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Ruben Gaona

Executive Director

Ruben Gaona, originally from El Paso, Texas, embarked on a transformative journey when he relocated to Milwaukee's Southside at the age of 15. Emerging from a challenging past, Ruben discovered his purpose in assisting others in rewriting their stories.

Following a remarkable journey, Ruben completed eight years of a ten-year Federal sentence by 2017. In 2019, fueled by his commitment to changing lives, he founded 2nd Chance Wisconsin. Through the power of motivational speaking, Ruben began guiding formerly incarcerated individuals toward brighter futures.

As a U.S. Navy Veteran and 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 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 assumed the role of Executive Director for My Way Out, Inc., solidifying 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 firmly 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.

Ruben Gaona, Executive Director, has received numerous accolades for his entrepreneurial leadership, including being named 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 the Hispanic Professional Greater Milwaukee Espiritu Award.

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