Why A Bigger Fleet Isn’t Always Better in Trucking

Jamie Hagen has spent almost his entire life around trucks. He remembers riding with his dad at four or five years old, eventually became an owner-operator himself and today runs Hell Bent Xpress, a 12-truck family-owned fleet in South Dakota.

But adding trucks was not the hardest part of that journey. Adding people was.

In this episode of Behind the Freight, Jamie explains why fleet ownership forced him to rethink the way he makes decisions. From why saying no can be a competitive advantage and driver retention strategies to why his fleet doesn’t need more than 12 trucks, he breaks it all down. The goal still remains driving, staying involved and knowing the people working beside him.

What You’ll Learn

What changes when an owner-operator becomes responsible for a team
Why good equipment is ultimately an investment in a driver’s time
How smaller fleets can compete for drivers without mega-carrier benefits
Why saying no to certain freight can protect both drivers and the business
How diversification gives carriers more room to react when a market changes

This episode also features Avery Vise, Chief Trucking Analyst at FTR Transportation Intelligence, who joins John and Scott for the show’s monthly freight market check-in. Avery explains why spot rates remaining roughly 40–45% above last year offers carriers some reason for optimism, even as diesel costs have climbed sharply. His key September watchpoint is simple: freight should show at least some normal seasonal firming around Labor Day. If it does not, that is when operators may need to pay closer attention.

Episode Highlights

[01:00] Spot Rates Are Holding Up Despite Higher Diesel

The monthly market update arrives as Avery Vise points out an unusual combination in the August market: diesel prices have risen sharply, yet spot rates have continued to follow a fairly normal seasonal pattern. Rates are also still running roughly 40–45% above last year across several major equipment types.

[06:45] The Hardest Part of Becoming a Fleet Owner

Jamie says moving into fleet ownership was his biggest professional adjustment because decisions stopped affecting only him. What is best for the business can conflict with what is reasonable for the people doing the work. That forces owners to continually balance revenue, service and employee needs.

[10:49] Equipment Decisions Outlive Market Conditions

A truck you buy today can still be generating payments years after the market that justified the purchase has changed. Jamie talks candidly about that tension as Hell Bent Xpress invests ahead of expected changes around 2027 equipment requirements and higher truck prices. The practical lesson is to understand exactly what you are committing to, keep the downside in mind and avoid treating a strong freight environment today as a guarantee about tomorrow.

[12:16] Learning That You Don’t Have to Say Yes

Jamie naturally enjoys the difficult loads and strange situations that make trucking interesting. The problem was assuming his drivers felt the same way. His wife eventually pointed out that not every opportunity needed a yes, especially when the demands were making life unnecessarily difficult for the team. It became an important leadership adjustment: a customer request can make financial sense and still be the wrong move.

[14:04] You’re Paying for the Driver, Not the Truck

Jamie offers a useful way to rethink fleet investment: trucking is a service business, so the person providing that service matters more than the piece of equipment carrying it. The truck is the tool that allows the driver to use their time effectively. Reliable trucks are not simply a recruitment perk. They reduce unnecessary headaches, help drivers work efficiently and show that the business respects the people expected to operate them every day.