Episode 018: Season 2, the $75 Consult and the Frankenstein Stack

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.

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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?" is over. What comes next requires something most small firm lawyers haven't done: build the knowledge infrastructure that makes AI work for your practice, not just anyone's.

In this episode:

  • Ron announces the shift from Season 1 (learning AI) to Season 2 (teaching AI your firm's knowledge and systems)

  • Why the Flintstones/Simpsons/Jetsons framework needs to evolve as AI adoption spreads across the profession

  • Jen Grondahl Lee on the trap of the Frankenstein Stack — why firms should design their workflow first, then pick the tools

  • The case for charging for consultations — and why free consults are really just sales pitches

  • How niching down and turning clients away can actually accelerate a bankruptcy practice

  • The FSJ-level homework assignment: Flintstones find your 10 best forms, Simpsons list your 10 most common client questions, Jetsons map your 10 most important firm systems

  • AI court orders and the problem of courts overreacting to bad lawyering — not bad AI

  • The contradiction hidden in a 3-part judicial AI order: disclose AI use, verify citations — and certify the document wasn't produced by AI

We also discuss:

  • Jen's AI-DR blog post — "copy pasta" AI content and how to train your tools to sound like you, not like everyone else

  • Heather naming her ChatGPT "Bosley" and why the reference fits

  • Claude vs. ChatGPT for brainstorming — and why power users play them off each other

  • The AI hiring test: give applicants an unhappy client email and watch whether they improve the AI's draft or just paste it

  • Jen's 1,000-hours-saved estimate and how she calculated it

  • Bankruptcy Toolbox, Rebel Roundtable, and Jen's course Building a Bankruptcy Practice from Start to Finish

Key Takeaway

Most lawyers using AI are still using it the way they used Google — as a tool they query, not a system they've trained. The difference between a Simpsons lawyer and a Jetsons lawyer isn't which tools they use. It's whether they've done the unglamorous work of documenting what their firm actually knows.

This episode is the on-ramp. The homework isn't hard — find your best forms, write down your most common client questions, name your most important systems. But most Flintstones and Simpsons lawyers haven't done any of it. That's what Season 2 is about.

Mentioned in This Episode:

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