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Edward Hennings’ story is one of resilience, transformation, and purpose. After spending 20 years behind bars, he made a conscious decision to take full accountability for his past and rebuild his life from the ground up. Rather than allowing his circumstances to define him, Hennings used his experiences as a foundation for growth, proving that redemption is possible with discipline, patience, and an unwavering commitment to change. Today, he is a thriving entrepreneur, motivational speaker, and author, using his journey to inspire others facing adversity.

As the founder of Go Time Trucking and the first Black-owned work boot company in the U.S., Hennings has not only built successful businesses but has also dedicated himself to creating opportunities for formerly incarcerated individuals. His passion for mentorship and community impact extends far beyond profit—his mission is to show others that they, too, can rise above their struggles. Whether through hiring individuals seeking a second chance or sharing his experiences with inmates still behind bars, Hennings leads with authenticity and purpose.

Despite his accomplishments, he remains deeply reflective about the time he lost with his children and the personal sacrifices that came with his journey. He is not just a success story—he is a living testament to perseverance, proving that the past does not have to dictate the future. With multiple businesses, books, and a growing platform, Hennings continues to push forward, living by his mantra: It’s go time.

There was a profound detail that stuck with me during our conversation where Edward shared a deeply personal moment that he hasn’t spoken about often. After spending over a decade in a medium-security prison, the time finally came for him to transfer to a minimum-security facility—the last step before his release. As he packed his belongings and waited for transport, he was called down to the recreation center, where he had worked as a barber. The guards, many of whom had seen him grow and transform over the years, wished him well and said their goodbyes.

As he walked out, one of the guards followed him into the hallway. At that moment, Edward noticed something unexpected—the guard turned his back, and his shoulders began to shake. Overcome with emotion, he started crying. “I’m so glad you’re leaving,” he told Edward, “But I can’t lie to you—it hurts. We’ve been here with you, day in and day out. We’ve watched you change, and now you’re moving on.” It was a powerful reminder of the impact Edward had made, not just on fellow inmates but on the very people tasked with overseeing him. It reinforced his belief that change is possible, and that even in the toughest environments, people take notice when someone is truly committed to transformation. Read on to learn more about how he turned his life around, built multiple businesses, and continues to inspire through his work.

Ed, your story is a powerful testament to resilience and reinvention. After serving 20 years in prison, what was the first step you took to begin rebuilding your life, and what mindset helped you move forward?

The first thing I had to do was take accountability. That was the foundation for everything because if I didn’t acknowledge my role in my situation, I could never fix it. I had to be honest with myself—I wasn’t getting it done. I had let myself down, and I had let others down. Once I faced that reality, I was able to start rebuilding. I identified where I had fallen short and worked on those areas, step by step.

You’ve said that not understanding patience led to some of your earlier decisions. How has patience played a role in your success today, particularly as an entrepreneur and mentor?

Patience is everything. Money, knowledge, and experience all hold value, but patience is what allows you to apply those things effectively. I’ve learned from my past mistakes—when I was younger, I was impatient, and it led me into situations that could have been avoided. Now, as an entrepreneur, I recognize that success is a journey. When I reach moments where most people tap out, I remind myself that I’ve been in tough spots before. That uncomfortable feeling? I’ve been there. I’ve pushed through it. And that’s what keeps me going when the challenges come.

Launching the first Black-owned work boot company in the U.S. is groundbreaking. What inspired you to start this company, and what message do you hope it sends to others?

My entire journey has been about inspiring people. Even while I was incarcerated, I was trying to motivate those around me, telling them, we can do better than this. We can be better. But in that environment, positivity isn’t always welcome. You’re in a maximum-security prison with people who’ve been there 15–20 years, leading cliques and surviving a certain way. And here I was, this 147-pound guy coming in saying, We’re better than this. It wasn’t easy, but I had a no-fear mentality. I was dedicated to changing my life, no matter what.

