Jamie Hagen always knew he was going to be a trucker. He came from a South Dakota trucking family, after all.

But apart from knowing what industry he wanted to be a part of, his plans were vague. And like a lot of young people starting out in the world, he endured a couple of false starts before he got on track to start a small fleet all his own.

Hagen was still in diapers the first time he went out with his truck-driver father on a trip.

“When you add it all up, I’ve spent my entire life in a truck,” he says now.

By the time he was a teenager, Hagan’s father owned three trucks. South Dakota didn’t have an in-state CDL law, so Jamie could legally drive one of the trucks to help out. Which is how he learned the business.

When he turned 21, Hagen decided to go into business for himself. He bought a used truck and became an owner-operator.

Although work was hard to come by in largely agricultural Aberdeen, where Hagen is from, he hustled.

“I spent three years as an owner-operator honing my craft and learning the hard lessons,” he says. “And things worked out well."

A little too well, as it turned out.

Flush with a little success, Hagen decided to upgrade to a nicer truck. As it turned out, it was too nice.

“It was a lack of experience on my part,” Hagen says. “And within three years, I was out of business.”

Try, Try Again

Hagen went back to being a fleet driver, working for Viessman Trucking out of Gary, South Dakota. He spent the next 12 years learning the trade and understanding the mistakes he’d made as an owner-operator.

In 2010, Hagen was once again in a position to purchase his own truck. He became an owner-operator and leased to Viessman. This time, he had a radically different perspective about business.

“I wasn’t thinking about starting a small fleet,” Hagen says. "But I had spent a lot of time thinking about the decisions I saw my employer making. From a company driver’s perspective, I couldn’t understand some of the decisions they made. I thought they were foolish.

"But, when I looked at it from the perspective of providing for a large group of people, it turned out there was a method to the madness!”

Boiled down to its essence, Hagen realized that being smart with money was the primary directive for a small business owner.

“So that's what spurred me on after I became an owner-operator,” he says. “I had a friend who needed a job. And I thought, ‘Well, how hard can it be to own a second truck?’”

Minding his pennies paid off. After a few years, Hagen and his friend bought a third truck. Then a fourth.

“Things just kind of slowly progressed over the years,” he says.

In 2020, Hagen took the plunge and went into business as an independent, for-hire fleet. Hell Bent Xpress currently has 12 trucks – all Macks, thanks to the social media influencer relationship he has forged with the OEM over the years.

Hagen plans on keeping his fleet at this size for the foreseeable future.

Expanding His Small Fleet's Customer Base

The company recently made a shift away from tankers to dry vans.

Viessman specialized in food-grade tanker hauling. But Hagen wanted a bigger playing field for Hell Bent Xpress.

“There are only so many liquid food-grade facilities in the world,” he says. "But when it comes to dry vans, there’s no limit to what you can put in that box.

"That meant we can offer our services to every Mom and Pop establishment out there, as well as big customers.

"It really opened my eyes to all the possibilities in the freight world. It was pretty astonishing. I fell in love with it at that point, and that's why it took off."

His business grew from one truck hauling freight and three trucks pulling tankers to a fleet of 12 over the next three years.

"We got excited and ran out and did it!”

Managing A Fleet With A Truck Driver’s Perspective

No matter what kind of freight, Hagen's time has a company driver gave him important perspective when it comes to fleet management.

“Sometimes, what a driver would like and what the business needs don’t align,” he says. “And in those cases, it’s the driver that takes the brunt of that – whether it’s delivering a load in the middle of the night or dealing with weird customer demands.”

When these situations come up, Hagen says he always tries to sweeten the deal for his drivers.

“As a small fleet owner, I can hand-pick my guys. And now, I’ve got a great group that I really love working with. We are very fortunate.”

Not pushing his drivers too hard is key part of Hagen’s management philosophy.

“From a driver's point of view, you don't mind sacrificing your time,” he says. “But you also want something for the effort, right?”

Which is why Hagen works to be very flexible when it comes giving drivers time off when they need it.

“Sometimes it hurts,” he says. “You need 10 trucks, but you only have eight available drivers. But you learn to adapt to those things. It’s a balancing act.

"I’ve learned not to push people too hard. Because if you do, sooner or later, they push back.”

And sometimes, Hagen says, that includes telling a customer “No.”

“That’s a hard lesson to learn,” he admits. “But if you’re up front with people: ‘I don’t have enough trucks this week. Can we make this run next week?’ It usually works out for the better in the end.”

Managing Expectations When Starting A Small Fleet

If you’re thinking about striking out on your end and starting a small fleet, Hagen's biggest piece of advice is to manage your expectations.

“Getting bigger is not a license to print money,” he cautions. “Having 10 trucks doesn’t mean you make 10 times the money.

"And understand that as your fleet grows, your problems grow along with it. You quickly go from being able to easily solve a few issues to dealing with a lot of big things that can go wrong in a single day.

"Trucking has always been a game of pennies. And when you get bigger, understand that there will be a whole lot more pennies to count.”

UPDATE: A Million Dollar Deal

Hell Bent Xpress is getting some new equipment, too.

Since HDT talked with Hagen a couple of months ago, he’s put in an order for five brand-new Mack Pioneer tractors.

In fact, Hagen’s personal truck, set to be delivered in a few days, is the very first customer-ordered Pioneer rolling off the plant floor.

“New truck prices are going to start going up soon,” he says. “So timing is a factor. But also, a good chunk of our fleet is around four years old with over 500,000 miles on them. So I figure it’s time."

The new trucks are all going to be a striking orange color not normally seen on Mack trucks.

Hagen was considering a custom color, but there wasn’t available production time to accommodate that request.

“I had to choose from what they had available,” he says. “And we went with Bronze Orange Pearl Metallic,  which they don’t use very often. But we’re going to call it ‘Hell Bent Orange.’”

Hagen’s association with Mack as a social media influencer is paying dividends, too. On top of being the first non-demonstrator truck produced, his personal Pioneer is absolutely jam-packed with features.

“This truck has everything under the sun on it,” he says with a laugh. “You couldn’t build a more expensive Pioneer if you wanted to!”

Asked if there are any new features on the truck he is particularly excited about, his answer is immediate.

“The rearview camera system,” he says. “I was hesitant about the technology at first. But then I drove a demo truck with it and I was very impressed. I think that technology is going to be the future of rearview vehicle safety.”

The remaining Pioneers, which won’t be delivered until October, aren’t quite so tricked out.

“I was trying to keep the price tag under a million dollars,” he says. “Plus, I want to keep the weight of each truck down.”

But, Hagen adds, the Pioneers are going to be “game-changers” for his drivers.

“My guys are giving me grief because my truck is so loaded,” he says. “But they don’t understand yet how big a difference these new trucks are going to be for them. The cab and sleeper are so much bigger. The truck is so much more comfortable. All of these things are going to be huge for guys who work and live in these trucks day in and day out.”

Asked if he ever thought he’d be negotiating million-dollar deals running a small trucking fleet, Hagen shakes his head in disbelief. 

“No,” he says. “Never imagined such a thing. Not even close. I’m just a farm boy from South Dakota. This is incredible.”