The Monopoly Report – Episode 54: The Enshittification of Everything (including digital media)

Host: Alan Chapell
Guest: Cory Doctorow (Author, Activist, Journalist)
Date: November 5, 2025

Overview

In this episode, host Alan Chapell sits down with Cory Doctorow to dissect the concept of “enshittification” – a term Doctorow uses to describe the worsening quality of digital platforms and services as they become monopolized. The conversation weaves together themes of platform decay, the erosion of privacy, antitrust challenges, regulatory capture, labor dynamics in tech, and the continual battle over data rights in advertising and digital media. Doctorow shares thought-provoking insights from his latest book and from two decades of activism, sparking a lively debate over the future of enforcement, the promise of privacy legislation, and possible frameworks for meaningful change.

Main Topics & Key Discussion Points

1. Book Tour & The Rise of Enshittification (00:09 – 04:02)

• Cory's Book Tour Success: Doctorow shares that his new book is an international bestseller, having sold out multiple printings rapidly.
  • “This book sold through four printings in the first three days and it’s an international bestseller.” (02:10, Doctorow)
• The Power of a Term: Alan appreciates the universality of “enshittification” as a descriptor of tech decline, noting its immediate resonance, even outside expert circles.

2. Defining “Enshittification” (04:02 – 07:00)

• Origins & Meaning:

  • The term is a framing device for the decline in platform quality, typically under monopoly conditions.
  • Stages of enshittification:
    1. Platforms benefit users while locking them in.
    2. Platforms degrade user experience for business customers’ benefit.
    3. Platforms extract all remaining value for shareholders, leaving a “homeopathic residue” for users and clients.
  • “...we get this platform decay, what I've been calling insidification, where in stage one, platforms are good to their end users while finding a way to lock those users in… Once it's hard for those users to leave, you move on to stage two...” (04:47, Doctorow)

• Not Just Greed: The process is enabled by monopolistic dynamics and is not simply a function of corporate greed.

3. Enshittification vs. Business as Usual (09:16 – 12:09)

• Distinction from Corporate Greed:

  • Doctorow explains that while product quality degradation (like in fast food) is common, enshittification is unique to modern tech because of:
    • Extreme market consolidation eliminating competition.
    • Regulatory capture diminishing oversight.
    • Eroded labor discipline and interoperability being legislated out of existence.

• Example: Consolidation in various sectors, not just tech, leads to consumer harm (12:09, Doctorow).

4. Forces That Once Disciplined Tech (13:17 – 20:05)

• Labor Power in Tech’s Golden Era:

  • Tech workers historically wielded significant influence due to scarcity and high productivity.
  • As layoffs and oversupply hit the market, their bargaining power diminished.
  • “A lot of tech workers...wanted to fight for the user...But as supply caught up with demand...they just lost the ability to fight with their bosses.” (15:38, Doctorow)

• Interoperability & Legal Crippling:

  • The tradition of modifying, reverse engineering, and customizing digital tech (interoperability) is now criminalized under laws like the DMCA, making user empowerment illegal.

• Example: Chamberlain garage door openers requiring users to view ads to open their doors due to app exclusivity (19:13, Doctorow).

5. Where to Focus: Privacy Law, Enforcement, or Antitrust? (20:05 – 27:28)

• No Silver Bullet:

  • Doctorow argues against prioritizing a single intervention (privacy law, regulatory reform, antitrust, etc.), emphasizing that these disciplines reinforce one another. Improving any of these areas strengthens the whole ecosystem.
  • He references Lawrence Lessig’s framework: code (tech limits), law, norms, and markets all interplay.

• Section 230 Clarification:

  • “Section 230 does not belong in that list... If that were not there, no one could launch a service except a billionaire...” (20:33, Doctorow)

• US vs. EU Enforcement:

  • Doctorow and Chapell discuss regulatory shortcomings, noting Ireland’s role in stalling GDPR enforcement, and how European reforms like the Digital Markets Act might finally enable action.

6. Consent, Friction, and Behavioral Ads (27:28 – 37:15)

• Consent Regimes & Small Businesses:

  • Alan expresses concerns about friction from consent requirements, disproportionately hurting small publishers.
  • Doctorow contends that industry claims of needing data for monetization are overblown, pointing to a not-so-distant era where contextual ads were valued.

• Prohibition vs. Regulation:

  • Doctorow favors a flat ban on behavioral advertising as administratively simpler and more effective than trying to police purpose limitation or minimization.
  • “A flat prohibition on behavioral ads gets you there…” (33:53, Doctorow)

• On Dark Patterns:

  • Doctorow expresses skepticism about the term, preferring to call them what they are: cheap tricks made easier by faster computers.

