Long argument short, Times New Roman isn’t bad, but it isn’t good. It is the median choice. But most of the circuit courts use it: the Third, Fourth, Sixth, Eighth, Ninth, Tenth, and Eleventh. It could be worse: the First circuit not only uses Courier New (the worst version of Courier, so of course it’s the one Microsoft shipped with Windows), but fully justifies their text — contrary to the nature of a monospaced font. (The Fourth circuit only recently switched from Courier New to Times New Roman — an upgrade, to be sure, but a disappointingly mediocre one.) It could be better: the Second and Seventh use Palatino. (Note how much better that Seventh Circuit decision looks than the Second’s, with its wider margins creating a narrower column of text.)

But it can be much better. The Fifth Circuit was long typographically superior to its peers, using Century Schoolbook — a highly legible font with great tradition and the right vibe. But in 2020, the Fifth Circuit upgraded, switching to Equity, Matthew Butterick’s excellent type family (which, of course, is used throughout Butterick’s own web book, Typography for Lawyers). Here’s a before and after tweet noting the change. The results are typographically sublime (including improved margins).

The gold standard is the U.S. Supreme Court, which uses Century Schoolbook. Yes, I just praised the Fifth Circuit’s change from Century Schoolbook to Equity as an upgrade, but tradition and consistency have their place. The Supreme Court’s typographic style has been stunningly consistent for — no pun intended — well over a century. (If only that were true of their recent decisions. Rimshot.) Here is last month’s Louisiana v. Callais decision — the gerrymandering / redistricting case. Here is 1954’s Brown v. Board of Education. I’d give the nod to the older one, which made better use of proper small caps, but the overall consistency is obvious.

Here is the 2026 edition of the Rules of the Supreme Court. Not only does the Court use Century Schoolbook for its own decisions, it requires submissions to the Court to use the same (p. 44):

The text of every booklet-format document, including any appendix thereto, shall be typeset in a Century family (e. g., Century Expanded, New Century Schoolbook, or Century Schoolbook) 12-point type with 2-point or more leading between lines. Quotations in excess of 50 words shall be indented. The typeface of footnotes shall be 10-point type with 2-point or more leading between lines. The text of the document must appear on both sides of the page.

Every booklet-format document shall be produced on paper that is opaque, unglazed, and not less than 60 pounds in weight, and shall have margins of at least three-fourths of an inch on all sides. The text field, including footnotes, may not exceed 4⅛ by 7⅛ inches.

Why the extra one-eighths of an inch instead of just 4 × 7? I don’t know. But 4⅛ × 7⅛ is exactly the size of the text field in the court’s own decisions.

Now compare the current 2026 rulebook to this edition printed in 1910 (with rules adopted in 1884). The consistency is striking — but, once again, the older version makes better use of small caps and just has a bit more vim and vigor to it. Just look at page 44, for example. It’s perfect. The current Court’s document formatters should aspire only to more closely ape the confidence and sturdiness of this older one. A century from now, U.S. Supreme Court decisions should look as similar to today’s as today’s do to those from a century ago.

The various circuit courts using lesser typefaces, looser margins, and lazier formatting should follow the Fifth’s lead and get their shit together. Tuck your shirt in, comb your hair, straighten your tie, and pop a mint in your mouth. If you’re a United States federal court, your typographic style should reflect that.

Back in 2020, Butterick took a well-deserved victory lap when the Fifth Circuit adopted Equity.¹ He quoted Fifth Circuit Judge Don Willett, a typography fan who spearheaded the restyling project, on its rationale. Willett wrote:

[Why] did the circuit devote finite judicial energy to swapping typefaces and widening margins? Simple answer: Our job is not just to present clear opinions, but to present our opinions clearly. Getting the law right is, of course, our tip-top priority. Nothing matters more. ... But good enough is never good enough. Our work is consequential, impacting the lives and livelihoods of real people walloped by real problems in the real world. The stakes are high, and we must present our best opinion, not merely a passable one. And that presentation begins before the first word is ever read.

