In this powerful episode of Second Chances @ Work, host Arti Finn sits down with Keidren Brewster, a formerly incarcerated entrepreneur, author, and founder of the Big Reform Movement. After serving 13 years in the Texas Department of Criminal Justice—beginning at just 17 years old—Keidren has transformed his life and is now the CEO of Brewster Logistics, a growing trucking company employing more than 15 people.

Keidren shares how the loss of his younger brother and mother during his incarceration served as turning points, inspiring him to take full advantage of education and personal development opportunities behind bars. From earning his GED to completing every class available, he made the decision to invest in himself. That mindset shift—combined with relentless hard work—set the foundation for his success on the outside.

Today, Keidren is a passionate advocate for second chances, mentoring justice-impacted individuals through his Big Reform Movement and speaking at reentry events across the country. He encourages incarcerated individuals to start their transformation while still inside and reminds correctional leaders of the power of lived experience in reentry programming.

This episode is a must-listen for anyone seeking proof that redemption is possible—and that belief, education, and opportunity can change lives. Keidren also shares why trucking is such a promising career path for people coming home from prison: it offers strong pay, doesn't penalize individuals for their record or appearance, and provides a tangible sense of freedom and purpose. With the launch of Orijin’s new CDL prep course, more justice-impacted learners will be able to follow that same road to opportunity.

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At Alameda County’s Juvenile Justice Center, a dramatic transformation is underway. Once operating near its 300-bed capacity, the facility now serves between 42 and 60 youth—a shift driven by intentional reforms, collaborative leadership, and a strategic embrace of technology.

This episode of Second Chances at Work dives into how Alameda County partnered with Orijin to integrate a digital learning platform that does far more than deliver education. Orijin is now embedded into behavior management, skill-building, and reentry planning—helping young people earn privileges through positive choices and access high-quality educational content, soft skills modules, and workforce training.

Superintendents Albert Bañuelos and John Ebrahimi share how Orijin’s Incentive Engine motivates youth to stay engaged, meet goals, and demonstrate accountability. From GED prep to entertainment, access is earned through pro-social behavior. The result? Improved facility safety, calmer living units, and a stronger culture of growth.

The conversation also highlights the power of voice calls through tablets, which have replaced conflict-prone shared phones. With over 648,000 minutes logged, these calls provide vital emotional connections that reduce tension and encourage reentry readiness.

Reentry Services Coordinator Rakeya Cherry-Hill discusses how technology supports individualized case plans and cognitive behavioral interventions—helping youth stay on track from day one through release. She also shares a promising initiative to grant school credit for tablet-based programming.

Whether you’re a correctional leader, educator, or policymaker, this episode offers valuable insight into how Alameda County is redefining rehabilitation—and why they believe in sharing their success with others.

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In this inspiring episode, Arti Finn, Co-Founder and Chief Strategy Officer, sits down with Tanaine Jenkins—TEDx speaker, award-winning recidivism strategist, and national advocate for probation and parole reform. Her journey spans military service, banking, incarceration, and ultimately finding her voice as a national leader.

Today, Jenkins serves as Director of the Florida Safety Coalition and State Organizer for Reform Alliance, the nonprofit founded by Meek Mill and others after Meek’s probation case exposed deep flaws in the system. Since 2018, Reform has helped pass 18 laws in 11 states, creating real second chances.

Jenkins shares stories from her childhood in Jacksonville, her military service, and the financial struggles that led to her incarceration. But it’s her post-release journey that stands out. She explains the "second sentence"—the 33,000 invisible barriers justice-impacted individuals face after prison, from employment discrimination to blocked access to licenses and insurance.

She also breaks down the hidden traps of probation and parole: monthly fees, drug testing costs, and violations for things like crossing county lines to reach a hospital. It’s a system stacked against success—and one Jenkins is working hard to change.

But her story isn’t just about barriers—it’s about breakthrough. During the pandemic, she paid off nearly $20,000 in restitution by delivering DoorDash orders. She invested in herself, refined her public speaking skills, and began sharing her story—first at the Florida Capitol, then on the TEDx stage.

Today, she's leading change. In Florida, Jenkins helped push for SB 752, which rewards probationers with time off their sentences for maintaining steady work or earning credentials like a GED or vocational certificate.

Jenkins and Finn discuss what’s needed to break the cycle: fair chance hiring, mental health support, and ending the stigma facing returning citizens. Jenkins reminds us that justice-impacted individuals aren’t liabilities—they’re often the hardest-working people, if given a real shot.

She leaves listeners with this powerful message: "Starting over isn’t starting from scratch. It's starting with experience. Forgive yourself, make a plan, and know that your best days are still ahead."

Whether you're a correctional leader, policymaker, employer, or someone rebuilding after incarceration—this conversation is for you.

Tune in to hear Tanaine’s incredible story and be part of the change.

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