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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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: tommy@docketdrafter.com
• 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.

Most AI training for lawyers is shiny-object stuff — nine prompts, the "ultimate playbook" — and that's exactly why none of it sticks. My old golf instructor figured this out decades ago, and he taught me the fix before AI even existed.

In this episode I tell that story and show you the one approach that actually works when you're learning to use AI in your practice. It's slower than chasing the next shiny thing, but it's the only thing that's ever worked.

Resource Links

• 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, we cover Perplexity—what it is, how it works, and why it deserves attention from solo and small firm lawyers. Ernie explains how Perplexity differs from traditional Google research by using AI to search the live web, synthesize answers, and provide footnoted citations so lawyers can quickly verify the sources behind the response.

You'll also hear practical examples of how lawyers are using Perplexity to research opposing counsel, evaluate expert witnesses, get oriented in unfamiliar areas of law, and test assumptions with sourced answers. Whether you are new to AI research tools or already using ChatGPT, Claude, or Gemini, this episode gives you a clear foundation for understanding where Perplexity fits—and why the next episode's conversation with Richard Serpe will make much more sense.

Chapters

0:05 Perplexity Episode Overview
1:17 Smith AI Sponsor
2:49 Perplexity Basics
4:35 AI Landscape Comparison
6:27 Lawyer Use Cases
8:00 Paid Features
8:59 Perplexity Computer Preview
10:08 Inner Circle Invitation

• AI Lab (a weekly AI workshop for lawyers)
• LinkedIn post by attorney offering AI chatbot that protects privilege
• The Inner Circle (my online community for lawyers)
• The 80/20 Principle (my techlaw newsletter)

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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.