Formerly incarcerated duo share their successes in the trucking industry with a podcast and online course

Facing the consequences of their crimes, Ed Hennings and Aaron Smith vowed to right their lives.

“I paced in my cell, I made some promises to myself," Hennings, a Milwaukee native, said of the time he waited for a guilty jury verdict. "I wasn't living up to my full potential. I walked out of school when I shouldn't have, trying to get instant gratification."

Meanwhile, Smith said while in prison, he had an awakening.

"I went back to the essence of who I was, I began to dream again," he said. "I had the chance to spend time around men that were inspiring entrepreneurs and white collar offenders who taught me a lot about business. ... I learned more on the streets, including prison, more than I learned in college."

The pair are working to help others benefit from what they have learned. They've teamed up for "The Urban Trucker Podcast," which focuses on the trucking industry, with its second season set to begin in the coming weeks. They also teach an online box trucking course.

Smith, who is from Chicago, uses his knowledge to produce much of the course’s content, while Hennings is the instructor. Hennings is no stranger to public speaking, as he gives speeches across the U.S. on his experiences being a formerly incarcerated man who has found success outside the prison walls.

"This course was a no-brainer," Hennings said. "I was already preaching, instructing to anybody in the urban community."

"It's more than a course, it is a mentorship as well," Smith said.

The pair met during an interview on Smith's podcast — "Escaping the Odds" — in which Smith interviews formerly incarcerated people who become successful entrepreneurs. Smith also has a trucking business in Chicago — U Turn Transport.

Hennings had always wanted to own his own barbershop and beauty salon, which he accomplished within a year of being released from prison in 2016. One of his customers ended up introducing him to the trucking industry, and that changed his life, he said.

"I immediately went and bought me a box truck and got into the business," Hennings said.

His company, Go Time Trucking, began in 2017 and has been doing last-mile trucking ever since. Last-mile delivery is the trucking of items from a local warehouse or fulfillment center to the customer. He typically handles a lot of furniture delivery. He currently employs five people in the Milwaukee area.

Hennings spent 20 years in prison for fatally shooting Milwaukee man

Hennings spent 20 years incarcerated for shooting and killing Michael Bailey in Milwaukee in 1996. He intervened in an argument between his uncle and Bailey and shot Bailey twice, he admits. He was charged with first-degree intentional homicide, but a jury found him guilty of a lesser charge of first-degree reckless homicide.

Hennings argues he was the product of an environment he calls the "street game," and he was really good at the game. He made a lot of money selling drugs and developed status among his family and friends. His status got the best of him when he decided to shoot Bailey, he said.

Smith spent a little more than nine years in federal prison; he was released in 2019. He admits to engaging in a conspiracy to distribute heroin and fentanyl resulting in death.

Similar to Hennings, Smith said he had "arrogance" that he could sell more drugs than anybody and he was good at it. He says his drug operation produced $15,000 a day.

"I'm going to school at the same time. I knew I was going to get my degree, but when you see $15,000 a day, how could you do anything else? I became addicted," Smith said.

"When I found out I was directly involved with the death of people, that fell heavy on my heart, so I decided to fall back," Smith said.

At that point, it was too late, he had been in the drug operation for five years and was under federal investigation. Smith said his phones were tapped and that ended up being the anchor of the prosecution's case.

Having a job can help people stay out of prison

Smith and Hennings connected with a company, Stretch Finance, to help get the online trucking course off the ground. "I'm in the trucking industry, I understand how lucrative it can be if done properly," Smith said.

Taking the course will provide an opportunity for poor people to earn a living quickly, Hennings said. "When I was in prison, I would say 90(%) to 95% of people in prison were poor," Hennings said.

Hennings said more people living in prison need opportunities to learn how to be successful. He says he was inspired by a young girl wearing a backpack at a middle school where he was speaking. The backpack contained the message: "Please forgive me for what I did while I was hungry."

"That summed it up for me," Hennings said. "This thing called poverty is more vicious than any motivation someone can put out there. You got to have a way to put food on the table. We all are better people when our bills are paid."

To take Hennings' and Smith's course, visit www.stretch.money/box-truck-class.

The duo is joined by Hennings' co-host Crissy Blue Jai on "The Urban Trucker Podcast," where they interview successful people from the trucking industry.

Contact Drake Bentley at (414) 391-5647 or DBentley1@gannett.com. Follow him on Twitter at @DrakeBentleyMJS. 

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This article originally appeared on Milwaukee Journal Sentinel: Formerly incarcerated share their successes in the trucking industry