November 05, 2025

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

1 hour 6 minutes

Cory Doctorow is a prolific writer of both fiction and non-fiction. His latest book is Enshittification: Why Everything Suddenly Went Wrong and What To Do About It. Cory and host Alan Chapell discuss the three stages of enshittification, its root causes, and the underlying social movement that is critical to addressing (and perhaps even reversing) its impact.

Recognizing that they come at this from very different perspectives, Alan and Cory also go deep into some of the endemic challenges of the ads space while wrestling with pro's and con's of data minimization, contextual advertising and how to offer a private right of action to the enforcement of privacy laws. Alan's Substack on CIPA the VPPA and anti-SLAPP laws is at https://chapell.substack.com/p/can-anti-slapp-save-ad-tech-from and should complement the discussion.

Cory's bio is at ⁠https://craphound.com/bio/⁠ and you can find out more about his book Enshittification at ⁠https://tinyurl.com/y7u698a6⁠.

Takeaways

Enshittification describes how digital platforms decay under monopoly power, shifting value from users to advertisers and then shareholders.

Monopoly and weak regulation allow corporations to capture markets and regulators, eroding user rights and competition.

Loss of interoperability and restrictive IP laws (like the DMCA) prevent users from fixing or improving technology.

Privacy and data exploitation are central to tech monopolies’ power, stronger, simpler rules are needed over complex consent systems.

Behavioral advertising should be replaced by contextual models to reduce surveillance and restore balance for publishers.

Private right of action can help enforce privacy rights when regulators fail.

Global antitrust movements in Europe, Canada, and Asia show more progress than the U.S.

Coalition building across privacy, labor, and antitrust advocates is key to countering corporate concentration.

Chapters
00:00 Introduction and Enshittification explained
04:20 How monopolies cause platform decay
11:15 Market consolidation and regulatory capture
13:30 Tech worker power and the loss of interoperability
20:25 Key issues, privacy, competition, and IP
27:25 Problems with consent-based privacy systems
29:45 Case for banning behavioral advertising
41:25 Enforcement and the role of private litigation
51:00 Antitrust progress and shifting global momentum
55:30 Building coalitions to fight tech monopolies

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