By Alexandria Staubach Ruben Gaona is ushering in an era of reimagined reentry services, led by the formerly incarcerated and aided by technology and a willingness to meet those returning to the community where they are. Gaona, a U.S. Navy veteran, served eight years in federal prison. Out since 2017, he knows personally the challenges of people transitioning out of incarceration. WJI recently talked with Gaona about his two initiatives: The Way Out, a tech start-up and “fair chance” employment platform, and My Way Out, a reentry service provider. Gaona described The Way Out as a blind dating app between individuals with a criminal history and those willing to hire them. On the employee end, the platform creates a cloaked applicant profile that leaves out all identifying information—“things that can introduce bias,” Gaona said. The employers only see qualifications—education, training, experience—and an individual’s criminal history. Because of the cloaking, an applicant can be honest without being unnecessarily public about their criminal convictions. On the employer end, the app lists job requirements, pay, and location while cloaking the company. Gaona said this permits the employer to be fully transparent and up front about what convictions are disqualifying and to participate anonymously. “Employers can shop for what they’re willing to accept” and “you’ll never have a bank get matched with someone who’s got a conviction for bank robbery.” Gaona and business partner Eli Rivers founded The Way Out following the pandemic, while Gaona was attending the University of Wisconsin-Milwaukee. The platform is live in Wisconsin, and Gaona hopes he’ll be able to expand the market. He is considering opening it up to veterans, who face some of the same challenges as the formerly incarcerated when they reenter the civilian world. More recently, Gaona’s focus has shifted toward the nonprofit My Way Out, which he founded in 2021. While working with The Way Out, Gaona keyed into a need to provide support services. “I wanted to help people sustain the employment opportunities we were helping them find,” he said. My Way Out has served approximately 1,000 clients since 2021. Its services vary based on the client. “Instead of creating something prepackaged, we focus on the individual and what the individual thinks they need,” Gaona said. Some things are recurring, however, with housing, employment, and transportation always at the top of the list. The organization has no physical office. The staff, who are not case workers or case managers, but rather “reentry partners,” go to the individual. “All of our work is on the ground,” Gaona said. My Way Out initially found clients through advertisements in a newsletter sent by The Community to men and women inside Wisconsin’s prisons. After that, clients came to the organization by word of mouth. “Social workers even reach out now,” said Gaona. Individuals scheduled for release or recently released fill out an onboarding application, identifying what support services they need. “We focus on three at time,” said Gaona. “Then we can scale up. Once you’re with us, we’re always with you.” Housing is the most consistent need, Gaona said. “How different does reentry look when you don’t have to worry about where you’re going to lay your head, especially in a state where seven to six months are cold?” Although housing has been difficult, it is also one way Gaona sees My Way Out growing. Earlier this year My Way Out secured a small grant from United Way and used it to pay the first three months of rent for clients. He hopes to expand that aspect of services. WJI asked Gaona about data supporting the effectiveness of his methods. Although My Way Out has significant volume in Milwaukee, “the tracking will take time,” he said. “The next three years will shed a lot of light.” But he believes that expanded access to housing will have a significant impact—that by addressing housing first, they’ll significantly disrupt recidivism. He’s not alone in that thought. "Housing first" is a homeless assistance approach that prioritizes permanent residence without preconditions and has greatly reduced chronic homelessness in Milwaukee over the last decade. Conor Williams, facilitator of the Milwaukee Reentry Council, told WJI that he, too, is a strong proponent of applying the housing first model to reentry. The council works to improve reentry outcomes and reduce incarceration. Nothing about the My Way Out program is court mandated, but Gaona has worked with the court system to make sure clients get credit with the court for his programming. In some cases that credit can affect the duration of supervision.
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