The Email That Ruined a $10M Lawsuit ft. Kat Mateo

What lawyers don’t realize is that most litigation problems start long before anyone files a lawsuit. In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Kat Mateo, Counsel of Litigation at Olshan Frome Wolosky LLP, to talk about the client decisions that make cases harder. Kat breaks down the fatal decisions clients make before entering court, why attorneys must review deals early and how an emotional email turns into Exhibit A. She also shares her story as a first-generation immigrant, explaining why cases are won on paper and how AI impacts litigation strategy.

Litigation does not begin when a lawsuit is filed. By then, the story has often already been written in contracts, emails, missed deadlines and the very human decision to wait because “maybe it’ll blow over.”

In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Kat Mateo, Counsel of Litigation at Olshan Frome Wolosky LLP, for a practical, lively conversation about what clients, founders, business owners and legal teams often misunderstand about litigation.

What You’ll Learn:

Why clients should involve attorneys before disputes escalate
How litigators can spot risks in deals that transactional teams may miss
Why most cases are won or lost on papers, not dramatic courtroom moments
How emotional emails, sarcasm and jokes can become serious evidence
Why discovery now reaches work emails, personal phones, WhatsApp, Signal, Slack and social media
Why attorneys can manage bad facts, but not surprise facts
How storytelling helps juries understand complex commercial disputes

Good litigation strategy is not just about fighting well. It is about preventing problems early, documenting carefully, communicating wisely and knowing when to call the lawyer before things get expensive.

Highlights:

00:00 Introduction

01:09 Kat’s Journey From the Dominican Republic to Litigation

03:44 How Culture and Community Shape Kat’s Advocacy

05:04 The Pressure and Responsibility of Being First-Gen

07:08 Staying Hungry Through a Hard Journey

08:50 Kat’s Advice for First-Gen and Immigrant Law Students

10:52 Why Litigation Starts Before the Lawsuit

11:16 The Biggest Mistake Clients Make Before Litigation

15:01 What People Misunderstand About Litigators

15:36 Why Most Cases Never Go to Trial

16:41 Why Emotional Emails Can Wreck a Case

18:06 The Courtroom Poster Test for Client Communications

21:22 Why Clients Should Never Hide Bad Facts

25:16 Why Storytelling Matters in Litigation

25:47 The Difference Between Truth and What You Can Prove

30:15 How Kat Approaches Storytelling for Juries

34:38 Kat’s Love-Hate Relationship With AI

35:33 The AI Privilege Trap Clients Need to Understand

38:51 What Kat Learned Inside a Judge’s Chambers

39:34 How Judges Really Approach Decisions

43:55 Kat’s Hot Take on Technology and Lawyers

44:48 Closing Thoughts

Quotes:

“Usually cases are not hard because the law is hard. They’re hard because of the decisions the clients have made before litigation even commenced.”
“The biggest mistake that I see clients make is that they don’t involve attorneys early enough.”
“Most cases are won or lost on papers.”
“I can deal with bad facts. I can’t deal with surprise facts.”
“Technology is changing what things look like, but it doesn’t mean that lawyers go away.”