Episode Summary: Cory Doctorow on Enshittification – Why Everything Suddenly Got Worse and What to Do About It

Podcast: New Books Network (Peoples & Things)
Host: Lee Vinsel
Guests: Cory Doctorow, danah boyd
Date: November 17, 2025

Overview

This episode brings together science fiction writer and activist Cory Doctorow, researcher danah boyd, and host Lee Vinsel for an in-depth conversation about Doctorow's latest book, Enshittification: Why Everything Suddenly Got Worse and What to Do About It. The conversation explores the phenomenon of platform degradation ("enshittification")—the process by which digital services and platforms become exploitative, frustrating, and less useful for ordinary users while enriching their owners. The discussion expands to examine broader themes of technological and social decline, monopoly, financialization, work, and the future of AI.

Key Discussion Points & Insights

1. The Concept of “Decline” and Jenga Politics

• Lee Vinsel frames the discussion by distinguishing between knee-jerk narratives of decline and more specific, "measurable forms of decline" (ghost towns, obsolescence, digital platform decay) [03:00].
• Danah Boyd introduces "Jenga politics," a metaphor for how institutional and infrastructural brittleness accumulates as officials and external shocks remove pieces—until the whole thing collapses:
  • "The whole game of Jenga...is that somebody takes out pieces...so that the tower will eventually fail." [07:00]
  • In the real world, "Everybody loses" when institutions crumble, not just those who 'pull the last piece.' [08:05]

2. What Is "Enshittification"? (Doctorow’s Theory)

• Cory Doctorow describes “enshittification” as a three-stage process by which digital platforms go from serving users, then businesses, and ultimately only themselves and shareholders [12:00]:
  1. The platform is good to users to attract and lock them in.
  2. Once users are locked in, the platform shifts to extract value from them for business customers.
  3. Both users and businesses are now locked in and value is extracted for the platform’s owners/shareholders.

"You end up with a platform where all the value...has been taken away from the users." [15:40, Doctorow]

• It’s a process catalyzed by monopoly power and exacerbated by a policy environment that rewards harmful rent extraction and prevents people from easily leaving for better alternatives [16:30].
• Doctorow emphasizes policy choices and regulatory failures as foundational; this isn't just about individual greed or consumer choices:

"We don't have to be prisoners of the terrible policy decisions of the first two decades of this century." [17:55, Doctorow]

3. Monopoly, Financialization, & Structures of Incentive

• Danah Boyd highlights the deep connections between monopolistic tech companies and the financialization of the economy (VC funding, shareholder value, financial engineering) [18:45].
  • Tech workers, managers, and shareholders are now entangled in a “perverse incentive” structure—"coming from inside the house and outside the house”—where everyone's fortunes are tied to stock performance [24:00].
  • The ecosystem encourages everyone (even employees and society at large through index funds and retirement accounts) to be "enrolled" in the platform’s relentless monetization [25:00].
• Doctorow elaborates on how Chicago School economics enabled these structures, including “shareholder supremacy” and lobbying for beneficial tax treatments [19:50].

"Shareholder supremacy is...a willful act of brain damage." [21:00, Doctorow]

4. Regulatory Capture, Worker Power, and the Uberization of Employment

• Doctorow notes that tech worker leverage came from scarcity, not unionization. Mass layoffs quickly erode that power [28:00].
• These policies enable "work without a boss" (gig economy), which removes avenues for redress and makes workforce exploitation easier [29:00].
• The winner-take-all market structure has shifted culture: today’s students are looking to become investors, not builders or entrepreneurs [31:56, boyd].

5. How "Venture Capital Makes the Monsters"

• Investors and VCs, not just founders, drive the extractive behavior—demanding abuses that maximize profit, not out of "sadism" but perceived rationality [34:00].

“It’s not Elon Musk that’s actually configuring that reality. It’s people behind him whose names we don’t know...far gnarlier than what we could separate out under monopoly.” [32:12, boyd]

• The only way to break the cycle is to build structural safeguards: robust APIs, unionized labor, decentralization—so it’s harder to “enshittify” later [36:00].
• The narrowing of capital sources and the inevitability of “shittier and shittier” business practices on mature platforms (e.g., Facebook) is discussed [37:00].

