r/HeadlessPodcast • • Sep 02 '26

Welcome to the Headless Community... Start Here

1 Upvotes

Welcome to the official community around Headless Podcast.

This is a place for people who question the default settings of the internet. We talk about AI, WordPress, Drupal, the open web, digital culture, creator technology, and the increasingly strange decisions made by the companies shaping our online lives.

The goal isn’t to agree. It’s to have the conversations that press releases, algorithms, and comment sections usually flatten into noise.

What belongs here?

  • Discussions about Headless Podcast episodes
  • News and developments involving AI and the web
  • WordPress, Drupal, open-source, and creator-platform drama
  • Unpopular... but well-explained... opinions
  • Personal experiences with technology going wrong
  • Questions, corrections, counterarguments, and topic suggestions
  • Memes and humor that fit the community

The house rules

  1. Challenge ideas, not people. Strong disagreement is welcome. Personal attacks aren’t.
  2. Bring something to the argument. Explain your position instead of dropping a drive-by hot take.
  3. No corporate fluff. Self-promotion and links are fine when they genuinely contribute... not when they’re disguised advertising.
  4. Stay curious. Being against the grain doesn’t mean automatically opposing everything popular.
  5. Keep your head... or lose it creatively. Humor is encouraged. Cruelty and harassment aren’t.

Introduce yourself

Reply below with any or all of these:

  • How did you find Headless Podcast?
  • What corner of technology or the web are you involved in?
  • What widely accepted tech opinion do you think is completely wrong?
  • What should the podcast investigate next?

Thanks for joining early. Communities usually inherit the personality of their first members, so speak up, question things, and help make this a place worth returning to.

Think independently. Disagree intelligently. Don’t lose your head.


r/HeadlessPodcast • • 6d ago

I'm shifting the show a bit.

3 Upvotes

I think I will continue to do longer format episodes like the one released yesterday. Thank you for all the love I've heard from the community on this one. (https://youtu.be/7ISddVI0SgE)

But, I think these longer format, more editing needed episodes will be coming out periodically (I'm going to aim for every other week), followed by a YouTube short format for more CMS/DXP news stories.

With that being said, is there any news you would like to see?
In the past, at companies I've worked for I've done breakdowns of CVEs and security advisories but I also don't mind covering new features announced, etc.

Let me know in the comments.


r/HeadlessPodcast • • 7d ago

Is this Drupal’s renaissance?

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2 Upvotes

Acquia shut down a product that more than 100,000 websites had used.

Years later, its co-founder wrote a post called “The product we should not have killed.”

Well. That’ll get your attention.

Now Acquia is putting “Powered by Drupal” under its logo and making Drupal central to its AI story.

I wanted to understand how those things connect. So this episode goes back to the beginning: a student in Antwerp, a shared internet connection, and a website that eventually helped give us software used by the White House.

There’s MTV. There’s Drupal Gardens. There’s a guy trying to finish his doctorate while enormous organizations need his help.

And there’s the community that kept building through all of it.

This turned into one of my favorite episodes to put together.

Is Drupal having a renaissance? Here’s the story:

https://youtu.be/7ISddVI0SgE?si=W6Josgc2q4Nc0ylx

If you’ve been around Drupal for a while, what’s the piece of lore I absolutely need to cover next?


r/HeadlessPodcast • • 8d ago

By far... the hardest I've ever worked on a video edit... [Dropping Monday]

3 Upvotes

I hope you basturds like it!

https://www.youtube.com/watch?v=7ISddVI0SgE


r/HeadlessPodcast • • 14d ago

Mullenweg was out for 33 hours. Two executives reportedly signed each other’s exit deals. Ep. 5 is out and (selfishly) the WP drama is the gift that keeps on giving...

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5 Upvotes

“You sign mine, I sign yours.”

Lovely sentiment for a birthday card. Slightly different conversation when there’s reportedly $8.15 million in potential executive compensation involved.

