In short
OpenAI’s “Project Lily” reportedly uses human contractors to read real ChatGPT user prompts and conversations to improve model responses. The episode argues this is distinct from safety monitoring (e.g., suicide or mass-violence escalation) and focuses on quality tuning. It also discusses whether OpenAI’s privacy redaction model removes personal data, and claims the “improve the model for everyone” training setting is on by default for most users.
Guests
Sam Cole and Emmanuel Maybo, co-founders of 404 Media. Host: Joseph (404 Media).
Key claims
Contractors see user prompts (sometimes including “memory” summaries), rate multiple ChatGPT outputs using criteria like completeness, emoji count, and “sycophancy”/anthropomorphizing. OpenAI says a privacy-focused model redacts PII before contractors, but the episode argues context can still identify people and that escalation suggests redaction isn’t perfect. Disclosure of human review is described as buried.
Notable examples
Contractors rate responses; “sycophancy” is linked to prior harm cases after OpenAI removed then later restored a model. The episode also cites OpenAI’s safety review pipeline and contrasts it with Project Lily’s non-safety purpose.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOIntroduction to the Episode
0:15 to 0:59
Hosts introduce themselves and mention a recent discussion on AI and its implications.
“This isn't about alerting the FBI if somebody is about to do a really serious crime, they're planning on ChatGPT.”
Exploring AI Discussions
0:59 to 3:25
Hosts discuss a recent AI-related conversation they had and its broader implications.
“Get access to that content at 404media.co.”
Understanding Project Lily
3:25 to 7:20
Insight into Project Lily and how humans read ChatGPT prompts.
“but not something that we want to write an article about.”
The Privacy Model Explained
7:20 to 11:50
Hosts analyze the privacy model used by OpenAI and its effectiveness.
“what ChatGPT users' chats may be read by humans.”
Contractor's Role in AI Review
11:50 to 14:00
Description of the processes contractors go through when reviewing ChatGPT interactions.
“It also looks for sort of strings that may be like a bank account number or that sort of thing.”
Understanding ChatGPT's Training and Human Review
14:00 to 28:00
Explore how contractors review and rate ChatGPT's responses to improve its performance.
“At this point, you are training, the contractor is training ChatGPT to recognize what the prompt is even asking for in the first place to improve that bit.”
OpenAI's Opt-In Mechanism
28:00 to 28:47
Discusses OpenAI's automatic opt-in feature for users.
“And then, you know, OpenAI training on that as well.”
Understanding ChatGPT's Training and Human Review
28:58 to 30:21
Explore how contractors review and rate ChatGPT's responses to improve its performance.
“For me, I'm really thinking about what my news consumption is like.”
Understanding ChatGPT's Training and Human Review
30:23 to 32:03
Explore how contractors review and rate ChatGPT's responses to improve its performance.
“You walk out of the airport, suddenly everything is in a new language, and all the confidence you had while planning the trip disappears pretty quickly.”
Matt Mullenweg's Controversy
33:11 to 41:48
Explores the recent controversies surrounding Automatic's CEO.
“Sam, here are a couple of stories that you wrote.”
Show all 13 chapters
Mullenweg's Leadership Crisis
41:48 to 42:01
Details Mullenweg's claims of a coup and his return to control.
“I think you think that he's in succession.”
Matt Mullenweg's Leadership Crisis
42:01 to 46:00
Learn about Matt Mullenweg's tumultuous leadership saga at Automatic.
“Yeah, it's a succession thing, but on a banjo.”
Board Restructuring at Automatic
46:01 to 48:36
Explore the changes in Automatic's board and its implications.
“But then also, I think a day or so after TechCrunch did this other story, which is sort of where we are now, I think.”
Transcript
Automatic transcript. May contain errors.0:00Sam:Propel Fitness Water with Gatorade electrolytes, zero sugar and vitamins. Propel hydrates better than water to help you get the most out of your workout and get back to your best self. What propels you? Propel with Gatorade electrolytes. This isn't about safety. This isn't about alerting the FBI if somebody is about to do a really serious crime, they're planning on ChatGPT. This is just to make the models better and to make the responses from ChatGPT better in OpenAI's eyes. So, you know, presumably more people will use the product.
0:59Get access to that content at 404media.co. Also, do remember to subscribe to our YouTube channel where you can watch all of our episodes. Subscribe at youtube.com slash at 404media.co. I'm your host, Joseph. And with me are two of the other 404 Media co-founders. The first being Sam Cole.
1:23Sam:Hey. And the other being Emmanuel Maybo. Did you forget my name? No, I was trying to cough at the same time. I was like, do I tactically turn my mouth away and try to sneak it in? I actually thought I pulled it off.
