Ruben Gaona

Executive Director

Ruben Gaona, Executive Director of My Way Out, has been honored multiple times over for his entrepreneurial leadership including as the 2021 Veteran Social Entrepreneur of the Year, one of Wisconsin’s 2022 Most Influential Latino Leaders, the 2022 Google Latino Founders Fund, the 2022 Michael Boyce Outstanding Entrepreneur Award from the University of Notre Dame, and 2023 Hispanic Professional Greater Milwaukee Espiritu Award.

Ruben's path led him to complete eight years of a ten-year Federal sentence by 2017. In 2019, driven by his commitment to change lives, he founded 2nd Chance Wisconsin. Through the power of motivational speaking, Ruben started guiding formerly incarcerated individuals toward brighter futures.
With a dynamic background as a U.S. Navy Veteran and a former Department of Defense employee (NAVY), Ruben brings unique insights to the table. His personal experience within the justice system fuels his determination to make a positive impact. This very commitment led him to co-found The Way Out a fair chance employment platform, inspired by his tenure in re-entry initiatives in the State of Wisconsin.
In 2022, Ruben became the Executive Director for My Way Out, Inc., cementing his leadership in the realm of re-entry support. He has graced multiple re-entry events across Wisconsin, sharing his inspiring journey and championing second-chance employment opportunities. Ruben is a steadfast advocate who strongly believes that mistakes do not define who you are but rather what you do afterward, working diligently to create a fairer future for all in the United States.

Ruben Gaona's story is one of resilience, dedication, and a passion for empowering others to seize their second chances. His journey from adversity to advocacy exemplifies the transformative impact that a single individual can have on the lives of many.