Why everything on the internet is getting worse | The Gray Area - October 20, 2025 -

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Search results that look like ads. Social feeds that you don’t control. Streaming platforms that are packed with ads. Services that used to be free, but are now behind paywalls. It’s not your imagination — it’s enshittification, the process by which good platforms turn bad … and it’s starting to happen outside the internet as well.
Sean’s guest today is Cory Doctorow, author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It. They discuss how the web became enshittified, why monopolies are the true engine behind our digital decay, and what it would mean to build a freer, fairer, and more human internet.
Host: Sean Illing (@seanilling)
Guest: Cory Doctorow (https://x.com/doctorow), author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It.
00:00 Intro
00:45 What is enshittification?
11:48 Is this techno-feudalism?
25:53 You didn't shop wrong.
35:14 How to win a trade war.
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