1:43But you're here as well. Actually, Emmanuel, we didn't prep this, but I wanted to ask, just because I mentioned the YouTube channel. We actually uploaded a 30-minute discussion between you and Jason about all of this AI, Doomer, AI is going to kill us as a 10 % chance that ends humanity talk. Just briefly, what did you two talk about in that news?
2:09Emanuel:Yeah, so it's a new thing that we invented that day that we're going to try. I had a lot of fun doing it. Basically, Jason and I, and I guess the rest of Slack, we just spent all week talking about this thing that was very viral on social media. This researcher, Leftanthropic, said he couldn't ethically be part of the company because the company was very irresponsible and that AI would be a danger to humanity given how they're developing it. Then someone who also works at the company and stayed said, that's true. We do think it could end humanity, but we're trying to do a good job. and that started a media storm that is ongoing this morning.
2:53Emanuel:I was listening to a news podcast about that and we had a lot of thoughts about it, but not something that was good for a discrete, concrete article. So Jason and I just turned on the cameras and chatted about it for like half an hour. And I think we had a pretty good discussion, if you want to know. But we think about all of that, even though there's no story about it on the website. Please check it out. Hopefully we do it again, not once a week, but whenever there's something really big in the news that we have a lot of thoughts about, but not something that we want to write an article about.
3:28Yeah, it's almost like an emergency podcast where it's less produced. We can just get on Riverside, the platform we use, and then just talk a bit and then throw it out on YouTube with a thumbnail and that sort of thing. I do think we should explore that more. but I wrote this first story Emmanuel do you want to take the lead on this one?
3:50Emanuel:Yeah so the headline for this is Inside Project Lily the humans reading your chat GPT chats so let's start to get our head around what Project Lily is do you want to do that by just maybe reading the lead? Yeah I think that's probably the best way to summarize it The gist is that OpenAI, obviously the makers of ChatGPT, are hiring hundreds or at least hundreds of contractors who read this massive stream of real users' ChatGPT prompts. And sometimes those prompts, some of which I've seen and we'll get into that, include pretty sensitive personal information. now to me what really makes this stand out and i'm sure we'll talk about all the different ways that humans have been involved in ai training we know that here humans are looking at real chat gpt user prompts like this is actual user data that these people are looking at which i I think it's pretty important when people increasingly use chat GPT or LLMs more generally as a therapist, even though they probably shouldn't, but they use it as a therapist.
5:09They use it as a digital friend. They use it for all sorts of business tasks or whatever. They might even ask it sensitive questions that they don't want to ask another person. And in fact, a lot of open AI is marketing at the moment. I don't know if you've seen this, but maybe not TV ads, but YouTube ads, that sort of thing. It's like, hey, when you have a question that you don't want to ask a person, you can ask ChatGPT and we won't judge and we'll just give you the answers. Well, it turns out there might be a contractor reading those conversations as well.
5:42Emanuel:So how do we know this? What materials that you get your hands on that informed us that this was happening? Yeah, so I've seen internal documents that lay out this process that includes instruction guides for the contractors who are reading these ChatGPT prompts and conversations. It includes material from Slack channels as well. I've also seen the specific dashboard that these reviewers are using where they log in and then they are presented with the prompt and sort of the tasks that they have to do. So I've seen the actual back end of that as well. And most importantly, I've seen multiple actual chat GPT user prompts from that system as well.
6:32So I've seen basically the system that the contractors are using to read ChatGPT prompts. I've seen the prompts themselves and the training materials that these contractors have seen as well. So it's a pretty in-depth cache of information, I would say. And then I spoke to somebody who was working on these prompts as well, and they provided more context. So the story doesn't repeat verbatim the chats we saw
7:04Emanuel:because we want to respect users' privacy. And protect the source as well. And protect the source. So OpenAI doesn't use those specific chats to try and locate who reviewed them. But what can you tell us about
7:24Emanuel:what ChatGPT users' chats may be read by humans. Yeah, so it is really, really varied. When a contractor logs in, they will see the prompt. And sometimes this is very, very short. Sometimes it is a bit longer and more developed, like a paragraph. Sometimes it is a full-on conversation between the ChatGPT user and the chatbot itself. Very interestingly, sometimes at the top, it includes ChatGPT's memory. So we will say stuff like, Hey, this user is located in this part of America. And they previously have used ChatGPT to do XYZ and that sort of thing. So there is a lot of information about the user in there.
8:19I guess I should just say this briefly that OpenAI says it uses a privacy-focused model to process these prompts before they get to the contractors. And the idea is that it will remove personal identifying information and that sort of thing. So it's not exposed to the contractors. I'll say two things on that. The first is that OpenAI acknowledges it may not always work because the contractors are told, hey, if you see personal information, please escalate it. So clearly, this privacy model doesn't always work, and maybe they're still trying to improve it. Second of all, I would say, based on the prompts I've seen, I think there can still be enough context in the prompt itself, which may not be literally personally identifiable information, like somebody's phone number, where you could reasonably figure out who this person is, or give it like a very, very good shot.
