The 80/20 Principle

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.

A few weeks ago, one of Sarah Persich's clients dropped an AI agent into their Slack workspace. Sarah gave it the criteria her client's intake team is supposed to follow on calls — build rapport, handle objections, gather the right information — and asked it to listen to the recorded calls and grade every person against those criteria. It came back ten minutes later with work that would have taken weeks by hand. The tool is Viktor. We spend a good chunk of this episode on it, because it runs inside Slack or Teams and it's proactive. It doesn't wait to be asked. But the tool isn't the whole story. Sarah calls herself a fractional integrator, and it's a role many small firms need without knowing what to call it. Which means they never go looking for one. We talk about where Zapier still fits, why connecting Claude to your email and calendar matters more than it sounds, and where I'd draw the line on giving AI access to your browser. Chapters 00:00 The tool that graded weeks of intake calls in ten minutes 02:17 From law firm employee to the "automation lady" 03:34 Why an automation request is usually a systems problem 07:04 What a fractional integrator does, and where the name came from 09:29 Where Zapier still fits now that AI has caught up 13:21 Claude, MCP connections, and the browser access red flag 17:31 Why connecting email and calendar is the real shift 19:31 Meet Viktor, the autonomous agent living in Slack 21:31 Grading every intake call and catching leads that slipped 25:48 Acting without approval, proactive nudges, and what it costs 31:22 Why firms under ten lawyers need this role, and how to reach Sarah Resource Links Automation Lady Zapier Make Granola Filevine Traction: Get a Grip on Your Business The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) 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.

Carolyn Elefant has been practicing law for thirty-five years and writing about solo practice for almost as long. In this episode she and Ernie get into how AI is changing litigation — not in theory, but in the cases she's handling right now. Carolyn walks through experiments she's run and posted publicly, including having AI draft the judge's opinion from both briefs before she wrote her reply, and hiding instructions inside a brief to see which AI tools would follow them. One tool refused. One followed them. The third declined the part it considered unethical and went along with the part it considered harmless — which is the interesting one, because it looks a lot like judgment. They also cover which tools she reaches for and when, why she pays for the business version instead of the free one, where a lawyer should start if all of this feels overwhelming, and her upcoming 'Bellwether AI Litigator' conference on September 17 and 18. Chapters 0:05 Episode Overview 1:45 Smith.ai Sponsor 2:30 A Small Firm That Fights Big Energy 7:09 Her First AI Experiments 10:46 Making AI Write the Judge's Opinion 12:59 The Prompt Injection Test 14:44 When AI Starts to Look Like Judgment 17:38 Connecting Claude to Email, Files, and Court Listener 25:02 Where a Lawyer Should Start 27:02 Free vs. Paid, and What Happens in Discovery 28:35 The Bellwether Litigator Conference Resource Links The Bellweather AI Litigator Conference info Early Bird Registration (special price) Carolyn's LinkedIn profile (follow her from here) The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) Follow and Review: I'd appreciate 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.

In this episode, Ernie Svenson talks with Docket Drafter co-founder Tommy Eberle about what lawyers need to understand to use AI tools like Claude more effectively. They unpack why Word documents consume so many tokens, why AI performance can decline during long chats, how context windows and compaction affect results, and when to use different Claude models and thinking levels. Tommy also explains how lawyers can use AI to organize files, automate repetitive document work, and build more efficient workflows—without needing to become programmers themselves. Chapters 0:05 Why AI Frustrations Make Sense 3:03 From Coding To Legal AI 8:05 Making Word Agent-Friendly 16:20 Why Claude Gets Dumber 26:21 Models, Thinking, And Compaction 34:33 Files, Folders, And Better Prompting Show Notes The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) Tommy Eberle's LinkedIn page Tommy's Email Address: [email protected] Docket Drafter https://www.youtube.com/@DocketDrafter 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.

Most lawyers using Claude are only scratching the surface of what it can do. In this episode, Ernie Svenson talks with former litigator and software founder Nick Chapleau about using Claude as more than a chatbot—as a chief of staff that can help run a modern law firm. They explore email triage, workflow automation, firm knowledge bases, custom dashboards, security, and what it takes to build a truly Claude-native practice. Chapters 0:05 Using Claude as Chief of Staff 2:34 Nick's Legal and Software Background 8:07 Building a Claude-Native Law Firm 14:55 Automating Email and Firm Workflows 19:54 Creating a Central Firm Wiki 31:06 Hosting, Security, and Implementation Resource Links The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) 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.