Episodes
AI Builds: Gmail Digest
13:57
Most AI advice for lawyers stops at prompting. Ron Drescher goes further, walking through the automated newsletter-digest system he built with make.com, Gmail, and ChatGPT — one that runs itself every morning and hands him a curated legal-tech briefing before he's finished his coffee. It's a real build, roadblocks and all, and a look at what "Jetsons" actually looks like for a solo practice.
Field Note: In Defense Of AI Notetakers
5:40
The internet's latest AI panic is about note-takers secretly turning your meetings into data — except your meetings were already data. Ron Drescher breaks down why the real question was never "do I trust AI," but whether you trust the vendor, the security model, and your own information governance. It's not an AI problem. It's the same due-diligence problem lawyers have been addressing since the first firm moved a file to the cloud.
Episode 021 Law Firm AI: Custom Made Or Off The Shelf?
53:43
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 origin story, the pricing, and the pitfalls — no punches pulled.
Episode 020: Pain Points, Grok And The Homeless Summer Associate
46:32
Solo lawyers don't need Big Law's budget to compete in the AI era — they need to find their pain point first. Dr. Sara Kubik, Ph.D, MBA, a family law and estate planning attorney turned professional AI trainer, joins Ron and Heather to make the case that small firms may hold the real advantage right now, and why a Reddit post about a homeless summer associate proves AI still can't replace human involvement.
Episode 019 Bankruptcy Meets The AI Revolution
54:01
Jenny Doling didn't wait for AI to be ready for bankruptcy practice — she built it herself, one skill at a time. This episode digs into the analyzer stack she's running for pay stubs, tax returns, bank statements, and Chapter 13 objections, and why she thinks the real win isn't time saved but better legal work. If you're still deciding whether AI belongs in a bankruptcy practice, Jenny's already three steps past that question.
Episode 018: Season 2, the $75 Consult and the Frankenstein Stack
45:58
Season 1 was about learning AI. Season 2 is about something harder. Jen Grondahl Lee — bankruptcy consultant, disruptor, and self-described bankruptcy nerd — joins Ron and Heather to kick off a multi-episode series on what it actually takes to make AI work inside a small firm: organizing the knowledge you already own. Plus: the argument for charging for consultations, the Frankenstein Stack problem in law firm tech, and your first homework assignment.
Episode 017 Training AI to Think Like Your Practice
43:34
Most lawyers talk about what AI might do for their practice. Ron and Heather are in the middle of actually doing it — a bankruptcy intake workflow pack, an 11-module paralegal course with a Claude Code-powered chatbot, and a portable markdown system that runs in any AI environment. This episode is what it looks like when practitioners stop theorizing and start training AI to think like their practice.
Episode 016: Can an AI Judge Train You Better Than the Real One?
45:01
For generations, lawyers learned advocacy by getting knocked down in front of a real judge. Litigation partner Chris Ryan built BenchSim AI to change that, letting lawyers argue their actual brief against an AI judge that interrupts, pushes back, and grades the performance before the real hearing ever happens. Ron and Heather dig into how this stacks up across the Flintstones, Simpsons, and Jetsons spectrum, and whether AI training tools like this fix the courtroom "reps problem".
AI Builds: Ground Zero
24:09
Every ad promises you can build an AI agent in 20 minutes. Ron spent over 12 hours building the simplest one he could imagine — a bankruptcy motion to extend time — and tested it across Claude, ChatGPT, Gemini, and Copilot to find out which platform actually delivers. The winner surprised him, and so did the lesson about what "regenerating a document" really costs you.
Field Note: Can Apple Intelligence Pass the File Cabinet Test?
9:26
Apple spent years letting others fumble with AI before stepping in — and WWDC 2026 may be the moment it finally does. This Field Note cuts through the keynote noise to focus on the two announcements that actually matter for lawyers: natural language Shortcuts that could make workflow automation accessible to anyone, and Apple Intelligence's potential to finally unlock the files already sitting in iCloud and Finder. The real question isn't whether Apple built the smartest AI. It's whether it can pass the File Cabinet Test.
Episode 015: The Last Flintstones Lawyer
37:39
The lawyers at your bar association panel aren't asking whether to use AI anymore — they're asking which tool, at what tier, and how to keep client information out of the wrong one. Ron sits down with co-host Heather Gardner and Maryland legal educator Donna Mandl to map out concrete Monday-morning moves for Flintstones, Simpsons, and Jetsons lawyers — including a practical workaround for Claude fans who can't justify the Enterprise price tag. The gap between lawyers who've figured out the tiers and those who haven't is widening fast.
