Joe Robinson: 24 Years in Prison to Financial Literacy Advocate

“We don’t have to be defined by the worst decision we’ve made.”

Joe Robinson’s story starts with one of my favorite movies: An Officer and a Gentleman. As a kid in Brooklyn, he watched it over and over on his mom’s color TV while babysitting his siblings. He wanted to be a pilot. He took flying lessons in high school. He had goals.

Then crack cocaine hit East New York in 1985, and everything changed.

When Crack Destroyed a Family

Joe was born in 1970 and raised mostly in East New York, Brooklyn. There were five kids, a working-class family, not much money but plenty of love. His mom constantly told him how smart he was, how much he could accomplish if he put his mind to it. That message stayed with him for decades, even through the worst of it.

“In 1985, my whole family life changed,” Joe told me. “Crack hit New York City by storm.”

He was 15, in tenth grade, walking to school and seeing crack paraphernalia littered everywhere. Women in their twenties propositioning him for sex in exchange for drugs. He didn’t understand what was happening at first.

Then one day, babysitting in his mom’s room, watching An Officer and a Gentleman on her color TV (they had black and white everywhere else), he bumped into a jewelry chest by accident. Crack vials spilled out.

“I said to myself, my mom is one of them. It was devastating.”

His baby brother found the paraphernalia too, brought it to Joe asking what it was. Joe snatched it out of his hand, never answered the question. The family went from tenement buildings to homeless shelters. His mom was in and out, spending less and less time with them.

From A Student to Rikers Island

Joe was the oldest of five. Without his mom around, he started drifting toward the neighborhood crowd. By 16, he was on Rikers Island for four months.

“I wasn’t as tough as I thought I was,” he admitted. “It was brutal. I saw people being violent like it was a sport.”

He survived, got his GED while inside, got out in May 1987. Worked a little, then went to college the next year at SUNY upstate. He was studying for the A&P (airframe and powerplant) program since he couldn’t afford Embry-Riddle, his dream school for becoming a pilot.

But college exposed a painful truth: Joe wasn’t ready. Not emotionally, not developmentally. He got caught up in parties, lost his way. That first semester his girlfriend back home got pregnant. He couldn’t concentrate knowing he had a child on the way.

“I didn’t want to be a deadbeat dad like my father,” Joe said. He left school, moved in with his girlfriend’s mom in Harlem, worked minimum wage jobs that paid three or four dollars an hour. It wasn’t enough.

The Fast Money Trap

Desperate and without a college degree, Joe connected with some guys he’d met at school who were making fast money selling crack upstate. Within an hour or two, everything he bought was gone. He was hooked on the lifestyle.

“I was a good salesman, good communicator, good with people,” he recalled. “I got addicted to the fast money, the fast women, the fast everything.”

But there was always that yearning for a normal life underneath. Even while dealing, he knew he had bigger dreams. He moved down to North Carolina with family, trying to get out, but kept getting pulled back.

In October 1991, Joe was 21 years old. He walked into a bar to meet a young woman. The guy who approached him had threatened him months earlier over a robbery attempt Joe had nothing to do with. The guy was armed. Joe disarmed him in a panic. The gun went off.

Joe ran. He was on the run for five and a half months, exhausted, terrified every time a cop car passed. Eventually he was arrested in Brooklyn after a combination of malt liquor, NyQuil, and sleep deprivation left him disoriented and fighting with strangers at a bodega.

He woke up handcuffed to a hospital gurney, told he was wanted for the crime upstate.

Twenty-Five to Life

Joe went to trial. The plea started at 20 to life. He countered with eight years. They couldn’t agree. In February 1993, he was convicted. In April, sentenced: 25 years to life.

“I was 22 going on 23. I hadn’t even lived 25 years. I couldn’t fathom what that was like.”

The first prison was Elmira. Joe spent almost every day in the law library, searching for that magic key that would get him out. The correctional officers noticed his dedication. One of them gave him a standing callout so he didn’t have to fill out forms every day.

He worked out to keep his sanity. Minded his business. Kept his circle small. And he started reading books on personal finance and entrepreneurship in the general library.

Teaching Money in Prison

The financial education came from a painful realization. Every time Joe had gotten arrested, it was about money or material things. He needed to understand money the legal way.

“I took to it naturally. Investing in stocks and bonds, mutual funds, business. It just made sense.”

By 1995, someone overheard him talking about investing and asked him to teach their organization’s members. Joe was intimidated. He was 25, teaching guys 10 or 15 years older. But he put together a curriculum, taught his first class, and never looked back.

“It was like a high. The responses I got, the fact that I was making a positive difference in someone’s life. I never turned back from there.”

He became known throughout the New York state prison system. Even the tough guys would pull him aside in the yard asking for investment tips. Joe realized he needed to monetize his knowledge. In 2007, still inside, he published his first book: “Think Outside the Cell: An Entrepreneur’s Guide for the Incarcerated and Formerly Incarcerated.”

His wife made it happen. They’d met through correspondence while he was inside and married while he was still incarcerated. She’d worked at the New York Times for 31 years. When Joe told her his idea, she said she didn’t know anything about business but would do whatever he needed.

Coming Home After 24 Years

Joe served 24 and a half years. He got out in 2016 at age 46. He was lucky: he had a wife, a home in the West Village, and a $50K job waiting for him.

But the internal reentry was brutal.

“The palpable and strong feeling of sense of loss,” Joe said. “25 years. That was half my life. Gone.”

He’d sit at breakfast with his wife, unable to articulate what he was feeling. The technology was overwhelming. He went in before the internet existed. Passwords, apps, constant notifications. He felt incompetent some days.

And his relationship with his son, born right before everything fell apart, remains difficult. Joe watched him grow up in pictures sent to prison. They were close for a while after release, but things have been strained for the past several months.

Mindful Money

Today Joe runs Mindful Money, a personal finance education company for people impacted by the criminal legal system. He does speaking engagements at reentry organizations throughout New York City. He’s writing a memoir, set to release next December to honor a brother they lost. He’s writing a book profiling formerly incarcerated entrepreneurs. And he’s working on a ghost-writing book to help people who have stories but don’t feel like good writers.

“I care about this stuff,” Joe told me. “I don’t want people, especially young people, to have to go through half the crap I went through. Financial literacy is a tool to shift mindsets. Not to serve money, but to have money serve them.”

His biggest takeaway from 24 years? “We don’t have to be defined by the worst decision we’ve made. That doesn’t define me. That’s not who my mother raised.”

You can find Joe’s book “Think Outside the Cell” on Amazon and reach him at mindfulmoneyllc@gmail.com.