Podcast: Humans Are Reading Your ChatGPT Conversations
404 Media podcast examines contractors who read real ChatGPT user conversations, plus Automattic CEO turmoil and a16z's enshittification essay.
404 Media's weekly podcast leads with an investigation into 'Project Lily,' the human contractors who review real ChatGPT users' prompts and conversations; the reporter reviewed internal documents about the program. It also covers leadership upheaval at Automattic, where CEO Matt Mullenweg was put on leave of absence and then claimed he was back in control. A subscriber-only segment discusses a16z's argument that enshittification is not real.
- Investigation details contractors reading real ChatGPT user prompts and conversations
- Reporter reviewed internal documents about the human review program
- Automattic CEO Matt Mullenweg placed on leave of absence, then claimed he was back in control
- a16z publishes argument dismissing platform enshittification concerns
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· Sep 16, 2026 at 10:19 AM
The contractors reading real ChatGPT users' prompts; the big out-and-back-in around Automattic; and a16z thinks enshittification isn't real.
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.
Listen to the weekly podcast on Apple Podcasts, Spotify, or YouTube. Become a paid subscriber for access to this episode's bonus content and to power our journalism. If you become a paid subscriber, check your inbox for an email from our podcast host Transistor for a link to the subscribers-only version! You can also add that subscribers feed to your podcast app of choice and never miss an episode that way. The email should also contain the subscribers-only unlisted YouTube link for the extended video version too. It will also be in the show notes in your podcast player.
- 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
About the author
Joseph is an award-winning investigative journalist focused on generating impact. His work has triggered hundreds of millions of dollars worth of fines, shut down tech companies, and much more.
Text extracted automatically; images, tables and formatting may be missing. Original: https://www.404media.co/podcast-humans-are-reading-your-chatgpt-conversations/