Field Note: Tiers Of The Clown
9:58
The debate over which AI tier is "smarter" is a trap — and solo lawyers are walking right into it. This Field Note breaks down the six capabilities that actually separate AI tiers (context window, retrieval, usage limits, connectors, memory, governance) and explains why the best tier for your practice isn't the most powerful one — it's the one that matches the task. Ron's own File Cabinet Test experiments are the proof.
Episode 014: Billable Hours and the AI Native Law Firm
40:25
Startup attorney Rich Rodgers has been building AI-native legal tools since before most lawyers had a working definition of the term — and what he's built challenges the assumption that AI and legal practice are on a collision course. This episode goes deep on what an AI-native law firm actually means operationally, how the billable hour is the real casualty of AI adoption, and what every lawyer — Flintstones to Jetsons — should be doing right now to stay in the loop rather than get cut out of it. The future isn't AI replacing lawyers. It's clients arriving informed, organized, and AI-assisted before the first meeting — and the only question is whether you're ready for that client.
Workflow Options: Claude for Legal and Strongsuit
22:07
The legal AI conversation has been obsessed with which model is smartest. That's the wrong question. This episode maps the split between enterprise ecosystem platforms like Claude for Legal and vertical workflow tools like StrongSuit — and explains why the winner for solo and small firm lawyers will be the platform that removes the most friction, not the one with the most features.
Episode 013 BigLaw, Privilege and an Unexpected "Wow!" Moment
42:37
The conversation about AI and privilege usually stops at hallucinated citations. This episode goes somewhere more dangerous: the moment you choose the wrong tier of AI tool, you may have already compromised your client's confidentiality. Matt Lafferman, a Dentons partner on the firm's AI task force, breaks down exactly how to build privilege defensibility into an AI workflow — from output labeling to mandatory human review to policy documentation that holds up in court.
Field Note: I WannAI Hold Your Hand: Learning AI From AI
21:46
Most lawyers searching for AI training are drowning in options — and most of those options are aimed at the wrong lawyer. In this Field Note, Ron Drescher offers a simple, portable method for learning AI on your own terms, plus three diagnostic questions that will tell you immediately whether any trainer — human or bot — is worth your time or money.
Episode 012 AI CLEs, Flintstones Lawyers & the Problem With Legal AI Training
35:20
Ron Drescher, Heather Gardner, and Kathryn Boling reflect on a live AI CLE panel presented at the 2026 Maryland Bankruptcy Bar Association Spring Break Weekend. The discussion explores why legal AI education remains so difficult, how Flintstones, Simpsons, and Jetsons lawyers experience AI differently, and what law firms should actually focus on before adopting new AI tools.
Field Note: How BigLaw Associates Are Actually Using AI in Legal Drafting
13:41
If AI hallucinations are the problem, how are lawyers still using it in drafting?
In this Field Note, Ron Drescher breaks down real-world workflows from BigLaw associates to show how AI is actually being used today—safely, strategically, and with clear limits. The result is a practical roadmap for using AI where it works—and avoiding it where it doesn’t.
Field Note: 21 Ways AI Can Hallucinate in Your Legal Brief
10:56
While most commentary about case hallucinations has focused on fake citations and misquotes, Ron Drescher highlights the more subtle—and more dangerous—types of hallucinations that appear in legal filings. From structurally corrupted citations to mutated judicial language, this episode explores how AI doesn’t just make obvious mistakes—it makes mistakes that look like law.
Episode 011 From Dabbling to Deployment: How Lawyers Actually Use AI
34:59
When does AI stop being a toy and start becoming part of your law practice?
In this episode, Ron Drescher talks with bankruptcy attorney Matt McCune, who is actively rebuilding his firm around AI. From automating client communication to analyzing financial documents in seconds, Matt shares what real deployment looks like—and why the lawyers who get this right will define the future of legal practice.
Workflow Options: Foundation AI
9:30
Most legal AI conversations focus on drafting, research, discovery, and analysis. But what if some of the most valuable AI for law firms has nothing to do with writing? In this Workflow Options minisode, Ron Drescher explores Foundation AI, a company focused on one of the oldest and most frustrating business problems in history: incoming document chaos.
