June 3, 2026
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58:48Now PlayingClick here for full show notes including episode mentions and recommendations
Jim talked with @corydoctorow—prolific sci-fi and nonfiction author, journalist, activist, EFF special adviser, and author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It—about how structural forces degraded the internet, and what citizens (not consumers) can actually do about it.
They discussed:
The origin of “enshittification”—Cory’s January 2023 blog post, its viral spread, and its naming as Word of the Year by the American Dialect Society
Two-sided markets & the persistence of intermediaries
Crad Kilodney as a self-publishing illustration, and why platform middlemen survive even when they shouldn’t
Monopsony vs. monopoly
The real statistics of Amazon’s dominance of book sales
The three-stage enshittification life cycle, using Facebook as the case study
The brittle equilibrium of late-stage enshittification—the thin line between “I hate this but can’t leave” and mass exodus
The metaverse as Facebook’s terminal pivot—Zuckerberg’s “legless, sexless, low-polygon” avatar world stolen from a 25-year-old cyberpunk novel, and why it still served him by forestalling investor sell-offs
Zuckerberg as Rich Uncle Pennybags, not Willy Wonka
Amazon’s early history & Bezos’s “your margin is my opportunity” mantra
Amazon’s junk fees (now 50–60% and rising) and the $80 billion/year advertising payola business
The consumer welfare doctrine—Robert Bork’s antitrust theory that monopoly is efficient, and why allowing monopsonies inevitably produces monopolies
Jim’s personal experience with the Thomson-West legal publishing merger
Tech workers as a structural check on enshittification
The convergence enabling enshittification: merger to monopoly → regulatory capture → loss of worker leverage → DMCA blocking entrants → abuse
The moral decay of business culture—from “we won’t do profitable things we think are wrong,” to “do whatever’s arguably legal,” to “do whatever’s illegal if the fine is less than the benefit”
Google’s $20 billion/year payment to Apple to stay off the search market
Why predatory pricing cases went unenforced
What citizens (not consumers) can do
The death of federal antitrust enforcement and international ripple effects
State-level antitrust action as a remaining avenue
The right to repair as an easy entry point
Trump’s “Liberation Day” tariffs as a paradoxical opportunity
Tech as geopolitical weapon—Microsoft accounts bricked for a Brazilian judge who sentenced Bolsonaro; the ICC chief prosecutor’s accounts shut down after the Netanyahu arrest warrant
The vision for open, auditable, sovereign digital public goods to replace the enshittified American Internet—run internationally, controlled locally
… and much more.
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