From Prison to the Oval Office - Glenn Martin

From Rikers to the Oval Office

Okay Nightmare Success lifters, we are back, and man am I excited about this guest. Glenn Martin had a conversation with President Obama in the White House about criminal justice reform. But that’s not where his story starts. It starts at 16 years old, getting stabbed on Rikers Island with a melted pen turned into a shank.

“I grew up in Brooklyn, Bedford-Stuyvesant, relatively tough neighborhood back then we’re talking about the late 70s early 80s,” Glenn told me. “Single parent ultimately, mom at work most of the time just trying to make ends meet, and you know the streets were calling.”

His dad was a chief of police. His older brother became a U.S. Marshall. Glenn took a different path. At Macy’s on 34th Street, he was arrested for attempted shoplifting. The judge looked down at him and said he was sending him to Rikers with $1,500 bail “to teach you a lesson.”

It taught him something, all right. But not what the judge intended.

The Lesson Rikers Actually Taught

Three days into what was supposed to be a short stay, Glenn faced his moment of truth. A guy approached him and demanded his jacket.

“That really is your moment to decide whether you’re gonna survive,” Glenn explained. “We got into a fight and before you knew it four guys were on top of me and one of them was stabbing me with a pen that was melted into a shank.”

The lesson Glenn took wasn’t fear. It was the opposite. “If I can toughen up enough to survive this then I can survive anything this world has to offer,” he reasoned. He was trying to escape poverty by any means necessary. In his neighborhood, shoplifting seemed like more of an opportunity than college.

Eight years later, he graduated to robbing jewelry stores. Multiple robberies, 120 counts, and a first plea offer of 20 to 40 years. He was 24.

The System’s Ugly Truth

Glenn hired one of Brooklyn’s best lawyers. The lawyer became friends with the judge. The judge bought a boat from the lawyer during Glenn’s case. Glenn’s sentence dropped from a potential 40 years to three to nine.

The prosecutor was furious. “Your honor I want to go on the record as disagreeing with the plea you are about to get Mr. Martin,” the prosecutor said. “In fact this was one step short of organized crime and Mr. Martin was the head of it.”

Glenn learned something that would fuel everything he did afterward. “It left me with a fire in my belly particularly when I got to state prison because I realized we lock up some of America’s best and brightest and that’s not the story we tell about who’s in prison,” he said.

The connection between money and justice bothered him. There were brilliant people rotting in prison for decades who could never buy the kind of legal help that cut his sentence by more than half.

Finding College Behind Bars

Prison surprised Glenn. He expected something like Rikers. Instead, within his first hour, people were helping him get set up. A guy at his bunk told him he didn’t look like he’d ever been there before and gave him help navigating the system.

During orientation, a corrections counselor looked at Glenn’s test scores and told him he should go to college. Glenn thought it was BS. But the counselor made sure Glenn landed at a prison with a college program born out of the Attica rebellion in the early 70s.

Glenn started taking classes. He remembers being in statistics class, trying to convince the professor that buying more lottery tickets improved his odds of winning. The professor helped him understand how wrong he was. “Moments like that and then also moments like you know guys like hey help me write your paper help me understand let’s talk about the book that we’ve read together,” Glenn said.

He took Russian literature as an independent study. He read the Wall Street Journal and New York Times, looking up every word he didn’t know. Prison became his education.

The Gift of a Painful Truth

On his release day, Glenn walked alone to the administration building with his wheelbarrel of belongings. The sergeant processing his release didn’t recognize him after five years.

“How long have you been here?” the sergeant asked. When Glenn said five years, the sergeant laughed. “You know you being here help me get my boat. When your son gets here he’s gonna help my son get his boat.”

Glenn calls it a gift, even though it was painful. “The truth is always a motivator for me even when it’s painful,” he told me. His son is now a U.S. Marine who owns multiple businesses and has been to 22 countries in the last three years.

The Reality of Reentry

Glenn landed in Midtown Manhattan after years of no fast movement, no cars, no cell phones. The sensory overload was jarring. Then came the job search. He visited 50 employers in 30 days and was turned away solely because of his felony conviction.

One guy finally offered him a job selling designer sunglasses. “You’re perfect,” the man said. “I need a person of color who’s articulate, a salesperson, I think you can sell.” That evening, the man called back. He’d done a background check and rescinded the offer.

Glenn started thinking about robbing jewelry stores again. Then he found a small reentry organization run by a formerly incarcerated man who told him, “You’re me, I’m you 10 years ago. I’m not gonna allow you to fail.”

The job paid $16,000 a year answering phones. Glenn owed $83,000 in fines, fees, and restitution. But it was a start.

Building Something Bigger

Glenn worked his way up from $16,000 to $73,000 at that nonprofit. He learned a key principle: if you can figure out 60 to 70 percent of something, you’ll figure out the rest. A mentor once told him he wasn’t ready to start his own organization yet. He took the advice, spent six and a half more years learning, then launched Just Leadership USA.

The organization became nationally known. Glenn raised over $43 million in the nonprofit sector. He founded multiple organizations and consulted with others. In 2016, he received the Robert F. Kennedy Human Rights Award.

And in 2015, he sat in the Oval Office with President Obama, discussing criminal justice reform. The kid who got stabbed on Rikers was now advising the President of the United States.

Glenn’s journey proves something he learned in prison: the people closest to the problem are closest to the solution, but farthest from power and resources. His life’s work has been bringing those two things closer together.