An update to More Magic Math from OpenAI

The final mad dash to IPO is on for the big AI companies. SpaceX, OpenAI, and Anthropic have all made their intentions clear. And nothing could be more obvious about OpenAI’s intent than today’s new funding announcement. A few things have changed since I wrote that piece. Some confirm my thesis, and one surprise, though not really.

So, the company says the round closed. $122 billion in committed capital, up from the $110 billion announced in February. Does committed mean money has passed the transom? We won’t know. What we do know is that at a post-money valuation of $852 billion, the anchors are Amazon, Nvidia, and SoftBank. Microsoft participated again, though not clear for how much. The additional $12 billion came from a who’s who of institutional money, including a16z, Sequoia, BlackRock, Blackstone, Fidelity, Temasek, D1, and Dragoneer. The FOMO gang!

So many brand-name investors show up at the last minute because none of them want to miss out on the sweet IPO pop. It surely will win them points with their own (limited partner) investors. I guess FOMO is also an affliction for the super rich.

By the way, nothing puts more in “t “less is more,” than more itself. In 2024, OpenAI raised $6.6 billion and sold about 4 percent of the company. In 2026, they raised $122 billion, twenty times more, by selling roughly 14 percent. Existing insiders and early employees must be in heaven.

To be clear, the circular financing problem hasn’t gone away. Amazon’s $50 billion is tied to an eight-year AWS contract. Nvidia’s contribution is compute, not cash. When I wrote about this in March, it was just an observation. Now it has a name. Bloomberg, Reuters, and others are now calling it “circular financing.”

OpenAI says it now has a $4.7 billion credit line from JPMorgan, Goldman Sachs, Citi, Morgan Stanley, and Wells Fargo. That’s not a lending syndicate. That’s an IPO underwriter roster auditioning for the job. It reminds me of those lining up outside Don Corleone’s room on his daughter’s wedding day. The credit facility is the gift they bring to get in the room.

Now let’s talk about the fix. The $3 billion in investments from individual investors. Axios reports that they are customers of three of the largest banks. Wait, the same three large banks that extended the credit facility and want to be part of the IPO underwriting syndicate. More circular economy at work.

OpenAI CFO Sarah Friar told Axios, “We are really trying to take to heart our mission, which is AGI for the benefit of humanity and thinking about access. Not just access to the technology, but also access to the economic upside that it’s driving.” That’s a nice line. It’s also an IPO marketing strategy.

OpenAI said it will be included in several ARK Invest ETFs. Cathie Wood, who previously invested in OpenAI through her venture arm, now gets to channel her retail base into pre-IPO OpenAI shares. Think about what that is. A private company, not yet public, getting into retail ETFs. That’s a new thing. It’s smart, too. You create demand before the IPO. You distribute the story. You make millions of people feel like they have skin in the game before you even file. That’s the fix.

ARK is overrated, to put it mildly. ARK’s flagship fund peaked in February 2021, then fell 75 percent. Five years later, a thousand dollars invested then is worth about $573 today. And ARK is the vehicle OpenAI chose to democratize the upside. Make of that what you will.

One last thing. OpenAI is quietly pivoting, shutting down Sora, its much-hyped video app, and concentrating resources on a “superapp” for developers and business users, with coding assistants at the center. Why? Because enterprise is exactly where Anthropic is eating their lunch. The $122 billion has bought more time to beat the competition. And did you notice that CFO Friar is doing all the press versus Sam?

You focus this hard because you want to go public. Fast. After all, you don’t want to be the one without a chair when the music stops. Your move, Dario!

Previously on this topic:

• More Magic Math from OpenAI?
• OpenAI Has New Focus (on the IPO)
• $110 Billion in Name Only
• The Debt Beneath the Dream

1

You’re welcome

I don’t hate April Fools Day. I’m just too busy to participate. So this is a fooling-free blog post.

Much to munch on

Getting great hang time with Jon Udell (who also manifests here) lately. Here are two of his recent publishings ya’ll might dig:
• Introducing XMLUI
• Beyond The Dip

Is there also a Gander?

Just discovered Goose.

Also, while we’re not at it, A2UI.

Bad try

This appears to be an interesting story, and available to free (as well as to paying) subscribers, but the shakedown is so hard and blunt that I moved on.

Good song title

Sycophantic Chatbots Cause Delusional Spiraling.

Another example of how BigAIs have become the Great Typicalizers of Everything

Florian Roth is tired of reading AI-written posts. His main take: “They all sound like the same guy.”

