Driven for Success
If you run a small trucking company — whether you’ve got one truck or forty — and want to run a smoother, smarter business, you’re in the right place.
I’m Mike Ritzema, founder of Superior Trucking Payroll Service, and each week I break down the business side of trucking: payroll, per diem, driver recruiting and retention, and all the back-office stuff that small carriers just don’t have time for.
You’ll get real-world stories, straight talk, and practical tips to help you avoid costly mistakes, stay on the road, and grow with confidence.
Driven for Success
W-2 vs. 1099 at Scale: Why Mid-Size Trucking Fleets Face Higher Risk
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.