Jamie Hagen didn’t just build a fleet—he built a following. The South Dakota native and founder of Hellbent Xpress has become a respected voice in trucking, both behind the wheel and on social media, where he’s known for sharing hard-earned insights from life on the road. His story isn’t just about growing from owner-operator to small fleet—it’s about resilience, financial discipline, and staying true to driver-first values.
Learning the Hard Way, Early On
Hagen’s trucking roots run deep. Raised in a family of drivers, he was already moving rigs in his teens. By 21, he was an owner-operator. But early success led to a costly mistake: an expensive upgrade that pushed his business beyond its limits and forced him off the road within three years.
He didn’t quit. Instead, Hagen went back to driving for Viessman Trucking, where he spent more than a decade learning what it really takes to manage a profitable trucking business—lessons that would eventually fuel his second shot at ownership.
A Smarter Second Start
In 2010, Hagen leased a truck back on with Viessman—but this time, he approached it with patience and strategy. Growth would come slowly and deliberately, with a focus on financial stability.
With the support of his wife, Hillary, Hagen started scaling. What began with one truck turned into two, then three, and eventually more. By 2020, Hellbent Xpress had become a fully independent operation, now running 12 Macks. That partnership with Mack Trucks has only grown stronger, in part due to Hagen’s influence and online presence.
Switching Gears: Tanker to Dry Van
The company originally hauled tanker freight, but making the switch to dry van was a turning point. “With dry vans, the freight possibilities are endless,” Hagen says. The move opened up more flexibility and access to broader lanes, allowing the business to adapt to market demands more easily.
Leading with Empathy
Having spent so many years in the driver’s seat, Hagen manages his team with that experience top of mind. Fairness, communication, and understanding are central to how he runs things.
“I hand-pick my guys,” he explains. “We’re a small, tight-knit team. When challenges arise, we adapt rather than push too hard.”
Drivers at Hellbent Xpress aren’t just numbers—they’re part of a crew where work-life balance actually means something. Hagen gives time off when needed and keeps communication open about loads and expectations.
Big Growth, Bigger Caution
While some fleets chase rapid expansion, Hagen is more cautious. “More trucks mean more problems,” he says. He’s focused on quality, not just quantity—and understands that real success in trucking often comes down to the smallest details.
“It’s a game of pennies,” he explains. Waste a little here or there, and it adds up fast. That mindset is what keeps Hellbent Xpress running lean and stable, even when the market shifts.
A Big Step Forward
In a major milestone, Hagen recently ordered 10 of Mack’s brand-new Pioneer tractors—including the first customer-ordered unit in the U.S. Painted in bold “Hellbent Orange,” the trucks reflect the company’s brand and commitment to progress, complete with safety upgrades and improved driver comfort.
Despite the size of the investment, Hagen hasn’t lost his down-to-earth approach. “I never imagined I’d be doing million-dollar deals,” he admits. “I’m just a farm boy from South Dakota who loves trucks.”
The Road Ahead
Jamie Hagen’s journey from a teenage driver to the head of a 12-truck fleet isn’t just impressive—it’s proof that persistence, smart planning, and a driver-first mindset still go a long way in trucking. His story resonates because it’s real—and because it shows what can happen when someone sticks to their values while adapting to a changing industry.
Source: Trucker’s Report
