333: Why AI feels more like email than the web

In this episode, Ernie Svenson talks with Greg Siskind, who has practiced immigration law for 35 years and wrote a book about marketing on the internet back in 1996, when that was a peculiar thing for a lawyer to do. Greg says AI reminds him of email more than any other technology wave he's lived through — the web, the cloud, and social media each changed a slice of legal work, while email changed the day-to-day job itself.

They talk about the drafting shift that surprised him most, a 25-page visa petition that used to take two days and now takes 20 to 30 minutes, and about the lawyers who got spooked by the hallucination headlines and won't touch AI even for low-risk work like marketing and firm management. They also get into the ABA's fee opinion, the argument for flat fees, and Greg's new ABA book, "The AI-Ready Law Firm," written for firms with no IT department and no consultant.

Chapters

00:00 Meet Greg Siskind, immigration lawyer and early internet adopter
02:34 Why Nashville in 1994 forced him online
05:21 How technology pulled both of us out of big firms
06:41 Decision trees on steroids, DAPA, and the travel ban apps
09:48 The CoCounsel demo that came before ChatGPT
13:12 Supervised agents and the 25-page petition in 30 minutes
16:07 Running a 1,000-prompt immigration library from inside Claude
20:09 Where lawyers trust AI too much, and where too little
22:40 Writing a book for firms with no IT department
26:33 AI note takers and the Zoom terms-of-service problem
29:13 Formal Opinion 512, fraud, and the push toward flat fees
33:49 Using AI as a brutal writing coach
36:12 Why AI belongs inside your case management system
38:57 Why this wave looks more like email than the web
42:36 What he tells law students about relying on AI

Show Notes

• The 80/20 Principle (my techlaw newsletter)
• The Inner Circle (my online community for lawyers)
• Greg Siskind Website
• Greg Siskind Linkedin
• The AI-Ready Law Firm

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