The Playbook

Adam Wingfield Wednesday, May 7, 2025

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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Adam Wingfield Thursday, May 1, 2025

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 Tuesday, April 29, 2025

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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Adam Wingfield Monday, March 3, 2025

Is a noticeable market shift around the corner?

The freight market has been all over the place for small carriers, and right now, there’s a feeling that something’s about to give. The big question is whether this shift is going to work in your favor or just keep the squeeze on spot market rates a little longer. Truckload demand (the need for your […]

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