Episode notes
Automattic's board voted founder Matt Mullenweg onto a paid leave he opposed. The CFO is interim CEO. WordPress.org says the free project did not change. The company has not said why. Also: Shopify bought Tailwind Labs after AI chat ate the docs traffic that paid the bills; 404 Media says Border Patrol targeting teams used financial patterns to cue local traffic stops; Google Ads labeled a signed Mac app malware, then reinstated the account after Hacker News, still with no trigger. The side of tech news nobody talks about.
Hosts: Alex & Jordan
Show: Chief Skeptic Officer — The side of tech news nobody talks about.
Drop: Daily at 7:00 A.M. America/New_York
Episode date: 2026-09-10
In this episode
Board parks the founder — On 9 September Automattic's board put Matt Mullenweg on paid leave against his vote. Mark Davies is interim CEO. Mullenweg stays on the board. Mary Hubbard said WordPress.org is unchanged. Automattic confirmed the leave and did not give a reason.
Tailwind's docs funnel dies, Shopify buys — Adam Wathan said Tailwind Labs is joining Shopify. MIT stays, new Tailwind Plus signups close. In January he had said revenue was down about 80 percent after AI tools answered from the docs. Price undisclosed.
A plate stop, a bank memo — 404 Media named Border Patrol Predictive Intelligence Targeting Teams. In the Olson case, Montana troopers cited an obstructed plate. A DHS note had already flagged financial patterns. CBP will not name the data source or a warrant.
Google said malware — The RACE developer spent 500 dollars on Google Ads for a signed Mac terminal app. Google suspended the account for malicious software. An edit on his post says Hacker News heat got it reinstated, with no explanation.
Links
AI disclosure
This episode was created with artificial intelligence. Alex & Jordan are AI hosts; their voices and conversation are generated with AI. Research and editorial judgment shape the skeptic angles; we do not invent quotes, scores, or viral claims about the news.
Transcript
Alex and Jordan, turn by turn. Tap a line to jump in the player.
0:00
Alex
Automattic's board put founder Matt Mullenweg on a paid leave he voted against. The CFO is interim CEO.
0:07
Jordan
Shopify bought Tailwind Labs, the small company behind a popular way of styling web pages.
0:14
Alex
A 404 Media investigation says Border Patrol teams used Americans' financial patterns to cue local traffic stops.
0:23
Jordan
Google Ads suspended a developer for "malicious software" after he spent five hundred dollars promoting a signed Mac app.
0:33
Jordan
That's the board. Stay for the audit. We open those up. Today's Chief Skeptic Officer.
0:49
Jordan
What if there was an AI that researched the tech news, checked the sources, and asked what the tech news is not telling you?
0:57
Alex
That's us. I'm Alex.
1:00
Jordan
And I'm Jordan.
1:02
Alex
You're listening to Chief Skeptic Officer. The side of tech news nobody talks about.
1:07
Jordan
Every day at seven A.M. New York time. Wherever you get your podcasts.
1:13
Alex
Automattic is the company behind WordPress.com, Tumblr, WooCommerce, Pocket Casts. On September ninth, its board voted founder Matt Mullenweg onto a paid leave of absence. He voted no.
1:25
Jordan
I'm on Hacker News. The TechCrunch thread is the live one. People are pasting his Slack.
1:31
Alex
He wrote that CFO Mark Davies "conspired" with directors Ann Dunwoody, Toni Schneider, and Sue Decker. The resolution landed fifty minutes before the meeting. He asked for a few hours with independent lawyers. That was denied.
1:45
Jordan
Wait. Leave, or fired?
1:47
Alex
Leave. Paid. Davies is interim CEO. Davies also told staff Mullenweg stays on the board.
1:54
Jordan
So WordPress itself just... lost its person?
1:59
Alex
That's the part I almost wrote down wrong. WordPress.com is the paid hosted product Automattic sells. WordPress.org is the free software anyone can download. Mary Hubbard runs the free side. She said that side did not change. Matt still leads the free project. She still is executive director.
2:17
Jordan
Same name. Two bosses.
2:20
Alex
Automattic confirmed the leave in an email. Full confidence in Davies. It did not say why.
2:27
Jordan
Last years he fought a host called WP Engine over money, and a hundred and fifty-nine staff took a buyout. That is background. The board still did not say why today.
2:38
Alex
Right. Do not treat Burning Man as the cause either. That was gossip.