I fear that guy is, at least in part, me. The sentence fragments, the short paragraphs, the em dashes. (These: —.) As source material, my writing is thick on the Web’s ground, going back to the early ’90s. Example.

I’ll cop to one of his tells: absurd certainty. Some of mine turned out to be the opposite of absurd. Examples: personal computing, outlining, the Net, the Web, Linux, open source, Cluetrain, blogging, smartphones. And some not (at least so far, or not yet in a big way): home Web servers (or “personal clouds”), desktop Linux, VRM, EmanciPay, the intention economy, MyTerms, personal AI, news commons, market intelligence that flows both ways…

Anyway, AI-style writing is now like Received Pronunciation in the UK: the way things are done.

Something I didn’t know

Ben Collier in the MIT Press Reader: The Secret History of Tor: How a Military Project Became a Lifeline for Privacy

Not  looking good

Thomas P.M. Barnett on the current war:

History doesn’t grade on effort. It grades on outcomes. And right now the outcomes are running about 3-to-1 against anything resembling the vision that justified the operation in the first place.
As usual, the postwar is everything.

Free at last

NiemanLab: The Salt Lake Tribune will drop its paywall.

I’m really excited to introduce a project I worked on with various AI agents the other night, which I think represents a new way we might build things in the future.

First, the problem: My WordPress site has 5,600+ posts going back decades, and I had some categories that were old and I didn’t really use anymore, and I wasn’t happy with the structure. Every time I made a new post, it irked me a little, and I had this long-standing itch to go back and clean up all my categories, but I knew it was going to be a slog.

Let me present Taxonomist, a new open-source tool you can run with one copy-and-paste command line that solves this problem. Here’s the idea:

1. You run this code in your terminal, and it spins up a Claude Code instance that asks you for your URL.
2. Then it takes that and figures out what type of site you have, which APIs are available, and starts downloading all your posts locally for analysis.
3. Sub-agents analyze every post against your current categories and thinks about suggesting new ones.
4. It previews all the changes.
5. Tries a variety of ways to authenticate against your site and make all the changes.
6. Logs everything locally, so anything is reversible later.

THIS IS VERY ALPHA. PROBABLY BUGGY. BE CAREFUL WITH IT. PATCHES WELCOME. MAYBE MAKE A BACKUP OF YOUR SITE BEFORE YOU CHANGE IT.

It kind of just worked. I ran it live against ma.tt and it cleaned up a ton of stuff pretty much exactly how I wanted. But there’s a lot of weird stuff happening here, so I don’t know quite what this is yet.

1. It’s very non-deterministic! There is some pre-written code, and probably could be more, but a lot of the code is generated on the fly by your agent. This creates interesting bugs where people testing with less powerful models had some odd behavior.
2. I kind of want a directory of these useful AI agents on WordPress.org, but also, there’s something a little strange about trusting a remote shell script to run on your machine.
3. I tested this with Claude, but there’s no reason Codex couldn’t use the repo in the exact same way, and I’d love to improve the quick start script to start by detecting all the agents you have, asking which you’d like to use, and also which directory you’d like to work in. I think we could kill the cd taxonomist-main && claude "start" part of it.
4. Because much of the code and commands are generated on the fly from prompts, it’s very resilient! I’ve seen people try it, and it ran into errors with libraries or whatever, but it just figured out how to work around them.
5. I’d love it if, at the end of every session, there was a moment for self-reflection where the agent would take the repository and suggest upstream issues and PRs based on anything that went wrong. Then this could recursively self-improve very quickly.
6. There are some obvious improvements to this, for example, doing this for tags. Sometimes it creates too many categories when you might only want 3-5 for your theme.
7. One fun thing is a bunch of the work of this just uses public WordPress APIs, so you can run it against any site! I like using distributed.blog as a demo. It’ll still do all the fun downloading and analysis and everything, you just won’t be able to make changes.
8. I now have a local cache of all my WordPress posts I can do other interesting things with, and that’s cool.
9. The logging and reverting probably still has some bugs in it.
10. You can riff with it along the way, so for example, it suggested I get rid of my Audrey category because it didn’t have enough posts, and I asked it to look at all the companies on Audrey.co website and categorize any posts that talk about them as Audrey, which created like 50 more.
11. I want to check the GitHub repo for any updates before it starts, and maybe periodically, because it’s iterating and improving really fast.
12. It’s not the default but the entire thing is way more pleasant if you run it with skip-permissions. So testing I usually run the one-liner, exit, resume with skip.
13. You can see some of my prompt history in the Github but I apologize it’s not comprehensive, I also used Gemini and Codex with this and got lots of value from them.

