The 404 Media Podcast

Humans Are Reading Your ChatGPT Conversations

The 404 Media Podcast

Show Notes

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.

Inside ‘Project Lily’: The Humans Reading Your ChatGPT Chats

Automattic CEO Matt Mullenweg Put on 'Leave of Absence'

Automattic’s Matt Mullenweg Claims He’s Back 'In Control'

Sources say Automattic’s board is out after failed attempt to oust CEO Matt Mullenweg

A16z Says You Actually Love Social Media, Enshittification Isn’t Real

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

Subscribe at 404media.co Learn more about your ad choices. Visit megaphone.fm/adchoices

More from The 404 Media Podcast

Oct 21, 2026

We start this week with Jason’s article about how everyone is apparently reverse-engineering everything. After the break, Joseph tells us about a big AI shakeup at consulting giant Accenture. In the subscribers-only section, Sam and Jason discuss the Character[.]ai bankruptcy.

Oct 19, 2026

Big tech is rushing to build hundreds of data centers across the planet to keep up with the computing demand of artificial intelligence. The tech companies are promising the massive buildings will bring jobs and prosperity when they’re built, but communities across the country aren’t buying it and they’re fighting back. People are concerned about water, noise, pollution, and the rising cost of electricity. Anyone who already lives next to a data center knows those fears are well founded.

Oct 14, 2026

We start this week with Joseph’s article about Raven, previously known as Geospy. This is an AI tool that can geolocate photos, and now says it can pinpoint a specific house based just on one photo taken inside. After the break, Jason explains why a judge ruled a particular Flock search as unconstitutional. In the subscribers-only section, we talk about the wild AI video that has derailed a manslaughter case.

Oct 9, 2026

Sponsor: Take back control today: go to incogni.com/404media and use code 404MEDIA for 60% off an annual plan. That's incogni.com/404media, promo code 404MEDIA—risk-free with a 30-day money-back guarantee.

Oct 7, 2026

We start this week with a story from our old friend Lorenzo Franceschi-Bicchierai, about how cops can bypass the inactivity reboot on iPhones. After the break, Jason tells us how people are losing their minds over an LLM ‘torture’ prison. In the subscribers-only section, Sam explains what happened in a wild ChatGPT case in New Mexico.

See all episodes →