7. Monopoly, Opacity, and Publisher Disempowerment (37:15 – 41:36)

• Monopoly’s Impact on Publishers:

  • Google and Meta now capture the majority of ad spend, forcing intermediaries and publishers into dependency.
  • Analogy: “...going to court...and you find out you're both being represented by the same lawyer who's also the judge and also trying to match with both of you on Tinder. And then...the house...goes to me.” (37:40, Doctorow)

• On Platform Preferencing:

  • Chapell calls for anti-preferencing provisions so that dominant platforms can’t use privacy controls to benefit their own ad products.

8. Enforcement & The Private Right of Action (41:36 – 50:01)

• Class Action Litigation:

  • Chapell questions the efficacy and fairness of private rights of action (PRA), citing burdens for small businesses.

• Doctorow’s Defense of PRA:

  • Argues that PRA is essential, especially when regulatory capture limits government enforcement capacity.
  • Cites the ADA as an example where PRA has meaningfully shifted business norms: “...just do it. Right. We have got pretty good ADA compliance in this country because of the no win, no fee bar and the private right of action.” (41:36, Doctorow)

• Debate on Tangible Harm:

  • Alan distinguishes between systemic privacy harms and “frivolous” cookie breaches; Doctorow stresses that all data collected irresponsibly presents risk due to its inevitability of leaking, drawing analogies to storing plutonium.

• Industry Solutions:

  • Doctorow suggests insurance companies could motivate better compliance by denying policies to businesses using risky software.

9. Momentum in Antitrust & Global Shifts (50:01 – 56:29)

• Antitrust Prospects in the US:

  • With the political winds shifting, Doctorow is pessimistic about US antitrust action under a Trump administration, foreseeing enforcement weaponized for personal vendettas, not public good.

• Global Policy & The US Backlash:

  • Global policymakers, especially in the EU and “Eurostack” nations, are now emboldened to diverge from US tech policy due to unpredictable American trade and foreign policy.
  • Possibility of “technological liberation” tools being sourced from foreign jurisdictions, much as Americans now source drugs from abroad.

10. Solutions & The Path Forward (56:29 – End)

• Coalition Building:

  • Doctorow argues that just as “ecology” united disparate environmental concerns, a broad coalition of those harmed by consolidated tech is needed. Labor, privacy, antitrust, and electoral reform advocates should see themselves as working in concert.
  • “...defeating inshidification, the shortest path to it, is building out that much broader base. Not people who all come to work on inshidification, but people who march side by side.” (56:41, Doctorow)

• Reasons for Hope:

  • Doctorow points to the global, largely unexplained resurgence in antitrust activism and legislative muscle as a “pocket miracle,” bucking the conventional wisdom that billionaires always get their way.

Memorable Quotes

• On the ironies of platform capture:
  • “We’re at the tail end of 20 years of monotonic expansion of IP law...making it illegal to defend your privacy.” (17:23, Doctorow)
• On the “opacities” of the adtech supply chain:
  • “It's like going to court...your lawyer’s also the judge and also trying to match with both of you on Tinder.” (37:40, Doctorow)
• On government enforcement vs. PRA:
  • “If all you have is public enforcers...then what you're going to end up with is regulatory capture.” (41:36, Doctorow)
• On the unlikely rise of global antitrust:
  • “I can't overstate how profoundly weird this is ... this is like gravity reversing itself, water flowing uphill, pigs flying. It is a pocket miracle.” (58:41, Doctorow)
• On coalition-building:
  • “Just like my issue might be the ozone layer and your issue might be owls, but...we’ll have each other’s back, because we’re both ecologists. Maybe you’re working on labor issues, maybe you’re working on privacy ... but we’ll understand that we’re working on the same thing.” (56:41, Doctorow)

Notable Timestamps

• [04:02] – Cory defines the term “enshittification” and describes its stages.
• [13:17] – Discussion on lost disciplinary forces in tech: labor and interoperability.
• [20:33] – Why Section 230 isn't the enemy, and interconnections of law, code, norms, and market.
• [28:50] – Chapell and Doctorow debate the adminstrability and effectiveness of consent and behavioral advertising bans.
• [37:15] – The rise of adtech intermediaries and their capture of publisher value.
• [41:36] – Debating the pros and cons of private rights of action in enforcement.
• [50:42] – A shift in optimism about US antitrust enforcement.
• [56:41] – The solution: coalition-building, modeled on the rise of the ecology movement.
• [58:41] – Doctorow’s “pocket miracle” remark and analysis of global antitrust resurgence.

Tone & Style

Throughout the episode, the discussion is lively, direct, and laced with Doctorow’s characteristic wit and metaphor. Both speakers are passionate and detailed—Doctorow leans activist-academic, Chapell brings the advertiser’s pragmatism and skeptic’s eye.

For Listeners

This episode is a broad, bracing examination of how monopoly economics and regulatory failures shape not just digital media, but the very structure of the modern internet—illustrating why things “suddenly got worse” everywhere online, and what audiences, policymakers, publishers, and platform users can do about it.