I confess I am very bad at newsletters. My bad habit is to always try to write something very big and important, like The Grand Unified Theory of AI, or else to write something really baldly transactional, like Please Hire Me To Build An AI Content Operations System in Sanity.
But oftentimes the best newsletters are just someone taking a moment to say hey and share some links.
Since the last one of these newsletters — last October 😅 — I've posted several new articles to the B&L blog; here's a roundup of the latest stuff.
Train your AI like a dog was adapted from a talk I gave at Decoupled Days last August in NYC. Like anything AI-related, it was written about the latest goings-on at the time, and a lot has happened since then. But I stand by the basic thesis and tips in the post.
Because AI agents talk like people, it's tempting to think they're capable of thinking or acting like people. This leads users to give overly broad or open-ended prompts—the kind we'd give a fellow human—only to get frustrated when the AI returns random, broken answers.
If you think of AIs as trained animals rather than peers, it reframes your expectations and helps you keep requests smaller and more focused. I work with ChatGPT much the same way I interact with my French bulldog, Johnny Cash—simple commands, patience, repetition, breaks, and lots of treats. (Okay, the treats are just for the dog.)
In What does it mean for websites to scale?, I unpack a word I've found myself using a lot to describe differences between basic websites and more robust ones, which I think a lot of folks (including developers) think they understand, but covers a lot more surface area than you might expect. In the post, I get into four kinds of scaling: Reach, Performance, Collaboration, and Change.
…if I've learned anything from working in some of the world's biggest tech companies, it's that 90% of scaling is handling those messy middle states. There are almost no websites or web apps operating at such a big scale that there isn't a team somewhere constantly watching and planning so that things keep running smoothly from one day to the next. And if this is true for Google or Stripe, it's even more true for startups and even small enterprises.
On designing with AI artifacts was inspired by day recently when I used the Claude Design beta to gin up a landing page around the same time that a client sent me some Claude-generated wireframes for their website, and I noticed some… similarities.
Large language models find common patterns in their training data, then generate text, visuals, etc that follow the pattern that seems most likely based on your prompt. Put another way, AI’s job is to find a common template that most closely matches what you’re looking for, then fill in blanks. That’s not a secret — it’s how they’re designed to work, the whole point of them.
This year marks the tenth anniversary of my weird little book about Git, Git for Humans, so I wrote a post reflecting on the anniversary and sharing the few things that have changed big time in the Git world since 2016, and what's remained stubbornly the same.
The biggest sea change in software development is, of course, the rise of agentic AI coding tools like Claude Code, Cursor, and Codex. (Note to self: found an AI startup starting with the letters ‘A’ or ‘B’.) While you don’t have to use Git to use these tools with codebases on your own computer, you really, really should — Git branches and commits are the best insurance policy you have against an AI agent breaking things, as you can always roll back to an older version, or use a diff tool (including the one built into GitHub Pull Requests) to see exactly what the AI changed.
Finally, Static vs. dynamic websites, explained is intended as something I can send to clients, prospects, or anyone struggling to grok the differences between the kinds of web pages one makes in Webflow or Squarespace, and the kinds of pages that are generated by more robust CMSes based on well-structured content and data.
The logic of static content is pages; the logic of dynamic content is types of information. When you have dozens of pages built from the same handful of patterns — locations, providers, case studies, events, resources — your site is probably a good candidate for dynamic content. Especially if those dozens could someday become hundreds.
Next up, I have posts in the old drafts folder about hidden costs of design and deployment, when it's time to graduate from a page-builder to a decoupled CMS, and dev tips and tricks for using variable fonts in Tailwind.
I've also been working with the legendary Joanne McNeil on some interviews with longtime web designers about the current state of the web; watch out for these later in the summer.
Also coming very soon: the next major refresh of bitsandletters.com. The current website has a lot of swagger and inventive design. Unfortunately, it's also not super well written (says the guy who wrote it), and I've reviewed hours of session recordings in PostHog and concluded it's also not particularly usable. The next version puts content and case studies front and center, with clearer navigation, a lighter color palette, and 100% human-crafted copy.
I didn't blur the beta site URL; feel free to check it out if you're interested!
Finally, on a sad-but-hopeful personal note: our Chief Canine Officer, Johnny Cash — shown here in a lightly AI-edited image staring at my laptop — is currently in the hospital recovering from spinal surgery.
He's a Frenchie (obviously), and like many Frenchies he's always been at high risk for back problems, including intervertebral disc disease (IVDD) where one or more spinal discs become inflamed and push on the nerves in the spinal cord. A few years back Johnny had a big, initial IVDD flare-up that was treatable with steroids, pain meds, and weeks of crate rest. This time we and his doctors thought something similar was happening. But Johnny suddenly lost the ability to use his hind legs — though he impressively tried to get around with just his front ones — so we rushed him to Red Bank Veterinary Hospital's ER and neurology department.
As of this writing, the excellent news is that Johnny went into surgery earlier today to remove his herniated disc, it was a success, and he's expected to make a full recovery. ❤️🐶❤️
Bits&Letters has availability coming up in June-July for new web projects. Along with the new site I'm trying out a new tiered pricing structure that's a lot clearer and more accessible to seed-stage startups with big ambitions, clear goals, but not a huge budget.
The Sprint tier starts at $25,000 for a 4-6 week engagement where we'll tailor one of our in-house project starters for WordPress or Astro + Sanity to your content and brand — a great foundation for a full design system and content architecture, or a good next step to move to from a page-builder or design-first platform that's started to get in your way.
I piloted versions of the Sprint package and process with two recent Astro clients with great success, and I'm excited to expand this to help more startups improve their design and content ops with better tools at a price point that's not too scary.
If you're in the market for a hyper-experienced, super opinionated website consultancy — or if you know someone who is — please reach out to david@bitsandletters.com.
And with that, thanks so much for reading. I'll try to be a little less of a stranger and for the next newsletter to come out less than 7 months from now. 😅
