Jamie Hagen, founder of Hellbent Xpress, turned his lifelong passion for trucking into a thriving 12-truck fleet—and became a respected social media voice in the process. Born into a South Dakota trucking family, Hagen was exposed to life on the road early. By his teenage years, he was already behind the wheel of his father’s trucks, absorbing both the craft and the business side of trucking.
Early Trials and Lessons Learned
Hagen first became an owner-operator at age 21, but his early success led to an overambitious truck upgrade that ultimately put him out of business within three years. Not one to be deterred, he returned to company driving with Viessman Trucking, where he spent 12 years learning the intricacies of running a successful fleet.
In 2010, Hagen made a second attempt at ownership, leasing his truck to Viessman. This time, he approached the business with a clearer focus: make smart financial decisions and grow slowly.
Building Hellbent Xpress
With support from his wife Hillary, Hagen gradually expanded his operation. A second truck for a friend led to a third and a fourth. In 2020, he launched Hellbent Xpress as a fully independent fleet, which now runs 12 Mack trucks—a partnership strengthened through Hagen’s social media influencer relationship with Mack Trucks.
Hellbent Xpress transitioned from tanker hauling to dry van operations, significantly expanding their market reach. “With dry vans, the freight possibilities are endless,” says Hagen, who appreciates the flexibility the switch offers.
Managing Drivers with Empathy
Drawing from his own experience as a driver, Hagen emphasizes fairness and balance in fleet management. He prioritizes driver well-being, offers time off when needed, and maintains open communication about workloads and expectations.
“I hand-pick my guys,” he shares. “We’re a small, tight-knit team. When challenges arise, we adapt rather than push too hard.”
Keeping Growth in Check
Hagen warns against overestimating the benefits of fleet expansion. “More trucks mean more problems,” he says. Success depends on smart planning, realistic expectations, and careful money management. He sees trucking as “a game of pennies,” where even small inefficiencies can add up quickly.
A Million-Dollar Move
Recently, Hellbent Xpress placed an order for 10 new Mack Pioneer tractors, including the very first customer-ordered unit. Finished in a bold “Hellbent Orange” color, these trucks will bring advanced safety features and improved driver comfort.
As his fleet modernizes, Hagen remains humble. “I never imagined I’d be doing million-dollar deals,” he says. “I’m just a farm boy from South Dakota who loves trucks.”
From owner-operator to small fleet trucking leader, Hagen’s story is proof that persistence, smart decision-making, and driver-first values can fuel long-term success in the industry.
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