AI Tools for Practicing Lawyers

SHOW NOTES Maryland has about 40,000 lawyers. Roughly half a percent of them work in civil legal aid. Add more lawyers and you still hit a ceiling, because every lawyer can only serve so many people. Reena Shah, Executive Director of the Maryland Access to Justice Commission, joins Ron and Heather to ask what happens when technology breaks through that ceiling, and what happens when the general-pu...

SHOW NOTES Every CLE season produces a stack of materials that make sense in the room and mean nothing six months later. NACBA's "Me, Myself, and AI" program is the exception. Four consumer bankruptcy lawyers — all past guests on this show — didn't just talk about using AI, they handed over the actual prompts and skills they run in their own cases. Ron got NACBA's permissi...

SHOW NOTES Lawyers are building Claude skills, custom GPTs, and homegrown intake bots faster than ever. Most of what they're building will be obsolete in six months, because the foundation models keep swallowing whole product categories. Sabih Siddiqui left Big Law to co-found Irys.ai , a general-purpose legal AI platform. What started as a $299 off-the-shelf app turned into something closer...

SHOW NOTES Every lawyer who's ever complained that no software vendor understands their practice has secretly wondered the same thing Tara Salinas actually did something about: what if you just built it yourself? Tara, a consumer bankruptcy lawyer in Denver, didn't buy a client intake system — she built one, on a stack most lawyers have never heard of, and she's convinced you could...

SHOW NOTES A legal industry business professional spends her career building expertise, then watches AI automate the most valuable parts of that work. That's not a hypothetical — it's what this week's guest proved could happen. Yvonne Nath, founder of Counsel Commons, joins Ron and Heather to talk about a marketplace where lawyers and legal professionals can buy and sell the AI prom...

SHOW NOTES A lawyer running a massive document production doesn't read every page anymore — she can't, and nobody expects her to. So when does that stop being lawyering and start being blind faith? Jim Casey, Chief Privacy Officer at Akamai Technologies, joins Ron and Heather to argue there's a real answer, one that depends entirely on whether a bad AI output can still be caught bef...

SHOW NOTES Chad Van Horn built an AI petition review process that cut his firm's amendments by 80 percent. He also thinks AI is making lawyers dumber. Both are true in the same law firm, and figuring out how to hold both truths at once is the whole game. If AI can teach a new associate everything a senior partner knows, what happens to the judgment that only comes from doing the reps yourself...

SHOW NOTES A federal bankruptcy judge just told us she doesn't personally use generative AI in her own chambers - and that's exactly why this conversation is worth your time. Judge Elizabeth L. Gunn, who sits on the U.S. Bankruptcy Court for the District of Columbia, spent nearly an hour with Ron and Heather working through what AI actually changes about the practice of law, and what it...

SHOW NOTES An insurance company just spent $300,000 fighting a pro se litigant who had no lawyer — just ChatGPT. That number should worry every practicing litigator. What happens when the other side has access to an inexhaustible junior associate that never bills, never tires, and never stops drafting the next motion? In this episode: - Nippon Life Insurance Company of America's lawsuit again...

Show Notes Lawyers wear exhaustion like a badge of honor — but what if the data on your wrist already knows you're running on empty? In this episode, Ron sits down with  consultant Megan Grover of MBG Wellness and physician Dr. Kathryn Boling to talk about what happens when you point AI at your own biometric data. The question isn't whether lawyers work too hard — everyone already knows...

Has AI fundamentally changed the law of evidence, or has it just forced us to revisit principles that have always been there? That's the question at the center of this episode, and there's no better person to answer it than retired federal judge Paul Grimm — one of the people who has literally tried to write the new rule. IN THIS EPISODE: - Judge Paul Grimm's background: 25+ years o...

Show Notes How much work has to happen before AI can actually help a law firm? Everyone wants an AI-native practice, but almost nobody asks what has to be true before the AI can do anything useful. This episode answers that question with someone who's already built the answer from the ground up: Leisa Wintz , a Florida family law attorney and founder of Legal Authority Lab, whose firm runs on...

