ClioCon takes place October 26 and 27 in Boston. You can watch sessions online for free (see link below). If you register and miss a session you can also watch the recording, so I recommend registering with the link below.

In this episode I discuss why the keynotes will be especially helpful for solo and small firm lawyers, and recommend a few key sessions that will be well worth your time. I also explain how you can participate in a virtual discussion of the conference sessions with other lawyers like you.

Information about conference

Keynotes sessions

• Malcolm Gladwell, "Weak Links, Strong Links: How AI Will Reshape Justice" (closes Day 1, Monday)
• Ethan Mollick, "From Disruption to Opportunity: Embracing the AI Revolution" (opens Day 2, Tuesday)
• Mechele Dickerson, on access to justice and the economics of legal services
• Jack Newton, Clio's CEO, on where Clio is headed

Recommended sessions

• Taking On Clients Who've Already Asked AI (Oct 26)
• How to Automate Your Firm End-to-End as a Solo Practitioner (Oct 26)
• AI in Action: What Early-Adopting Law Firms Have Learned So Far (Oct 26, also virtual)
• Pricing with Confidence: 4 Steps to Charging What Your Work Is Worth, with Molly Kremer (Oct 27, also virtual)
• Promise and Perils in the Judicial Adoption of AI (Oct 27, also virtual)

Resource Links

• ClioCon 2026 (October 26–27, Boston) — https://cliocon.com
• Free virtual ClioCon (register to watch a selection of sessions live or later) — https://cliocon.com/virtual-experience/
• Full ClioCon agenda — https://cliocon.com/agenda/
• The 80/20 Principle (my Substack newsletter)
• The Inner Circle (try it for 30 days for just $1)

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.

If the 80/20 principle never worked for you, you weren't doing it wrong. You were missing a part never gets discussed. In this episode I cover that part. It has to do with perfectionism, and with whose trial and error you rely on.

Then I show how it works in a free automated scheduling tool many lawyers still resist. Why they resist and how to overcome mental blocks with the 80/20 principle are explained in a way that you'll find surprisingly helpful.

Resource Links

• Calendly (automated scheduling software)
• The 80/20 Principle (my Substack 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 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.