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Episode 7: Ruben Gaona of The Way Out

Second chances. Our society loves stories about second chances. They make great plots for movies like “It’s Wonderful Life.” But when it comes to the formerly incarcerated or justice-involved, the data tells a different story. Annually, 2.3 million people are incarcerated in this country with 12,500 being released every week according to a report from The Brookings Institution. Of those who are released, almost two-thirds will return to prison within three years and 55% find employment within the first year of release. Not much of a second chance, right?

The formerly incarcerated face many challenges to get a second chance in our country from employment to housing to dealing with the stigma our society places on them. Even after they have paid their debt to society, they continue to pay long after they are released as they struggle to hold jobs and find housing.

However, there is a startup founder who is not only trying to solve this problem but has also experienced these issues as a justice-involved individual. He spent time in the federal prison system.

From 88Nine Radio Milwaukee, this is Diverse Disruptors, a podcast about leaders, entrepreneurs and trailblazers who found their own way to innovate and did so with inclusion and accessibility at the forefront.

This is the first episode of the second season and our guest is Ruben Gaona, co-founder of The Way Out. The Way Out is an anti-bias employment platform that specializes in the hiring of justice-involved job seekers and also provides additional social support services and technologies to help them integrate into their new roles successfully.

The Way Out even developed an app called My Way Out that that establishes real-time communication between returning citizens, reentry service providers and additional supportive service providers.

But before we learn more about The Way Out, I wanted to know more about Ruben’s story and his journey from a promising military career to time in federal prison to becoming a startup founder. His story is powerful and emotional and at times moved me to tears. We even shared a couple of things in common -- being veterans and loving chess. His story illustrates that you don’t have to be from Harvard or Stanford to build a successful startup.

Director of Digital | Radio Milwaukee