6. Policy Solutions and Alternatives

• Doctorow’s solutions focus on policy shifts and rebuilding coalitions:
  • Enact meaningful privacy regulation (“the last privacy law was in 1988!”) [41:50]
  • Legalize and encourage interoperability and reverse engineering, undermining rent-extraction scheme [42:00]
  • Seize global geoeconomic opportunities as the US relinquishes its grip (“time to make America sad” by ending automatic American platform supremacy) [44:00]
• Open Source and Free Software: necessary but not sufficient. Doctorow sees a blend of state investment and commons-based production as the way forward—“a fusion of the open source promise ... and the free software promise...” [47:32]
• Worker cooperatives: Doctorow advocates worker-led co-ops as more resilient than consumer co-ops, provided switching costs to join can be lowered (via policy change, interoperability, etc.) [62:20]

  “Worker co-ops...treat their workers right just as a baseline. Workplace democracy...means when they're wrong, you can do something about it.” [66:36, Doctorow]

7. The AI Bubble and Future of “Enshittification”

• Both Doctorow and boyd agree that generative AI is ripe for enshittification—opaque, error-prone, and full of opportunities for extractive rent-seeking [73:47].
• Doctorow predicts many foundation models and big AI companies will collapse under business models that simply don’t add up:

“Stein’s Law: anything that can’t go on forever, eventually stops...the number of foundation models...might drop to zero.” [75:41, Doctorow]

• boyd is less worried about the tech and more about the social and institutional destruction it will cause—the “enshittification of work” and the mass loss of skilled process knowledge and community fabric [79:00].

8. Loss of Knowledge: Agnotology and Process Knowledge

• The group discusses “agnotology” (the study of ignorance), especially how institutional knowledge is lost not due to malice or fakery, but simply from neglect, disuse, or over-reliance on automation [82:00].
• Loss of “process knowledge”—the lived, informal expertise within organizations—can cripple entire systems, and digitization/AI threaten these communities of practice [86:48].

Notable Quotes & Memorable Moments

• Doctorow: “We have this policy, these series of policy choices that created an enshittogenic environment that ensured that these bad people would always be on top.” [16:20]
• boyd (on incentive structures): “It’s coming from inside the house and from outside the house.” [24:05]
• Doctorow (on solutions): “We could just stop them. We could just make it illegal. And then they wouldn’t.” [41:55]
• Doctorow (on AI): “All the jobs that supposedly it can do, it can’t do. Which doesn’t mean your boss won’t fire you and replace you with an AI that can’t do your job because your boss is relentlessly horny never to pay you again.” [76:01]
• boyd (on agnotology): “There are three kinds of ignorance...what’s not yet known, what is forgotten or lost, and what’s polluted or undermined. ... I actually am more worried...of that second tier—we’re going to lose so much shared knowledge.” [81:44]
• Doctorow (on co-ops): “Their margin could be our opportunity, but we need to...” [65:28]

Timestamps for Key Themes

• [03:00] — Vinsel: Opening thoughts on decline, disinvestment, and digital degradation.
• [06:49] — boyd: "Jenga politics," census, and civil service resilience.
• [11:00] — Doctorow: What is “enshittification”? The three-stage degradation model.
• [16:30] — Doctorow: Monopoly, captured regulators, policy history.
• [18:45] — boyd: Financialization and venture capital’s role.
• [24:00] — boyd: Employee incentives & societal "enrollment."
• [28:00] — Doctorow: The rise and collapse of tech worker empowerment.
• [32:12] — boyd: Venture capitalists as "monsters behind the monsters."
• [34:00] — Doctorow: Investors rationalizing exploitation.
• [41:43] — Doctorow: Concrete policy solutions.
• [47:32] — Doctorow: Role of open source and government in public technology.
• [62:20] — Doctorow: Worker co-ops versus consumer co-ops.
• [73:47] — Doctorow: Enshittification and the coming AI collapse.
• [80:37] — Doctorow: Dangers of losing entire institutional functions to failed hype cycles.
• [81:44] — boyd: Agnotology and societal knowledge loss.
• [86:48] — Doctorow: Process knowledge—what gets lost that tech can’t duplicate.

Tone & Atmosphere

• The conversation is lively, intellectually rigorous, and deeply intertwined with both humor and urgency.
• Both Doctorow and boyd frequently use colloquial and irreverent language (“greedy as fuck,” “relentlessly horny never to pay you again,” “wobbly tower,” “temporarily embarrassed entrepreneurs”).
• There’s camaraderie among the speakers—this is a group of old friends poking fun, citing doctoral-level theory, and swapping war stories about tech, policy, and academia.

What’s Next from the Guests

• boyd: Working on research about “decoys” and abstraction traps in AI justice and policy, as well as a forthcoming book on the US Census and politics of data (“Data Are Made, Not Found”) [89:45].
• Doctorow: New book, The Reverse Centaur’s Guide to Life after AI (coming June 2026), and graphic novel adaptations of both Unauthorized Bread and Enshittification [90:57].