By the end of this episode, you'll understand how lawyers are actually AI maxxing in 2026, and how you can, too.

Timestamps:

0:00 Intro

1:58 Why it's the best time to be a lawyer

3:03 Hallucinations and cognitive surrender

5:33 Quality over efficiency

8:13 Why AI upends legal work

15:20 60% of contracts filed to EDGAR have mistakes

20:04 How LLMs actually work

25:59 Zero data retention, explained

29:16 The privacy risk beyond training

39:16 How to prompt

47:03 Michael Showalter's AI-native litigation stack

55:27 Spellbook's Compare to Market Feature

1:03:10 Building a regulatory agent

1:09:50 The judgment crisis for junior lawyers

1:12:15 Cooley's AI training method

You'll hear from 10 people at the cutting edge of legal AI:

Zack Shapiro, Founder and Managing Partner at Rains LLP
Molly Abraham, General Counsel at Coinbase
Sujit Raman, Chief Legal Officer at TRM Labs
Michael Showalter, Founder of Showalter PLLC
Erich Dylus, attorney, programmer and creator of CamoText
Aaron Kelly, General Counsel and open source AI expert
David Wang, Chief Innovation Officer at Cooley
Scott Stevenson, CEO of Spellbook
Justin McCallon, CEO of StrongSuit
Samson Enzer, Partner at Cahill Gordon & Reindel

This episode is presented by Altitude, visit altitude.xyz/law to learn more about their financial operating system.

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Sponsors: Thank you to the Hyperliquid Policy Center and Solana Policy Institute for supporting this podcast.

To get in touch with the Cahill team about how any issues discussed in this episode apply to your situation, email mtomsky@cahill.com.

Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by guests are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.