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Much more recently, I quizzed Ternus and global marketing head Greg Joswiak about Apple’s future, specifically its plans to get ahead of the AI transformation. Ternus acknowledged that AI is “an immense kind of inflection point,” but couched it as one of many leaps that Apple has navigated. Each hit product — the Apple II, the Mac, iTunes, the iPod, the iPhone, iPad — piggybacked on a previous product. “We never think about shipping a technology,” he said. “We want to ship amazing products, features, and experiences, and we don’t want our customers to think about what [underlying] technology makes it possible. That’s the way we think about AI.”

That’s fine, but I look back to the mid-2000s when everybody was waiting for Apple to come out with a phone. When Jobs finally delivered in January 2007, the product defined the mobile era. It’s a big ask for Ternus to do something similar for the AI age — but it’s an opportunity that must be seized. AI threatens to disrupt the entire iPhone ecosystem. By the end of this decade, it’s unlikely that people will swipe on their phones to tap on Uber or Lyft. They will just tell their always-on AI agent to get them home. Or that agent will have already figured out where they need to go, and the car will be waiting without the friction of a request. “There’s an app for that,” may be replaced by “Let the agent do that.”

I’m a huge longtime Steven Levy fan, but this is nonsense. It’s hard to read this and not worry that he too has lost his mind to the AI snake-oil hypesters. What Ternus told him is exactly right. The Apple way is never to ship a technology. The iPod wasn’t about MP3 files. It wasn’t about 1.8-inch hard drives. It was about music. The iPhone did define the mobile era (which we’re still very much in), but Apple doesn’t need to capitalize on every single market the mobile era opened up. Social media is a defining component of the mobile era. It comprises the entirety of Meta’s value and a sizable slice of Google’s (via YouTube). Apple doesn’t have a social network business. It’s fine — because the way people consume and create social media is using their phones.

Does AI “threaten to disrupt the entire iPhone ecosystem”? It’s possible, but it doesn’t seem nearly as likely to me as Levy asserts. Changing the iPhone ecosystem? Sure — that’s already true. Obviating the iPhone ecosystem? I don’t see it. Levy’s argument reminds me of the hype around “the cloud” when that first became a term. It’s so meaningless when used broadly (e.g. “Everything will soon be in the cloud”) that it could mean anything. It’s step #2 in the gnomes-stealing-underpants master plan.

The idea that AI agents “will have already figured out where [we] need to go, and the car will be waiting without the friction of a request” strikes me as pure fever dream high-on-the-hype fantasy. I’m just going to step outside a restaurant when I’m done eating a meal and a ride-share is going to be there, waiting for me, without my having hailed it? Every time? And I’m going to find this pleasing, not creepy? And ride-share drivers are going to respond to all these requests, because the requests will never be wrong? And this is going to happen, somehow, without my carrying a phone with me? And this is going to happen in the next four years? I don’t think I’d want this even if it were plausible, but it doesn’t sound plausible.

Actual products have to be real. Actual experiences have to rely on actual products. How exactly in Levy’s end-of-this-decade scenario will we tell our “always-on AI agent” to get us home? What microphone is listening to the command? What speaker is telling us the request was understood and acted upon? What screen do we look at to see how far away the hailed car is? I’d bet a pretty large sum of money that in 2030, when someone hails a ride-share vehicle to take them home, the most common product they’ll use to do that will be their phone. Whether they’re doing it via a verbal command issued to an “always-on AI agent” or good old tapping and swiping, it’ll be a phone.

If you think that people will buy smaller devices to replace their phones, and use those to talk to “always-on AI agents” instead, you have to answer some questions. What company is the best in the world at making smaller-than-phone personal computing devices? What device will people use as their camera? What device will people use as their screen, for watching videos, playing games, texting, and (one hopes) reading? My answers to those three questions: Apple, phone, phone. Why would smaller devices — you know, like watches, earbuds, and, say, glasses — work independently rather than pair with the phone that you’re almost certainly still going to be carrying with you?