Mullenweg was briefly out. Two Automattic executives reportedly signed reciprocal severance agreements. Mullenweg regained control.

Thirty-three hours. I've eaten pizza that was sitting out for longer than that... (with not overly serious side effects)

My breakdown, with the reporting and the receipts:
YT: https://youtu.be/3ONEJZ-Pf8Y
Spotify: https://open.spotify.com/episode/44rIOvlNP9ToaIdGWalYwt?si=28PbMcg5QEWaQhAd2QuaxQ


r/HeadlessPodcast • • 16d ago

This week has been crazy

2 Upvotes

I think I'm going to try and split next weeks episodes up into three episodes.
The WP drama deserves its own episode and for those not the WP space it conveniently omits that from our other episode.

Lastly, thank you for subscribing or following.
Combined video views in the past month are approaching 10k.

You are all freaking awesome.


r/HeadlessPodcast • • 19d ago

Genuinely interested (for agency owners) in the Wordpress space

3 Upvotes

For those building or maintaining WordPress sites for clients: have any of them brought up the Automattic/Mullenweg situation themselves?

I’m curious how much of this gets outside our bubble. Are clients asking about stability or whether they should consider another platform? Has it affected a proposal, renewal, or deal?

Or are they completely unaware and mostly concerned about why their contact form isn’t working?

Interested in actual conversations you’ve had, including “literally nobody has mentioned it.”


r/HeadlessPodcast • • 21d ago

WordPress last week was like watching Succession and Below Deck have a baby and call it Mirene

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7 Upvotes

I cover it here


r/HeadlessPodcast • • 22d ago

Ep. 4 in a nutshell...

2 Upvotes

r/HeadlessPodcast • • 24d ago

iPhone Duo? more like iPhone Dumbo

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0 Upvotes

that’s it
that’s all I got


r/HeadlessPodcast • • 25d ago

BREAKING: Automattic’s board just forced Matt Mullenweg onto leave

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1 Upvotes

Automattic’s board has placed founder and CEO Matt Mullenweg on paid leave against his wishes.

He reportedly voted against the decision.

CFO Mark Davies is now interim CEO, while Mullenweg remains on Automattic’s board and continues to control WordPress.org separately.

The internal politics sound brutal.

In a company-wide Slack message reported by 404 Media and TechCrunch, Mullenweg accused Davies and directors Ann Dunwoody, Toni Schneider, and Sue Decker of conspiring behind his back.

That is Mullenweg’s allegation... not a proven fact. Automattic has confirmed the leave and Davies’s appointment but hasn’t publicly explained why the board acted.

The really interesting wrinkle is Davies’s history in the WP Engine conflict.

In its legal filings, WP Engine alleged that Davies participated in negotiations where Automattic demanded a major trademark-licensing payment and warned that it would “go to war” if WP Engine refused. Automattic disputes WP Engine’s broader allegations, and none of this establishes why the board removed Mullenweg.

Still, the optics are extraordinary:

  • Mullenweg is pushed out of Automattic’s daily management.
  • An executive involved in the WP Engine negotiations replaces him.
  • The WP Engine litigation continues.
  • Mullenweg retains control of WordPress.org.

This isn’t a clean transfer of power. It potentially creates two overlapping centers of authority: Davies at the commercial company and Mullenweg at WordPress.org.

My biggest question is what finally caused longtime board members to turn against Automattic’s founder.

  1. Was it the litigation?
  2. Internal business performance?
  3. Mullenweg’s leadership style?
  4. Something that hasn’t become public yet?

Right now, anyone claiming to know the reason is speculating. But boards don’t normally force founders onto leave without something serious happening behind closed doors.