2:44
Jordan
Would you close this as "nothing changes"?
2:48
Alex
I'm mid-migration on logging at work. If Slack says nothing changes after the person who signed the contracts is parked, I do not close the ticket. .com can sideline the founder overnight. .org can say the project is the same person. Hosts still type one word into the search bar.
3:06
Jordan
Adam Wathan posted that Tailwind Labs is joining Shopify. Tailwind is a kit of short style names developers paste into pages, the colors and spacing. He says about a hundred and ten million installs a week.
3:20
Alex
HN is arguing the sale, not the classes. January is the missing paragraph.
3:26
Jordan
Yes. In January Wathan said revenue was down about eighty percent. Docs traffic down about forty percent since twenty twenty-three. He laid off three of four engineers. AI chat tools were answering Tailwind questions from the docs, so people stopped visiting the site that sold Tailwind Plus.
3:46
Alex
Usage never needed the company. The visit did.
3:50
Jordan
Today's post says the free license stays, the MIT one, meaning anyone can still copy the code. Same team, Shopify paying. New signups for the paid templates are closed. Existing customers keep access. No price on the deal.
4:05
Alex
"Stable long-term home" is his sentence. They can still change the license later. We only have the blog.
4:12
Jordan
Shopify already uses Tailwind in its shop builder. Wathan wants it built against a real store, including shops that talk to AI helpers.
4:20
Alex
So the style kit millions of sites already use now lives inside Shopify.
4:27
Jordan
The classroom tools I design already lean on it because teachers' portals were built that way. I did not pick Shopify. The classes were just there.
4:37
Alex
And the docs funnel that paid the maintainers is the thing AI made optional.
4:45
Alex
404 Media named Border Patrol units called Predictive Intelligence Targeting Teams, PITT, in the Spokane and Laredo sectors. They review financial activity and other law-enforcement databases, then tip local police.
4:58
Jordan
Reason has the case. Kyle William Olson, May, Interstate 90 in Montana. Troopers said the stop was an obstructed license plate.
5:07
Alex
Later, in the court file, a Homeland Security note from agent Matthew Phelps showed up. He had flagged money patterns he tied to drug traffic, plus prior history, and passed it to a Montana sergeant as a heads-up for stops.
5:20
Jordan
Olson says he works on a licensed cannabis farm in California and was taking product home to Wisconsin. He was charged with DUI and possession with intent. Charged is not convicted.
5:32
Alex
Customs and Border Protection will not say which financial feeds they used, or whether a warrant existed.
5:40
Jordan
The HN row is thin. Thirty-two points. One comment calling it a dupe. We are not pretending the thread exploded.
5:48
Alex
Jake Laperruque at a privacy group told 404 you cannot invent a legal reason to stop someone in a back office, then hide it. He called this parallel construction: the driver hears a plate, the memo shows a bank pattern.
6:02
Jordan
The constitutional rule is cops need a real reason to stop you. Here the reason they said out loud may not be the one in the file.
6:11
Alex
Yes. The public sentence is a traffic stop. The targeting is a flag local cops do not have to read out loud.
6:19
Jordan
A developer built RACE, a Mac app for extra terminal windows you can move around. Apple checked and stamped it. The website is a simple page, no secret server. He spent five hundred dollars on Google Ads. Google suspended the account for "malicious software" and "compromised site."
6:37
Alex
The HN title is a joke. He is not teaching you how to sell malware. He is quoting the label Google stuck on him.
6:45
Jordan
I'm on his post. After the old radio joke, there is an edit. Hacker News heat got the account reinstated. Still no explanation of what triggered it.
6:54
Alex
Frontpage as customer support.
6:57
Jordan
This is the product page. Windows you can place, shells that survive a restart. Not a mystery binary from a random host.
7:06
Alex
Appeals never said what file or line was the problem. You cannot prove "I am clean" to a form that will not name the dirt.
7:15
Jordan
Scam ads still run. A signed indie tool gets the malware stamp until enough people yell.
7:23
Alex
The default way to pay to be seen can freeze you, unfreeze you after a thread, and never say which filter fired.
7:33
Alex
That's our audit for today. Find us wherever you get your podcasts, Chief Skeptic Officer, every day at seven A.M. New York time.
7:41
Jordan
Tell us what you're skeptical about. Drop it in the comments, the angle you can't stop chewing on.
7:47
Alex
Stay curious. Stay skeptical.
7:51
Jordan
Doubt both.
