How A Milwaukee Entrepreneur Turned His Prison Experience Into A Business

Ruben Gaona is interviewed by St. Joan Antida High School Students. (Picture by Lily Shea Photography/Carvd N Stone)

From a prison cell to a self-made businessman, Ruben Gaona is changing incarcerated people’s lives. In 2010, Gaona was federally indicted on drug charges along with 21 other people, including his siblings. He then spent seven years in prison and one year in a halfway house. Throughout that time he knew he had to do more.

In 2019, he founded The Way Out with his Co-Founder Eli Rivera to help formerly incarcerated men and women achieve stability in their careers and lives.

Through The Way Out, Gaona and Rivera are connecting well paying jobs to those affected by the criminal system.  

“I never saw myself to be an entrepreneur,” he said. 

Even though he didn’t consider himself an entrepreneur at the time, when Gaona was younger, he began selling burritos in Texas to provide for his family. Eventually he stopped selling them out of embarrassment, but his late Godmother told him to never be ashamed to do the right thing. 

Inspired by his Godmother’s sons, Gaona joined the U.S Navy in 2001 and was eventually discharged and considered a hazard because of a back injury. Gaona then fell into a deep depression causing him to abuse drugs and alcohol. With Gaona having no savings, a wife and five kids, he had to find a way to support his family.

While working for the U.S. Department of Defense, Gaona trafficked drugs from Texas to Wisconsin. He eventually was caught because his kid’s Godfather, who was also his best friend, told on Gaona to reduce his jail time.

Ruben Gaona is the founder of The Way Out. (Picture by Lily Shea Photography/Carvd N Stone)

While in prison Goana realized that the path that he took didn’t lead him to where he wanted to be in life. He then made plans to change his life around once released. 

Upon his release in 2017, he decided to be a case manager to make a difference. 

“My number one regret was not being there for my family,” said Gaona. 

Gaona wanted to do more, which led him to meet Rivera where they collectively created The Way Out. 

To learn more about The Way Out, click here.

Written and interviewed by:

Natina Glover-Hunter

Imani Jenkins-Webster

Ayleen Cruz

Natalie Rangel 

Trinity Carter

Lidya Rose Allen

Kendi Johnikin

Ana Salgado 

Paola Guido

Aylen Hernandez

Noemi Vazquez

Paola Nieto

Elicia Power

Primavera Rivera 

Ayaa Omar

Jamya Price-Thomas