The Work of the Closing of the Internet Frontier
The boy masterminds once roamed its mIRC chatrooms and Usenet groups like herds of buffalo
You know the archetype: the boy mastermind of the internet.1 Snarky and full of himself, a know-it-all shielding his insecurities behind the anonymity afforded by cyberspace. Perhaps you were even such a mastermind yourself, back when the web was young and uncivilized, when the light of your monitor backlit a 1024 x 768 display. But his natural habitat has become crowded with "normals" and "sensitives" — types he probably thought he had left back in the real world. Much to his chagrin, the "IRL/URL border" has become much more permeable since the age of Mosaic and Netscape Navigator, and what was once a simple turf war has transformed into a bitter rearguard struggle to preserve a piece of a rapidly vanishing past.
This transformation raises an interesting question: is the culture of the internet mastermind something better left abandoned and forgotten, or does it represent a unique moment in digital history worth preserving?
Drive through certain parts of America, and you will see Confederate flags on display in states that fought for the Union. These flags are no longer shows of support for a rogue state; rather, they are nostalgic emblems of a make-believe era when society was static and people knew their place.2 Similarly, some beaten-down internet masterminds often invoke a halcyon vision of a benighted time when, as "problematic" as things were, they at least had a special and secretive room of their own.
I entered that "room of one’s own" when I was eleven. My family connected to the internet in 1993, and the version of it that I encountered through the Mosaic web browser struck me as an ugly, confusing place. It lacked meaningful curation and was navigated through primitive impressionistic path-finding, with the user directed from one pile of black text set against a white background to another. Images could be displayed, though even the most low-resolution image took an eternity to load (in spite of that limitation, smutty pictures and other vulgar content soon began to accumulate on FTP servers). In time, I discovered bulletin boards and forums relevant to my interests — comic books, wrestling, weightlifting, — and immediately started engaging in pissing matches with other awkward loners studying those subjects.
This early internet was a kind of messy bachelor pad, and the boy masterminds abounded. Each of us had independently discovered the web, as we had done with Roger Corman films or the music reviews of Mark Prindle, and we manspread across this open frontier. And it was male-dominated terrain in those days, in principal part because of a process of acculturation that still equated computer technology with "nerds" and discouraged women from participating altogether. There was a running gag about the AOL chatrooms, in which parties exchanged wholly fictitious a/s/l information with one another, that such conversations inevitably devolved into two men who were pretending to be teen lesbians "cybering" with each other.
This was the golden age of the boy mastermind, a time when regular usage of the internet coupled with a poorly designed Geocities homepage was sufficient to cause your out-of-touch parents to label you a "techie." The multifarious harassment methods perfected in later years by certain internet subcultures were still in their embryonic stages, but they were no less effective. mIRC, in particular, was a bloodbath: I recall vicious mastermind competition for chatroom status that led to the creation of special password-locked rooms for private cliques, empty boasting about physical and sexual accomplishments, and seemingly endless attempts to "dox" (discover private information about one another, up to and including posing as someone else, usually a woman, to score nude photographs) and "break" (i.e., trigger some kind of serious mental breakdown) our rivals.3
As this rough-and-tumble culture coalesced, it would prove a useful vehicle for media outlets looking to increase viewership via scary stories directed at flyover country. The Columbine murderers Dylan Klebold and Eric Harris, who played the bloody first-person shooters Doom and Quake together &c., were villainous boy masterminds straight from central casting: a two-man "trenchcoat mafia" who conspired to wreak vengeance on their normal high school classmates. After Columbine, the boy mastermind became more than just a social outcast; he was now a suspect, too.
This cultural shift coincided with rapid technological advancements. The late 1990s and early 2000s saw the rise of broadband internet, which dramatically changed how people interacted with the web. No longer constrained by the slow speeds of dial-up modems, users could now stream audio and video, download large files, and engage in more complex online activities. This technological leap forward would prove to be a double-edged sword for the boy masterminds.