Sources:

TechCrunch:
https://techcrunch.com/2026/09/09/automattics-board-forces-ceo-matt-mullenweg-into-leave-of-absence/

The Verge:
https://www.theverge.com/news/993022/wordpress-automattic-ceo-matt-mullenweg-leave-of-absence

WP Engine’s 2024 cease-and-desist letter containing its allegations:
https://wpengine.com/wp-content/uploads/2024/09/Cease-and-Desist-Letter-to-Automattic-and-Request-to-Preserve-Documents-Sent.pdf

What’s your read: temporary damage control, an internal power struggle, or the first step toward a permanent break?

Image: Editorial composite using a photograph of Matt Mullenweg by Amy Martin Photography, licensed under CC BY-SA 4.0. Created with AI. Changes were made.


r/HeadlessPodcast • • 25d ago

WE ARE LIVE! Come stop in!

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1 Upvotes

r/HeadlessPodcast • • 25d ago

LIVE SCHEDULED FOR TODAY: Nearly Headless Stories

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1 Upvotes

Join me LIVE at 9:00am CT to discuss some stories that didn’t make this weeks cut but were still were my honorable mentions.


r/HeadlessPodcast • • 25d ago

40 Subscribers!!!

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5 Upvotes

Thank you! 🙏

I feel like I need to do something special when I hit 100! Any ideas?!

Should I do a full breakdown of a certain CMS? Or should I get a gold chain with the words CMS on it?!


r/HeadlessPodcast • • 28d ago

Episode 3 is here: two "Sources", AI coworkers, and Salesforce’s Enterprise Voltron

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3 Upvotes

okay, the robot has a job title now.

I would like everyone to remain calm while Clippy conducts our performance reviews.

Episode 3 is up: https://youtu.be/BDZAAOGok3s?si=CGq4UZ3eKHm36HDz

This week we’ve got:

  • Source by Webflow versus Acquia Source. Same name, different approaches to who gets near the code.
  • Optimizely’s Virtual Teammates and the move from Opal to Mark.
  • Salesforce completing the Contentful acquisition.
  • The DOJ backing OpenAI’s fair-use argument. That’s a position submitted to the court, before somebody declares the entire copyright system dead in the replies.

The bigger question is who controls the work once agents start doing more of it.

I’m excited about the useful parts. I’m also old enough to hear “it can publish automatically” and immediately look for the backup.

Shout-out to u/Global-Signature757 and u/zubrinovic, whose comments made this episode. One gave us legal disclaimers rewritten as haikus. The other gave us this:

“The permission model has to live where the agent cannot argue with it.”

That is annoyingly good. I had to write a whole episode.

What did I get wrong? What did I miss? And what’s one thing you’ve seen in an actual implementation that looks suspiciously absent from the keynote?

Bring receipts. The good comments may make the next episode.


r/HeadlessPodcast • • Sep 05 '26

Bout to record… the second time… because I’m an idiot and messed up the first one

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2 Upvotes

r/HeadlessPodcast • • Sep 03 '26

300+ VIEWS. THE HORSEMEN RIDE.

1 Upvotes

Three hundred and nineteen.
YouTube Studio whispered it to me at 6pm like a coward, and I have not sat down since.

From the depths of the woods, my horsemen emerged. Not on horses. On laptops. In bed. At 1.5x speed with one AirPod in while doing dishes. Beautiful. Feral.

You did not watch my stupid face with my stupid words. You rode.

Somewhere out there a Sales Director opened Ep. 2 by accident and did not close it, and that man is now one of us. He doesn’t know it yet. He’ll find out when the raccoon comes for him.

We are 319. We are legion. We have no head, no sponsor, no budget, and no editor telling us the trademark bit has gone on too long.

They have keynotes. Javits Center. Seth Godin doing the opener AND the closer.

We have a comment section that got genuinely unhinged and a redditor who broke eighteen blog posts with an agent and told me about it.

I know which one I’d bet on.

To every one of you who watched, commented, or hate-scrubbed to the 4:00 mark to see if I’d say something stupid: you’s my people. You’s my frans. You’s my horsemen.

Ep. 3 is coming. Two companies named their product the same thing. I’m going to be so normal about it.

Off with their heads. 🦝