Only a fool would argue that Apple can stand on the sidelines and ignore AI. It’s very different from, say, social media that way. Social media doesn’t pervade everything in technology. You can ignore social media as a user. (And you’re probably more productive, and happier, if you do.) A company can eschew social media as a business. AI, on the other hand, is pervasive. It can’t be ignored. But it’s just technology.

Wireless networking is pervasive too. But Apple doesn’t have “a killer wireless networking product”.¹ Wireless networking simply pervades everything Apple makes. I’m hard pressed to think of a single product Apple makes that doesn’t use some combination of Wi-Fi, cellular, Bluetooth, and proprietary wireless protocols. There was a time, not too long ago, when Apple didn’t make a single product with wireless connectivity. Now it’s pervasive in all their devices. That’s more what AI is going to be like. There’s not going to be one “killer AI device”. Everything is going to be an AI device, to some extent, just like how everything today is a wireless connectivity device, to some extent.

Postscript: “Existing Stakeholders Have a Say in the Future”.

Notepad++ is a longstanding open source (GPL) Windows text editor by Don Ho, which debuted back in 2003. Just adding “++” to the name might be misleading. The name implies that it’s like Microsoft’s Notepad plus a little more. But Notepad++ is in fact a wholly independent programming text editor, with a rich plugin library. It doesn’t resemble Microsoft’s Notepad much at all anymore. It’s over two decades old but remains quite popular. To some extent Notepad++ is sorta kinda the Windows peer to BBEdit.

Nextpad++ is something new, from Andrey Letov. It’s a Mac port of the Notepad++ GPL code. It launched a few weeks ago under the name “Notepad++ for Mac”, but Letov had no right or permission to the name. That dispute has been settled, and Letov has renamed this project Nextpad++. The website’s About page has entire sections for “How Nextpad++ for Mac Was Built” and “Technology Stack”, and neither of those mentions AI, but this thing has to have been built using AI vibe-coding agents. That same About page also says the project only started on March 10, and the 1.0 version (under the defunct “Notepad++ for Mac” name) shipped just a few weeks after that. Something of the scope of this port couldn’t happen at that pace without AI. Update: On the Author page, not the About page, it states, “multi-agent AI development workflows are what make a one-person project at this scale practical.” Possible, sure, but I wouldn’t call this practical.

Nextpad++ feels like a fever dream. Like what Mac apps would be if the Nazis had won WWII. Look, there are all sorts of foreign apps on the Mac. Electron apps. Apps ported with Wine. Web apps running in browser tabs or saved to the Dock. The curious new generation of lean-and-mean apps that are, in a technical sense, “native”, but are decidedly not Mac-assed apps, like Zed and Tolaria. All those types of apps feel alien on MacOS. Like different species. They are apps for the Mac but aren’t Mac apps. The Mac, however, is welcoming to them all, like the Mos Eisley cantina. We do serve their kind here. Nextpad++ isn’t like that. It doesn’t feel like an alien. It feels like Vincent D’Onofrio’s alien-bug-in-human-skin character from Men in Black.

Letov’s website describes Nextpad++ as “A real Mac app, not a Wine wrapper: Objective-C++ on top of Scintilla and Cocoa, shipped as a Universal Binary for Apple Silicon (M1–M5) and Intel Macs.” Ostensibly that’s a good thing. The download is only 14 MB. But Nextpad++ looks and feels like something that should not exist. The promotional screenshots on the app’s own website show it with 50 inscrutable toolbar buttons. It closes document tabs on mousedown, not mouseup. Its default font is 10-point Courier New. This is a real dialog box. It offers four settings for font antialiasing — “Default”, “None”, “Antialiased”, and “LCD Optimized” — but the default is not “Default”. No human being would port a complex Windows app like Notepad++ to the Mac like this.