So, not sure what this is, but please check it out, play with it, submit improvements or ideas, and think about what’s next. Might host a Zoom or something to brainstorm.

The final thing I say is that this was a very different process of writing software for me. Instead of staying at the computer the entire time, I found myself going away for a bit, napping and dreaming about the code, coming back with new ideas and riffing on them. Maybe I’ll return to my Uberman polyphasic sleep days? Nap-driven development?

BTW I have lots of thoughts and feedback for Emdash but I thought this was more interesting, will try to get that out later tonight. One preview: TinyMCE is a regression; they should use Gutenberg! We designed it for other CMSes and would be fun to have some common ground to jam on.

Might do the same for you

In The Relentless Missionary Creating AGI: Demis Hassabis, the latest episode of the Founders podcast, David Senra compresses by Sebastian Mallaby's book, The Infinity Machine: Demis Hassabis, DeepMind, and the Quest for Superintelligence, into 55 minutes of pure inspiration. Not just because Demis is a hugely inspired and driven dude, but because a pile of ideas came to me while I was listening.

Big fact

YouTube has 2.7 billion monthly users.

Here's almost looking at you

Imagine scattered bits of coffee grounds, floating in space in front of your face, a few inches to a few feet away. Among them, blurred filaments float around, like zero-gravity worms. These are bits of debris inside my left eyeball, not far from my retina, exfoliated, I am told, by my cornea, which is slowly healing from the effects of cataract surgery that required a somewhat aggressive emulsification of the lens before a new replacement lens was installed.

An interesting thing: if I don't move my eyes, the debris slowly vanishes, erased by my brain as if by Photoshop's healing brush. Then they reappear when I move my eyes. Strange shit.

Observations

Explore these observatories. Read what they are about and how they are produced. One more way (within which are many more ways) that the world will never be the same. Bonus link in the same vein. Big HT to Jim Cowie of the Berkman Klein Center, the Internet History Initiative, and much else.

Unanswered

I still have questions about two Dorothy Parker quotes.

“A newspaper is not only a collective propagandist and a collective agitator, it is also a collective organiser.” — Vladimir Lenin

In 1902, Lenin argued that his revolution needed a newspaper of its own, and that newspaper was (unironically) named Pravda, which means truth in Russian.

“The standard communications playbook just doesn’t apply to us. We’re not a typical company. We’re driving a really big technological shift.” — Fidji Simo, 2026

Simo, OpenAI’s CEO of Applications, explained this to OpenAI staff as to why OpenAI had just bought TBPN. Different century. Same logic to explain an emerging new socioeconomic order, a new post-revolution reality.

To recap, OpenAI, weeks if not months before its public offering, has acquired the Technology Business Programming Network (TBPN). It is a daily, three-hour live tech talk show hosted by founders Jordi Hays and John Coogan. The show had 58,000 YouTube subscribers, $5 million in revenue last year, and a cult following in Silicon Valley. It was profitable, had no outside investors, and was growing fast. As a former media person, any media exit is a good exit. Congratulations to the founders.

Now let’s dig into what OpenAI really bought and why.

Think of TBPN as a room. A room where people in tech come and talk openly, without having to worry about the antagonistic queries that big media is often posing them. They go because it feels like peers talking, not press interrogating.

If you lived through Internet 1.0, CNBC’s morning show had the same vibe. ESPN’s SportsCenter did the same for the cable sports revolution. They don’t speak to power. They amplify power. TBPN made that playbook its own.

The best part of the announcement is where TBPN sits inside the OpenAI org and who it reports to. The show sits under “strategy” (and not communications) and will report to Chris Lehane. He is OpenAI’s chief political operative, the man associated with coining “vast right-wing conspiracy” as a deflection tactic during the Clinton White House years, who built Fairshake, the crypto super PAC that spent hundreds of millions targeting anti-crypto candidates in 2024.

You don’t put an editorially independent media property under your political operative. That’s not a media strategy. That is part of overall strategy. But they still have to sell it as keeping it editorially independent. Pravda was technically editorially independent too.

Anyway, maybe I have lost my rose-tinted glasses, but when a company says “do no evil,” you know what they are going to do. And if a press release mentions editorial independence four times, you know where that is going. And if you have to invent a new phrase, “Editorial Independence Covenant,” then I don’t really need to spell it out for you.

