What do you do after running 11 trucks nearly bankrupts you?

If you’re Kevin Rutherford, you build the industry’s most trusted voice for small fleet owners and owner-operators.

In this Greatest Hits episode of Freight Nation: A Trucking Podcast, Kevin sits down with host Brent Hutto for a deep dive into how personal pain became professional purpose. From growing up around trucks to reluctantly buying his first rig at 21, Kevin’s path was anything but smooth. He scaled quickly, up to 11 trucks, but did so without the systems or financial visibility needed to sustain growth. The result was crushing debt, missed paychecks, and a wake-up call from reality.

Rather than file for bankruptcy, Kevin chose a different route: accountability, discipline, and education. Over four years, he paid off every cent he owed and discovered a new mission, which was to help others avoid the same fate. That mission became Let’s Truck.

Brent and Kevin explore Kevin’s transition from driver to writer to SiriusXM radio host, where his blunt, no-nonsense advice made him a fan-favorite. They also reveal a big announcement about the return of the Certified Master Carrier program at the Mid-America Truck Show, a solid proof that Kevin’s legacy of helping drivers thrive is still going strong.

[05:40] Kevin opens up about a glaring gap in the trucking world, which is the lack of real education for owner-operators. In most industries, you’ll find courses, mentorship, and roadmaps. In trucking? Not so much. Kevin’s hard-earned credibility didn’t come from theory, it came from surviving real business failure. That’s what makes his advice different. It’s raw, practical, and rooted in experience. Without real-world education, most owner-operators are forced to learn the hard way, and that's exactly why Kevin is on a mission to change that.

[11:44] Growing up in a trucking family, Kevin learned to turn wrenches before he hit double digits. But while mechanical skills came early, business acumen did not. He shares how his love for trucking led him to scale too fast, reaching 11 trucks without a clear financial system. What looked like growth was actually leading him straight into financial chaos. Scaling a business without foundational systems is like building on sand, it’s only a matter of time before it crumbles.

[15:06] With more trucks came more problems—and eventually, $60,000 in debt. Bankruptcy attorneys told him to walk away. But Kevin couldn’t. Instead, he chose the hard way: selling off assets, cutting back, and paying every dollar back over four long years. That decision reshaped how he thought about business and became the foundation for everything he teaches now. He does embodies the fact that true leadership starts with ownership, especially when it would be easier to walk away.

[17:07] Most people would stop at survival. Kevin didn’t. After digging himself out of debt, he realized he didn’t just want to run trucks, he wanted to help other truckers avoid the same pitfalls. That purpose led to the birth of Let’s Truck, a platform built to deliver honest, actionable advice for owner-operators trying to make the numbers work. Kevin's story shows that sometimes your greatest failure becomes your most powerful tool for service and impact.

[24:25] Sometimes, opportunity knocks in strange ways. For Kevin, it started with correcting a mistake in a trade magazine. That one email turned into a call from radio legend Dave Nemo and before long, Kevin was live on SiriusXM. So many people called in that it jammed the phone lines. What began as a one-time guest spot turned into a 15-year radio career helping truckers across the country.

Kevin Rutherford is a third-generation owner-operator who started his trucking journey at 21 and quickly grew a fleet of 11 trucks, learning hard lessons about business the tough way. After clawing his way out of debt, he turned his experience into purpose, becoming the trusted voice behind Let’s Truck, a platform that has helped thousands of owner-operators improve their operations and profitability. Kevin spent over 15 years as the host of SiriusXM’s Trucking Business & Beyond, and his no-nonsense advice earned him a loyal following across the country. He’s also a passionate advocate for driver health, leading conversations on wellness through his show Destination Health. His work has been featured in top industry outlets like Overdrive Magazine, Pro Trucker, and the Partners in Business series. Whether he’s speaking at events or answering calls from the road, Kevin’s mission is simple: to help truckers run smarter, healthier, and more successful businesses.

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