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PODCAST

The 404 Media Podcast

Welcome to the podcast from 404 Media where Joseph, Sam, Emanuel, and Jason catch you up on the stories we published this week. 404 Media is a journalist-owned digital media company exploring the way technology is shaping–and is shaped by–our world. We bring you unparalleled access to hidden worlds both online and IRL through investigative reporting, smart blogging, and breaking news. At 404 Media you’ll read, and hear, stories you can’t find anywhere else written by journalists who are leading

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All Episodes

64:46

How the Internet Became Hell (with Whitney Phillips)

The 404 Media Podcast ·

2026/04/13

‘The Ambivalent Intent’ and ‘The Shadow Gospel’ author Whitney Phillips on how online got so badWhy does the internet feel like it’s getting worse every single day, and why does it feel like the political landscape is getting worse in response? The answer might seem obvious, especially if you read 404 Media on a regular basis, where we’ve been documenting this decline, but it’s important to occasionally zoom out and ask the big questions. That’s why this week on the podcast I’m joined by

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50:08

Wildlife Cops Are Searching AI Cameras for ICE

The 404 Media Podcast ·

2026/04/08

This week we start with Jason’s story about how wildlife cops are doing Flock lookups for ICE. It shows that ICE is gaining access to this sort of information through pretty unexpected ways. After the break, Emanuel tells us all about the AI ban at Wikipedia. In the subscribers-only section, Joseph breaks down a set of vulnerabilities in the ‘secure’ chat app TeleGuard. 0:00 - Intro 1:03 - Wildlife Conservation Police Are Searching Thousands of Flock Cameras for ICE 27:55 - Wikipedia Bans

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54:52

The Lawyer Fighting Government Surveillance for 30...

The 404 Media Podcast ·

2026/04/06

This week Jason brings you an interview he did with The Electronic Frontier Foundation’s executive director Cindy Cohn, who recently announced she would be stepping down from the legendary digital rights nonprofit after decades of service. Cindy's new book “Privacy’s Defender,” is a memoir of her work to protect Americans’ privacy and fight government surveillance.Privacy’s Defender weaves Cindy’s life story through three incredibly important court cases. Rather than being a dry recounting of three

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52:59

Inside the AI Slop Propaganda Wars

The 404 Media Podcast ·

2026/04/01

This week Matthew Gault joins us to discuss his article about Iran’s AI slop and LEGO-focused propaganda, and why the creators chose LEGO. After the break, Jason tells us all about the new automated system in baseball and the drama it’s causing. In the subscribers-only section, Sam walks us through perhaps one of the worst sex apps of all time.1:19 - Iran Is Winning the AI Slop Propaganda War 26:37 - 'You Can't Defeat the Robots!': Baseball's AI Strike Zone Is Must-Watch

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43:45

The Journalist Who Tracked Epstein Island Visitors’...

The 404 Media Podcast ·

2026/03/30

This week Joseph talks to Dhruv Mehrotra, a journalist and technologist at Bloomberg. Before that, Dhruv was at WIRED, where you probably saw a ton of his interesting work. Dhruv sits in a very unusual space in journalism: he is able to both write technical tools to dig through data, or collect information, or really anything else, and is also able to just write a damn good story. That is a very unique blend. The pair chat about Dhruv’s entry into journalism, how computational journalism has changed

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45:45

The Company Secretly Turning Your Zoom Meetings into...