With the bursting of the dot-com bubble in 2000, the boy mastermind started sharing his space. Various companies were aggressively trying to recruit internet users, and internet speeds increased beyond the limitations of dial-up modems. By 2004, the boy mastermind surely saw the writing on the wall. All kinds of regular folks had logged on, and no longer just to arbitrage their worthless, store-bought Beanie Babies on the eBay market. Now the boy mastermind was faced with a fast-rising wave of people, including women and older adults, weblogging about their vibes and feels. Not only that, but content that these people might want to read was migrating online too. Where media and newspaper websites had once been mere bookmarks amid a sea of fanfiction and other DIY material, they were now integral parts of those businesses.
The rise of blogging platforms like Blogger (1999) and WordPress (2003) democratized content creation, allowing anyone with an internet connection and a pulse to become a publisher. This shift challenged the boy mastermind's perceived monopoly on internet expertise and content creation. The internet was no longer a specialized tool for the tech-savvy; it was becoming a public square where a welter of diverse voices could be heard.
Where once all the virtual world had been men, it was at first slowly and then suddenly a place for everyone else. Eventually stories about grandparents having weblogs ceased to be novel; eventually they ceased to be stories at all. And so the boy mastermind retreated further, moving his shitposting and harassing operations to text-heavy forums that recalled the bare-bones internet of yore.
Social media made things worse for the boy mastermind. Friendster (2002) and Myspace (2003) began allowing users to associate faces with names, lifting the veil of anonymity. Facebook (2004) and Twitter (2006) universalized the process, creating privately owned landscapes where Second Lives collided with, and eventually just became, Extremely Online first lives. Boy masterminds still linger on these sites, but their anonymous accounts and viral shitposts4 are increasingly anomalous on a publicly monitored internet more inclined toward polite speech and "identity-in-bio" presentations of the curated self.
The rise of smartphones and mobile internet further accelerated this trend. The iPhone, introduced in 2007, brought the internet into people's pockets, making online access a constant, ubiquitous part of daily life: the post hand (PH) and goon hand (GH) at last found the powerful prosthetic that unleashed their true power. This mobile revolution meant that the internet was no longer a separate space to be visited; it became an integral part of how people navigate the world, blurring the lines between IRL/URL existence.
Along the way, the masterminds lost their games and comics, too. Now that nerdy popular culture is just plain old American monoculture — all Avengers, Pokémon, and Dungeons & Dragons. The boy masterminds found themselves having to accommodate an influx of minority characters, game designers, authors, illustrators, and programmers; they could choose either to go all-in as unhelpful, social justice-obsessed white knights and pick-me tryhards5 or become embittered reactionaries, stewing in their own juices as they bemoan the good ol’ days of homosocial hobby shops and comic conventions.6
In all cases, the response from the darkest corners of what was once the internet frontier boils down to an angry won't-you-leave-our-stuff-alone plea — but the process they're critiquing is inexorable. For good or ill, the internet is more populous and diverse than ever before, and individual users have further differentiated and diversified themselves to stand out in this marketplace of banal ideas.7 The once-niche world of gaming has become a global, multi-billion dollar industry — a bigger business than movies and television combined. Lousy YA fantasy story and comic book adaptations still dominate the box office. The insipid mainstreaming8 of these formerly niche interests has brought joy to millions of normies but has left some original enthusiasts feeling displaced.
But is the culture of the boy mastermind deserving of preservation, like the habitats of the spotted owl or the religious communities of the Shakers? It does indeed represent a historical moment in the evolution of the internet, a time when the digital frontier was still wild and largely unexplored. However, like many frontier cultures, it can be retroactively memorialized as exclusionary and hostile to outsiders — a way of life with no place or purchase in the modern, interconnected world.
The internet mastermind may elect to portray himself as a warrior who succumbed to a force greater than his own. But that's a romanticization of a bygone era. The reality is that the internet frontier, like any frontier, was destined to be settled.9 The question now is how, if such a thing is even possible,10 we might build a digital society that preserves the spirit of innovation and exploration that characterized the early internet, while rejecting some of the unsavory or stupid elements of mastermind culture.