I’m not anti-AI. I’m very much intrigued by the whole incipient vibe-coding phenomenon. But this app feels unholy.

My muse for the session was this quote from Walt Disney: “We don’t make movies to make money; we make money to make more movies.” To me, that’s it. That’s the thing.

Merlin and I were talking about independent writers and podcasters, because that’s what we were (and remain), but the concept applies just as perfectly to independent developers. This came to my mind after reading (and linking to) David Smith’s description of the new Pedometer++ today. Not just what it does, but why he spent six years making it. That’s the sort of productive obsession that fascinates me.

Ice water is always refreshing, but it tastes better when you’re on a road trip to hell. It feels like the world of software is bifurcating quality-wise. This whole thing about Adobe’s new craptacular “modern” UI language (a.k.a. “Spectrum”) exemplifies one side of that bifurcation — the bad-and-getting-worse side. Software that is the product not just of an ignorance of long-established principles of interaction design, but of a willful disdain for those principles. What Adobe is now shipping is just inexplicably bad UI, ignoring literally decades of great work and long-mastered concepts — a lot of which work was pioneered by Adobe itself!

The whole thing with MacOS 26 Tahoe is similar. To be clear, the UI crimes in Tahoe are deeply worrisome, but they are nowhere near as severe as those in Adobe’s Spectrum. But the problems with Tahoe are steps down the same fork in the road that Adobe took years ago. Spectrum is where Tahoe suggests that MacOS was headed under Alan Dye’s leadership: cross-platform sameness for the sake of sameness, with a complete disregard for longstanding platform nuances and idioms. In Spectrum’s case those platforms are MacOS and Windows and the web. In Tahoe’s case it’s MacOS and iOS.¹

The other side of the software fork is not deserted. It’s just populated, more than ever, by the products of small independent developers who obsess, first and foremost, over quality and artistic vision. Remarkable new software gems exhibiting spectacular UI design appear all the time. They’re just not coming from the biggest companies, the ones whose apps, alas, dominate not just our desktops and pockets but our entire culture today.²

There’s always been software with poorly designed user interfaces. Much of it has been successful financially, sometimes spectacularly so. I’d argue, in all seriousness, that that’s the story of Microsoft in a nutshell. What’s new today is poorly designed software from developers from whom we expect better. In the old days there were people who would argue that prioritizing good user interface design was a waste of time — like spending hours decorating cupcakes destined for kindergarteners who are simply going to mash them into their mouths. (Again: cf. Microsoft’s undeniable market success.) What’s new today is people holding up objectively bad interaction design and proclaiming it to be good, and the product of teams that purportedly prioritize “design”, when it’s clear they have no idea what they’re talking about. It’s one thing to make something poorly designed and shrug on the grounds that it doesn’t matter. It’s another thing to make something poorly designed and hold it up as good design.

We are justified to expect nothing short of insane greatness from Apple, and solidly good design from Adobe. In principle, all software ought to have well-designed user interfaces. That’s never going to be the case. But software for designers — Adobe’s raison d’être — absolutely demands to be well-designed itself, like how a book on writing must itself be well-written.

Perhaps I was wrong, though, to describe Adobe’s new UI as inexplicable. It’s just indefensible. The explanation for so much software going so rotten from a UI-design perspective is, the more I think about it, related to Nilay Patel’s “Software Brain” theory, which I’ve commented on both directly and indirectly. Here’s Patel’s definition of “software brain”:

The simplest definition I’ve come up with is that it’s when you see the whole world as a series of databases that can be controlled with the structured language of software code. Like I said, this is a powerful way of seeing things. So much of our lives run through databases, and a bunch of important companies have been built around maintaining those databases and providing access to them.

Zillow is a database of houses. Uber is a database of cars and riders. YouTube is a database of videos. The Verge’s website is a database of stories. You can go on and on and on. Once you start seeing the world as a bunch of databases, it’s a small jump to feeling like you can control everything if you can just control the data.