“The conscious and intelligent manipulation of the organized habits and opinions of the masses is an important element in democratic society.” — Edward Bernays, Propaganda, 1928

Bernays, who was Sigmund Freud’s nephew, invented the PR industry. He thought of it as a key part of corporate design. He was hired by corporations such as United Fruit and American Tobacco to do exactly what OpenAI is doing now. Build the perception layer around a product by presenting it as a massive societal shift.

The Soviet term was agitprop. The Silicon Valley term is earned media strategy. A century apart, history still rhymes.

Related Reading

• OpenAI: The Fix Is In — How OpenAI is engineering its IPO narrative through circular financing and retail ETFs.
• OpenAI Has New Focus (on the IPO) — On Simo, Facebook-style engagement loops, and the real game being played.
• More Magic Math from OpenAI — The PE deals, the JV structure, and why the real product is the IPO prospectus.
• The New Announcement Economy — How OpenAI mastered the press release as a capital-raising instrument.

I was invited by Janna Anderson and Lee Rainie, of the Imagining the Digital Future Center at Elon University, to contribute my thoughts to their latest study, titled Building a Human Resilience Infrastructure for the Age of AI: Experts Call for Radical Change Across Institutions, Social Structures, which just came out. Here is the full report, which runs 376 pages. I am generously sourced on pages 11, 16, 142, and 358. There is a lot of great stuff in the report, which I highly recommend. For what it’s worth, here is the full text of what I sent them.

We are digital beings in a digital world. That’s the main thing. And this world is still very new.

We’ve operated in the natural world for as long as we’ve been a species, and we are experts at it. But the digital world is not only new, but sure to be with us for many years, decades, centuries, and millennia to come. And we still lack countless graces we take for granted in the natural world, such as privacy and independence from algorithmic manipulation.

Making full sense of this new world is very hard because we understand everything metaphorically, and natural world metaphors mask what’s really going on in the digital world. So, while we speak of “domains” with “locations” that we “build” and “own” (though we only rent them), and speak of “loading” and “transferring” “packets” of data in “up” and “down,” data are actually collections of ones and zeroes that are by design immaterial non-things that are instantaneously both here and elsewhere, even though “where” only makes full sense in the natural world. How will all this change and make whole new kinds of sense after a few more decades of digital existence?

Progress is the process by which the miraculous becomes mundane. In the digital world, that transition is now happening almost instantly, and in many domains, because AI is endlessly useful.

Big AI does its best to ingest the totality of human expression in all digital forms, and then to make any and all of it available in the most useful ways it can. At the moment (for me, Noon in The Bahamas on February 2nd, 2026), it does this by bringing hunks of that expression back to us, on demand, in constructive conversational forms. Big AI is the world’s largest Magic 8 Ball, within which floats a polyhedron of answers with trillions of facets, each ready to help.

As with all tech, Big AI has its downsides. (Just ask Gregory Hinton or Gary Marcus.) But its usefulness verges on absolute, so we can’t stop using it, no matter how abyssal some credible prophesies may be.

But there is one saving upside. It’s the same one that saved us from HAL 9000 in the movie 2001: A Space Odyssey. It’s our humanity and independence. Specifically, in the form of personal AI.

We need personal AI for the same reason we need personal homes, shoes, and computers. We need it to know our natural and digital selves as fully as possible, and to participate with full agency in society, its economies, and its governance.

Think about all the data in our personal lives that is not in our full control, and could use some AI help: our schedules, our past and future work, our property, our finances, our obligations, our writing and correspondence, our photographs, our sound recordings, our videos, our travels, our countless engagements with other persons online and off, our many machines, you name it.

Truly personal AI—the kind you own and operate, rather than the kind that is just another suction cup on a corporate tentacle—is as hard to imagine in 2026 as personal computing was in 1976. But it is no less necessary and inevitable. When we have it, many of the questions that challenge us will have new and better answers. And new challenges.

Every form of life, from the microbial to the human, is fraught with challenges. Personal AI is necessary for us to meet and surmount our challenges in the digital world, and to answer all the questions posed to us in this very research exercise.

Amara’s Law says we overestimate in the short term and underestimate in the long. I’ve been doing both all my life, and in all my answers to good questions asked by Pew over the years.

Perhaps the most glaring example of short-term overestimation was my response to a request by The Wall Street Journal in 2012 to compress my new book, The Intention Economy, to a single cover piece for the paper’s Marketplace section. My editor at the Journal suggested writing about how the intention economy would look ten years in the future, which is three years ago as I write this. The piece I wrote was titled (by the WSJ) “The Customer as a God.” In retrospect, I was wrong. The economy I described still hasn’t happened. We are not gods in the marketplace. But there are encouraging signs, and I’m still sure my prophecy will prove out. Meanwhile, the first half of Amara’s Law applies.

