Regis Joseph Acosta
JD and AI systems builder.
I exist in a few worlds at once. I write, I build, I deploy. I co-run an online literary community. The throughline, if I had to name one, is that I keep finding myself drawn to the seam between things that are usually kept apart. Law and software. Literature and the internet. Machine learning and the question of what it means to make something honest.
For my day job I'm an AI Solutions Architect at Thomson Reuters, where I help attorneys and federal agencies actually use the tools that are reshaping their profession. On nights and weekends I work on Simon, an autonomous trading system I built mostly to see if I could build something that learns from its own mistakes without lying to itself about them. I also co-founded and run The Olive Branch Review, a writing platform for people who want to be read by other people, not by an algorithm.
Before all that, I went to Suffolk Law, where the clinical program let me build a docketing tool the Massachusetts Appeals Court adopted, and before that the University of Rochester, where I studied English and Computer Science and worked in admissions, which turned out to be the most useful training for everything I have done since.
Outside any of that: my wife, our two dogs, and a horror movie group I catch the newest releases with. I read more than I should and write more than I publish. Most of what I love is built on craft of some kind. The novel that knows exactly what kind of reader it's trapping. The horror film that earns its scares from character rather than cuts. The album that doesn't waste a second. I am, as a result, very hard to please and very easy to fall in love with something new.
I live in Rochester. The winters are bad and the city is interesting and the food is better than people give it credit for.
Selected writing
All writing →-
Where Do Junior Lawyers Come From Now?
The legal apprenticeship that produced every lawyer alive is breaking, and not in some far-off future. A note from inside the room where it's being dismantled.
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Two Sides of the Same Damaged Coin
On Don Draper, Tony Soprano, and why we keep returning to the antiheroes television was last willing to leave unresolved.
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On Staying Honest About AI
An attempt to write about AI from inside the deployments, without evangelism, without refusal, and without the comforts of pretending you aren't already participating.
Selected work
All projects →-
Simon
An autonomous trading system that separates prediction from strategy, fails loudly when it doesn't know, and learns from the things it gets wrong.
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Suffolk Law Clinical Program
Three years of clinical work. Client representation, civic legal tech that shipped to courts, and public-interest tooling.
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The Olive Branch Review
A community writing platform. Original work, peer feedback, and a publishing standard that takes both seriously.