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 **Follow and Review** I'd appreciate it if you could drop a review over on  Apple Podcasts. It only takes a few seconds and helps spread the word about the podcast. **Thanks to the sponsor:** **Smith.ai** Smith.ai is an amazing virtual receptionist service that specializes in working with solo and small law firms. When you hire Smith.ai, you're hiring well-trained, friendly receptionists who can respond to callers in English or Spanish. And they have a special offer for podcast listeners where you can get an extra $100 discount with promo code ERNIE100. Sign up for a risk-free start with a 14-day money-back guarantee now (and learn more) at smith.ai.