The Unlikely Journey of Chip Skowron: From Wall Street to Prison Entrepreneurship

Imagine a moment where the weight of your choices feels heavier than any burden you’ve ever carried. For Chip Skowron, that moment came during a quiet evening at home when he found himself staring into the abyss of his own life, realizing the duality he had created. On one side, he was the star student and athlete, excelling in school and leading his soccer team. On the other, he was a young man ensnared by the grips of drug addiction, a secret that gnawed at him from the inside.

This stark contrast defined his teenage years, a time when the allure of acceptance led him down a path of severe addiction and troubling choices. Chip grew up in Cocoa Beach, Florida, where his father worked as a rocket scientist, contributing to some of the most iconic missions in space exploration. His mother, a dedicated secretary, played a pivotal role in supporting the space program. With such a legacy, expectations were high, and Chip rose to meet them, achieving straight A’s in school and captaining his soccer team.

But it was during this time that the seeds of his addiction were sown, beginning with his first encounter with drugs at the age of 15. What started as a quest for belonging spiraled into a double life, where he stole money from his parents to fuel his addiction, all while maintaining the façade of a perfect student and athlete. As Chip navigated this turbulent period, he faced a devastating legal setback that would change the course of his life. Convicted of insider trading, he was sentenced to five years in federal prison a stark contrast to the life of success he had envisioned.

But it was during this time that a turning point emerged. His mother, concerned for her son’s wellbeing, reached out to church elders for help. Through their prayers and intervention, Chip experienced a profound moment of clarity. The addiction that had consumed him seemed to dissipate overnight, allowing him to reassess his life and the choices he had made.

This newfound perspective led him to a pivotal realization: he needed to prove his worthiness not through achievements on a tennis court or in a classroom, but through meaningful contributions to society. After serving his time, Chip turned his attention toward medical school, determined to forge a new path. However, destiny had other plans. As he transitioned from Wall Street to working with inmates, he discovered a deeper calling that resonated with his own experiences.

Now serving as the CEO of the Prison Entrepreneurship Program, Chip has dedicated his life to transforming the lives of incarcerated individuals. His mission is simple yet profound: to provide entrepreneurial education and mentoring to those who have lost their way. The statistics speak volumes less than 5 percent of participants return to prison, and 100 percent find employment within 90 days of release. Chip has witnessed firsthand the power of second chances, helping to launch over 100 businesses among those he mentors.

Reflecting on his journey, Chip often emphasizes the importance of understanding one’s purpose. He recognizes that every moment of struggle, every mistake made, has led him to a place where he can now help others navigate their own challenges. His story is not just about overcoming addiction or legal issues; it’s about the profound realization that our past does not define us. Instead, it is our commitment to growth and helping others that shapes our legacy.

As we engage with stories like Chip’s, we are reminded that the journey of transformation is complex and deeply personal. Each step he took, from the depths of addiction to the heights of advocacy, serves as a reminder that we all have the capacity to change and make a difference in the lives of others. In helping those reentering society, Chip Skowron has not only found his purpose but has also ignited hope in countless individuals striving for a better future.

Hear Chip Skowron’s Story