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

September 24, 2026 Adrian Cea

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, 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's 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

Want to watch this episode of Between the Briefs instead? Get the full video on YouTube.

About the Contributors

Adrian Cea

Adrian Cea is Steno's Social Media Manager, leading content strategy, audience engagement, and digital brand-building across platforms. He also produces and co-hosts Between the Briefs, Steno's podcast covering the intersection of legal technology, court reporting, and the future of litigation. With a background spanning content creation, field marketing, and sales at companies like Sell Better and Chili Piper, Adrian brings a multi-disciplined lens to making complex legal tech topics accessible and engaging.

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Joe Stephens

Joe Stephens, J.D., is Steno's Director of Legal Solutions as well as a Clinical Lecturer at Texas Tech University School of Law. With over 15 years of experience in criminal defense and public service, he founded and led Texas' largest rural public defender office, which serves a 12-county area. A graduate of The University of Texas School of Law (cum laude) and Vanderbilt University (B.A.), Stephens currently serves as a Board Member of the Texas Criminal Defense Lawyer's Association (TCDLA) and sits on multiple State Bar of Texas committees. His expertise spans the intersection of legal practice and technological innovation in the justice system.

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