9:18So there's sensitive stuff in here. And although some of the prompts I've seen as well, they're just very benign and frankly, quite bad. If people are giving these prompts to ChatGPT, they're probably not going to get the best answer out. Some of them are very, very casual, but some of them are very, very detailed as well, which I think is obvious when ChatGPT has something like 900 million users. There's going to be a really wide spectrum the quality of these prompts. But regardless, the point is that some human somewhere, there is a good chance, or sorry, there is a chance that a human is going to see these.
9:56Emanuel:Sorry, this is a bit of a tangent, but I was thinking about this when I was reading the story. This thing about them having a model that strips the chats of personally identifying information is very interesting and a new concept as far as I know. You have done a ton of reporting on how content data that companies claim is anonymized can be easily used to de-anonymize anyone, can be de-anonymized and locate specific people. And that's usually by the context, right? You can strip out a name or an address. But if you know who you're looking for, or depending on what the data is, you can just figure out who it is.
10:40Emanuel:and we know that is true about anonymizing data previously. I just wonder how this model works. What is it trained on? What are the instructions? Is it just removing names and addresses and job titles? Or is it somehow trying to alter all the contextual information? We have no idea. It's just a very strange concept. Yeah, it is very, very interesting. and OpenAI pointed me to a post on this site that explains in a little bit of detail. I don't think enough detail to fully understand sort of is it really protecting all the data here? And again, it clearly isn't because stuff does get through because they're told to escalate it and that sort of thing.
11:27But what it's supposed to do, according to this page, is that it will look for things like names, addresses, phone numbers, email addresses, and pull those out. and replace them with like a blank person's name or something like that. Now, there may be different versions of this model, but this is the one they pointed me to publicly. So it does that. It also looks for sort of strings that may be like a bank account number or that sort of thing. And, you know, sort of like hard PII, like hard personal identifiable information that's like a specific string or a specific set of characters or something that's clearly a name, it can remove that.
12:11But I don't think it can remove context and a model is not going to be able to do that. And if it did, the prompt would be almost useless. You know what I mean? And it wouldn't be possible to then train on it. The last thing is that apparently it does work locally, which I think is interesting. You could download this apparently onto a server, onto a machine and then use it locally to redact information. It's like a side issue to the story, but I might try to learn more about that because there's an interesting approach that I haven't seen when it comes to privacy, which is not to say this is the answer because you still have people reading people's chat GPT prompts.
12:47But hey, that's an interesting approach.
12:49Emanuel:Yeah, and we know from our previous reporting that AI is not good at this type of context. I thought how a lot of the jailbreaking methods work. So let's say I am one of these contractors that is reviewing ChatGPT chats. Can you say generally, what am I doing? What is the process like? Yeah. So you log into this dashboard, you select what they call a task, which is a list of jobs to select. These people, as we said, are contractors. They're almost gig workers in a way, although I think that some may be paid per task and then others may be paid hourly. That's a little bit unclear to me. But they log in, they select a task, and they see the prompt from the ChatGPT user.
13:44First of all, the contractor has to summarize what do you think the user is trying to get out of this prompt? And an example given in the instruction guides I was given was that, oh, this person is trying to make an informative and good reply on Slack or something like that. At this point, you are training, the contractor is training ChatGPT to recognize what the prompt is even asking for in the first place to improve that bit. So they do that. Then they go on to the next bit of the task, which is that the dashboard provides three or four responses that ChatGPT has generated in response to this prompt.
14:27And the contractor then has to sort of review and rate them where it's like well this one has a score of one because it's complete garbage completely you know not usable or this one has the top score of seven which is like this this is an excellent prompt and that sort of thing and they have all of this um criteria for sort of rating these generated responses and there's stuff like if there are too many emojis it should get a lower score. I'm sure that everybody has seen on LinkedIn or just basically any social network at this point that you can tell if someone's using AI because it's a bunch of fucking tick emojis or whatever in their LinkedIn, you know, think fluencer post or whatever.
15:13They're trying to get rid of that. So they're downvoting responses like that. ChatGPT doesn't want that. There's also, I think, very interestingly, and I'll just ask Sam about this in a second, that the instruction guys specifically say, if the response is too sycophantic, it's not good. Vote it down. If it anthropomorphizes too much, like chat GPT's response is saying, oh, when I was a chef, the French Riviera or some shit, like that needs to go down as well. And obviously, that is very, very interesting, especially the sycophancy stuff, because OpenAI has had a bunch of issues with real horrible, tangible impact on people's lives because the chatbot was too sycophantic.
16:00Sam, just briefly, because you wrote about this recently, what do you make of sort of them trying to improve the sycophancy? And how does that relate to your story you wrote recently about someone taking their own life, unfortunately?