The 404 Media Podcast ·

2026/03/25

This week we start with Emanuel’s crazy story about WebinarTV, a company that is secretly recording Zoom meetings and turning them into AI-powered podcasts. It’s nuts. After the break, Joseph tells us about the eccentric billionaire who tried to become a cocaine kingpin. In the subscribers-only section, we lament the lose of the metaverse. 1:06 - This Company Is Secretly Turning Your Zoom Meetings into AI Podcasts 25:58 - An Adrenaline Junkie Millionaire’s Quest to Become a Cocaine

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49:36

The Marketing Tricks of "Artificial Intelligence"

The 404 Media Podcast ·

2026/03/23

This week, Sam talks to Emily Bender and Alex Hanna about the marketing ploys of “artificial intelligence,” why ridicule works to keep big tech’s claims in check, and what makes them hopeful for the future. They’re the authors of The AI Con: How to Fight Big Tech’s Hype and Create the Future We Want.Dr. Alex Hanna is a writer and sociologist of technology, labor, and politics. She’s the Director of Research at the Distributed AI Research Institute (DAIR) and a Lecturer in the School of Information

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47:22

The Disappearing DOGE Depositions

The 404 Media Podcast ·

2026/03/18

This week we start with Joseph’s series of articles about the DOGE depositions. He watched hours and hours of them, then a judge ordered them removed from YouTube. But, they’ve already been archived all over the web. After the break, Jason tells us about the AI data labelers who are fighting back. In the subscribers-only section, Jason breaks down what’s wrong with all the AI job loss research at the moment.0:00 - Intro 0:51 - Google Street View's Unmappable City 3:40 - I Watched 6 Hours of

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17:29

Google Street View's Unmappable City

The 404 Media Podcast ·

2026/03/16

There's only one city in America that isn't on Google's Street View. Documentary filmmaker Chris Parr set out to map it, using North Oak, Minnesota's byzantine rules and the help of a drone. His experience shows who gets privacy in America, and who doesn't. 'I Mapped Google’s ONLY SECRET CITY' YouTube Version: https://youtu.be/3iGvHBr0mJw Subscribe at 404media.co for bonus content. Learn more about your ad choices. Visit megaphone.fm/adchoices

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44:25

How to Talk to Your Friend Experiencing 'AI Psychosis'

The 404 Media Podcast ·

2026/03/11

This week we start with Sam’s story discussing something that has come up a lot but no one has really answered: how do you speak to your friend or family member falling into AI psychosis? After the break, Joseph breaks down what happened when the FBI wanted data from ProtonMail. In the subscribers-only section, Emanuel tells us about the viral developers behind an app called Quittr, and how they exposed very sensitive data of hundreds of thousands of users.1:21 - 'How to Talk to Someone

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48:03

Understanding Roblox’s Grooming Problem

The 404 Media Podcast ·

2026/03/09

Cecilia D’Anstasio on Roblox efforts to protect children from pedophiles. Roblox is one of those games that is more popular than you can imagine, but unless you are of a certain age group and live in that world, you’ll rarely hear about it unless it makes the news for some terrible reason. More recently, for example, we wrote about the Tumbler Ridge shooter who created a mass shooting simulator in Roblox. But what is Roblox, how big is it exactly, and why does it seem like it's so

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57:20

The Depravity Economy

The 404 Media Podcast ·

2026/03/04

This week we discuss our coverage of the U.S.-Israel strikes against Iran, specifically how Polymarket and Kalshi are letting people profit from death, and that Amazon data centers were on fire after missiles hit Dubai. Then Emanuel talks about how AI translations are adding 'hallucinations' to Wikipedia articles. In the subscribers-only section, Sam tells us about a change with Amazon wishlists that may expose your address. 0:00 - Intro 1:32 - With Iran War, Kalshi and Polymarket Bet That the

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54:48

How to Detect Phone Spying Tech (with Cooper Quintin)

The 404 Media Podcast ·

2026/03/02

Joseph speaks to Cooper Quintin, a security researcher and senior public interest technologist with the Electronic Frontier Foundation (EFF). Quintin is one of the people behind Rayhunter, an easy to install tool that can detect nearby IMSI-catchers. This tech, sometimes known as Stingrays, poses as a fake cellphone tower to track a phone’s location, intercept calls and texts, and can sometimes even deliver malware.Rayhunter GitHub: https://github.com/EFForg/rayhunter YouTube:

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53:15

Ring Is Just Getting Started

The 404 Media Podcast ·

2026/02/25

This week we start with Jason’s follow up to Ring launching its ‘Search Party’ feature. It turns out, according to a leaked email he got, the feature is only starting with finding lost dogs. After the break, Emanuel explains why we’ve learned nothing about amplification when it comes to the recent looksmaxxing trend. In the subscribers-only section, Sam explains how Grok produced the real name of a sex worker who performs pseudonymously.1:11 - Leaked Email Suggests Ring Plans to Expand ‘Search

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44:50

Privacy Under Pressure (With Harlo Holmes)

The 404 Media Podcast ·

2026/02/23

In this week’s interview, Sam is joined by Harlo Holmes. Harlo is the Chief Security Programs Officer at Freedom of the Press Foundation. She’s a media scholar, software programmer, and activist. Harlo and Sam discuss the important work she does every day, and why it’s only becoming more crucial. They also get into how to fight back against privacy nihilism, digital security practices everyone can be implementing regardless of their threat model, and the recent arrests and raids of journalists in

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60:10

Inside an AI-Powered School

The 404 Media Podcast ·

2026/02/18

This week we start with Emanuel’s wild story about Alpha School, a very hyped AI-powered school. Emanuel got leaked documents and spoke to former employees. After the break, Sam tells us what happens when someone decides to make an AI nudify OnlyFans with your likeness. In the subscribers-only section, Joseph tells us about the agencies buying GeoSpy, an AI that can geolocate photos in seconds. 2:49 - Understood: Deepfake Porn Empire 5:47 - 'Students Are Being Treated Like Guinea Pigs:' Inside

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49:41

What It’s Like to Be a Data Labeler Training AI

The 404 Media Podcast ·

2026/02/16

I recently traveled to Kenya for a journalism and AI conference. While I was there, I really wanted to meet with Michael Geoffrey Asia, the secretary general of the Data Labelers Association. Data Labeling is a huge job in Kenya. Data labelers are the people who train AI, and who also work on ensuring the outputs are accurate. In some cases, data labelers are themselves pretending to be AI, in order to train AI. Often, data labelers don’t know exactly what they’re working on, because the work

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50:02

Ring Is Back and Scarier Than Ever

The 404 Media Podcast ·

2026/02/11

We start this week with exciting news: we bought a Super Bowl ad! For… $2,550. We explain how. After the break, Jason tells us about Ring’s recently launched Search Party feature, and gives us a very timely reminder of what Ring really is and how we got here. In the subscribers-only section, Joseph breaks down Lockdown Mode and how it kept the FBI out of a Washington Post reporter’s phone.Timestamps: 0:00 - Intro 2:49 - Watch 404 Media’s Super Bowl Ad 27:29 - With Ring, American Consumers

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85:54

The Screen Time Panic Sets Parents Up to Fail

The 404 Media Podcast ·

2026/02/09

Patrick Klepek on the reality of parenting in the age of Roblox and YouTube. I listened to hours of podcasts about how screen time affects kids of all ages and how parents should manage screen time but I still felt completely unprepared for this challenge when I had a kid. I think the reason for that is that there’s a lot of reporting about how screens are impacting kids, and a lot of reporting about the research into this subject, but rarely did I encounter a conversation between parents

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55:00

The Latest Epstein Dump is a Disaster

The 404 Media Podcast ·

2026/02/04

We start this week with Sam and Emanuel’s article about the latest Epstein dump, and how it’s really a disaster in a lot of ways. After the break, Matthew runs us through Moltbot and its terrible security. After the break, Emanuel breaks down his two recent stories about a fundamental issue exposing a bunch of very sensitive data.Timestamps: 0:00 - Intro 2:19 - DOJ Released Unredacted Nude Images in Epstein Files 25:08 - Silicon Valley’s Favorite New AI Agent Has Serious Security Flaws 34:55 -

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