World Series Coach Trent Clark on Mistakes, Leadership, and Building Winning Teams

My Favorite Mistake: Business Lessons from Failures and Success

My guest for Episode #291 of the My Favorite Mistake podcast is Trent Clark, CEO of Leadershipity and Founder of Courage Coach LLC. Having spent his adult livelihood among the top 1% producers in sports and business, Trent is dedicated to empowering people to reach their goals, peak performance, and attain their dreams.

Episode page with transcript, video, and more.

An entrepreneur of 12 companies and longtime Entrepreneur Organization Member, he is best known for being a two-sport Division I Collegiate Athlete and Coaching 12 years in Professional Baseball with three organizations - including three (3) trips to the World Series - working with the Detroit Tigers, two-time American League Champion Cleveland Indians and the 2002 World Champion Los Angeles Angels of Anaheim.

He’s the author of a new book, Leading Winning Teams: How Teamwork, Motivation, and Strategy Achieve Big League Success, and he’s also the host of his podcast, "Winners Find a Way."

Trent has worked on staff with famed personalities, coaches, and executives, including Nick Saban, Joe Maddon, Tom Izzo, Mike Scioscia, and my favorite from that list… Sparky Anderson.

This episode covers the importance of learning from mistakes, resilience, and the parallels between sports and business leadership. Trent shares impactful lessons from his career, including a pivotal mistake involving contract negotiations that shaped his approach to accountability and preparation.

The conversation explores themes such as embracing failure as a stepping stone to growth, the necessity of adaptability in high-pressure environments, and the role of coaching in fostering continuous improvement. Insights on balancing personal and professional commitments, the evolution of strength training in baseball, and cultivating high-performing teams round out a compelling discussion on achieving sustained success through intentional learning and reflection.

Questions and Topics:

• What’s your favorite mistake?
• Are you willing to share what the main promises were that the Angels made verbally but never included in the written contract?
• Do coaches typically have an agent or a lawyer, or is that something you just handle on your own?
• How has the thinking evolved about bulking up in baseball? Is it still considered risky, or is it more about how players approach strength training?
• As a strength and conditioning coach, were you traveling constantly with both the Major League and minor league teams? What was that like for your family life?
• What can we learn from athletes about bouncing back from mistakes that might apply to entrepreneurship or our own work?
• You told me you get excited about mistakes—why is that, and how do people respond when you show that enthusiasm?