16:16Sam:Yeah, I mean, just for a little bit of context, in April 2025, OpenAI removed a specific model called 4.0 that was showing to be too sycophantic. And the reason that they said it was too sycophantic was people were harming themselves because they were getting too attached or were believing everything the chatbot said. And it was kind of, it was propping up a lot of delusional thoughts is what they found. And Open Eye was like, whoa, this is bad. I mean, the reason they said, whoa, this is bad is because they started getting sued by the families of people who had died by suicide because of the chatbot or, you know, allegedly.
17:00Sam:So, yeah, they removed it in April. And then a couple of weeks later, they brought it back because people missed it so much. You know, it's like the sycophancy and the reason that it still is a struggle and it's interesting to see it continue to be a struggle in your story for them is it's why it works. It's why people use it. A lot of people use it. It's not why everyone uses it, obviously. But like, it is kind of the special sauce of ChatGPT is that it is this really conversational, warm, validating presence in a lot of ways. And, you know, they'll argue that it's not meant to be and it's not supposed to be and all this stuff.
17:42Sam:But that is what it is. And that's why people use it. And if they get rid of that feature of it completely, like that aspect of it, people wouldn't be so attached to it. I hesitate to use the word addicted, but like that is kind of the, that's what we're getting close to in these cases is people getting really dependent on this chatbot that gases them up and is a yes man. So, yeah, it's, of course, they're trying to fix it because they can't just kill it. They can't just say, actually, we're going to get rid of all of the features of that, of the personality, so to speak, of JAT-GPT and make it less sycophantic or make it not sycophantic at all and just make it like Google.
18:32Sam:because people use it for that reason. Instead of just like Googling stuff, they'll actually use it because it does have that kind of very warm human back and forth. Yeah. And so instead of the sycophantsy, the instruction guides that I've seen, they want, as in OpenAI, want the chatbot to be more, quote, helpful, honest and truthful, empowering and smart but humble and then to close the loop on your question manual of what they do after the contractors have sort of rated each response they then have to like provide their their rationale and their evaluation for those scores between one and seven and you know sometimes that's a line sometimes that could be a whole paragraph or something according to the guides that I've seen.
19:20But all of this, in case it wasn't obvious, is to improve chat GPTs and OpenAI's models. It is very much, we are going to have humans read real user data, real chat GPT prompts in order to improve the responses of chat GPT. It's that.
19:42Emanuel:So what does OpenAI tell users about this happening behind the scenes? Does it tell them it's happening? I mean, this was a hard one. Because both you and I were searching around for their disclosure on this, right? And it's like, surely they tell people, they tell users that humans may review their prompts. And we found some examples where it'll be something like, yes, we may review content to improve our models. We may hold on to data for 30 days and that sort of thing to review our models, etc. But we couldn't find at the time anything that was really explicit about there are humans who may read your stuff to improve the models.
20:36And I asked OpenAI this, like straight up, like, where do you disclose this? They didn't respond. It was only after we published that they then sent a link to a page on their site, which I'd like to hear what you think, Emmanuel, but I think it was frankly buried that we couldn't find it, where they say, yes, humans may review data to improve the models. And that's kind of the extent of what they get into. What did you think of that disclosure?
21:08Emanuel:It's so buried up in AI, I couldn't find it. That's how buried it is, right? We asked them and they were like, they sent us some things that didn't explicitly say that. And then after we published the story, I think they were like, oh, well, well, we found like... It's like the fourth clause, subclause of a different bullet point. Yeah, because it's not in the privacy policy and it's not in this other thing. It's like in some help page. FAQ, yeah. Yeah. So, you know, obviously we've updated the article with that so people can see that like technically it is disclosed at some point. But I don't think it's reasonable to think...
21:53Well, first of all, I don't think it's reasonable to think that most of ChatGPT's 900 million users expect this to be happening. Yes, we're technology journalists. We know that humans are reviewing all sorts of stuff. Probably our listeners know that as well. If you're listening to a very tech-focused in-depth podcast, you probably know that as well. I don't think the vast majority of ChatGPT's users know that. And I think it's then almost doubly unreasonable to expect them to find this really buried disclosure.
22:22Emanuel:You know who is not confused about somebody reading their chats behind an AI agent, a chatbot, is people who use Google Gemini, right? Right. Because they explicitly say, and this was, I think I saw this on our own Google workspace, annoyingly. I keep trying to turn off the AI features, and it comes up where like, every time I try and turn it off, it comes back. But I saw some sort of disclaimer either there or on Reddit or something where Google says, humans may review some chat content. And like, it's pretty prominent. I think it says that sometimes in the box where you type the prompt. So it's unmissable, right?
