A True Underdog Story: The Player-Agent Partnership (Doug Flutie and Kristen Kuliga)

In this powerful episode of Negotiation Warriors, Cliff Stein sits down with two true pioneers in the player contract ecosystem: Heisman Trophy winner, CFL and NFL legend Doug Flutie and trailblazing NFL agent Kristen Kuliga.

Doug challenged every assumption about what an NFL quarterback “should” look like — standing 5'9", proving doubters wrong at every level, winning three Grey Cups, earning Pro Bowl honors at 36, and playing in the NFL until age 40.

Kristen broke into a male-dominated industry when virtually no women represented NFL players. She became the first female agent to represent a starting NFL quarterback and has now represented NFL players for over 30 years.

Together, they discuss:

• How trust became the foundation of their player-agent relationship
• The adversity that shaped both of their careers
• What really happens behind the scenes before contract negotiations
• Lessons from the Giants vs. Patriots decision
• The evolution of women in sports representation
• NIL, revenue sharing, and the Wild West of college football
• The true traits of a great negotiator

This episode is about resilience, preparation, grit, and understanding what truly matters in a negotiation. A masterclass in trust, preparation, and championship mindset.

Episode 001: The Origin of Negotiation Warriors

In the first full episode of Negotiation Warriors, Doug Pires and Jessica DeBear of the Stopping By Podcast interview Cliff Stein about the origin of the podcast and the mindset behind great negotiators in professional sports. Drawing from more than 30 years in the NFL — as both an agent and General Counsel of the Chicago Bears — Cliff shares lessons on preparation, tactics, discipline, and the psychology of high-stakes negotiations.

What does it mean to be a Negotiation Warrior?

This episode lays the foundation for future conversations with elite negotiators across sports and business.

Introduction to Negotiation Warriors. Hosted by Cliff Stein.

Every negotiation is an opportunity to learn.

After more than two decades negotiating NFL player contracts and managing the salary cap, I realized something powerful: every conversation across the table — with agents, executives, players, and owners — was a masterclass in leverage, preparation, psychology, and strategy.

In this introductory episode of Negotiation Warriors, I share the journey behind the podcast — from my years inside NFL front offices to teaching The Art of the Player Contract Negotiation at Northwestern and Miami Law — and why I created this platform.

This podcast pulls back the curtain on the player contract ecosystem and features conversations with some of the greatest negotiators in professional sports. We’ll explore their philosophies, tactics, turning points, and the mindset that separates good negotiators from elite ones.

If you want to understand how deals really get done at the highest level — this is where the education continues.

Welcome to Negotiation Warriors.