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David Demaree

@demar.ee
298 followers 172 following 1.2K posts

Information artist. Owner & principal @bitsandletters.com, a design & product consultancy. Nerdy about fonts, design systems, coffee, and keyboards. Alum of Google, Adobe, Stripe, Webflow.

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David Demaree @demar.ee · 19/09/2026
If your agent says: - Nothing is redundant for the current shape. The shape carries more than the product needs. - What reaches the model, and what bounds it. - The product, and where the code diverges from it that's not your agent, that's J.R.R. Tolkien
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David Demaree @demar.ee · 19/09/2026
This morning I asked Fable to go over my website/ops monorepo with a vengeance, looking for stuff other agents (including previous Claude runs) had over engineered, overexplained, or generally left a mess. Four hours later, this was the result. This is an AI-generated diff I can get behind.
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David Demaree @demar.ee · 16/09/2026
For me, what's more surprising than the lack of results is just how bad the output was, and how stupid Astra was about approaching the problem. In each iteration, Astra just changed the sequencing of sentences/grafs/words, while keeping sentence/graf length inhumanly long.
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David Demaree @demar.ee · 16/09/2026
I asked Codex to work for ten passes, or until it had achieved a Pangram score of 100% Human. (Honestly, I'd have accepted 50%+.) The best it could do was _one_ attempt where Pangram didn't see any human-written content, but was willing to believe it was AI-assisted, not AI-generated.
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David Demaree @demar.ee · 16/09/2026
We all keep hearing about how advanced AI can break out of sandboxes, find novel workarounds for hard problems, yada yada. So I decided to try an experiment: I asked GPT-6 Astra (in ULTRA mode) to try to write a 3-paragraph blog post that could fool Pangram's AI detector.
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David Demaree @demar.ee · 10/09/2026
Love to see anti AI-slop slop that's 100% generated by AI
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David Demaree @demar.ee · 25/08/2026
Today in Apple enshittification: I saw this "Add Mac to AppleCare One" alert in the sidebar of my Mac mini's Settings app, and thought "oh no, I thought I had coverage! Let's fix it!"
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David Demaree @demar.ee · 16/08/2026
Love to see anti-slop thought leadership that's 100% slop 🫠
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David Demaree @demar.ee · 04/07/2026
Claude drugs will be enormous horse pills, but mostly placebos, because the real drugs are too dangerous for anyone but a select list of partners.
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David Demaree @demar.ee · 02/07/2026
Know what bothers me about Claude Design? It's not just the generic, template-y look, the obsession with eyebrow headings and numbered cards, the same warm grays everywhere… It's that, if you give Claude copy, you can't trust it not to rewrite stuff.
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David Demaree @demar.ee · 26/06/2026
Yes
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David Demaree @demar.ee · 21/06/2026
In a product newsletter I subscribe to, the author recently shared a link to a chat with Claude _three times_ in <500 words. He says this chat with an AI is more valuable than a Harvard MBA for understanding brand and marketing. Given space for actual insight or a real CTA, he linked to Claude.
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David Demaree @demar.ee · 19/06/2026
AI design be like
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David Demaree @demar.ee · 16/06/2026
That was Google's Gemma open-weight model. Qwen3.6 -- one of the latest Chinese-developed open source models -- answered The Question, and wasted no tokens on such frivolities as "explaining why."
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David Demaree @demar.ee · 16/06/2026
Installed a local LLM on my Framework laptop, unfortunately, it's useless garbage that can't answer The Question
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David Demaree @demar.ee · 11/06/2026
New pastime: making the most expensive and powerful AI model research its own limitations
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David Demaree @demar.ee · 08/06/2026
Lest you think Google's the only search engine peddling AI slop, here DuckDuckGo is mistaking a bug asking for WSL support in Codex for that feature existing already
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David Demaree @demar.ee · 07/06/2026
I’m sure this guy’s digital book is amazing but I’m not sure why anyone would pay $100-150 for a treatise on making software when established masters of design and engineering are out here blogging for free
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David Demaree @demar.ee · 06/06/2026
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David Demaree @demar.ee · 06/06/2026
Earlier I was trying to find a variation of the "Stop Using Math" meme and searched "Stop Using Math Meme Variations". Google replied, "Message received, loud and clear. No more 'stop doing math' formats, 'girl math' tropes, or overused calculator jokes" on a page full of the memes I asked for.
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David Demaree @demar.ee · 06/06/2026
We achieved perfection in 1995 and have been falling from grace ever since #trackballs4eva
A critique of trackpads on desktops, highlighting their inefficiency compared to trackballs, with sarcastic commentary on design choices.
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David Demaree @demar.ee · 05/06/2026
Echoing this passage from Chiang's piece, we know the moon landing happened not only because there was TV footage of Neil Armstrong bopping around in a huge silver suit, but because it was preceded by years of rocket launches and space journeys, getting progressively closer to the moon.
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David Demaree @demar.ee · 04/06/2026
Windows, my friend, if you're gonna encourage me to use AI search to fix settings, you can't just shrug when I ask for something you don't like.
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David Demaree @demar.ee · 02/06/2026
One true way to know copy was written by AI: 3+ variations on “The [thing] [synonym for ‘bottleneck’]” in one phone-sized screen of text.
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David Demaree @demar.ee · 29/05/2026
Goodhart's Law: When a measure becomes a target, it ceases to be a good measure
Tweet from Gergely Orosz:

Two months ago, inside anthropic someone suggested building a token leaderboard… the decision was made to *never* do it because several people simply thought ahead about the consequences.
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David Demaree @demar.ee · 28/05/2026
Introducing Opus 4.8! It’s marginally better at everything, except the one thing people consistently use Claude for. For that, Codex is better. BTW all tokens now cost double and there’s a 2 million token minimum luv u khxbai
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David Demaree @demar.ee · 28/05/2026
Wow, even Codex has jumped ship and joined Anthropic! 😂
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David Demaree @demar.ee · 23/05/2026
Nobody: Jellycat: PEANUTS WITH HATS! SMILING VEGETABLES! LITTLE CHEESE GUYS!
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David Demaree @demar.ee · 20/05/2026
Very relatable and resonant newsletter from Shreyas Doshi today: shreyasdoshi.substack.com/p/on-blunt-f... re “The real audience is the backchannel”, in a lot of corp cultures there’s a norm that feedback isn’t real until it’s been delivered, even if it was delivered confusingly or in bad faith.
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David Demaree @demar.ee · 19/05/2026
I caved and installed Arc. On macOS, Arc defaults to iCloud Sync, which was deprecated almost two years ago. If you switch to Arc Sync, there's a confusing-ass prompt to _also_ turn on iCloud Sync. You can't switch back to only iCloud Sync. The docs say don't use iCloud Sync. 🫠
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David Demaree @demar.ee · 19/05/2026
A few times a year I'm tempted to go back to Arc as my daily browser, but I just can't look past the fact that TBCNY has this giant ad for Dia — in full Arc-looking mode — on Arc's web page _yet still lets you download Arc_. Why not just make this redirect to Dia?!
Screenshot of the Arc browser homepage with a giant ad for Arc's successor Dia
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David Demaree @demar.ee · 17/05/2026
He’s home! Lots of meds, lots of bed rest, tons of sweetness.
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David Demaree @demar.ee · 17/05/2026
Mapped all the social networks
Hand-drawn 2x2 chart placing social network logos on axes labeled “Nazis”/“Vegans” and “Young”/“Old”.
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David Demaree @demar.ee · 16/05/2026
Pick a Bond from photos you already have on your phone:
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David Demaree @demar.ee · 14/05/2026
Look, writing a salty post title in the notes app and hoping it turns into a post is my process, okay?
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David Demaree @demar.ee · 14/05/2026
Our beloved CCO (chief canine officer), Johnny Cash, is in the hospital with a herniated disc in his spine that caused him to lose movement in his hind legs. His doctors seem optimistic, but please send all your love and good vibes his way
A French bulldog sleeping on a giant puffy bedDog looking at something only he finds interesting Middle-aged man playing video games on the couch with his equally middle-aged dog basically on his lap
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David Demaree @demar.ee · 06/05/2026
Sorry, if you say you’re not doing something for the money, my mind goes straight to Spaceballs
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David Demaree @demar.ee · 30/04/2026
“i use arch btw”
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David Demaree @demar.ee · 29/04/2026
For autism awareness month, I’d like to better understand whether online autism influencers — a phrase that I can’t believe is a real thing — think it’s helpful to tell folks that they were measured against the wrong standard while having no advice re what to do about it?
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David Demaree @demar.ee · 23/04/2026
Satellite imagery from NASA’s LANDSAT that appears to spell the word “FARTS”
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David Demaree @demar.ee · 20/04/2026
“Filmed in IMAX” is hilarious for a game so many of us played on Steam Deck or PS4 or whatever old gaming PC we had around because it looks great (and will kick your ass thoroughly) on any hardware
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David Demaree @demar.ee · 06/04/2026
Sometimes I’m in a photo and I’m like My god My head is HUGE. Does this explain why I’ve always felt so… different? All these years, have I always been… a FunkoPOP?
Man with large head posing with his tween daughter and French bulldogRender of a custom Funko Pop figurine styled to look like the man in the first photo
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David Demaree @demar.ee · 27/03/2026
What are you talking about? That dispensary has been open for months. You’re just imagining the paper in the windows.
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David Demaree @demar.ee · 17/03/2026
IRISH AVENGERS: Sure if we don’t have to stop Lucky from gatherin’ all the Infinity Charms, or else won’t he snap his wee fingers and pinch half the universe so
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David Demaree @demar.ee · 13/03/2026
…in _this_ economy?!
Apple iMessage conversation where one party shares a tweet about Steven Spielberg casting "8 former newsies" in West Side Story, and the other person shares a modified screenshot from The Onion with the headline "Fuck Everything, We're Doing Eight Newsies"Modified screenshot from The Onion with the headline "Fuck Everything, We're Doing Eight Newsies"
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David Demaree @demar.ee · 15/02/2026
paper.design is a new, Figma-like design tool with bleeding-edge features like "Copy as Tailwind" and "Insert weird shader effect", as well as something truly mind-blowing: It can access local fonts _without a local font server/app thingy_. Figma, take note!
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David Demaree @demar.ee · 13/02/2026
Just as a test to see how Notion's Granola-like AI transcription works on Linux, I had it record and summarize about a minute of my child playing Pokémon and yapping about it
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David Demaree @demar.ee · 13/02/2026
My new favorite kind of email: an AI notetaker was kicked out of a meeting, but was there long enough to catch 1 min of discussion about kicking out AI notetakers, then summarizes it as if it were a whole meeting.
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David Demaree @demar.ee · 31/01/2026
So much of our family’s conversation is in a hyperlocal dialect consisting of stuff Siri misheard one time, such as “creamy juice,” and now, “beef rice stoops.”
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David Demaree @demar.ee · 02/01/2026
What are y’all getting sworn in on? I’m going with the hardcover copy of T.S. Eliot’s complete poems and plays I’ve had since 11th grade
Very old, worn copy of T.S. Eliot: The Complete Poems and Plays
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