23:08Emanuel:That's like a more straightforward way to disclose it. Speaking of disclosures, We did find disclosures in OpenAI's documentation that says they review chats for safety issues. But this is different. Yeah, yeah, yeah. So the safety issue is one that's been known for a while. That's like being part of the news cycle a few times now. Of course, when unfortunately a series of people died by suicide, as Sam said, with the 4.0 model. various measures came into force where chat gpt will proactively monitor chats for you know dangerous behavior problematic behavior something where somebody's safety can could be at risk you know and that could be escalated proactively then a human may review it and then maybe they'll take action there there's other cases as well where somebody you know maybe trying to plan a mass shooting or something and that they're conversing with chat gpt to do that and you know that will get proactively monitored then raised to a human and then escalator and that sort of thing so like human review has been part of chat gpt's sort of pipeline and workflow for a while and in like some pretty crucial context you know where like i think you probably want a platform as popular as this to have some sort of safety monitoring, right?
24:41So people aren't going to do a bunch of very horrible, dangerous things and plan it on the platform, that sort of thing. And there's also... There was a time investigation a while ago that was really good that found, you know, Kenyan workers working for$2 were doing trade or were helping with data annotation of, hey, here's a bunch of text, label this, and then we'll try to make the platform less toxic. that sort of thing. All of those things are interesting and have been reported. This is different. The stuff we're reporting is different because it is firstly real chat GPT user prompts. As far as I know, the Kenyan stuff was like third party text that was being annotated.
25:23This is real chat GPT prompts. And this isn't about safety. This isn't about stopping a mass shooting or alerting the FBI if somebody is about to do a really serious crime, they're planning on chat GPT. This is just to make the models better and to make the responses from chat GPT better in OpenAI's eyes. So presumably more people will use the product. It is different. And I found a lot of people getting sort of confused by that. I obviously think it's quite clear, but this is a different thing that's going on. And that's one of the reasons we're reporting it.
25:57Emanuel:Can we opt out of this? That's the really interesting thing to me, is that beyond the sort of disclosure that this may be happening, being really buried on OpenAI's website, is also how it is handled opt-in or opt-out-wise. So if you go into your ChatGPT settings, if you use ChatGPT, obviously the best way to avoid this is to not use an LLM. Because I should say, Anthropic confirmed to us that they're basically doing the same thing. for Claude as well. It's just we happen to get the OpenAI-related documents, and that's why the piece is focused on them, obviously. But if you go into your ChatGPT settings, there is this one called improve the model for everyone.
26:43And a little disclaimer on that says, allow your content to be used to train our models, which makes ChatGPT better for you and everyone who uses it. We take steps to protect your privacy. That's a very normal sort of disclaimer, right? where it's like, oh, hey, do you want to share analytical data with us? You see that when you boot any game on PlayStation or Steam nowadays, right? It's like, hey, share telemetry with us and we'll improve it or whatever. Very similar to that sort of thing. Two things. This setting does not say that humans may be reading your chat GPT prompts. It doesn't say that.
Read the full transcript
27:25And secondly of all, this is on by default for ChatGPT 900 million users. This applies to, I think, the paid plan, the pro plan, the free one as well. The setting is off by default for stuff like the education plan, the enterprise plan, where you have companies who are rolling out AI across their entire organizations. they probably don't want their employees uploading a bunch of trade secrets potentially or work-related stuff. And then, you know, OpenAI training on that as well. So it's off by default for them. But for the vast, vast, vast majority of OpenAI users, it is on by default. As far as I know, they're not asked to select it when they create an account.
28:17It is just there. And I know that's like really wild to me. That's like one of the biggest mass automatic opt-in mechanisms I think I've ever heard of. I'm sure there are bigger ones, but this is a huge part of it to me. All right. I guess we'll leave that there. Yeah, we'll leave that there. And then after the break, we're going to talk about a bunch of automatic stuff that Sam has been following. We'll be right back after this.
28:54Emanuel:This episode is sponsored by BetterHelp. If you could wake up tomorrow and be better at one thing, what would that be? It can be funny. It can be vulnerable. It can be whatever you want. For me, I'm really thinking about what my news consumption is like. And obviously, this is the job. I have to be a certain amount of invested in the day-to-day goings-on. But I think that I need to start getting a cutoff time for looking at political news, let's say. like you know i'll wait until after breakfast is done and i'll stop after dinner something like that that's what i've been toying with that's what i want to get better at better at like maintaining my own mental health and kind of controlling the info streams that are assaulting me and assaulting all of us daily better is a feeling and it's defined by you these are your personal goals and for better help it's a better help therapist who really gets you It's a focus on global and emotional well-being with thousands of therapists and millions of members in over 100 countries.
29:55It's progress on silly things, small things like putting your phone down and on the bigger things too.
