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May 4, 2026

Firstly, happy Star Wars Day to those who celebrate.

Secondly, a bigger update: we have a kid.

If this is the first you’re hearing about it (and we know each other personally) we likely e-mailed you; but, as we bothered to individually mailmerge personalized messages along with the basics (photos, weight, height, name, etc.) your note may have been classified as spam. Oops.

Also, if you read my last update, it should go without saying that kid content will not be on bigco social media nor the public internet. So you wouldn’t have found out that way, either.

So we have a kid.

You will (read: won’t) be surprised to learn that the kid has their own website on a private, hand-rolled technology stack Building one’s own CMS (Content Management System) is a rite of passage for technologists, up there with building one’s own TODO list, notetaking app, and (increasingly) one’s own LLM orchestrator. But this CMS (codename: Cassette CMS) is pretty good—good enough that I’m thinking of making it FOSS. It’s a combination substack, exposure, asset library and mobile authoring app that you can run on commodity cloud hardware for a few $/mo.

It’s easy-to-use and built to prevent accidental content leakage.

It also fits into my thesis about how this AI thing plays out given the growing distrust in bigtech and their proprietary algorithms, and the increasing value in private online communities.

(More on this soon.) built by yours truly (in collaboration with LLMs).

Write for access.

The Usuals

Upcoming Travel

(While updating this section, I realized I have not left New York since August 2025, which is probably the longest stretch of time I’ve been in one place since I was enrolled in College. Whoa.)

  • Berkshires (Massachusetts)
  • UK (England, Scotland)

Vocational Notes

In what was meant to be a relaxed parental leave, sitting out the most transformative months industry has seen since the invention of industry itself felt—to put it mildly—fiscally irresponsible.

Simultaneously caring for a newborn while learning how to tame an alien, errant form of intelligence? Not on our bingo card, but we are making it work.

Without ego, I’m getting pretty good at both. The biggest challenge to me (and other AI-pilled folk) has been in what’s called “One More Turn”, referring to the addictive nature of Sid Meier’s video game series Civilization in which you manage and command an ever-growing dependency graph of resources in the pursuit of world domination. In the kid’s early days, when sleep was more abstraction than an old reliable, there was no end and no beginning to any day. Writing and reading in LLM context windows is what I did when I wasn’t sleeping, solo-caring for our child, or having quality family time.

LLMs work at incredible speeds For a wild demo, check out Jimmy and ask it to write some code for you. It is still live as of writing, and “printed” the open-source Llama 3.1 8B LLM model direct to silicon and produces 15,000 tokens/second, which is about 1,000 times faster than your laptop computer. Whew. but their outputs don’t necessarily constitute good software. Most interesting to me is that thousands upon thousands of engineers, thinkers, and tinkerers are all trying to figure out how to best work with these LLMs. Happily, the industry is converging on the same best practices that were true for the preceding decades. And not because these LLMs were trained on computer code designed for human authorship, but because the design patterns work.

Software is part creative pursuit, part factory. LLMs amplify skill… or lack thereof. Or that a product, process, or workflow translated into software is worth anything at all.

Software is a liability as much as it is an asset. Good software is good in that it can run consistently and predictably without failure, and—more importantly—in that it can be changed quickly.

This is what I’ve been doing with nearly all non-family awake time: learning how LLMs can build high-quality, highly-malleable, highly-secure software, quickly and reliably.

“But isn’t software dead?”

Short answer: no.

I continue to invest here because the great promise of the internet has yet to be realized, and the speed and capabilities that LLMs unlock for the competent practitioner put so many “that will never be economically viable” projects squarely into “fuck it”-levels for viable investment.

In whatever working hours I can find, I’m making basic tools to replace commercial software that no longer meet my feature needs or privacy requirements. While I’m building these for myself, I plan to release some for public consumption, either freely or commercially available. Likely both.

We’ll see.

Of note, I have recently “capped” my working hours to 40 per week, with no LLM-driven coding allowed after 7pm. (See “One More Turn” from above.) Weekends are for friends, family, and (non-tech) projects.

Lastly, I have been placing some small bets on some small(er) companies and startups as the opportunities present themselves. (n.b., I am not a professional investor.)

Avocational Notes

Having recently gotten out of baby (and vibecoding) jail, I have started to wade back into a gym routine. The time off was not inconsequential and I’m hopeful “it” will come back quickly.

Otherwise, between work, newkid, and seeing friends, there hasn’t been much available bandwidth other than what can be accomplished on a tiny pocket screen.

Balance is important.

Content Consumption (Abbreviated)

Television/Movies

  • Silicon Valley - Believe it or not, never watched beyond the first two seasons despite knowing the memes. (e.g., hot dog / not hot dog)
  • (Omitted: slate of should-only-watch-while-on-parental-leave drivel)

Books

Scant time blocks and drained willpower between trudging through LLMs’ daily Franzen-novel’s worth of generated text and hands-on kiddo care means that this section is going to look a bit different for a bit.

Children’s books

Given fierce shelf space competition at your local bookstore, you would think most kids’ books—typically made of thick “board book” stock—would be of quality. Surprisingly not true.

When I’m running bedtime, here are the titles I continually reach for and can recommend to those reading to a baby:

(This list will expand over time. Recommendations welcomed.)

Top gripes about other books include:

  1. Lazy scansion and/or rhyming schemes when attempting lyrical prose
  2. Low-contrast text on glossy-print pages (which is difficult to read by nightlight)
  3. AI-generated slop (amazing how quickly this infiltrated the market)
  4. “Coffeetable Quality”: if only the authors spent half as much time on the content as the trappings (children’s books are meant to be read many, many, many times over… not flipped through once and looked at from afar—have some pride in your craft, please!)

Non-Children’s Books

  • Mythos by Stephen Fry. “Reading” this one on audiobook, narrated by the author, as he is uniquely capable of reanimating very, very played-out stories. My 6th grade teacher famously tasked each one of his students to retell the stories of the Greek gods in a singular assignment, with no submission to be shorter than 60 pages on double-spaced 12pt font. It remains the most tedious assignment I’ve ever completed—but insanely effective. Decades later I still remembered how the pantheon came to be.
  • Enshittification by Cory Doctorow. Also via audiobook, also narrated by the author. (I linked to Wikipedia because it contains a very nice summary, but you should also read the book and donate to the EFF)
  • The Happy Sleeper by Heather Turgeon and Julie Wright. Highly recommended to me, and for good reason. Last physical paperback I’ve read in over six months.

Games

  • ARC Raiders - I have yet to try this, but it has been purchased and downloaded.
  • Dispatch - I don’t do the narrative/dialog-tree genre, but this was very well written and accessible.
  • Humanity - A nice puzzler with a good soundtrack that wasn’t too difficult to complete while forcing myself to stay up for the kiddo’s last nighttime feed. (We’re now sleeping through the night. Game changing.)
  • At any time I have a dozen Chess.com and Crossplay (NYTimes’ Scrabble knock-off) games going on. Message me directly for my usernames. (One is easier to guess than the other.)

Sundry Notes

The Formula 1 TV on Apple TV is still a bit glitchy. I remain concerned.

I’m also a fan of the new regs. Fight me.

Hat tip to nownownow.com.

• November 2, 2025 →