Blog posts

2026

What’s Wrong With Where Legal AI Is Heading

3 minute read

Published:

Full disclaimer before I begin: I’m not saying all Legal AI is wrong, and I won’t pretend I’ve evaluated every product on the market. My assessment draws from podcasts, YouTube videos, and articles I’ve read — so take it in that spirit. I’m also specifically focused on legal reasoning products, or products positioned to assist with legal reasoning.

Is AI Really Non-Deterministic? What Legal Practitioners Need to Know

5 minute read

Published:

I was listening to the Weekend Law podcast from Bloomberg Law this morning, where Justin Daniels — an AI and tech law expert and shareholder at Baker Donelson — shared how lawyers are using AI. One point he made stuck with me: AI is good at pattern matching, but you shouldn’t confuse probabilities with certainties.

Would AI Give You a Discount? Maybe — Just Not the Kind You’re Expecting

4 minute read

Published:

By now, almost everyone in the legal industry has heard: Kirkland & Ellis announced a $500 million, four-year investment to develop proprietary internal AI tools. The reaction was predictably mixed. With capable off-the-shelf solutions like Harvey and Legora already on the market, many observers questioned why K&E would build from scratch at that scale. Harvey co-founder Gabe Pereyra weighed in on the strategic logic behind the decision here.

Legal Practitioner’s Guide to LLMs

2 minute read

Published:

I recently attended the Bloomberg Law Symposium, where I had the opportunity to hear from two very different worlds: academic researchers presenting their latest findings, and legal practitioners and law firm representatives speaking candidly about the challenges their field is facing — what’s broken, and what they need.