The $800K Dispute That Could Have Been Prevented ft. Kai Jacobs

October 26, 2026 Adrian Cea

Litigation Strategy Legal AI Trial Preparation

An $800,000 dispute over a self-drafted contract sounds completely avoidable. And, for a business litigator, the kind of frustrating case they could do without.

In this episode of Between the Briefs, Adrian Cea and Joe Stephens sit down with Kai Jacobs, Partner at South Florida Business Law Group, to discuss how 33 years of practicing law have shaped his approach to litigation, client counseling, and preventative legal work. Plus, they break down what happens when clients bring AI-drafted agreements into a law firm, why Kai prefers pre-lawsuit mediation over arbitration, and how broken business relationships can make dispute resolution far more complicated than interpreting contract language.

What You'll Learn:

Why litigation can be a burning house and preventative legal work is insurance
How lawyers can use preventative agreements to reduce litigation risk and deliver greater value to clients
How to counsel clients who want to cut corners on contracts and legal documentation
What an $800,000 dispute reveals about the consequences of inadequate legal documentation
Why attorneys should establish clear ownership records and decision-making structures from day one
How 50/50 partnerships can create deadlocks without clear decision-making rules
Why Kai recommends pre-lawsuit mediation clauses over relying on arbitration
Why reviewing AI-generated contracts can create more legal work than drafting agreements from scratch
Why legal judgment and understanding the client matter more than a polished AI draft
Why broken trust is often the real issue behind business litigation
How to separate being right from reaching an effective resolution
What Kai learned about leadership, mindset, and business ownership after starting his own firm

Turns out, the best litigation strategy might be preventing the case altogether. Tune in for Kai’s compelling argument that lawyers should become better business advisers, not simply better litigators.

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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