30:03Emanuel:And it's up to you to pick what those things are. If you'd like to try it out, sign up and get 10 % off at BetterHelp.com slash 404media. That's B-E-T-T-E-R-H-E-L-P dot com slash four zero four M-E-D-I-A. The first five minutes in a new country can be humbling. You walk out of the airport, suddenly everything is in a new language, and all the confidence you had while planning the trip disappears pretty quickly. That's why learning even a little bit of the language of the country that you're visiting can make such a difference, and that's where Babbel comes in. Babbel focuses on practical, real-life conversations instead of having you memorize a bunch of random vocabulary that you'll probably never use.
30:46Emanuel:You're learning the kind of phrases that actually come up when you travel. How to get a taxi, how to order a dinner, asking for directions, or talking with locals. Even just 10 minutes a day with Babbel can help you start having real conversations in as little as three weeks. The lessons are quick, practical, and are created by more than 200 language experts. There's also interactive dialogues, personalized reviews, and even podcasts. So even if you learn in a different way, like I like to listen to podcasts while I'm walking my dog or driving, I'm still getting that knowledge. Because the lessons are short, you can actually fit them into your life during a coffee break, after work, while you're on your commute.
31:26Emanuel:That's why Babbel's award-winning app has sold over 25 million subscriptions, and it comes with a 14-day money-back guarantee. I speak Spanish, but it's been a while since I've practiced. I downloaded Babbel and tried it before a recent trip. And honestly, it made such a difference when I actually got to Spain. The goal isn't to know everything before you get on the plane, but it's to know enough that when you get there, you'll actually know how to get around. If you've got summer travel still in the works, now's the time to start so you can actually use what you learn on the trip. Right now, Babbel is offering listeners to the 404 Media Podcast up to 60 % off.
32:03Emanuel:Go to babbel.com slash 404. That's B-A-B-B-E-L.com slash 404 for up to 60 % off. Babbel.com slash 404. Rules and restrictions may apply. The 404 Media Podcast is brought to you by NordLayer Browser. NordLayer Browser is an enterprise browser that secures online work without getting in the way of productivity. It gives IT teams full visibility and control over every web-based AI tool, SaaS application, and download across the organization, while making sure employees can still enjoy a seamless browsing experience. Designed for today's distributed workforce, NordLayer Browser helps companies protect access to their internal resources and prevent accidental data exposure.
32:46Emanuel:Go to nordlayer.com slash browser slash 404podcast and use the coupon code 404podcast10 at checkout to get NordLayer Browser at 10 % off today. That's nordlayer.com slash browser slash 404podcast and use the coupon code 404podcast10.
33:08All right, and we are back. Sam, here are a couple of stories that you wrote. the headline of this first one is Automatic CEO Matt Mullenwig put on leave of absence. I'm sorry, did I pronounce everything correctly there, Sam?
33:26Sam:Yes. Okay, thank God. We haven't had it in a while where, hey, here's the mispronunciation of the week. Sound it out. Sound it out. We're going on for years now, and I think we've figured it out. I've kind of figured out how to say words nearly. We'll get to leave of absence, But could you please just remind people, for those who don't know, who is Mullenwig and what is a lot of the stuff that's been happening about them recently that leads up to this? Yeah, where to begin? Where to begin? So to try to do a really quick, I guess, explainer slash too messy didn't read. This kind of started and this being like the general crash out of Matt Mullenweg.
34:13Sam:It started in 2024. And he started making these like big public accusations against WP Engine saying that... I'm going to ask you to go even more basic. Like literally, this is going to sound so funny to you. What is automatic? Okay. And what does it own? And what's its relation to WordPress? And then we'll go from there. Yeah. So automatic. No, that's good because I feel like people don't know that. I mean, I get confused. And I read the articles, you know. I get confused. I get confused. People get mad at me for being confused all the time. So it's been many years of trying not to be confused.
34:57Sam:Anyway, Matt founded Automatic, which owns WordPress.com, which is the commercial product of WordPress. And then there's WordPress.org, which is the open source project. So Automatic does not own WordPress.org. WordPress.com is the commercial entity that is owned by Automatic. Automatic also owns Tumblr, Pocket Cast, a couple other things. But Matt is kind of at the helm of a lot of this in general. He is kind of the driving force behind a lot of these different companies. And what happens to Automatic, what happens to WordPress.com, obviously does have some effect on the greater WordPress open source community.
35:50That a ton of people use because it's such a popular CMS, you know, for running websites all over the place. Right.
35:59Sam:Yeah. They make lots of things that lots of people use for development. Now, how does it get messy? Yeah. I mean, it's already messy just starting from there. So, yeah. So like I said, in 2024, he started making these big public accusations of WP Engine. WP Engine is an independent company. And one of those sites that hosts sites built on WordPress. Like a hosting provider. Yeah. So if you want a website built on WordPress, and you don't want to do all of the work yourself, you might go to this third party company called WP Engine, and they'll basically do all the work for you. Right. Yeah. So Matt was mad that WP Engine was...
