
I write about education, AI, and building a Prototyping Mindset at https://xitter.cf/t.co/SuBJlnvt00. | Husband, Dad, Prof @harveymudd, Venture Partner @praxis_hq
Substack →
Joined June 2009
- Tweets3.5K
- Following1.1K
- Followers809
- Likes9.3K
Josh Brake retweeted
I have been a fan of @ezraklein's for so many years — a master of conversation. In this conversation, we got to the heart of our current dilemma: Chatbots offer the feeling of companionship without the demand for reciprocity, the illusion of empathy while deskilling our ability to deal with one another. I loved how Ezra pushed back on where companionate AI might actually offer relief — it sparked a sharp, necessary debate about the future of human community. nytimes.com/2026/10/14/opini…
Josh Brake retweeted
I’m in @asteriskmgzn this week, on virtue ethics and alignment, and what it would mean to make an AI model virtuous
Our newest issue, Flourishing, drops today! Join us as we try to untangle big questions around meaning, community, values, and the good life.
First up: @spaniel_bashir explains how AI alignment moved from optimizing outcomes to teaching our systems how to be "good" – and whether there is a place for virtue ethics in alignment science.
asteriskmag.com/issues/16/th…
Meta's Muse is the latest in a series of consumer products designed to make agentic AI tools more consumer friendly. It's also the first where I've noticed an emphasis that we can or should "make" these tools do things for us.
Josh Brake retweeted
This is a great book, by the woman who has done more than anyone to illuminate how technology changes human relationships
Today is the publication day for Artificial Intimacy. There are so many moments in the life of a book. The day you finished the proposal. The day you settled on the right outline. The copyedit. The corrected pages. But there is nothing like the day that you see your book in a bookstore. All of those other landmarks fall away. In winter 1978, I stood outside Harvard Book Store, nose pressed to the window, and watched a young woman take Psychoanalytic Politics off the shelf. She looked at it and put it back. But I was content. My book, my first book, was in the hands of strangers. And now, these feelings rush back: Artificial Intimacy is in the world, and I feel humbled. hachettebookgroup.com/titles…
Josh Brake retweeted
Here I argue that the original sin of generative AI and its chatbots is using the first person, and that this is most harmful to young developing minds. It’s key to my argument in Artificial Intimacy. theatlantic.com/ideas/2026/0…
Josh Brake retweeted
I’ve been looking forward to today for 3 years
Today we’re announcing Foundation - Chroma’s solution to memory
Our research preview of this technology builds self-improving memory from your agent sessions. Try it out at trychroma.com/foundation
Introducing Foundation
Chroma's solution to agent memory
Nice touch from the @conductor_build crew. A sign of good taste to use the time while the agents are cranking to write some handwritten cards.
It is easy for me to imagine that the next great division of the world will be between people who wish to live as creatures and people who wish to live as if the machines were people.
OpenAI: Here's this crazy postmortem of how our unreleased model used a message board to collude with other instances to escape the sandbox we tried to confine it in.
Anthropic: Messaging between agents? Seems cool! Hold our beer.
Josh Brake retweeted
Writing is the process by which you realize that you do not understand what you are talking about
Josh Brake retweeted
Someone asked me recently why I’ve become interested in aesthetics after having spent most of my life more interested in STEM-adjacent topics. I hadn’t really considered the question consciously before, but I’m certainly thinking about aesthetics more than I used to. I think it’s a confluence of things:
• Many things today are ugly and far uglier than they used to be or need to be. Once you see this, it’s kinda hard to stop perceiving it. (Early twentieth century phone boxes versus modern phone boxes; old water fountains versus new water fountains; etc.) As someone with a naively meliorist assumption that most things should be getting better rather than worse, it’s all a bit perplexing: why did we stop doing things nicely? Is it a choice? Was there a malevolent spell cast upon us? This vein led me to think more about modernism and why much of art became more intentionally "challenging", grotesque, opposed to prettiness, rebarbative, dissonant, etc. Can or should anything be done about this? Is this just how things ought to be?
• Relatedly, much of modernism involved a kind of explicit repudiation of cultural continuity and represented a schism with prior practices. This is maybe most evident in American architecture, where the International Style exhibition in 1932 initiated the displacement of a rich tapestry of prior styles. This cultural break seems important and interesting to me, and I suspect that the rejection had important consequences outside of the aesthetic domain. Samuel Hughes has been exploring this question in his recent writing at @WorksInProgMag; @RuxandraTeslo is also pulling on this thread. Elaine Scarry wrote about how beauty inspires creation. If so, the inverse may also be true: ugliness inhibits it.
• It’s clearly the case that changes in the aesthetic domain can at least inspire progress in other places. Petrarch helped set some of the preconditions for the Renaissance which in turn fostered the scientific revolution and Enlightenment. Things like World Fairs (the 1851 Fair at the Crystal Palace recorded 6 million admissions when the population was 21 million) reflect the popular interdependency that used to exist between aesthetics and material development.
