The Unfiltered Journey of Karlos Harris: From Helena to Empowerment

Karlos Harris had a question for me when we talked on the podcast. “I don’t know if I stated, but my dad died when I was six,” he said. “He was 23 years old.” Then he paused. “And my dad died from a heart attack.” Karlos just turned 52, and a couple weeks ago, he had his own heart attack. The parallels weren’t lost on either of us.

What makes Karlos’s story fascinating isn’t just that he survived 11 years in prison across three separate sentences. It’s what he built afterward. Today, he’s the co-owner and chief operations officer of DSDT, Detroit School of Digital Technology. He’s establishing partnerships with the Michigan Department of Corrections, the city of Detroit, and the U.S. Department of Labor. The school operates out of an old jail, which feels like the kind of detail you couldn’t make up.

From Helena to the Streets

Karlos grew up in Helena, Arkansas, raised by his grandmother after his mother left when he was three. “My grandmother would say I was bad as hell,” he told me with a laugh. At 15, he’d had enough of the Southern discipline. “She was going to whip me one day. You know, what about weapons? Southern weapons. I had one of those. We’ll pick some limbs that fought. Get your own switch and break it up. That weeping willow tree. I was done taking weapons. I just, it was over. I was 15.”

He left that day and never went home. His pastor eventually bought him a bus ticket to Michigan with three conditions: don’t have children too young, don’t get into drugs, and graduate high school. “I kept one of them,” Karlos said. “I’ll let you guys guess which one that was. I’ll tell you this. I graduated.”

Michigan gave him structure initially. His uncle got him jobs at Farmer Jack and Honey Donuts. He finished high school while working, even joined the dive team despite never having access to pools in Arkansas. But responsibility hit fast when he had his first child at 17.

The Technology Obsession

Even while navigating street life, Karlos stayed drawn to technology. “I remember when the first computers came online. And I can remember breaking into them, you know, in order to whether it was swapping out a motherboard or the CPU or whatever the case it was. I like to tell the students around here before there was Cisco that was me.”

His approach to learning was always hands-on, even destructive. “I believe in being auto-diabetic. It’s a word that I learned along the way. And it expresses who I am 100% to a fault. I don’t like to be told how to do anything. I like to sit down with it to break it. If it takes 10,000 times to get it right, I love the process of the 999 times.”

That obsessive quality would serve him in multiple contexts. “If I’m going to be a criminal, I’m going to be the best criminal period. I don’t care what it is. If it’s bank robbing, if it’s hijacking, whatever it is, I’m going to be the best. Because I’m obsessed with whatever I set my mind to.”

The Cigarette Business

The criminal career started almost accidentally. Karlos owed $29,000 from gambling, mostly shooting pool. When his mother’s boyfriend snatched a bank deposit bag and got caught, Karlos saw the money. “It had to been, I don’t know, maybe about $12,000 in cash. First thing that popped in my mind was I can do that.”

One liquor store break-in led to something bigger when Karlos grabbed cigarettes on impulse. A friend’s father, who owned a convenience store, offered to buy them at half price. “A pack of cigarettes, four thirty five, four dollars, thirty five cents. There’s 10 in a carton. That’s forty three dollars and fifty cents. If you get one hundred cartons, that’s four thousand three hundred and fifty dollars.”

The math was simple. The execution became systematic. “We would literally hit, we call them hit licks. So we would do breaking in rings into businesses that were next door to police offices. For the thrill of it. We’d scope out the business, scope out the station that was next door. Our whole plan is how fast can we get in to grab them? We can grab upwards of maybe 200 cartons in less than two minutes.”

Three Sentences, Eleven Years

The arrests came eventually. December 1999, July 2003. October 2005, November 2010. November 2013, September 2014. Three separate sentences totaling 11 years. The judge during one of his later appearances told him bluntly: “Mr. Harris, I see that you have all these and you’ve been to prison and yet you continue to do what you’re doing. Apparently you’re not that good of a criminal.”

Karlos’s response surprised me. “I just sat back like I was like the fat cat who ate the canary. Yes, Your Honor. Because I literally can count hundreds of times that I’ve gotten away.”

Prison taught him systems thinking in a different context. “Anybody that has done time before knows how difficult it is to reacclimate yourself once you come home. One of the hardest. It’s just it is what it is. It’s not that I wasn’t transforming my thought process, even from the first time, it’s just that I didn’t have the support and the opportunities that you have in 2025.”

Building Something Real

Today, Karlos applies that same obsessive energy to legitimate work. “When it came to even being a partner here at the school and building it out, I was obsessed with it for many years. I mean, there were many nights that I didn’t sleep because I had to figure out, how do we come up with systems in order to find what would be veterans or general students, our fast-paced students, or how do we hire people all sure to be members of the team?”

The technology skills he’d been developing since high school finally had proper outlets. “Nowadays, whether it is to set up a business and build the digital presence or whatever the case may be, I can normally do that in about probably at the latest. Three days. Build all the online content, build the website, register the domain, set everything up, set up the phone lines, do everything.”

His story illustrates something I’ve seen repeatedly: the same qualities that can destroy you in one context can rebuild you in another. Obsession, system thinking, and the willingness to break things to understand them. The difference is channeling those traits toward something that builds rather than tears down.

Karlos is 52 now, dealing with his own heart issues and thinking about legacy. His school operates from an old jail, training people in digital technology. Some of his students probably remind him of himself at various stages. The irony isn’t lost on him, and it shouldn’t be lost on us either.