Regis Joseph Acosta
JD and AI systems builder.
Day job is the Advisory Tier at Thomson Reuters — applied AI for Am Law 100 firms, Fortune 500s, and federal agencies including the U.S. Department of Justice. Independent work is autonomous systems that learn from their own mistakes.
Selected writing
All writing →-
On Staying Honest About AI
An attempt to write about AI from inside the deployments — without evangelism, without refusal, without the comforts of pretending you aren't already participating.
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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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Where Do Junior Lawyers Come From Now?
The legal apprenticeship that produced every lawyer alive is breaking — not in some far-off future, now. A note from inside the room where it's being dismantled.
Selected work
All projects →-
Simon
Autonomous trading system — XGBoost-driven prediction plus an LLM-driven strategy layer. Independent work.
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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.