'The Fall of a Financial King: The James Catledge Story'

What happens when a man builds an empire from ashes, only to discover the real treasure was learning how to rise from the fall itself?

When I sat down with Carlos Harris, I thought I was interviewing a successful tech entrepreneur who’d overcome his past. What I discovered was something far more profound, a man who’d turned his darkest chapters into the blueprint for helping others rewrite their own stories.

Carlos isn’t your typical technology executive. As co-owner and chief operations officer of DSDT (Detroit School for Technology), he’s spearheading second-chance initiatives and building partnerships with everyone from the Michigan Department of Corrections to the U.S. Department of Labor. But here’s what makes his story extraordinary: he’s doing all of this without a college degree, after spending 11 years in prison across three different sentences.

From Church Boy to Criminal Mastermind

Carlos’s transformation didn’t happen overnight. Raised by his grandmother in Helena, Arkansas, until age 15, he had the foundation of faith and discipline. But when life threw him curveballs, his father’s death at 23 from a heart attack, leaving home at 15 to avoid another beating, moving to Michigan with nothing but $60 from his pastor, those boundaries started shifting.

“My grandmother would say I was bad as hell, but good teacher,” Carlos told me, and that contradiction would define his early adult years. The kid who’d been raised Southern Baptist, who played in the band and made the diving team, slowly found himself drawn into a world where quick money trumped slow progress.

The turning point came when he saw more cash than he’d ever imagined, money from his mother’s boyfriend’s bank robbery. “First thing that popped in my mind was I can do that,” Carlos reflected. “Not one time did I think not to do it. I just thought about that I could do it better than what he did.”

That mindset, the obsessive pursuit of excellence, even in illegal activities, would both destroy and ultimately save him.

The Professor of Prison Economics

What fascinates me most about Carlos is how he approached crime like a tech startup. He identified a market inefficiency (cigarette distribution), built systems around it, and scaled ruthlessly. “We would literally hit, we call them hit licks… we would do breaking and entering into businesses that were next door to police stations… for the thrill of it,” he explained.

But here’s where Carlos’s story gets really interesting. Even while running this criminal enterprise, he never stopped taking classes at community college. He was literally straddling two worlds, attending accounting and typing classes by day, coordinating cigarette heists by night.

“If I’m gonna be a criminal, I’m gonna be the best criminal period,” Carlos said, and that obsessive mindset is exactly what makes him exceptional in legitimate business today. “I’m obsessed with whatever I set my mind to.”

The judge who sentenced him said something that stuck: “Mr. Harris, I see that you have all these felonies, 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.” Carlos just smiled, knowing she was seeing only the few times he’d been caught, not the hundreds of times he’d succeeded.

Building Systems That Actually Work

Here’s what blew my mind about Carlos’s reentry story: he stopped listening to the “experts” and started building his own path. While everyone told him he could get a job as a janitor with his custodial maintenance technician certificate, Carlos had bigger plans.

“I stop listening to those that were in a place to tell me this that other and start just doing what I thought would be best for me,” he explained. That rebellious streak that got him into trouble became his greatest asset in building something legitimate.

Today, Carlos can set up an entire business, domain registration, website, phone lines, state registrations, business plan templates, funding preparation, in three days. Those same systems-thinking skills that made him successful in illegal cigarette distribution now help him run a technology school and advocate for criminal justice reform.

The man who once owed $9,000 to a pool shark named Night Train now sits on Google roundtables discussing second chances in technology. He’s not just surviving reentry, he’s redefining what’s possible.

What strikes me most is Carlos’s honesty about the path. “It’s not easy,” he admits. “But guess what? It’s not supposed to be easy. Why? Because if it was easy, everybody would be doing it.”