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.