Regis Joseph Acosta
JD and complex systems builder.
I build systems and write about what they break. The systems are reshaping law, education, and how we read, and I'm inside each one. The throughline, if I had to name one, is the seam between things people insist on keeping separate: law and software, literature and the internet, new tools meeting old institutions.
For my day job I'm an AI Solutions Architect at Thomson Reuters, where I help attorneys and federal agencies actually use the tools reshaping their profession. On nights and weekends I build Simon, an autonomous trading system that learns from its own mistakes without lying to itself about them, and I co-founded and run The Olive Branch Review, a writing community for people who want to be read by other people, not an algorithm.
Selected writing
All writing →-
Who Signs When the Machine Is Wrong?
AI tools fail differently than people do. They fail fluently, confidently, and without a tell, and the legal profession's entire accountability structure was built for a kind of mistake that announces itself. A note from inside the deployments on what the signature on the filing now certifies.
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Where Do Junior Lawyers Come From Now?
The apprenticeship that produced every lawyer alive was never designed. It was a byproduct of cheap junior labor doing necessary tedious work, and automation is collapsing the trade that funded it. A note from inside the room where the bottom rung is being sawn off.
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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.
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.