The Three Pressure Points Small Carriers Are Facing Right Now with Adam Wingfield

Most owner-operators know how to drive. The part that trips them up is running the business. Compliance, rates, market cycles; each one is its own challenge. Together, they’re what separates the carriers still running five years from now from the ones who aren’t.

This includes:

• Increased enforcement focus during Roadcheck Week
• Margin compression caused by inconsistent rate outcomes
• Market cycles that continue to shape cash flow every 12–18 months

That came through clearly in a recent episode of Behind the Freight, where Todd Waldron and John Howland spoke with Adam Wingfield, founder of Innovative Logistics Group, at the Mid-America Trucking Show.

🎧 Access the full episode of Behind the Freight:

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Trucking is a contact sport

Adam describes the trucking industry as a contact sport because of the constant pressure and decision-making required to stay profitable. Many carriers get into the business without ever learning the financial side of running an operation.

However, mastering the business side is what he calls the “golden thing” that actually keeps a carrier in business.

One of the biggest misconceptions carriers have is thinking that ignorance of the law will protect them. Adam explains that you are responsible for everything in the regulations, even if you do not know about a specific rule yet.

Roadcheck week is an open-book test

International Roadcheck Week can be stressful for drivers, but Adam views it as an open-book test. The CVSA announces the focus areas ahead of time, so every carrier knows exactly what inspectors will be looking for.

Even with this information, many drivers get caught off guard because they assume they will not be the one pulled into a weigh station. Adam suggests that drivers should always assume they will be inspected. Checking things like tire tread depth or brake adjustments before the week starts can prevent simple violations from putting a truck out of service.

Using AI to improve your rates

Technology is changing how carriers operate, especially with ELDs and data tracking. Adam notes that it is becoming harder to hide violations like the overuse of personal conveyance because modern tools and AI are very intuitive.

Rather than fearing technology, Adam challenges carriers to use AI to help them make better decisions. He recommends a three-step challenge to improve freight rates:

1. Set the role: Tell the AI it is an expert in load negotiations.
2. Feed it your rate confirmations: Feed it your recent rate confirmations.
3. Find the gaps: Ask the AI to evaluate the information and tell you where you can improve.

This process allows carriers to use their own data to have a more profitable month.

The freight market cookout

The freight market is always cyclical and behaves like a roller coaster. Adam compares the market to a cookout where everyone is eating but no one is bringing more food. Eventually, the food runs out, and the market turns.

Market cycles typically last about eighteen months. Adam cautions that money is never permanent in this industry, so carriers must prepare for the next downturn while things are still good. Understanding these patterns helps owners stay steady when the market inevitably shifts.

The business side is where carriers win or lose

Running a successful trucking business requires discipline, preparation, and a willingness to use new tools. Compliance, rates, market cycles — the carriers who manage all three with intention are the ones who last.

Adam offers in-depth advice on how to identify what’s stopping you, and staying profitable through the ups and downs of the market.

Listen to the full conversation