The Unfiltered Journey of Karlos Harris: From Helena to Empowerment

When your business partner operates out of an old jail, it might raise some eyebrows—until you learn that your partner spent 11 years behind bars and transformed that experience into a mission to change lives.

I’ve been having some incredible conversations on Nightmare Success, but my recent chat with Karlos Harris left me thinking about how our worst experiences can become our greatest qualifications. Karlos is the co-owner and chief operations officer of DSDT, Detroit School of Digital Technology, where he’s training people in fields like AI and digital marketing. What makes his story so powerful is that he built all of this without a college degree—and after serving three separate prison sentences.

From Helena to High-Speed Chases

Karlos grew up in Helena, Arkansas, raised by his grandmother after his mother left when he was three. His father died of a heart attack at just 23 years old. By 15, he’d had enough of the strict discipline and moved out on his own. “My grandmother would say I was bad as hell, but good hearted,” Karlos told me, and that combination of trouble and heart would define his next few decades.

When he moved to Michigan at 17, chasing dreams of being a rapper, life took a different turn. Working factory jobs, living paycheck to paycheck, and owing $9,000 from gambling debts, Karlos found himself looking for any way to make quick money. When his mother’s boyfriend got caught snatching a bank deposit bag, Karlos saw all that cash and thought, “I can do that better than him.”

That decision launched him into a criminal career focused on cigarette theft—breaking into stores, building distribution networks, even hitting businesses next to police stations for the thrill. “If I’m gonna be a criminal, I’m gonna be the best criminal period,” he said. That obsessive mindset would serve him differently later, but first, it led to multiple arrests and eventually an 11-year journey through the prison system.

The Education No One Wants

Here’s what struck me most about Karlos: even while living this street life, he never stopped taking classes at community college. He was literally straddling two worlds—studying accounting and typing classes while running cigarette operations. As he put it: “We are pre-programmed that you need higher schools of education… but I learned that wasn’t actually the truth. You just need to be educated. You can go to the military and be educated or you can go to college and get your degree or you can get out here in these streets and end up in prison and get educated. Just depends on what the education is.”

That last stint—triggered by a high-speed chase after another cigarette heist that left both his legs broken—became his turning point. While serving time, he was already planning differently. He studied business essentials, wrote business plans, and made a crucial mental shift: he decided to chase opportunities, not money.

Building Systems Instead of Schemes

When Karlos got out the final time, he went to a Detroit homeless shelter by choice. He wanted something completely different—new city, new people, new possibilities. Within a week, he met his mentor Ezra Brown at the parole office, who was teaching a business course. That connection changed everything.

The same systematic thinking that made him successful as a criminal now fueled his legitimate business ventures. “Whether it’s setting up a business and building the digital presence or whatever the case may be, I can normally do that in about probably at the latest three days,” he explained. All those years of trial and error, of building distribution networks and managing operations—those skills transferred directly into the business world.

Today, Karlos has partnerships with the Michigan Department of Corrections, the City of Detroit, and the U.S. Department of Labor. He’s training people in cutting-edge technology fields, providing second chances to others who’ve walked similar paths. Google even featured him in a roundtable discussion about people who’d made the most of their second chances in tech.

The guy who once thought he’d never measure up to Bill Gates or Mark Zuckerberg is now creating his own lane in the technology space. And he’s doing it all while carrying the weight of karma—knowing he violated the sanctity of many businesses over the years, but using that understanding to build something meaningful.

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