#206 - How lawyers are using AI in 2026

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

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