While AI note-takers grab the headlines, the real issue at stake in this episode is one lawyers have been dodging for decades: "Is AI notetaking actually riskier than everything else already sitting in your practice?" In this episode: - Why the claim "AI note-takers turn everything into data" misses the point — meetings were already data, AI just organizes it - Ron's take...

Most lawyers think about AI as a chat box. Ron argues that's already the old way of thinking — and the real leverage is in systems that run without you, remember what they're supposed to do, and hand you a finished result before you've had your coffee. In this episode: - Why the podcast is shifting focus from prompting skills to persistent, automated AI workflows - The "airport...

SHOW NOTES Most AI pitches to law firms start with a product. This one starts with an audit — and a question about whether buying software was ever the right move for a solo or small firm in the first place. Jerry Dearden of David AI joins Ron and Heather to unpack what it actually takes to build AI around a firm instead of forcing a firm into someone else's software. It's the David AI o...

SHOW NOTES What if the smallest law firms are actually the best positioned to win the AI era? That's the provocation Ron opens with this week — and it comes from someone with a genuinely rare vantage point: a solo attorney who also works as a professional AI trainer for the labs building these models. In this episode: Dr. Sara Kubik's path from a gerontology-focused PhD to family law, es...

Show Notes Most bankruptcy lawyers still don't know what their own firm actually makes each month. Jenny Doling built a revenue dashboard in Claude to find out — and then kept going, building analyzer skills for pay stubs, tax returns, bank statements, and Chapter 13 objections that her staff now runs without her. If a nationally recognized bankruptcy attorney and NACBA's incoming presid...

Show Notes Episode 018 | Season 2 Premiere | Guest: Jennifer Grondahl Lee Season 1 taught you how to use AI. Season 2 is going to be harder. The question isn't whether to adopt AI anymore — it's whether your firm's knowledge is organized enough for AI to actually use. When almost every hand in a room full of lawyers goes up to confirm they're using AI, the era of "should I...

Show Notes What are you actually doing with AI — and does it work? Ron and Heather put their tools down long enough to talk about what they've been building with them. This isn't a roundup of tools you might try. It's an inside look at two practitioners who have spent serious hours creating AI-powered workflows for their own legal and legal-adjacent businesses — and what those proje...

What if you could lose your case to an AI judge tonight, so you don't lose it to a real one tomorrow? For generations, lawyers learned advocacy the hard way: draft the brief, argue the motion, get knocked down by the judge, learn why you were wrong. Litigation partner Chris Ryan built a different path. BenchSim AI lets lawyers upload their brief and opposing counsel's brief, then argue o...

Are "build an AI agent in 20 minutes" ads lying to you?  Ron spent way more than 12 hours trying to find out. Ron set out to build the simplest possible AI legal workflow — a motion to extend time to file bankruptcy schedules — and discovered that "easy" and "AI-assisted" don't always mean the same thing. In this episode: Why Ron decided to test AI workflow-build...

SHOW NOTES NOTE: The File Cabinet Test is used to determine whether AI can discern the contents of every file in a connected drive. The star of Apple's WWDC 2026? Apple Intelligence. Apple announced how Apple Intelligence is being incorporated into Siri. This prompts us to ask: Can Apple Intelligence finally make workflow automation accessible to ordinary lawyers? In this episode: Why Apple&a...

Most conversations about AI and legal writing focus on the tools. This one focuses on the lawyers. What does a Flintstones lawyer actually do on Monday morning after they've finally decided to move? What does a Simpsons lawyer do when they discover their favorite tool isn't safe for client data? And what happens when the question isn't whether to adopt AI — but whether you'll s...

The question everyone is asking is wrong. When lawyers debate which AI tier is "smarter," they're arguing about a label — and labels end analysis. The better question isn't which tier is best . It's what capabilities am I actually buying , and whether those capabilities match the task in front of you. Ron's File Cabinet Test experiments proved this the hard way: Enter...

SHOW NOTES  Is the billable hour a liability you're voluntarily handing to your clients — and is AI finally giving lawyers a way out? Rich Rodgers has been building AI-native legal tools since before most lawyers knew what a large language model was. He's a practicing startup attorney, a four-time founder, and the creator of Start Legal — an AI platform designed to give founders a runnin...