Cory Doctorow doesn't just recount the history of the internet; he diagnoses the precise moral failure that allowed it to rot from the inside out. In a landscape often dominated by technical post-mortems, Doctorow offers a startlingly human explanation for the current digital decay: it wasn't a lack of intelligence that broke the web, but a surplus of shamelessness. For busy readers trying to navigate the era of algorithmic manipulation, this piece reframes the crisis not as an inevitable technological evolution, but as a series of conscious choices made by people who simply stopped caring about the user.
The Moment the Web Broke
Doctorow anchors his argument in a personal flashback to the late 1990s, specifically his time co-founding Opencola, a peer-to-peer search project that predated many modern recommendation engines. He describes brainstorming sessions where his team, aware of a nascent competitor called Google, deliberately reverse-engineered how to destroy it. "We were pretty sure we could extract a list of the 100,000 most commonly searched terms from Google, and then we could use our web-crawler to capture the top 100 results for each," Doctorow writes. The plan was to generate thousands of pages of "word-salad" to trick the search algorithm and harvest ad revenue.
The crucial pivot in the narrative isn't the technical feasibility of the scheme, but the emotional reaction to it. "The idea of someone deliberately poisoning it this way churned our stomachs," Doctorow recalls. This visceral disgust stands in stark contrast to the modern tech landscape, where such tactics are not just accepted but are the core business model of the industry's largest players. The argument here is that the early internet was protected by a specific kind of technologist—what Doctorow calls "Tron-pilled"—who viewed the network as a shared space to be nurtured rather than a resource to be strip-mined.
The thing that distinguished these monsters wasn't their genius — it was their callousness.
This distinction is the article's most potent insight. It suggests that the current state of the internet—characterized by what Doctorow has previously termed "enshittification"—is not a bug of the code, but a feature of the culture. When the team at Opencola considered the spam strategy, they felt fear and were inspired to save the web. In contrast, Doctorow observes, "When they brainstormed ways to break the internet, they created pitch-decks." This shift from moral hesitation to financial optimization marks the transition from the "old web" to the current era of extractive platforms.
The Death of Shame and the Rise of the Grift
Doctorow expands this historical anecdote into a broader critique of the modern tech elite, naming figures like Zuckerberg and Musk as the antithesis of the early "Tron-pilled" nerds. He argues that the capacity to imagine destructive strategies has always existed; the difference lies in the lack of shame required to execute them. "Evil genius is just a lack of shame," he asserts, stripping away the mystique of the "evil genius" archetype to reveal a much simpler, more banal reality.
The commentary here is sharp because it refuses to let the industry off the hook by blaming complexity or unintended consequences. Instead, it places the blame squarely on the decision-makers who chose profit over integrity. Doctorow notes that while the early internet had its share of trolls, they were "vastly outnumbered by the legion of Tron-pilled nerds who wanted to make the internet better." The current crisis, therefore, is a failure of that protective culture to hold the line against a new wave of actors who view the user as a product to be sold.
Critics might argue that this romanticization of the early web ignores the significant harms that existed even then, such as rampant spam, privacy violations, and the digital divide. While the early internet was certainly not a utopia, Doctorow's point is not that it was perfect, but that it possessed a foundational ethic of care that has since been systematically dismantled. The comparison is less about the quality of the technology and more about the intent of the builders.
When we brainstormed ways to break the internet, we felt scared and were inspired to try to save it. When they brainstormed ways to break the internet, they created pitch-decks.
Rebuilding the Post-American Internet
The piece concludes with a call to action, urging a new generation of technologists to reclaim the "Tron-pilled" ethos. Doctorow envisions a "post-American internet," a concept he is exploring in an upcoming book, which implies a geopolitical and structural shift away from the current US-centric, corporate-controlled model. He argues that defending the web requires more than just building new tools; it requires a fundamental shift in values. "We're going to need a multitude of Tron-pilled technologists, old and young, who build, maintain — and, above all, defend it," he writes.
This framing is particularly relevant given the current regulatory and political climate. While the source text mentions the administration's actions in passing, the core argument remains focused on the agency of the technologists themselves. The solution, Doctorow suggests, is not waiting for government intervention but cultivating a culture that rejects the "callousness" of the current giants. This is a hopeful, albeit demanding, path forward that places the responsibility for the internet's future on the people who build it.
Bottom Line
Doctorow's most compelling contribution is his redefinition of the internet's decline as a moral failure rather than a technological inevitability. By contrasting the shame-filled brainstorming of the 1990s with the pitch-deck-driven destruction of today, he provides a clear, actionable diagnosis for the current crisis. The argument's greatest strength is its emotional resonance, but its biggest vulnerability lies in the difficulty of scaling this ethic of care across a global, profit-driven industry. For the reader, the takeaway is clear: the internet is only as good as the shame of the people who build it.