A man with a mission: Driver, company owner tackles challenges, enjoys freedom of the road

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A man with a mission: Driver, company owner tackles challenges, enjoys freedom of the road
As a child, Jamie Hagen loved the “Star Trek” series and had a lofty mission of traveling to the stars. While he doesn’t get to go to outer space, he does enjoy traveling the highways of the U.S. as a professional driver and owner of Hell Bent Express. (Courtesy: Jamie Hagen)

Growing up in a family with trucking connections, you would think that the obvious choice for a child would be to follow in the family business. That was not the case for Jamie Hagen, who started driving in his teens. Now, at 48, he is the owner and operator of Hell Bent Xpress.

Hagen’s earliest travel plans — more of a mission, really — wouldn’t have just taken him across the country. He would have left the planet entirely. Born and raised in Aberdeen, South Dakota, Jamie was a big fan of the sci-fi series “Star Trek,” and he dreamed of a life in the stars.

“It was a little ambitious of a dream,” Hagen said. “Once I got into my teenage years, my uncle and my dad both drove trucks, and it became my passion. I started driving when I was 16. My dad had trucks on the farm and I kind of worked my way into it from there.”

His father, Norman Hagen, started bringing Jamie with him on the road when Jaime was only 3. Hagen says he considers himself to have been “raised on the road.”

Jamie and Hillary Hagen
Jamie Hagen, a truck driver and owner of Hell Bent Xpress, enjoys spending time with his wife, Hillary. (Courtesy: Jamie Hagen)

Those early experiences are part of the reason Hagen followed in the footstep of his family — that and the fact that there are, at times, virtually “no co-workers,” Hagen joked.

“It’s the freedom to do your own thing,” he said. “Someone tells you, ‘Here is A; now get it to B.’ You’re the master of the ship, and that’s the part of driving that I love the most. That and being in charge of my own day, so to speak, and nobody micro-managing you. That’s how I treat my guys too.”

It’s that spirit of freedom that made Hagen realize he wasn’t entirely happy with the way the trucking business treated him and other drivers like him. He says he was often treated not as a person, but just as another piece of equipment. That’s what inspired him to found Hell Bent Xpress in 2020 — he wanted to create an environment where those who work for him feel respected, valued and trusted.

“When my guys call and ask what they think they should do, I tell them that they are the master of their ship,” Hagen said. “You do whatever you think you need to do get you from A to B. That’s all that I ask of them.”

The creation of Hell Bent Xpress was the chance for Hagen to grow and build something bigger, and to take on the challenges of ownership.

“There’s no better challenge than to be completely on your own,” Hagen said. “When you’re leased to a carrier, they handle all of the ups and downs. You’re sort of isolated from the situation to some degree. I wanted to get a real good ‘kick in the teeth’ of trucking.”

Hagen is not only the owner of Hell Bent Xpress; he is also part of the driving team because, he says, he still has that passion for driving. He enjoys listening to audiobooks and “a lot of podcasts” to pass the time on the long hauls.

“My days are pretty full, dispatching my trucks and dealing with issues of running a business,” Hagen said. “I have a pretty full day on the phone.”

Hagen is typically gone for one to two weeks at a time on a run, depending on the scenario, but he likes to be home with his wife and children as much as possible. The father of five girls, his blended family includes his wife, Hillary, and daughters Taylor, 27, Grace, 20, Elizabeth, 13, Camille, 11, and Celeste, 7.

Continuing the family tradition begun by his father and uncle, Hagen has brought the kids along on his trips, just as his father and uncle did with him.

“(With my daughters) it was when they were younger,” Hagen said. “When they get to those teenage years, the trips kind of loses their shine. It’s fun when they can load up in the sleeper and watch movies … all of them have been with me at some point.”

Hell Bent Xpress has two different fleets with four trucks leased to Cliff Viessman Inc. in Gary, South Dakota, which handles food-grade liquid tanks. In addition, he has six trucks that haul dry vans (according to Hagen, this freight is “whatever you can stick in a box”).

For Hagen, what he loves most about the job is that it offers adventures.

“Some people hate it for that aspect, but I love it for that aspect,” Hagen said. “Every day is a new problem that has to be solved, whether it’s weather or a mechanical issue or a shipper or receiver issue — in my opinion, there’s always an adventure.”

Jamie Hagen and Michael Douglas
Jamie Hagen, left, and driver Michael Douglas enjoy a laugh together during Douglas’ training. (Courtesy: Jamie Hagen)

Hagen bought his first truck, a 1992 Freightliner FLD, in 1995. Even though the tractor was only 3 years old, Hagen said it had already seen its better days. Still, he was elated at the purchase. After nearly three decades in the industry, he still loves trucking.

When queried about his opinion on the truck driver shortage, Hagen said that’s part of the reason he founded his company.

“There is no driver shortage; there is a shortage of treating people like decent human beings,” Hagen said. “We create a lot of drivers every year with people getting their CDLs. We don’t retain those people to a large degree. They are burned right out of the gate with some of these mega-carriers, and in some of the little ones too, that mistreat people.”

Numbers wise, Hagen said he believes there is somewhat of a driver shortage simply because many drivers are retiring, and there are not enough younger drivers entering — and staying in — the business.

For those who are entering the trucking industry, Hagen says the No. 1 thing a new driver needs to have is patience.

“You’re not going to make seven figures the first year,” Hagen said. “It takes a while to grow and find what you like and master the craft. I look back at my first few years, and they were kind of a disaster. It takes time to learn the way of the trucking life. Even though I was born into it and definitely traveled a lot, it’s a whole different story when you’re on your own and doing it. Had I given up then, I would have never gotten to this point where I have a small fleet and I’m loving it.

Hagen said it is his mission to do things differently in the trucking industry.

“I try desperately every day to treat my people like decent human beings. I want them to feel like they’re part of the company and not just working for it,” Hagen said. “I want to them to feel like they have ownership of it, to some degree.”

He said he feels that, in some cases, truck drivers feel like they’re just another number, and that their opinions don’t matter.

“That’s the biggest reason I created Hell Bent Xpress,” he explained. “It’s one thing to talk about it, but another to actually do it. Every day we are trying to grow and evolve and be profitable, but still have our people be a part of it.”

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