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'I'm not finished yet': Milwaukee man starts third business following his release from prison

After two decades behind bars, Ed Hennings is using his businesses and his story to help other formerly incarcerated people get back on their feet.
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After taking the darkest time in his life and turning it into a lesson, Ed Henningsis now moving forward and giving back. After being sentenced to 40 years and spending 20 in prison, he is on his third business endeavor; but it all started in 2016, once he was released.

“A lot of people say ‘You had 40 years!’ and all I seen was I got a chance,” said Hennings. “20 years later, I got out, and that’s what I was able to hold on to, that I had a chance.”

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Over the past seven years, Ed has done a lot with that second chance. He started a barbershop within a year of being released from prison, and just four months after his shop opened, was inspired to take on another challenge.

“A client sat in my chair, I was cutting his hair, and he was telling me about a truck that he had purchased and the type of work he was doing with it, and I thought to myself ‘wow, man, I think I got in the wrong business.’”

That week he bought his first truck and began another business called Go-Time Trucking.

“Six in the morning to six in the evening I would be doing deliveries and I would get out of the truck and cut hair from six at night to eleven-o-clock at night, seven days a week.”

After two years of working double duty, Ed is now focusing on trucking full-time. But if you ask him what he does for a living, driving won’t be his answer.

“My main business really is inspiration," he said. "So, I will always push and have different endeavors as I go forward.”

He’s using that inspiration to hire other formerly incarcerated people to work under him and make a living. He says being someone that has walked the same path makes a difference in understanding people in that position.

Todd Jones has been driving for Ed for almost a year now and says that understanding the system and what they both went through, means everything.

“I’m incredibly grateful that I had especially him, someone that I knew because so much of it boils down to trust of the individual,” said Jones.

Now, Ed has started a new chapter: a shoe company made by truckers for truckers called Ed Hennings Shoes & Boots. As he steps into this new role, his goal remains the same: setting an example for others that hard times come with hard-earned lessons and a path toward a better future.

“There’s some things that a piece of coal has to go through before it becomes a diamond,” Hennings said.

Ed is also an author and spends time speaking to current inmates about his story.

His new shoes are for sale now on his website.

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