AI Tools Podcast

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.

018 Episode 018: Season 2, the $75 Consult and the Frankenstein Stack (45 min)

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.

017 Episode 017 Training AI to Think Like Your Practice (43 min)

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.

016 Episode 016: Can an AI Judge Train You Better Than the Real One? (45 min)

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".

Your hosts

About the show

Ron Drescher

Attorney & Host

After more than 40 years in the trenches of bankruptcy law, Ron Drescher has seen legal practice evolve from paper and fax machines to cloud software—and now to artificial intelligence.

He’s not a technologist. He’s a practicing lawyer who understands how law firms actually work—and where they break.

Through his podcast, AI Tools for Practicing Lawyers, Ron helps attorneys move beyond hype and confusion to practical, ethical use of AI in their day-to-day work. His focus is on what matters: tools that save time, improve client service, and fit within the realities of legal practice.

If you’re trying to figure out what AI actually means for your practice, Ron is the guide who speaks your language.

Heather Gardner

Co-Host & Founder, Propel Paralegal Services

Heather Gardner is the Founder and CEO of Propel Paralegal Services, a virtual legal support company providing experienced bankruptcy paralegal services to attorneys nationwide. She has spent her career working extensively with consumer bankruptcy practices, supporting debtor-focused Chapter 7 and Chapter 13 cases through every stage of the bankruptcy process.

An early adopter of AI in legal practice — from GPT to Spellbook — Heather uses AI extensively in content marketing, workflow development, and creating SOPs. She frequently speaks on practical ways attorneys can use AI tools for drafting, business operations, and everyday practice management.

40+

Years in Law

1000s

Cases Handled

Weekly

New Episodes