But that doesn’t always work.

You might think it counterintuitive that a movement obsessed with software would be spearheading a severe decline in the design quality of software, but in Patel’s definition, there’s no concept of software as art, as a practice, as a craft. Software brain is purely an obsession with software as a medium in and of itself. A means with no consideration for the end.

Framed in Walt Disney’s adage, software brain makes software only to make more money. The idea of making money in order to make more software — to afford the time and talent to craft it — does not compute. Framed in the metaphor that Steve Jobs used to close his introduction of the original iPad, and returned to again to close his final keynote at WWDC 2011, software brain is nowhere near the intersection of technology and the liberal arts. Software brain is so far down Technology Street that it’s no longer in the same zip code as Liberal Arts Avenue. Another way, perhaps, to define software brain is that it’s the utter rejection of Jobs’s maxim that “technology is not enough”. With software brain, technology is all there is.

Sam Altman was the president of Y Combinator for several years, and left to become the full-time CEO of OpenAI. The New Yorker quotes Y Combinator co-founder Paul Graham multiple times, in the context of Altman’s trustworthiness. (Some of those quotes are firsthand, others secondhand.) Graham’s role in the story — particularly his public remarks after publication — comprised an entire section in my own take on the New Yorker piece, wherein I concluded:

I would characterize Graham’s tweets re: Altman this week as emphasizing only that Altman was not fired or otherwise forced from YC, and could have stayed as CEO at YC if he’d found another CEO for OpenAI. But for all of Graham’s elucidating engagement on Twitter/X this week regarding this story, he’s dancing around the core question of the Farrow/Marantz investigation, the one right there in The New Yorker’s headline: Can Sam Altman be trusted? “We didn’t ‘remove’ Sam Altman” and “We didn’t want him to leave” are not the same things as saying, say, “I think Sam Altman is honest and trustworthy” or “Sam Altman is a man of integrity”. If Paul Graham were to say such things, clearly and unambiguously, those remarks would carry tremendous weight. But — rather conspicuously to my eyes — he’s not saying such things.

The thing that stuck in my craw is this: Does Y Combinator own a stake in OpenAI? And if they do, given OpenAI’s sky-high valuation, isn’t that stake worth billions of dollars?

OpenAI was seeded by an offshoot of Y Combinator called YC Research in 2016 — when Altman was running YC. In December 2023, the well-known AI expert (and AI-hype skeptic) Gary Marcus wrote the following, in a piece on Altman’s trustworthiness in the wake of the OpenAI board saga that saw Altman fired, re-hired, and the board purged in the course of a tumultuous week:

After poking around, I found out that “I have no equity in OpenAI” was only half the truth; while Altman to my knowledge holds no direct equity in OpenAI, he does have an indirect stake in OpenAI, and that fact should have been disclosed.

In particular, he owns a stake of Y Combinator, and Y Combinator owns a stake in OpenAI. It may well be worth tens of millions of dollars; even for Altman, that’s not trivial. Since he was President of Y Combinator, and CEO of OpenAI; he surely was aware of this.

So it’s well known that Y Combinator owns some stake in OpenAI. But how big is that stake? This seems like devilishly difficult information to obtain. I asked around and a little birdie who knows several OpenAI investors came back with an answer: Y Combinator owns about 0.6 percent of OpenAI. At OpenAI’s current $852 billion valuation, that’s worth over $5 billion.

Graham and his wife Jessica Livingston are two of Y Combinator’s four founding partners. The fact that Paul Graham personally has billions of dollars at stake with OpenAI doesn’t mean that his public opinion on Sam Altman’s trustworthiness and leadership is invalid. But it certainly seems like the sort of thing that ought to be disclosed when quoting Graham as an Altman character reference. A billion dollars here, a billion there — that adds up to the sort of money that might skew a fellow’s opinion.