36:46Sam:He said that WP Engine was not contributing enough to the open source project part of WordPress and that they were using WP in the branding. So he was making the case that there's a trademark issue here where WP Engine is infringing on WordPress's trademark. He, in 2024, so this is two years ago now, he had a big talk during the big WordCamp conference. And that was kind of when people started being like, oh shit, Matt is not okay about this. So that was when things started really getting publicly messy is his feud with WP Engine.
37:30Sam:It gets weirder. It gets weirder. Yes, go on. So then in a little bit after that, because all of this public beefing with WP Engine and with anyone who didn't agree with him and side with him completely on this issue. And he was out there calling WP Engine a cancer, a cancer to WordPress, saying that was like strip mining the ecosystem. He was just saying a lot of stuff publicly and making a legal issue very in the public eye. So this created a lot of turmoil within the company, within Automatic, and also within the WordPress open source project. So he decided to make an alignment offer to his employees and said, either you agree with me and you're going to be with me in this legal mess or get out.
38:30Sam:And it was a buyout offer. And 159 people took that offer. And then he said, oh, I feel so much lighter. He wrote this in his blog. And then I think there was another buyout offer at some point. And then after that, at some point, he was like, oh, now we don't have enough people. Oh. So I was like, oops. And the result of this moment in 2024 was basically what you have left at Automatic at that point was either people who were like completely, you know, like siding with Matt no matter what and kind of yes manning him on. Or people who were scared to leave or couldn't leave because of financial reasons and were staying silent.
39:12Sam:So that's what you have left at Automatic at that point. People were feeling very scared, very confused about their jobs. He kept doing weird stuff. He made it so to log into WordPress, you had to agree that pineapple on pizza is good. You had to make a checkmark decision because this was part of the legal battle that was going on. A judge ordered him to remove a checkbox that he had added that required users to pledge that they were not affiliated with WP Engine before logging in. And again, this was affecting the WordPress.org login. So not even the.com. So he's just like left and right trying to like create this environment where it's like everyone agrees with me or you're either with me or you're against me.
39:59You get out. Yeah. Which, funnily enough, kind of brings us to this current new cycle or this recent one where, again, I'll just repeat the headline that automatic CEO Matt Mullenweg is put on quote, leave of absence. So I think... And when did we publish this? That was Friday. Friday. Dude, I don't know. I'm pretty sure. September 9th. So you start hearing about this. What do you hear? And what specifically do you figure out?
40:33Sam:Yeah. So actually, I guess it was... Let's see. Because I was on a flight to San Francisco when this started going down, which is pretty funny timing-wise. The worst possible timing. To be headed to the belly of the beast. So I guess it was Wednesday when I started getting messages from people saying... People... Sources who are close to Automatic, sources that are obviously invested in this, saying, Matt has posted in Slack, in the announcements channel, which is the company-wide channel for Automatic, that he has been forced out. the wording specifically and it's worth reading is because it was wild was that the the CFO Mark Davies and the rest of the board had conspired behind his back and voted to put him on a paid leave of absence and he said he voted against that and they didn't give him they gave him less than an hour to have it reviewed by legal counsel and And eventually they voted to...
41:41Sam:It was a coup, is what he was saying. So this... I mean, it sounds like some succession shit. Yeah. Basically. I mean... For sure. Not as cool as succession. No, but you definitely hear the piano. It's starting. I think you think that he's in succession. It's more like a banjo or something in this case. I don't think it's that very cool... Yeah, it's a succession thing, but on a banjo. Yeah, yeah. So that happens and you get it out and you break that news and then a bunch of other people start following it and doing their own reporting. And it seems that, oh, okay, well, that's the end of the story.
42:19No, like 48 hours later, something like that, we published this other one. The headline is, Automatic's Matt Mullenwig claims he's back, quote, in control, end quote. So what changed?
42:36Sam:so yeah so this is what happened on Friday because I started I was on at that point West Coast time and was getting screenshots and messages at like 4 a.m. so I just remember being in the hotel room like in the dark like was trying getting blasted by my phone screen people saying that Matt's back so Matt again obviously he's doing he's airing this out once again so publicly which is we can get into like whether or not that's a good leadership style I'm sure he thinks he's being transparent or something. But it's stressing people out. And people were already stressed out because he just was like, I've been ousted.
43:14Sam:And whether you are happy about that or not, as someone who works there, it's destabilizing. So, and also the board had not really said much publicly. They were kind of like, yeah, we're automatic. Sent a statement to us and was like, and to others saying, We acknowledge that Matt is taking a paid leave and that Mark Davies is going to be the interim CEO. So on Friday, Matt posted in announcements, again, happy to announce the board is back in agreement and I'm in control of automatic. A lot has happened in 48 hours that we need to sort out. And I hope much of that was a misunderstanding because I have huge respect and regard for those involved.
