How AI Is Helping Lawyers Find Cases They’d Never Find Manually ft. Maxwell Weiss

Maxwell Weiss has investigated everything from stolen historical artifacts and match fixing to counterfeit medicines, privacy violations and questionable health plans. Now, he is working at the intersection of plaintiff-side litigation and AI-powered case discovery.

In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Maxwell Weiss, a partner at Don Bivens and Litigation Counsel at Darrow AI, to unpack how lawyers can find the facts that actually matter, investigate complex wrongdoing and use technology to uncover cases that traditional methods may never reach. Maxwell explains the 80/20 rule he applies to litigation, why brevity matters in legal writing, what federal judges taught him about courtroom advocacy and why the best lawyers often sound more like they are having a conversation than delivering a performance.

The conversation also gets into Darrow AI and how technology can monitor prices, identify potential privacy violations and analyze complicated health-plan structures at a scale that would be nearly impossible for lawyers to handle manually. Maxwell explains how those findings are turned into something lawyers can actually use: a clear case theory, the relevant law, precedent and an evidentiary roadmap.

And then there is Maxwell’s biggest concern about AI: junior lawyers may become so dependent on it that they skip the foundational work that teaches them judgment in the first place.

What You’ll Learn:

How Maxwell applies the 80/20 rule to litigation strategy and focuses time on the facts that actually drive a case
Why investigative work often requires lawyers to bring in private investigators, technical experts and other specialists
What Maxwell learned from his federal clerkship about brevity, courtroom advocacy and communicating with judges
Why strong advocacy looks more like a conversation than a rehearsed courtroom performance
How class actions can create meaningful relief by stopping harmful conduct, not just recovering money
How AI can surface potential privacy violations, misleading pricing practices and health-plan problems at a scale that would be difficult to investigate manually
Why translating AI findings into clear legal analysis is still a deeply human part of the process
How lawyers identify and recruit strong named plaintiffs for class action cases
Why Maxwell is concerned that AI could leave junior lawyers without the foundational skills needed for good legal judgment

The big takeaway: AI can expand the scale of legal investigation, but lawyers still need the judgment to turn what they find into a real case.

Highlights:

00:00 Introduction

01:25 The Stolen Artifact Investigation

03:52 Maxwell’s Unusual Path Through Big Law and Federal Court

05:05 Investigating Counterfeit HIV Medicines

08:01 The 80/20 Rule for Litigation Strategy

09:10 How Lawyers Actually Investigate Complex Cases

11:19 The Ethics of Representing Clients

14:00 Why Brevity Matters in Legal Writing

15:30 What Federal Court Taught Maxwell About Advocacy

18:04 The Real Purpose of Class Actions

21:31 How Darrow AI Finds Hidden Legal Wrongdoing

24:46 The Problem With Dominated Health Plans

27:34 AI Cases That Would Never Be Found Manually

28:59 Will Lawyers Actually Adopt Legal AI?

30:42 What Happens When Both Sides Have AI?

31:47 Maxwell’s Next Big Litigation Target

35:17 Why Purpose Drives Maxwell’s Practice

36:45 Using Targeted Advertising to Find Plaintiffs

38:42 What Makes a Good Named Plaintiff?

41:27 The Emotional Side of Plaintiff Litigation

42:28 Maxwell’s Biggest Fear About AI and Junior Lawyers

43:47 Closing Thoughts

Quotes:

“The 80/20 rule is just so true.”
“The best advocates are having a conversation with the jury or the judge.”
“You don’t have to be absolutely perfectly polished.”
“I worry that junior lawyers will grow to rely on artificial intelligence so much that they’ll never get the basic skills.”