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 →-
Where Privilege Breaks
Attorney-client privilege rests on a confidentiality that most AI deployments quietly dissolve, at a layer of the system that sits below anything the doctrine was written to inspect. A procedural walk through where the protection survives, where it fails, and why those turn out to be two different questions.
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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.
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.