The 404 Media Podcast The 404 Media Podcast

Humans Are Reading Your ChatGPT Conversations

Sep 16, 2026 · 50m

Summary

404 Media investigates "Project Lily," revealing that OpenAI hires contractors to read real ChatGPT user prompts to improve model responses, despite buried privacy disclosures. The episode also covers the chaotic leadership crisis at Automattic, where CEO Matt Mullenweg was briefly ousted by the board before claiming to regain control and replacing key executives. Hosts Joseph, Sam, and Emmanuel discuss the ethical implications of human data review in AI training and the ongoing turmoil in the WordPress ecosystem.

Topics discussed

Sponsor: LinkedIn Hiring Pro 404 Media subscription and bonus content Intro and AI ethics discussion recap Project Lily: Humans reviewing ChatGPT chats Reviewer dashboard and user data exposure Privacy model limitations and PII leaks Anonymization techniques and context removal Contractor tasks: rating prompts and responses Sycophancy risks and user safety concerns ChatGPT's conversational personality and utility Rationale for scores and model improvement Buried disclosure of human review practices Comparison with Gemini and safety monitoring Distinction from previous Kenyan worker reports Opt-in settings and enterprise data risks Sponsor: BetterHelp Sponsor: Babbel language learning Sponsor: NordLayer Browser Matt Mullenweg put on leave of absence Background: Automatic, WordPress, and WP Engine 2024 feud and internal company turmoil The board vote and Mullenweg's reaction Mullenweg claims he is back in control Board statement and executive support The tugboat blog post and trolling Board changes and removal of members CFO departure and current board status Outro and subscription call to action
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