As we move further into the age of social media, artificial intelligence, and virtual reality, the landscape of the internet will continue to evolve. The challenges we face today — misinformation, privacy concerns, the devolving of consciousness into PH and GH — are far removed from the territorial squabbles of the early internet. Perhaps it's time for a new kind of internet mastermind: one who can navigate these complex issues with empathy, wisdom, and an unwavering commitment to building a unique digital world not predicated on the cash-on-the-barrelhead values of the speculator and the carnival tout.11
For now, the story of the internet mastermind will remain a cautionary tale about the dangers of gatekeeping and the inevitability of change. As we continue to shape our digital future, we would do well to remember both the innovative spirit and the pitfalls of that early internet culture. The frontier may be gone, but the need for pioneers — clever, weird, and forward-thinking ones — remains as strong as ever.
This is a comprehensive reworking of an article I wrote years earlier for The Awl. At the time, The Awl — like every other semi-mainstream publication — demanded the insertion of “Trump content” (see, e.g., what I had to do here). I have removed this offensive material, given that it was unnecessary and included only to ensure that I satisfied the editor and thus could collect my fee ($300 in 2024 money, in the case of this piece).
Things ain’t like they used to be and they never were!
All pictures of pictures of pictures of the original online culture of the 1980s and 1990s, to be sure.
She won’t pick you, dude.
Regardless of the option chosen, most remain creeps — something I discussed in this Paris Review article that (more or less) holds up.
“Every humanzee a brand-zee,” you might say.
Consider the following: “From the conditions of frontier life came intellectual traits of profound importance. The works of travelers along each frontier from colonial days onward describe certain common traits, and these traits have, while softening down, still persisted as survivals in the place of their origin, even when a higher social organization succeeded. The result is that to the frontier the American intellect owes its striking characteristics. That coarseness and strength combined with acuteness and inquisitiveness; that practical, inventive turn of mind, quick to find expedients; that masterful grasp of material things, lacking in the artistic but powerful to effect great ends; that restless, nervous energy; that dominant individualism, working for good and for evil, and withal that buoyancy and exuberance which comes with freedom—these are traits of the frontier, or traits called out elsewhere because of the existence of the frontier. Since the days when the fleet of Columbus sailed into the waters of the New World, America has been another name for opportunity, and the people of the United States have taken their tone from the incessant expansion which has not only been open but has even been forced upon them. He would be a rash prophet who should assert that the expansive character of American life has now entirely ceased. Movement has been its dominant fact, and, unless this training has no effect upon a people, the American energy will continually demand a wider field for its exercise.
But never again will such gifts of free land offer themselves. For a moment, at the frontier, the bonds of custom are broken and unrestraint is triumphant. There is not tabula rasa. The stubborn American environment is there with its imperious summons to accept its conditions; the inherited ways of doing things are also there; and yet, in spite of environment, and in spite of custom, each frontier did indeed furnish a new field of opportunity, a gate of escape from the bondage of the past; and freshness, and confidence, and scorn of older society, impatience of its restraints and its ideas, and indifference to its lessons, have accompanied the frontier. What the Mediterranean Sea was to the Greeks, breaking the bond of custom, offering new experiences, calling out new institutions and activities, that, and more, the ever retreating frontier has been to the United States directly, and to the nations of Europe more remotely. And now, four centuries from the discovery of America, at the end of a hundred years of life under the Constitution, the frontier has gone, and with its going has closed the first period of American history.”
I would argue that it is not, but that’s not the point of this peroration.
Once again: Ain’t gonna happen, but isn’t it pretty to think it could?
I feel attacked by this relatable content, dear sir! I was 16 or 17 when I first met the internet, thanks to being at NCSSM. I am actually more likely to say something somebody doesn't like to their faces. In any case, I don't say anything that I wouldn't say to their faces, if that makes sense. This week in as the internet turns, I learned that certain progressives don't want to hear or understand why any candidate who is a veteran... shouldn't that vet get out in front of any and everything that could trip them up from their military career? It's soooo hard not to be like "you idiots, you just created another swift boat situation" but... can't be out here calling the people idiots, right?
In early 00s I used mIRC and usenet to snag warez and thought torrents were mainstream when they came out. It felt very underground having the latest moviez, gamez and mp3z on CDR.