How Keidrain Brewster Drove His Life from Prison to Prosperity

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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