He Spent 20 Years in Prison

Now he’s spending his life helping those who have been incarcerated

By Princess Safiya Byers

This story was originally published by Milwaukee Neighborhood News Service, where you can find other stories reporting on fifteen city neighborhoods in Milwaukee. Visit milwaukeenns.org.

After 20 years in prison, Ed Hennings has dedicated his life to giving back to Milwaukee residents who have been incarcerated.

Now the owner of Go Time Trucking, which employs Milwaukeeans with experiences similar to his own, Hennings also works as a speaker, author and life coach helping formerly incarcerated people reacclimate to society.

Hennings was sentenced to 40 years in prison for first-degree homicide in 1996.

‘I didn’t understand patience’

He said he was a few months from graduating college in Phoenix when he decided to take a break and come back home to Milwaukee.

“I didn’t understand patience,” he said. “Almost everyone I knew was making quick money, and I wanted to keep up. I felt I was trying to do the right thing, and it wasn’t paying off.” So he told his mother he needed a break from college, and she sent him money to come back to the city.

“I told her I needed a little over $300 for a plane ticket but instead of buying a plane ticket, I bought a train ticket for $69.99 and pocketed the rest of the money,” he said. “I’d already plan to turn the money in my pocket into more money when I got home.”

He said that was the worst decision he ever made.

“When I got home, I hit the streets and started making fast money, and it was addicting,” he said. “I was 19 to 20 and I got hooked on the independence I had.”

Learning from his mistakes

Hennings said he made a lot of money in the few years before his arrest.

“I determined the day I was arrested that if I was given a second chance, I wouldn’t need a third,” he said.

Hennings said he has grown to appreciate his two decades spent in prison.

“That whole 20 years I was making myself the best version that I can be in every way possible,”

Hennings said. “So it was like a boot camp to serve to a certain extent. I took every class, every program, I just did a total overhaul on the person that I was.”

A new beginning

After his release, Hennings did some odd jobs before working in a barbershop and eventually opening his own.

“One day a client came in talking about how much money you can earn truc-king, and I immediately got intrigued,” Hennings said. “I started educating myself in the business and seeing what skills I had that would apply.”

He started Go Time Trucking five years ago, and things took off.

On top of his mentoring and trucking, Hennings now owns a clothing line, has two published books and is a podcast host.

“Because of the trucking business, I can do the community work that is important to me,” he said.

‘He gives his all’

Mary Roby, Hennings’ mother, said her son is passionate and determined.

“He is so concerned with the well-being of the community that he gives his all,” Roby said. “He’s very open about it. He’s willing to help wherever he can.”

“Ed is a positive role model to our members because of his powerful life experience,” added Steve Lied, the program administrator at Partners in Hope, a prisoner re-entry program. “He hits on important topics that resonate with people. I wish we could have him more.”

A love for Milwaukee

Hennings said he does all this work because he loves Milwaukee.

“Some of my heroes are from Milwaukee,” he said. “When I was younger, I was fascinated with our culture. We were a place that brought people from all over the country together.”

He said one of his goals is to help Milwaukee get back to a place where people want to be.

“Some of the best advice I ever received was to be great where you are and let it carry over,” Hennings said.

For more information, Hennings holds Zoom calls every Saturday to help people learn how to get into the business and get a truck of their own. He has information about those classes available online.