Startup aims to create meaningful employment after incarceration

Formerly incarcerated job seekers face not only a stigma, but also a five-times-higher unemployment rate.
person walking out of bars

After Ruben Gaona paid his debt to society, he was ready to work. Thirteen days after his release from federal prison for drug-related crimes, the U.S. Navy veteran applied for a nearly $20-per-hour job as a case manager for a workforce development company. Its operations manager said his skills and experience made him a great fit, and he was sent to the staffing agency that handled all company hires. It was supposed to be a formality, but when the agency recruiter learned of Gaona’s criminal record, she suddenly told him that job had a one-year waitlist and offered him a $7.50-per-hour janitorial position instead. “My kid’s working at Taco Bell — he makes $9.50 per hour, and I’ve got to go home and take care of him still,” Gaona recalls. “I got into the car and started crying.”

As embarrassed as he was, Gaona’s wife insisted he let the original manager know what had happened. That manager confirmed there was no waitlist, arranged for him to interview directly with the company and Gaona got the better-paying job for which he was qualified.

Formerly incarcerated job seekers face not only a stigma, but also a five-times-higher unemployment rate (pre-COVID-19), which leads to recidivism; 70% are unemployed a year after reentry and 65% return to prison within three years. According to the U.S. Department of Justice, each prisoner costs taxpayers about $35,000 a year to house, to the tune of more than $80 billion a year — to say nothing of the economic hardship faced by families with a loved one in jail, the ripple effect on communities and the well-documented racial disparities permeating through the criminal justice system.

“Our mission is to close equity gaps in America, and we believe that social innovation and entrepreneurship can play a major role in that,” says Shayna Hetzel of The American Family Insurance Institute for Corporate and Social Impact, or The Institute, which was already researching the staggering rates of incarceration in communities of color and hoping to address these issues through innovation.

Nationally ranked startup accelerator gener8tor has also expanded its focus over the last several years, casting a wider net to include artists, musicians and social impact entrepreneurs. After examining startup solutions to mass incarceration and recidivism, gener8tor teamed up with The Institute to expand social impact programming this May, announcing six gALPHA and two gBETA Social Impact cohorts focused on criminal justice and equity in education.

That’s how Gaona met Eli Rivera. Together, they founded The Way Out, a sophisticated employment platform that connects qualified justice-involved job seekers with the right employers. The technology is being developed by University of Wisconsin–Madison computer sciences professor Vikas Singh.

“Once you have the job, you have the financial resources for a home to support your family. It’s about that first step of reclaiming your dignity,” says Rivera, who also served federal time for drug-related crimes. He considers himself lucky he was able to build a successful hospitality industry career, including creating the ShyftFly app to help restaurant owners train employees.

Now, like Gaona, he wants to help all individuals struggling with a criminal record. By the time they met through gener8tor, Gaona — who is still working toward a social work degree at UW–Milwaukee — had helped start Destined to Succeed, a staffing company. The duo combined their experiences and were accepted into gALPHA, a free four-week program that guides participants in developing ideas and making connections. They hope to be accepted in the seven-week intensive gBETA Social Impact program to refine their business model to attract investors and ultimately bring The Way Out to market.

“Don’t allow society to put that stigma that just because you’re a felon, you’re a failure,” Gaona says. And Rivera adds: “We want them to have careers. … We want them to become completely functioning and self-fulfilled individuals involved in our society.”

Maggie Ginsberg is a monthly columnist and senior contributing writer for Madison Magazine.