The 404 Media Podcast

Latest Episodes:

OpenAI Admits AI is Killing the Internet Sep 23, 2026

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We start this week with Jason’s story about OpenAI and Microsoft’s big admissions from court records that they are destroying the internet in all sorts of ways, and stealing intellectual property on an unprecedented scale. He admit it. After the break, Emanuel explains how he hijacked a real band’s Spotify page with AI-generated slop. In the subscribers-only section, we hear all about iLands, the AI agent platform that is basically just spam.

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Is AI Making Us Less Human? Sep 21, 2026

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When chatbots become our closest “friends,” what happens to our capacity to care?

This week I'm joined by Professor Sherry Turkle. Sherry is a licensed clinical psychologist, the founding director of MIT's Initiative on Technology and Self, and the Abby Rockefeller Mauzé Professor of the Social Studies of Science and Technology at MIT. She's a the New York Times bestselling author of multiple books including Alone Together, Reclaiming Conversation, and The Empathy Diaries.

Her latest book, Artificial Intimacy: Who We Become When We Talk to Machines, comes out on September 29. In it, Turkle explores how conversational chatbots have changed the ways we relate to other humans, empathize with each other, and what that could mean for our future.

“The progression is: First we talk to each other, then we talk to each other through machines, and now we drop the middleman and we're happy to just talk to machines,” she said in our conversation.

We get into what happens when people stop placing importance on emotionally connecting with other people, and whether it’s too late to pull back from the path we’re on.

Youtube Version: https://youtu.be/whqDsYhCl0s

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404 Media x The Intercept LIVE: How AI Is Used to Surveil and Kill Sep 18, 2026

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In this bonus collaboration with our friends at The Intercept, 404 Media's Jason Koebler and the Intercept's Sam Biddle and Akela Lacy discuss the ways AI is already used to empower private surveillance companies that filter data to the government, how AI is used in war, and the prospect of an AI apocalypse. This podcast was recorded live in Los Angeles at The Loved One on September 12.

Check out The Intercept Briefing podcast wherever you get your podcasts, and find a full transcript of this pod here.

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Humans Are Reading Your ChatGPT Conversations Sep 16, 2026

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We start this week with Joseph’s story about the people who are reading real ChatGPT users’ prompts and conversations. He got a bunch of documents all about these contractors and saw real prompts himself. After the break, Sam tells us all about the Automattic CEO getting kicked out. Then coming back again. In the subscribers-only section, Emanuel tells us why a16z thinks enshittification is not real.

YouTube version: https://youtu.be/AyPuYrjLk1E

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Fighting for the Future of Libraries (With Jennie Rose Halperin) Sep 14, 2026

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This week we’re joined by Jennie Rose Halprein. Jennie is the executive director of Library Futures, a non-profit that advocates for a fair digital future for libraries and the communities they serve. We have written a bunch of stories about libraries over the years, and I have talked to Jennie a few times for those stories. I always have really interesting conversations with her, but a lot of what we talk about never makes it into a story. That’s why I wanted to share one of those conversations with you today. We of course touch upon censorship but also many other subjects, so I hope you enjoy this conversation as much as I did.

YouTube Version: https://youtu.be/mS0xofGW2hE

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DHS’ Secretive ‘Predictive Policing’ Unit Pulling People Over Sep 09, 2026

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Take control of your data footprint risk-free with a 30-day money-back guarantee. Go to https://incogni.com/404Media and use code 404MEDIA for 60% off an annual plan. That's code 404MEDIA at https://incogni.com/404Media

We start this week with Joseph’s story about the secretive predictive policing units inside DHS that are analyzing Americans’ financial data and having local cops pull them over. After the break, Jason tells us about the funky shirt designed to fool AI-camera systems. In the subscribers-only section, we talk all about our third anniversary events.

YouTube version: https://youtu.be/o0AG6A5MIRg

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This Innocent Woman Spent 13 Days in Jail Because of a False Flock Hit Sep 07, 2026

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This week Jason talks to Lindsey Isaacs and her lawyer, Patrick McGeehan. Last year, Lindsey was falsely arrested and imprisoned after authorities used Flock’s license plate reader system to pull over the wrong person in a hit-and-run that killed three people. Lindsey spent 13 days in jail because of this screwup.

This all happened because authorities were looking for a black dodge Durango, and used Flock’s freeform search to look for a black SUV. Lindsey happened to be driving a black dodge Durango 3 miles west of where the crash happened a few minutes beforehand. Lindsey was arrested even though there was no damage to her car. She again, spent 13 days in jail before the charges against her were dropped. This is one of the worst cases of Flock-related policing screwups we’ve ever seen, and an innocent person had their life upended because of it. We spoke to Lindsey and Patrick about what happened, the case, Flock surveillance, and their lawsuit against the police who did this to her.

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We Spoke to an Amazon Worker Destroying Books for AI Sep 02, 2026

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We start this week with Emanuel’s follow-up to his Amazon book scanning story, in which he spoke to someone who worked in the Amazon warehouse which destroys books to train Amazon’s AI products. After the break, Emanuel and Sam tell us about the same few names appearing in LLM output over and over again. In the subscribers-only section, Joseph tells us why ICE is buying loads of data about ‘voter fraud’.

Youtube Version: https://youtu.be/PcNdLnLF7mo

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How Cyber Sleuths Tracked Down a Nigerian Scammer Aug 31, 2026

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This week Joseph talks to Paul Raffile, a cybercrime researcher, and Erin West, founder of Operation Shamrock. The pair recently traveled to Nigeria to track down a scammer and meet a bunch more. This conversation is some fascinating insight into how scammers live, how they can be identified, and platforms like Meta’s responsibility.

I Hunted the Men Who Blackmail Children Online

Youtube Version: https://youtu.be/973m4leS25c

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Cops Are Making Fake Flock Cameras and Amazon Packages Aug 26, 2026

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We start this week with Jason’s piece on a cop making a fake Flock camera to catch a vandal. How can you be charged with destroying expensive property if… the camera wasn’t real? After the break, Sam tells us about how Darth Vader loves Flock. In the subscribers-only section, we talk a bit about three years of 404 Media.

YouTube Version: https://youtu.be/rYCvhAOGAjM

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