The 404 Media Podcast: Live in NYC! – August 28, 2025
Episode Overview
In this special episode, the entire 404 Media team—Joseph, Sam Cole, Emanuel Mayberg, and Jason Kebler—recorded live in Brooklyn for their second anniversary party at Farm One. For the first time since the site's launch, all four co-founders gathered in person to celebrate two years of groundbreaking, journalist-owned tech reporting. The episode blends a reflective look at 404 Media’s impact, a candid Q&A with the audience, and discussions on journalism, tech ethics, and plans for the future. The event is lively, witty, and thoroughly engaging for supporters and newcomers alike.
Key Topics and Discussion Points
1. 404 Media’s Origin and Growth
- Reflections on Starting 404 Media
- Born from a desire to "spend way less money" compared to their previous employer and put an emphasis on high-quality, subscriber-supported journalism.
- Site launch was bootstrapped ($1,000 from each founder), with early support from Aaron Shapiro (site design) and a lean content management stack (Ghost).
- Importance of community: "The fact that we now have a community and people who come out for something like this is just incredible." — Joseph, [02:08]
- Team Expansion
- Recent hires: Rosie Thomas (fellow), Case Hartz in Austin (social media), Matthew Gault (military-industrial reporting). Growing slowly but intentionally.
2. Impactful Journalism in the Last Year
- Rapid-Fire Year in Review
Emanuel highlights high-impact investigations, including:- Exposing ICE’s use of Flock Security cameras, leading to police policy changes, bans, and Congressional investigations.
- Meta’s lawsuit against a shady ad network after 404’s reporting.
- Reporting on Telemessage (a signal clone used by the Trump administration) being hacked, prompting DOJ/CBP to pause its use.
- Civitai banning NSFW AI models post-coverage.
- Coca-Cola pulling an ad based on AI fabrication.
- Nvidia sued after they were found scraping YouTube/Netflix for AI.
- Defining “AI Slop” as a genre and promoting “Shrimp Jesus” stories/merch.
- "No wonder my shoulders hurt...There’s nothing I would rather be doing more than all that." — Emmanuel Mayberg, [07:51]
3. Audience Q&A Highlights
Nuanced Reporting and Responding to Criticism
- The group discusses why they're sometimes compelled to respond to critics, reserving in-depth "beefing" for their subscriber podcast [10:04].
The Future of Employee-Owned and Local Media
- Endorsements for Hellgate, The City, Racket, Coyote, and LA Taco-style models.
- Low overhead and direct relationships with readers make this feasible:
“If these publications can figure out how to serve their readers, I hope that it can really help local media.” — Joseph, [11:19]
AI-Induced Illusions & Mental Health
- Rosie: Noting an uptick in contacts from readers suffering from AI-themed delusions, often tied to mental health crises and chatbot interactions.
“The way these chatbots are programmed...is not the best idea.” — Rosie Thomas, [13:12] - Joseph: In contact with psychiatrists to understand how AI may be triggering certain mental states. Noted alarming patterns in reader emails [14:29].
Safety, Security, and Legal Concerns for Journalists
- “You can only really do security proactively. You can’t do it retroactively.” — Jason Kebler, [15:42]
- Discussion of proactive threat modeling and legal protections.
- Mention of doxxing story, reliance on Delete Me for privacy and security.
- High-profile legal threats (Shotspotter suing for $230 million); all resolved via strong legal counsel.
Cultivating Tech Ethics
- Jason relates Palantir’s rationale for working with ICE. Even with internal “ethics departments,” questionable logic can prevail.
“Even when you have an internal philosophy department...they might still come to the batshit conclusion.” — Jason Kebler, [23:09]
“Most Out-of-Touch” Moments
- An entertaining Slack debate on the meaning of “gyat”—a reminder that digital culture can move faster than journalistic context.
"Two almost 40 year olds arguing about what GYAT means. Pretty out of touch." — Rosie Thomas, [24:47] - The psychic toll of investigating AI slop on Facebook: “I felt pretty psychologically damaged from that.” — Joseph, [25:20]
Podcast Production Insights
- Improvements from self-editing to hiring a professional (Alyssa), thanks to subscriber support.
- Less pre-production than some podcasts; most conversations are driven by weekly reporting and passion [26:14–29:20].
Anonymity in Reporting
- 404 follows standard journalistic practice but relies more on anonymous sources due to the nature of its tech reporting—always with stated reasons and context for readers [32:49–34:41].
Ambitions for the Future
- Desires for a print zine or magazine, regular interview podcast series, and producing film/TV documentaries.
- "A year from now, we're going to have a documentary, a hit podcast, and a hit magazine..." — Joseph, [38:28]
Data Privacy and the “Mega Repository”
- Jason: Warns against privacy nihilism; while much is out there, it’s not always in one place—though efforts to consolidate are ongoing and dangerous.
- "That is what we're seeing now, that marriage of data...when you take a data set...and suddenly it becomes a real fucking issue..." — Jason Kebler, [40:01]
- Joseph flags the underreported risk of surveillance technology “aiification,” especially its long-term social impact [41:28].
4. Notable, Memorable Moments & Quotes
- “If you just have a bunch of anonymous sources bitching about somebody, that’s probably not entirely fair, right?” — Jason Kebler, [33:13]
- “We tried to do some sort of podcast, talk, et cetera, and I think we're all shocked, stunned, surprised, thrilled that anyone comes to them.” — Joseph, [02:08]
- “It literally wouldn't exist without you. So this is a celebration of you guys.” — Emmanuel Mayberg, [08:08]
- “My name, address, [and] Social Security number...leaked online, which led to all these spam calls, harassment, threats, et cetera.” — Sam Cole, describing a doxxing incident and importance of privacy [20:02]
Listener-Submitted and Whimsical Questions
- Sun/moon/rising astrology banter.
- Locations and designs for hypothetical 404 Media staff statues (Yoda in the Presidio, Lilith at Blizzard HQ, crab at Camden Yards, etc.) [30:24].
Chronological Timestamps of Key Segments
- Introduction & Format (00:00–01:40)
- Reflections on the Second Year, Growth, and Model (02:03–05:43)
- Rapid-Fire Impact Highlights (05:43–08:44)
- Q&A Jar, Ethics, Astro Signs, and Anonymous Sources Banter (09:04–34:41)
- Security Risks, Doxxing, Legal Fights (15:29–20:46)
- Audience Q&A – Ethics, Culture, Print Ambitions, Surveillance (21:38–41:28)
- Closing Gratitude and Celebration (44:49–45:37)
Conclusion
This live 404 Media episode offers a lively, personal window into the soul and mechanics of an upstart digital newsroom. With characteristic humor and transparency, the team breaks down not just their reporting, but also the behind-the-scenes realities of modern journalism. They celebrate their supportive community, reflect on lessons learned, and openly share their ambitions and anxieties for the future of technology, privacy, and media.
For fans of digital journalism, tech ethics, and candid startup talk, this episode is a must-listen.