ason Lee Sharp’s story is one of hardship, discipline, service, and transformation. Raised in Chicago amid drugs, homelessness, and the pull of the streets, Jason learned early that suffering could either break him or build him. Today, he is a businessman, author, soldier, mentor, and leader dedicated to helping others turn adversity into strength.

In this episode, Jason shares how his challenging childhood shaped his mindset, how military school redirected his life, and how leadership became the throughline of his journey. From founding Sharp Leader and Sherris Lounge to serving as an infantry company commander in the Kansas Army National Guard, Jason’s path reveals what it means to stay alert, endure pain with purpose, and grow through discomfort.

We also dive into his book, Eyes Wide Open: Learning to Suffer, his work with youth through gritKC, and the lessons he has learned about mentorship, resilience, and choosing growth when life gets hard.