Outside Providence: How to Fire Up a Growing Solo Law Firm

This week's vexing problem: solo attorney Ernie DiGregorio has no IT department and no fractional vendor to help him weigh AI tools against data security and client confidentiality. Michael Santomaro, principal of Santomaro Law in Providence, walks through how he actually uses AI across his personal injury and criminal law practice, from proofreading pleadings to finding federal court rules he'd never needed before. We also get into hallucination risk, the malpractice argument for using AI at all, and how Michael turned a deeply personal passion into a growing corner of his practice. Key Takeaways Run every draft through AI before it goes out. Michael caught over twenty typos in a single complaint once he started running documents through AI, and in his book, typos in 2026 read as laziness, not just error. Using AI to rework a sentence or a closing argument isn't cheating, it's the same move as using a thesaurus or asking a colleague at the water cooler. AI can get you to an unfamiliar rule fast, but it can't replace reading the cases yourself. Hallucinated citations have already gotten lawyers sanctioned. If you've never touched AI, start small: feed ChatGPT an email you already wrote and see what it changes. Think of it as a curator, not a mystery box. Solo and small firms without in-house IT can still build real AI infrastructure with off-the-shelf add-ins for Microsoft, Adobe, and Lexis. Links and Resources Santomaro Law: https://santomarolaw.com Red Cave Law Firm Consulting: https://redcavelegal.com Keywords legal tech, legal technology, AI for lawyers, legal AI tools, solo practitioner, small law firm, law practice management, law firm technology, ChatGPT for lawyers, AI hallucinations, legal ethics AI, client confidentiality, law firm marketing, personal injury law, legal research AI, document automation, shadow AI, Jared Correia, Adventures in Legal Tech, Red Cave Law Firm Consulting, AI malpractice risk Episode Highlights [00:02:00 - 00:04:00] Michael explains Ernie DiGregorio's Providence College basketball legacy and his own family connection to him. [00:05:00 - 00:06:00] Michael shares the malpractice warning that pushed him to adopt AI: skip it, and you're falling behind opposing counsel. [00:07:00 - 00:08:00] Michael describes running a redacted complaint through AI and catching over twenty typos his staff missed. [00:08:00 - 00:09:00] Michael uses AI to find unfamiliar federal court rules on his first case removed from state court. [00:09:00 - 00:11:00] Michael pushes back on the idea that using AI to write is cheating, comparing it to a thesaurus or a colleague's input. [00:10:00 - 00:11:00] Michael flags the real risk: hallucinated case law and the sanctions lawyers have already faced for not checking it. [00:13:00 - 00:15:00] Michael's advice for AI beginners: run an email you already wrote through ChatGPT and see what changes. [00:20:00 - 00:23:00] Michael opens up about his personal connection to plant medicine and his work with the Psychedelic Bar Association. [00:26:00 - 00:30:00] Michael breaks down how referral relationships, not big ad spend, drive his caseload.