Ed Hennings Explains How 20 Years In Prison Helped His Boot Brand – Sourcing Journal

Ed Hennings is aware that he’s not just selling shoes; he’s selling his story of perseverance and redemption right along with them.

When sentenced to prison for 40 years as a 24 year-old in 1996, his attitude wasn’t one of despair or hopelessness. It was one of resolution to get to work because his release date—whenever that might be—would be the fruit of a second chance he’d already received.

Freedom came finally for Hennings in 2016, two decades after he was sent to the Wisconsin state penitentiary for a first-degree reckless homicide conviction resulting from a confrontation with a neighborhood man who had been attacking members of his family, and who, according to court records, was threatening to again.

Prosecutors had been pushing for intentional first-degree murder charges, and with it life in prison, but given some of the extenuating circumstances, the jury came back with the lesser conviction.

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Ed Hennings cutting hair in a barber shop he opened a year after getting out of prison after 20 years on a homicide conviction.


“I was sitting there, facing the rest of my life [in prison], and I made some promises that if I got a second chance, I wouldn’t need a third,” Hennings said. “Everybody is saying ‘man, you got 40 years.’ But to me, that 40 years sounded like my second chance… So my whole time in, that’s always on the forefront of my mind, even on my bad days. I have to say, ‘you know what, this is the chance you asked for’.”

Forty-four years old at the time of his release, Hennings reentered the world armed with a barbering and cosmetology license he attained in prison. Within a year he turned that expertise into his first owned barber shop. Hennings soon switched his career path to trucking at the suggestion of a customer. Trucking was lucrative enough during the pandemic, but through both of those entrepreneurial adventures, the lifelong passion of a self-professed “shoe junkie” left Hennings with a desire to start his own footwear brand.

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Ed Hennings in his second post-prison career as a delivery truck driver and mover.


“I always thought of the problems I had with the shoes that I was wearing in the workforce,” he told Sourcing Journal. “In the barber shop, you might wear some Timberland boots, but they’re pretty heavy to be wearing in a barber shop. Then you might wear tennis shoes, which are very comfortable, but if you got some Air Jordans on, you’re gonna get hair all over it and after two haircuts the shoes are done. Then I went over to the trucking industry and a lot of the shoes I wore driving, I liked for the comfort and the safety, but I didn’t like the look of the shoe. That’s why I started to formulate my ideas for what I wanted my work shoes to look like—versatile enough to get you through your working hours, but stylish enough to get you through happy hour.”

Hennings’ trucking business mostly involved delivery and assembly, which made him keenly aware of a gaping hole in the footwear market.

“When you’re in a customer’s home, you’ve got to look presentable. You can’t come walking in with these big, muddy boots,” Hennings said. “The other thing is safety. We would love to wear tennis shoes on that truck. But if you deliver a refrigerator or stove, you want to have safety. So I came up with a steel-toe protective shoe that also has the style of a tennis shoe, which I’ve been able to buy from different manufacturers and branded with my brand and, man it has been something. I just did a fashion show this last weekend, and when I told them that that was a steel-toe shoe, you could hear the crowd just gasp.”

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These counterpoints of a work boot with style and an athletic shoe with steel toe, all under the mantra “Ed Hennings Trucker Wear” and a logo with the phrase “For Truckers, By Truckers,” jump off the edhenningsco.com website.

Hennings himself is not a footwear designer and his white label business means he sources products from manufacturers in Asia and applies his own branding. Shoes, made from mesh and leather, are shipped by air directly to customer addresses.

Hennings said scoured the internet to find a manufacturer who could produce his best-selling Sports Steel Toe shoe to his specifications.

“When I first thought of the idea of shoes, my first thought was always delegating,” Hennings said. “Just find some manufacturers who are producing what I was looking for.”

Hennings’ career running a footwear brand began in October of 2022 and he says the business is going well so far, though he has no profits to report, as yet. He said he currently has four employees and targets truckers and other blue-collar workers through television and social media marketing.

After attending his first fashion show recently, Hennings had his first popup event at Wisconsin’s Bayshore Mall in Glendale, which he hopes will be the first of many brick-and-mortar endeavors.

Hennings said he’s also soon to be featured on Master P Reviews, a viral show dubbed an ‘urban Shark Tank,’ hosted by the ’90s rap star.

“I studied financial literacy while I was in prison… and I’ve got mentors I didn’t even know existed. I know how to work, save and invest,” Hennings said. “I came home [from prison] making $7.25 an hour cutting hair. By the end of that year I had saved up $7,500 and that was seed money for my barber and beauty salon. So I continue that same formula—you stack up, you save up and when the opportunity presents itself, you position yourself.”

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A steel-toed athletic shoe available on the Ed Hennings Co. website.

Footwear, celebrity