May - 2025 -
15 May
Adam Wingfield

How to Read Your Rate Con Like a Pro

Too many carriers treat the rate con like a formality, but buried in those few pages are the traps that can cost you detention pay, shift liability, or delay your check for weeks. In this guide, we walk through how to break down a rate confirmation like a fleet manager, flagging sneaky clauses, protecting your rights, and building a system to manage paperwork at scale. In trucking, reading the fine print is financial survival.

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Adam Wingfield

The Truth About Deadhead and How to Fix It

Deadhead miles don’t show up on rate confirmations, but they quietly bleed small carriers dry, fuel, time, equipment wear and revenue lost every mile you roll empty. This guide breaks down what deadhead really costs and offers five practical strategies, from triangle hauls to smarter rate negotiation, to cut it down, tighten your routing, and boost profit without needing a dedicated lane or a giant customer list.

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09 May
Adam Wingfield

How to Craft a Shipper Outreach Strategy That Works Part 2

It takes work to land shippers as a small carrier, but a few small changes can mean the difference between winning and losing freight.

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08 May
Adam Wingfield

How to Save on Commercial Truck Insurance in 2025 Without Cutting Corners

Commercial insurance rates have ballooned over the last few years. Small carriers can use some techniques to reduce their costs.

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07 May
Adam Wingfield

Shifting Gears: New Rules, New Rivals and the Road Ahead

Independent Contractor Fight Reignites — DOL Backs Off Biden-Era Rule for Now The U.S. Department of Labor just announced a major shift: It’s officially putting the brakes on enforcing the 2024 Biden-era independent contractor rule — at least for now. In a memo sent May 1 by acting Wage and Hour Administrator Donald Harrison III, […]

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06 May
Adam Wingfield

Why the problem with the CDL system is bigger than just ‘non-domiciled drivers’

Non-domiciled CDL holders are just a small sliver of a bigger issue with how CDLs are issued and regulated.

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Adam Wingfield

Crafting a shipper outreach strategy that works

For small carriers, you have to have a solid strategy to win freight directly from shippers. Here are the steps to make it happen.

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05 May
Adam Wingfield

How to Track Driver Performance Without Micromanaging

Managers walk a fine line between tracking performance and stepping on toes.

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Adam Wingfield

Fuel-Saving Tech Tools Worth Trying in 2025

Fuel strategy is essential to running a profitable business. Here are some pro tips to help you maximize your fuel strategy.

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02 May
Adam Wingfield

Pressure Points – Safety, Enforcement and the New Realities Facing Trucking

New Federal Push on CDL Enforcement Targets a Growing Concern Last week, the White House issued a formal directive aimed at cracking down on what it calls “commonsense violations” in commercial driver licensing. The Executive Order, signed on April 24, sets the stage for stricter federal oversight of state licensing practices — particularly focusing on […]

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01 May
Adam Wingfield

How to Get From Lease-On to Authority in 90 Days

The jump from leased-on driver to running under your own authority feels easy when you’re frustrated with your current situation. You start thinking, “Man, if I’m doing all the work, why am I giving up 20%, 30%, even 40% of the money?” And you’re not wrong to feel that way. But emotion doesn’t pay for […]

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Adam Wingfield

Masterclass Recap: How to Go Direct and Ditch the Spot Market (Part 2)

If Part 1 of this series was about the mindset shift—getting off the hamster wheel of the spot market—then Part 2 is all about the muscle: the actual steps to build, pitch, and maintain shipper relationships that bring consistency to your business. This is where the rubber meets the road. In the Playbook Masterclass, we […]

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Apr - 2025 -
30 April
Adam Wingfield

From Driver to Business Owner – A Roadmap Snapshot

How do you get from running your truck to running your business? Find out in this Roadmap Snapshot.

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Adam Wingfield

A Light That Moved Fast and Shined Bright: Honoring Brittany Traylor

Brittany Traylor was a light in the trucking industry; she is remembered by friends and honored by those who she knew.

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Adam Wingfield

Masterclass Recap: How to Go Direct and Ditch the Spot Market (Part 1)

Let’s be honest. If you’re still relying solely on the spot market to run your business in 2025, you’re not building a business—you’re gambling with your livelihood. I’ve said it before and I’ll say it again: The spot market load board is not a business model. It’s a temporary solution. In a recent Playbook Masterclass, […]

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29 April
Adam Wingfield

When to Add a Second Truck (And When to Wait)

If you’re reading this, you’ve probably got one truck that’s doing okay—or maybe just surviving—and you’re thinking: “Is it time to grow?” “Should I get another truck?” “Can I afford to scale, or am I just chasing the dream too fast?” Let me say this up front. The worst time to add a second truck […]

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28 April
Adam Wingfield

Building a Carrier Packet That Wins You Freight

Your carrier packet is the first handshake for potential clients. Here are some tips to make sure yours wins you business.

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Adam Wingfield

What the Latest Rate Dip Means for Small Carriers (Part 2)

The freight recession is dragging on and getting deeper as tariffs throw a wrench into any possible recovery. What does this mean for small carriers?

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