tools. They would be owning it.”

In fact, a different set of values had grown out of (and grown up with) the digital world, values that mirrored the men and women present through its birth and adolescence. Since the earliest phase of the electronic age, counterculture and digital culture—indeed, sex and tech—had shared the same fertile mulch in the Bay Area hothouse.

The Internet’s roots, oddly, had first grown from the right, not the left. The Net’s forerunner was developed for the military, and its earliest users, as well as many of the earliest evangelists for the computer, were often affiliated with research labs, corporations, or academic institutions that had strong military ties. But as 1960s America splintered politically and socially, the region around San Francisco helped propel the counterculture. And this vocal and sizable amalgam of progressive individuals—espousing free speech, self-empowerment, youthful experimentation, consciousness expansion, and a set of ideals that ranged from libertarian to communal to utopian—deeply influenced the San Francisco–area engineers, programmers, and hackers, along with the nation’s wider community of netizens. In ways large and small, the ’60s youth rebellion, the mind-set of the so-called New Left, and the attendant sexual revolution had all helped lay the track for the digital revolution.

John Markoff, the Pulitzer Prize–winning technology writer for the New York Times, makes this point persuasively in his book What the Dormouse Said: How the Sixties Counterculture Shaped the Personal Computer Industry: “The Vietnam war, drugs, sexual liberation, women’s liberation, the Black Panthers, the human-potential movement, the back-to-the-land movement—at the end of the 1960s, all of these were concentrating with wicked force on the San Francisco Peninsula.” These elements, he says, helped shape the values and priorities of the computer culture vanguard.9

There was a loose but undeniable confederation between various groups in the area: the statistical analysts who assisted the Pentagon during the Vietnam War and the antiwar activists; the early acid trippers and the pioneering propeller-heads at local electronics companies and research labs; the Merry Pranksters and the participants at clothing-optional parties hosted in the mid-’60s by math professor turned computer wizard Jim Warren (where, according to Markoff, “a whole range of worlds seemed to intersect in the parties at his mountain cabin: hippies, academics, rock and rollers, and people from the nude beach scene… [enticing a BBC film crew to shoot] part of a documentary on the ‘Now’ generation”) and, later that decade, guests at parties thrown by real estate lawyer John Montgomery (which, in Markoff’s words, were “attended by many of the Valley’s more liberated techies.… There were nude sunbathers, peacocks strolling in the backyard, a PA system playing rock-and-roll music, and a light organ, an electronic device that projected colored lights to accompany music. Inside… there were orgy rooms and a room where everyone could try laughing gas”).

As Markoff recalls, some of the region’s visionaries believed that the insights derived from mind-altering substances mirrored the nonlinear thinking that was central to tech innovation. There was Douglas Engelbart (seer of the modern computer network and personal computing, as well as father of hypertext and the computer mouse), who headed up the Stanford Research Institute in the 1960s—“a tiny band,” as Markoff describes them, “distinguished by their long hair and beards, rooms carpeted with oriental rugs, women without bras, jugs of wine, and on occasion the wafting of marijuana smoke.” There was the aforementioned Stewart Brand, who, in a no-holds-barred story for Rolling Stone in 1972, discussed the use of psychedelics among a key sector of the computer community. (A generation later, he would offer the elegant decree, in a 1995 Time essay on the computer boom: “We Owe It All to Hippies.”) There was Steve Jobs, the cofounder of Apple, who in 2001 showed Markoff an early demonstration of iTunes, which produced “dancing color patterns that pulsed on the computer’s screen in concert with the beat of the music,” the author recalls. “Jobs turned to me with a slight smile and said, ‘It reminds me of my youth.’… He explained that he still believed that taking LSD [in the early ’70s] was one of the two or three most important things he had done in his life.”

The makers and shakers of the Silicon Valley—like the information that graced their creations—wanted to be free, and freewheeling.

And in terms of sex, how freewheeling was it?