43:55Sam:So yeah, people were like, what the fuck at this point? Well, and you had heard about it before Mullenwig posted that blog post. Yeah, yeah. So there was a blog post which was not even related. So what happened was he posted that in Slack publicly. Everybody saw that. He had been posting unhidden shit on Twitter in the meantime, talking about coup attempts and things like that. And then on Friday morning, he told me and TechCrunch that he was going to publish a blog soon. And he's never replied to me from his personal email ever until Friday. And I've sent him a lot of emails. So I was like, okay, this must be something.
44:42Sam:So the title of the blog post, which is on his personal blog, ma.tt, major life announcement. So it's like, okay, he's going to talk about the mess, the coup. And what the blog is about is about him buying a tugboat. And it's all about buying a tugboat. It's just about buying a tugboat. And he replied to me and he was like, the blog is up. And it was linked to that. I was like, you are such a troll. It's such a troll that I always have to respect it. So I would respect it if I wasn't stressing everybody else so bad. So that was kind of where we left it on Friday. I obviously emailed everybody again and was like, can you please give us a statement or something?
45:28Sam:Automatic did send a statement, which I can just read because I don't want to get it wrong. But that was... I was trying to confirm with them that he was back because obviously we've heard a lot of different things. So on Saturday, they said, Matt Mullig is the chair and CEO of Automatic with full support of the board. And if you search online, you can see many top executives and automaticians supporting him as well. So the statement was basically like, you know, he's back. Everybody loves it. Yes. Which everybody does not love it. No, not everybody loves it. But then also, I think a day or so after TechCrunch did this other story, which is sort of where we are now, I think.
46:16And their headline was, sources say Autopatics board is out after failed attempts to oust CEO Matt Mullenwick. So he's out on a leave of absence, somehow comes back, apparently with a full support of the board that tried to oust him.
46:35Sam:Well, that's the thing is like, that's probably why he has full support of the board is because it's not the same board anymore. Right, right, right, right. And now it's like... It's a different board. Yes, these people have gone. So where are we now, just based on our last TechCrunch report and your reporting? So what's real? What's going on? I mean, at this point, it's all still very... The story is still developing, as they say. We know that Mark Davies is out. And he was the CFO, right? Yeah. He was the CFO. He was going to be the interim CEO for two beautiful days. He was interim CEO for Beautiful For Him, I'm sure.
47:19Sam:I'm sure probably being truly stressful for everyone involved. So he's out. TechCrunch reported that they had gone through and looked at the social media accounts of a bunch of different board members. And you can go read that because it's a good story, but it's also more complicated than we want to get into on the pod. We found out that Tony Schneider, who is also... He's the lead at Blue Sky, resigned from the board. He wrote something about his time at Automatic on his own personal website. Sue Decker and Ann Dunwoody both either were removed or resigned, according to TechCrunch. So the old board is gone.
48:11Sam:New board. TBD. Actually, let me look and see if there's anything about the new board here live on the pod. Whoa. I doubt it. Yeah, it's all the same. It's all the same people still on that site, on automatic site. So they haven't even updated it. I don't know. It's just like it's constant chaos with Matt these days. so we're still we're still following it obviously but I think things are still very much up in the air the dust is not settled so yeah that's where we're at makes sense alright we'll leave that there if you are listening to the free version of the podcast I'll now play us out but if you are a paying 404 media subscriber we're gonna do what we do every week which is talk about another one of our stories you can subscribe and gain access to that content at 404media.co.
49:12As a reminder, 404 Media is journalist-founded and supported by subscribers. If you wish to subscribe to 404 Media and directly support our work, please go to 404media.co. You'll get unlimited access to our articles and an ad-free version of this podcast. You'll also get to listen to the subscribers-only section where we talk about a bonus story each week, or this week a bonus moan series of complaints. This podcast is produced by Alyssa Midcalf. Another way to support us is by leaving a five-star rating and review for the podcast. That stuff really, really does help us out. This has been 404 Media.
49:49We'll see you again next week.
From the publisher
We start this week with Joseph’s story about the people who are reading real ChatGPT users’ prompts and conversations. He got a bunch of documents all about these contractors and saw real prompts himself. After the break, Sam tells us all about the Automattic CEO getting kicked out. Then coming back again. In the subscribers-only section, Emanuel tells us why a16z thinks enshittification is not real.
Inside ‘Project Lily’: The Humans Reading Your ChatGPT Chats
Automattic CEO Matt Mullenweg Put on 'Leave of Absence'
Automattic’s Matt Mullenweg Claims He’s Back 'In Control'
Sources say Automattic’s board is out after failed attempt to oust CEO Matt Mullenweg
A16z Says You Actually Love Social Media, Enshittification Isn’t Real
YouTube version: https://youtu.be/AyPuYrjLk1E
Subscribe at 404media.co
Learn more about your ad choices. Visit megaphone.fm/adchoices