• @tedgioia and others have written about stuck culture and how so many domains seem to have ceased to straightforwardly advance in the way that they did up until the nineties or thereabouts. This is obviously peculiar and interesting. What changed, and what does it mean? Is it about the internet and fragmentation? Is it about a loss of supply? Is it just about having reached the zenith of various mediums?
• I’m generally interested in markets and the dynamics of creation. In aesthetics broadly, I find the reflexivity between supply- and demand-side factors to be very thought-provoking. There’s a natural desire to view satisfaction of individual preferences as the yardstick to measure market success, but things get interesting and even a bit unsettling when we start to think about how the supply might start to shape the demand. I often think about this in the context of food. Why is food so much worse in Germany than many of its neighbors? Germany certainly doesn’t have less material ability to produce good food; indeed, Germany is richer than the countries around it. There’s probably something about German food supply chains that is impoverished relative to France and Italy, but the Germans themselves don’t seem too upset about it. It just seems that the Germans are stuck in an objectively worse market equilibrium than their neighbors: the food is bad and they’ve gotten used to it. The obvious question then is where else these kinds of reflexive patterns apply, and where else we’re stuck in some objectively inferior equilibrium, even if preferences are in some superficial sense being sated.
• While this is an extremely banal and obvious point, I hadn’t until recently thought much about or internalized how much one can study reasonably objective things ("the status of women in society", say) through artwork. (Thanks to @_alice_evans for opening my eyes here.) In this vein, I’m pretty excited about the possibilities over the coming years in computational art analysis. I want something that’s conceptually similar to Google Ngram timelines but for the visual arts.
• We've always tried to do things well at Stripe. I've come to see that attempting to do them beautifully is often a helpful way to break out of standard practices and to do something with greater novelty and in a way that might have other benefits besides. (Also, excellent people want to do great work because it is intrinsically satisfying. Explicitly allowing aesthetic considerations to carry weight avoids having to justify every assessment with some kind of torturous empiricism.)
• In his Nobel Lecture, Solzhenitsyn said that, among the Platonic virtues of goodness, truth, and beauty, that beauty is special, for it possesses a unique kind of irrefutability. He notes that arguments, writing, and philosophical systems can all be predicated on misapprehensions, but that “a true work of art carries its verification within itself.” He proceeds to observe that when goodness and truth are threatened, the “ever surprising shoots of beauty will still force their way through.” There is a lot of specious and motivated reasoning in the world today and plenty of questionable value systems. I don’t think that beauty directly reflects any definitive trait, but I’m intrigued by the idea that it can be a marker of deeper metaphysical coherence.
Can confirm, this stack rocks.
Pro tip, use this as a startup script to jump right into your tmux session when you launch it from Termius.
tmux new-session -A -s main
Termius + Tailscale + tmux
You don't need your laptop to build with Claude Code, Codex, or any other AI coding agent:
→ Run your agent inside tmux to keep the session alive
→ Use @Tailscale for secure access to your laptop
→ Connect with Termius over SSH from iPhone, iPad, or Android
Start coding at your desk. Continue on the go.
Josh Brake retweeted
A huge amount of the Anti-AI code sentiment massively overestimates the quality of human code outside of a very small set of open source and high quality company codebases. Human Slop is everywhere and can trivially be improved on by any opus level model.
Ya think Nike wishes they made some more of those USMNT jerseys right about now? Sold out all over the place.
This is boss. Got Conductor hooked up to my local AI compute now through OpenCode, running inference on my @NVIDIAAI DGX Spark.
Where has @Tailscale been all my life. My word. So simple and so useful.
Really enjoy Readeck, but like to read on my Kindle Scribe instead of the app and my phone/tablet. But the full featured website is not a good experience on the Kindle web browser. So naturally, built myself a custom web interface for the Kindle today, from my phone, with Claude Code in approximately 3 prompts. Just crazy.
Just can’t quite shake the intuition that there are real limits to motivation via machine. My working thesis is that lasting, authentic motivation requires human relationship, in one form or another. Feels like this is a really central thing to get straight as we think about integrating AI into education.
As one example, I’m thinking about how activity rings on my Apple Watch, Strava streaks, or other sorts of machine-generated nudges or reminders are way less effective for motivating you than a running or walking buddy who expects you to show up at a specific time every week.
To the degree that the nudges work, it’s because they are actually just reflecting your own expectations back to you. This is why the technology can help you to build a habit if you bring the motivation to the table, but isn’t much good otherwise. Same paradigm applies in education, where a motivated learner can use AI to learn but it will be net negative for a student who doesn’t already come motivated to learn. The technology can help to facilitate or amplify motivation, but it can never create it.
That said, I’m very curious to hear how this lands with you. What are the best arguments/narratives for and against this thesis?
Josh Brake retweeted
70k words, 600+ illustrations, and 1000s of hours (so far).
Making Software is now available in early access.
makingsoftware.com/early-acc…


