I brought that same mindset into business. Yes, I want financial success, but just as important is showing people that change is possible. A lot of people, especially in urban communities, feel stuck. They feel like their circumstances define them. But I want them to look at me and know, I was in a worse situation than you, and I turned it around. You can too.

Starting the work boot company was an extension of that. I didn’t even realize at first that no Black entrepreneur had entered this space. But when I did my research, I saw the gap. And since my brand has always been about the grind—whether in prison, business, or life—it only made sense to combine that with work boots. It’s a symbol of hard work and resilience.

Go Time Trucking has become a vital source of employment for formerly incarcerated individuals. What motivated you to focus on providing opportunities for people with similar experiences, and what impact have you seen so far?

It started when I opened my barbershop in 2017, about a year after I came home. A client sat in my chair one day and told me about the trucking business. He broke down the process—the type of deliveries, the income potential, and the freedom it provided. I was immediately intrigued. I bought a truck, never drove one in my life, but I got behind the wheel and figured it out. That was six years ago.

Since then, I’ve hired and trained people coming home from prison and others from underserved communities. When I first got into trucking, it was incredibly lucrative. It was a way out of poverty for a lot of people. But as the industry evolved, some people struggled to adapt. Many got used to making easy money, and when things got tougher, they quit. I stayed in it, running five trucks at one point, employing guys from prison, giving them a fresh start.

Now, with my focus shifting to the work boot company, I still keep one truck and drive it myself. I’m up at 6 AM, loading up, delivering, and then coming home to work on the boots. It’s all about staying in motion, staying committed to the vision.

You’re deeply committed to community work in Milwaukee. Can you share a particularly meaningful moment you’ve had while mentoring or working with someone reentering society?

There have been so many, but one that stands out happened recently when I visited a prison here in Milwaukee. Families often reach out to me saying, my son is locked up. He’s about to come home. Can you talk to him? So, I went in to speak to the inmates.

When I walked in, the reaction was overwhelming. It was almost like being at a concert and seeing people react to a major celebrity. But one moment really hit me—one of the guys who had been locked up with me before had gotten out but ended up back inside. When he saw me, he ran up, grabbed me, and started crying. The guard reminded him he couldn’t touch me, but he didn’t care. He just kept saying, I’m getting it together. I’m getting it together. It was like he felt he had let me down.

That moment reminded me how difficult it is to stay on track after prison. People want to change, but the world isn’t always forgiving. Seeing him struggle made me even more committed to my work.

With two published books, a podcast, and multiple businesses under your belt, what legacy do you hope to leave behind, and what’s next for Edward Hennings?

I’ve learned not to place limitations on anything. 28 years ago, I promised myself that if I got a second chance, I wouldn’t waste it. And I meant it. I don’t need a third chance because I’m giving everything I’ve got right now.

I’m leaving this earth on empty—no untapped potential, no wasted opportunities. I want my legacy to show that no matter where you start, you can rewrite your story.

What’s something people may not know about you that you’re willing to share?

People see my success and assume I’ve got it all figured out, but one thing I don’t talk about enough is the time I lost with my children. I was gone for 20 years, and I missed their upbringing. No accomplishment—no business, no book, no speech—can ever replace that. That’s something I have to live with every day. So, while people celebrate my turnaround, I want them to know that I also carry regrets.

What does a typical day in the life of Edward Hennings look like?

My day starts early—between 4:30 and 5:00 AM. I make sure I have content ready for social media, whether it’s something for the boot business or an inspirational message. By 6:00 AM, I’m at the dock loading my truck. I’m on the road until about 1:00 or 2:00 PM, then I head home to box up boots and take them to the post office. Some days, I have a speaking engagement in between. By the evening, I wind down, study, or watch sports—I’m a big fan.

What is your favorite mantra or words to live by?

“It’s go time.” That’s my mindset. That’s the name of my trucking business. That’s how I approach life. No excuses. No hesitation. Just action.

For more information visit,  www.EdHenningsco.com

 

Photo Credit: Edward Hennings