Once you grow past a small fleet, the W-2 vs. 1099 conversation changes — fast.

At five trucks, classification mistakes may slide under the radar.
At 30, 40, or 80 trucks, the same decisions can trigger audits, penalties, and six-figure exposure.

In this episode of Driven for Success, we break down W-2 vs. 1099 specifically for mid-size trucking fleets — without legal jargon, scare tactics, or internet myths.

You’ll learn:

• Why worker classification gets riskier as fleets scale
• What regulators actually look at (and what they ignore)
• The most common misclassification myths that trip up growing fleets
• Where mid-size fleets go wrong in real-world operations
• The true cost of getting this wrong once you’re more visible
• What a clean, scalable classification setup looks like

We also mention a free self-assessment tool you can use to pressure-test your current setup.
If you’re unsure whether your drivers should be paid W-2 or 1099, you can take the quiz here:

👉 https://www.truckingpayroll.com/1099-vs-w2-quiz/

This isn’t about fear.
It’s about understanding how running a 20–80 truck fleet is fundamentally different than running five trucks — and building systems that hold up as you grow.

If you’re an owner or executive who wants clarity instead of gray areas, this episode is for you.