The Journey of Ben Robinson: From Solitary Confinement to Entrepreneurial Success

From the Streets to Tech School

When I talked with Ben Robinson on the podcast, one thing stood out immediately. Here’s a guy who dropped out of high school, spent a year hanging around the block, then walked back into Roosevelt High School and re-enrolled himself. “Me and one of my friends was like, hey, man, there’s nothing going on out here until like two thirty three o’clock, man. We might as well just go get back in school, man,” Ben told me.

That decision led him straight through graduation and into ITT Tech, where he earned an associate degree in computer networking. But Ben was straddling two worlds. He’d leave his friends on the corner, saying “I’ll be back. They like, where you going? I’m like, man, I gotta go to night class. I’ll be back. I’ll see y’all later.”

Ben grew up in St. Louis as the baby of the family with two brothers and two sisters. Early on, his family moved to Kansas City, where he attended Seminary Academy and got into gymnastics and swimming at a competitive level. When they moved back to St. Louis around age eight, he shifted into football, playing tight end and wide receiver. The sports background served him well, but the streets were calling too.

Building an Illegal Business

After tech school, Ben dove deeper into selling marijuana and cocaine. What started as survival mode evolved into something more calculated. “Once I climbed the ladder, you know, a couple years later, I started looking at it as a business because I was protecting myself, I was, you know, raising myself, semi, and I was raising a little girl at that as well,” he explained.

By 21, Ben had his own house and was supporting his 18-month-old daughter. The business skills were real, even if the product was illegal. He understood distribution, clientele, and cash flow. But the lifestyle had trapped him. When ITT Tech connected him with a potential job at Boeing fresh out of school, he couldn’t take it. “They tell us the after the interview, you know, it was like a grouping, but it was only like a few of us there from ITT Tech. And it was like seven or eight people from other colleges so I’d be like, Hey, you guys after this go down the street to your UA. I’m like, I can’t do that. You know, I smoke weed every day.”

That missed opportunity at Boeing eating at him. Starting pay was good, benefits were solid, and it could have been his way out. Instead, he stayed locked into street life.

The Federal Trap

The dominoes started falling in 2008. First, Ben almost got caught by police while getting into his car near the corner where he parked. “I was dirty,” he said plainly. He made it out of that one, but then someone snitched. “I got guinea pigs, you know, there’s, you know, how that is. Just when I actually got it and got jammed up with the time, it’s when I got guinea pigs and told the police to protect the sex. I was the one that he was doing when it was actually the other way around.”

The federal system doesn’t play games. Ben was facing a mandatory minimum of 120 months, 10 years. When his lawyer first came with a deal for more time, Ben’s response was immediate: “I was like, no fucking way. I said, my daughter’ll be 12, man. No fucking work.” But federal conviction rates sit at 95 percent. The odds were stacked.

The trap closed when Ben went downtown to retrieve personal property the police had taken during his arrest. His girlfriend went with him to the federal building. “Go downtown, turn off first, get on it. Now they call me back down there to get my bag. Go back down there to get my bag to the check is walking in behind me. Yeah. Oh, you got a federal indictment.”

Ben called his mom from the back of the police car while handcuffed, watching them decide whether to turn left toward county jail or right toward the federal building. They turned right. That was March 2008, and he wouldn’t sleep in his own bed again for over a decade.

The Prison Tour

Ben spent eight months in Lincoln County jail before getting shipped to Oklahoma’s transfer center during the holidays. Weather delays and lockdowns at other facilities kept him there for three months. “I was in Oklahoma from the first week before Thanksgiving and to the first week before Valentine’s Day,” he said. The whole unit was stuck together, cycling through the system.

His first real stop was USP Lee in Virginia, literally carved into a mountain in the middle of nowhere. Ben was supposed to go to a medium-security facility, but the computer said otherwise. As he put it, old-timers at the transfer center asked where he was going: “They’re like, man, what the hell you do?”

USP Lee was an eye-opener, but Ben adapted. That became his strategy throughout the whole sentence. He kept his profile low, stayed out of trouble, and focused on getting closer to home. From Virginia, he transferred to Pollock, Louisiana, then to Oakdale, and finally made it to the minimum-security camp at Fort Leavenworth.

Two Weeks from Freedom

At Leavenworth, Ben worked at the Fort Leavenworth golf course, one of the best jobs you could get. Community custody meant leaving the prison grounds every day, seeing regular people, cutting grass, trimming around sand traps. After years behind fences, it felt like a taste of society.

With two weeks left on his sentence, Ben was working hole number two when he saw a scanner pull through. Prison vehicles came through the golf course regularly, so he didn’t think much of it. That changed fast.

“They came and kicked me up out there and I was like, yo, I actually honestly thought like something caught up with me from before my case, like before everything, but once they took me to the big house and I looked around, I was like, y’all got the wrong guy,” Ben told me.

Someone had made an allegation. Ben spent the next three months in solitary confinement while they investigated. He could have lost his release date entirely. For someone who’d already served over nine years, that was devastating.

Through it all, Ben held onto two things that kept him grounded: his mother and his daughter. Every time he wanted to lose it, make bad decisions, or crash out, he thought about them. “Every time it was coming to a time for me to crash out,” he said, “moms and daughter kept me grounded the entire time.”

The investigation cleared him. Ben walked out of Leavenworth as scheduled, but those final three months in the hole were perhaps the hardest part of his entire sentence. Two weeks from home, back in solitary, wondering if someone’s lie might cost him another year.

Today, Ben’s building something legitimate. The business skills that got him in trouble are the same ones helping him succeed on the outside. The difference now is the product is legal, and the only bars he sees are the ones on his phone checking stock prices.