Field Note: Even Biglaw Gets The AI Hallucination Blues
10:52
Even elite firms can get burned by AI hallucinations. In this field note, Ron Drescher breaks down the recent Sullivan & Cromwell filing controversy, where an emergency brief reportedly contained multiple citation and quotation errors that opposing counsel exposed first. The lesson is not that one firm slipped—it’s that polished AI output can create false confidence in any lawyer, especially when they're under severe deadline pressure.
Episode 010 No Harvey FOMO: AI On A Budget
25:10
How can lawyers get into AI without overspending or getting burned? In Episode 010, Ron Drescher and Heather Gardner compare premium tools like Harvey with affordable options like Gemini, ChatGPT Enterprise, Claude, and Copilot. They explain how to build a smart AI stack, avoid common traps, and use AI to create a more efficient—and possibly more independent—law practice.
Episode 009 Lawyer Moms (and Dads) and the 7-Minute AI Solution
38:20
In this episode, we talk with Carolyn Elefant about her AI for Lawyer Moms workshop and the idea that AI isn’t about massive overhauls—it’s about using the small pockets of time in your day more effectively. We also explore the rise of MSOs, shifting client expectations, and what solo lawyers need to understand to stay competitive in an AI-driven world.
Workflow Options: Ivory Mind
10:00
In this kickoff “Workflow Options” episode, Ron Drescher takes a closer look at Ivory Mind, an AI document assistant designed to help professionals quickly understand and organize their materials.
Field Note: Building the Stool — How to Implement the AI Discovery Standards
15:00
In this companion Field Note to Episode 008, Ron walks through the practical steps lawyers can take to implement the emerging AI discovery standards. He breaks the process into a simple three-legged stool: choosing the right vendor, properly configuring the tool, and handling the lawyer-side workflow and documentation needed to make AI use in discovery more defensible.
Episode 008 AI Discovery: A Safer, Defensible Way to Use AI in Discovery Work
34:44
AI can dramatically improve discovery work — summarizing productions, organizing documents, spotting patterns, building timelines, and making massive email chains usable. But most lawyers still lack a clear, defensible framework for using AI on discovery materials safely.
Episode 007: Folder Mania — When AI Comes to You
37:27
Every AI tool claims it can read your folders. We actually tested that claim — across ChatGPT, Claude, Gemini, and Microsoft Copilot — using a real-world 48-document Chapter 13 case file. The results were all over the place.
Field Notes: Confessions Of An AI Hallucinator
25:03
In this Field Note episode, Ron Drescher shares a candid story about relying on hallucinated legal citations in a client memo — and explains why “just verify it” is not enough. He offers a more practical framework for lawyers who want to use AI safely, effectively, and without compromising their work product.
Episode 006 729 Hallucinated Cases Later ... Lawyers Still Don't Get Ai
37:05
A conversation with Professor Nancy Rapaport on legal ethics, AI risk, and what lawyers are getting wrong about AI adoption.
Episode 005 How Lawyers Should Talk To AI
29:22
Using a simple framework to get better results from ChatGPT, Copilot ane other AI Tools
Episode 004 AI In Tools You're Already Using
36:37
Conversation about how AI is already built into the tools lawyers use every day —
from email and Zoom to Google Workspace and Microsoft 365.
Episode 003 AI Specialists: Where Do They Fit In Your Law Practice?
43:33
In this episode, Ron and Heather step back from the “latest tool” conversation and ask a more useful question:
Where do AI tools fit inside a law firm’s systems?
Episode 002 Primary Care AI Tools For Lawyers: ChatGPT, Gemini, Claude
36:02
A practical, non-hype discussion of ChatGPT, Gemini, and Claude for lawyers—how they’re similar, where they differ, and how to use them responsibly in real legal workflows.
Field Notes: Why Lawyers Should Stop Chasing AI Tools
7:44
In this episode, Ron Drescher discusses the overwhelming influx of AI tools available for lawyers and emphasizes the importance of integrating these tools into existing systems rather than getting lost in the multitude of options.
Episode 001 What Practicing Lawyers Need to Know About AI Right Now
24:56
Welcome to the inaugural episode of AI Tools for Practicing Lawyers.
In this first episode, we explain what artificial intelligence actually means for lawyers today — separating practical tools from hype, speculation, and fear.
