The True Cost of Being an Owner Operator in Trucking

Episode 5 • 20th March 2026 • Built in the Midwest • Midwest Truck Driving School

00:00:00 00:38:19

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Andrew Krueger got his start hauling freight in box trucks around Chicago in his early twenties. A decade and a half later, he's running his own trucks, hiring his own drivers, and filing for his own motor carrier authority — and he's doing it from the Upper Peninsula.

Then the company he'd been leased to for years pulled the plug. Right before Christmas. Instead of walking away, he went all in.

This week, his first truck rolls out under his own name.

WHAT WE GET INTO

What it actually costs to become an owner-operator — and the $4,000 bet that started everything
The stuff CDL schools don't teach you — blown airlines, brake adjustments, and the road etiquette nobody mentions
Why most owner-operators will tell you not to do it — and why Andrew did it anyway
The real numbers: what a motivated reefer driver can earn, what it costs per mile to survive, and why your business checkbook and personal checkbook can never be the same account
Electric trucks, autonomous semis, and where Andrew thinks the industry is headed in five years

ABOUT ANDREW KRUEGER

Andrew got into trucking in his early twenties after working sandblasting and painting jobs around Chicago. He's driven over the road, worked the repair side, and built a multi-truck operation hauling reefer freight to California. After relocating to Michigan's Upper Peninsula, he grew from a single leased truck to running his own drivers.