I’ve been young for so long that I now have the life expectancy of a puppy. So I don’t expect to see personal AI or the intention economy prove out in my lifetime. But I am sure both are worth working toward, so that’s what I do. And I advise anyone wishing to make the world better to look for their best work to manifest somewhere beyond their own life’s horizons.

So, two other Matts at Cloudflare announced EmDash — the spiritual successor to WordPress that solves plugin security.

(Is it nominative determinism or a simulation glitch that everyone trying to terraform the web has some variation of “Matthew” in their name? I was in a call set up by Matthew Prince, talking to Matt Taylor and Matt Kane, with my right hand there, Matías.)

First, I’m going to tell you why this isn’t spiritually tied to WordPress at all, then why they haven’t solved plugin security, and finally offer some suggestions.

The Spirit of WordPress

WordPress exists to democratize publishing. That means we put it everywhere. You can run WordPress on a Raspberry Pi, on your phone, on your desktop, on a random web host in Indonesia charging 99 cents a month, and you can run it scaled up on AWS or across multiple datacenters.

The same code. When you download WordPress Playground you’re running the same code that’s being attacked a thousand times a second at WhiteHouse.gov. That’s what we mean when we say democratization.

It’s all built on open source and web standards. You can run it anywhere; there’s no lock-in.

That’s why we do what we do. It’s really hard. You can come after our users, but please don’t claim to be our spiritual successor without understanding our spirit.

The Spirit of EmDash

I think EmDash was created to sell more Cloudflare services. And that’s okay! It can kinda run on Netlify or Vercel, but good stuff works best on Cloudflare. This is where I’m going to stop and say, I really like Cloudflare! I think they’re one of the top engineering organizations on the planet; they run incredible infrastructure, and their public stock is one of the few I own. And I love that this is open source! That’s more important than anything. I will never belittle a fellow open source CMS; I only hate the proprietary ones.

If you want to adopt a CMS that will work seamlessly with Cloudflare and make it hard for you to ever switch vendors, EmDash is an incredible choice.

Claimed Plugin Security

In another example of them not understanding the spirit of WordPress, the fact that plugins can change every aspect of your WordPress experience is a feature, not a bug! And their sandboxing breaks down as soon as you look at what most WordPress plugins do.

I know we get a bad rep because there are 62k plugins with wildly variable engineering quality, and more every day, and when one installed on 0.01% of our user base has a vulnerability, a bunch of websites write breathless articles that get clicks saying “122,000 WordPress Sites Vulnerable!”

That, by the way, I think we’ll be able to fix in the next 18 months with AI. The plugin security only works on Cloudflare.

Critical Feedback

As I said, we had a call with Cloudflare on March 23rd, where they asked for feedback on this thing they built but didn’t tell us the name, said it would probably launch in their developer week towards the end of April, and some top colleagues and I offered to help. I wish I could say the things I’m saying in this blog post on that call, and if they had just shared the announcement post I could have, but in the spirit of open source here’s what I would have said:

1. If they had said the name I would have asked if they had any other options because I have an amazing colleague named Emdash who is doing some of the most exciting stuff with WordPress and AI. (BTW I think our Em will have more impact on the web than this in five years.)
2. I actually think the product is very solid, there’s some excellent engineering, migration tools, it’s very fast, and the Astro integration is nice.
3. I’d be surprised if this doesn’t get tens of thousands of sites on it.
4. The UI is in the uncanny valley of being sorta-WordPress sorta-not. I know it wasn’t a weekend vibecode project, but it has some of that smell. Stuff breaks at the edges.
5. I think using TinyMCE is a regression, and they should adopt Gutenberg, which we licensed and created to be used by other CMSes.
6. The Skills are amazing, a brilliant strategy, and we need to do the same as soon as possible. I’ve been working on something similar and got some good ideas from their implementation.
7. I’m not going to say which parts, but they copied a lot of things we’re planning to kill. Build from first principles. Make it better. Skate to where the puck is going.

There’s a new CMS every other day. And that’s great! I love building CMSes and I totally get why other people do, too.

In Conclusion

Some day, there may be a spiritual successor to WordPress that is even more open. When that happens, I hope we learn from it and grow together. Until then, please keep the WordPress name out of your mouth.