Ruben Gaona, BS

Executive Director

Ruben Gaona, Executive Director of My Way Out, is a visionary leader whose entrepreneurial spirit and commitment to social change have earned him numerous accolades, including being named the 2021 Veteran Social Entrepreneur of the Year, one of Wisconsin’s 2022 Most Influential Latino Leaders, a recipient of the 2022 Google Latino Founders Fund, the 2022 Michael Boyce Outstanding Entrepreneur Award from the University of Notre Dame, and the 2023 Espiritu Award from the Hispanic Professionals of Greater Milwaukee.

Ruben’s journey has been one of extraordinary resilience. After completing eight years of a ten-year Federal sentence by 2017, he emerged determined to turn his experiences into a force for good. In 2019, he founded 2nd Chance Wisconsin, using motivational speaking to help formerly incarcerated individuals chart new paths forward.

A U.S. Navy Veteran and former Department of Defense employee, Ruben blends his diverse professional background with personal insight into the justice system, fueling his unwavering commitment to creating opportunities for others. This dedication led him to co-found The Way Out, a fair chance employment platform inspired by his work in re-entry initiatives across Wisconsin.

In 2022, Ruben took the helm as Executive Director of My Way Out, Inc., solidifying his leadership in the field of re-entry support. He frequently speaks at events throughout Wisconsin, sharing his powerful story and advocating for fair chance employment opportunities.

In 2025, Ruben achieved another milestone by earning his Bachelor’s degree in Social Work from the University of Wisconsin-Milwaukee, further equipping him to drive impactful changes in the community.

Ruben Gaona’s life stands as a testament to resilience, determination, and the transformative power of new beginnings. He firmly believes that mistakes do not define a person, but rather what they choose to do afterward, and he continues to work tirelessly toward a fairer future for all.