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Image courtesy Hellbent Xpress
Can trucking be a challenging headache? Definitely. Is it also a rewarding journey? Absolutely, according to Jamie Hagen, president of Hell Bent Xpress, a small trucking company based in South Dakota.
We caught up with Hagen to learn how his small fleet is weathering market swings and diesel prices, plus his biggest lessons learned from early career mistakes.
—Interview by Shefali Kapadia, edited by Bianca Prieto
What is the hardest part of operating a small business trucking company today?
The hardest part for me has been competing with outlaw chameleon carriers that can beat me on price and equipment utilization. You can run pretty cheap if you don’t have to follow the rules. We refuse to compromise our beliefs in the process. People have to come first. After all, there is a human in the cab. We offer a service. The truck is just the tool we use to provide the service.
How have rising diesel prices impacted your business? Are things starting to level out?
Diesel prices rising definitely hit us in the cash flow pocketbook quickly. We were already on the edge, so this was a tough one to endure. Eventually, we were able to negotiate some fuel surcharges. With prices slowly coming down, it has helped immensely. We are a fuel-efficient fleet, so this was something we could battle.
What's one thing you've done that you believe has helped you stay in business through market ups and downs?
I’ve always planned for the downs. I try to keep the expenses low by analyzing different ways to optimize practices we are already doing. Continuous improvement has to be the goal. Have a war chest built up. You’re going to need it.
What's your No. 1 piece of advice to other small business trucking owners navigating tough times?
Treat it like a business. Pay yourself a moderate salary, then grow your business with discipline. Be careful of salespeople. They don’t always know what they are talking about. Do your own research.
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Your 2026 fleet software pricing guide
Managing a modern fleet requires balancing efficiency with tight budget control. Beyond just features, finding the right platform means understanding the total cost of ownership and how a vendor scales with your business.
Software Advice has researched the 2026 market to cut through the marketing fluff. Our latest Pricing Guide compares top providers, including One Step GPS, OptimoRoute, Azuga Fleet and others, so you can invest with confidence. Download the report to get:
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What's a mistake you've made in your career, and what did you learn from it?
Mistakes are plenty when you come from nothing, trying to succeed. There was no road map. When I first got started, I may have gotten carried away with living large and not limiting myself to a salary. I may have believed I could work myself out of any missed step. Don’t stay invested too long in a bad idea. Cut those losses quickly and start a new path.
What do you see as the most rewarding part of a career in trucking?
The best reward by far is having a great team. It’s not about the financial success. Lord knows if that will ever happen! But working with a team you created and succeeding, and getting praise from customers—now that makes trucking worth every bit the headache it can be. Trucking has been about the journey since I started it. Right now, our journey is epic, and I wouldn’t have it any other way.
(Image courtesy Jamie Hagen)
The Inside Lane’s Take
The operators still standing after the last few years of rate chaos share one trait. They planned for the down before it came. If your war chest isn't built yet, Hagen's advice is simple: start now, pay yourself a salary and cut losing bets fast. The market will test you again.
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The Inside Lane is curated and written by Shefali Kapadia and edited by Bianca Prieto.
