Software, Bicycling, Brooklyn
Fifteen years: junior engineer to VP of Engineering. I personally ship code every day. Engineering Leadership, AI, Product, Security. I studied poetry because it's elegant and packed with meaning. Then I designed software architecture for the same reasons. Now I make the second by writing the first.
Thoughts
Software always suckedIt was built for the median user, and the median user is nobody.
Every app you've used was a compromise between what you needed and what a few million other people needed. The settings screen is the fossil record of that fight. We called it good software when the compromise was tolerable. Now that a program for one person costs about as much as a long email, the compromise is optional, and I'm starting to notice how much of it I'd absorbed.
The factory is the wrong metaphorFactories make the same thing a million times. Nobody wants the same software.
A factory wins by repetition. It stamps out identical parts and the whole point is that mine matches yours. Software made with AI goes the other way: each thing is shaped for one person, one week, one problem. A better picture is a garden. You plant something small, it grows toward how you actually live, you pull up what stops being useful. The gardener's skill is in the tending, not the stamping.
Software is free againThe fun we had in 1999, before the business got big.
The first time software was free, we were teenagers with GeoCities pages and a view-source habit. Then it became an industry and the industry needed everything to be a product, and products need users, and users need onboarding. The feeling I have building with these tools is the one I had then. I can make the thing in an evening, and nobody has to agree that it's a business.
Tell your phone what you needState the need. Get the app. Throw it away when you're done.
Picture no app store. You say what you need, out loud or in a few words, and something appears in the shape the moment calls for: a list, a map, a voice that answers back, a button on your watch. It lasts as long as the need does. The hard engineering is in the layer that chooses the shape and keeps your data yours. I've started to sketch what that layer looks like.
When software gets paid forIf anyone can make it, when is it still worth buying?
For thirty years the answer was at the point of sale, for the software itself. That's ending for anything one person can describe in a paragraph. Payment moves to the moments a homemade version can't cover: when the data has to come from somewhere, when the thing must not go down, when nobody on hand knows what good looks like, and when it breaks at two in the morning and someone has to answer for it. Businesses that sold the first thing will have to find out which of those moments they actually own.
Projects
- Heyyy HealthAn LLM-powered health coach. Designed, built, launched, still maintained.
- Daily ScoopA daily newsletter, written and sent by an AI pipeline I run.
- NYC Alternate Side ParkingAn app that tells you when to move the car, and when you can leave it.
- Parenting newsletterNotes from raising a kid in Brooklyn, sent to parents who asked.
- My Career CopilotCareers for teens and veterans, through a thousand day-in-the-life videos.
Learnings
- BendHead of Engineering, then fractional CTO. Moved the backend from Elixir to Node without users noticing, then pointed a model at BigQuery and it found an audience we had never marketed to.
- ForerunnerVP of Engineering. Took fifteen people through SOC 2 by treating every control as a setting, so the audit was a day of screenshots instead of a quarter of archaeology.
- Bowery FarmingSenior Director of Engineering. The software decided when the plants got light and water, so a bad deploy browned a crop. Launches still got 90% faster.
- Care/ofSenior Director of Engineering. Incidents fell 90%, mostly by changing who ran the post-mortem. Then I wrote the technical diligence for the Bayer acquisition.
- NBCUniversalSenior engineer, principal, then engineering manager. Helped launch Peacock and moved twenty channels to the cloud, so the show on your TV came out of a data center we didn't own.
- AdvomaticSenior Software Engineer. Sites for the ACLU and the American Federation of Teachers, where traffic spiked the moment the news did.
- Institute for Integrative NutritionSoftware Engineer. Tools health coaches used to open their first practice. The first time my code carried someone else's livelihood.
- Poets & WritersJunior Web Developer. First job in tech, and I got it because of the poetry degree, not despite it.
- Binghamton UniversityBA in English and Creative Writing. Four years of saying more with fewer words. Still the job.
My favorite articles elsewhere
- We are all Product Engineers now
- Don't be a meat proxy
- AI enthusiasts are in a race against time, AI skeptics are in a race against entropy
- Revised rules of engineering leadership
- “Doctor, it hurts when agents create unreviewable PRs.” “Don’t do that.”
- Understanding is the new bottleneck
- The Tower Keeps Rising
- Trying the Software Factory pattern