Midwest Truck Driving School

Built in the Midwest

Business EN ↓ 21 episodes

There are careers that pay six figures, have massive demand, and take months to get into — not years. The reason most people never consider them has nothing to do with the work. It has to do with what they were never told. Built in the Midwest is where we have real conversations about careers in the skilled trades. From truck driving and electrical line work to heavy equipment and beyond. We bring in the people doing the work, the employers hiring for it, and the instructors training the next generation — because most people make career decisions with almost no real information. They pick a pa...

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Midwest Truck Driving School

Category

Business

Latest episode

Jul 10, 2026

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Episodes

Why Most Tradespeople Stay Broke Despite Earning Big 10.07.2026

WHY THIS ONE MATTERS Something happens when the paycheck gets bigger. A lineman finishes his apprenticeship. A driver moves up to a better lane. A operator finally hits the top of the scale. And for the first time in their life, there's money left over at the end of the month. Most people know exactly what to do with it. They go buy the truck. Or the four-wheeler, the side-by-side, the skid steer,...

First Year Trucking and the "Driver Shortage" 03.07.2026

Thinking about a truck driving career? This is part two of our Q&A with Josh Barron, director at Midwest Truck Driving School. We cover what your first year on the road is like, how to choose a CDL school, and whether the driver shortage is real. RJ asks the questions. Josh answers. We cover three things. First, how to evaluate a CDL school. Josh explains what separates a solid truck driving p...

Your Truck Driving School May Be Setting You Up to Fail 26.06.2026

A guy with twenty years on the road climbs into the cab for a road test, asks if he can float the gears, and proceeds to grind metal on metal the whole way down the block. That moment is the whole point of this episode. Experience isn't the same as doing it right, and a lot of what gets argued about online falls apart the second someone who teaches this for a living walks you through it. RJ pulled...

Four Questions That Beat 'What Do You Want to Do When You Grow Up?' 19.06.2026

Trent Bellinger grew up being told the same thing a lot of kids hear — that college was the only road that led anywhere good. He went and got the degree. But somewhere along the way he figured out that the thing setting him apart wasn't the diploma, it was the 4,000 hours he'd already put in at his dad's shop. Now he runs career and technical education for two counties, and he's spending his days...

Why This Former Marine Leader Started Over as an Apprentice 12.06.2026

You want a stable career that pays well with room to grow — but with all the noise out there, it's hard to even know where to start. Johnny Rogers didn't have a map either. He left the Marine Corps at 28 and started over in the trades at the bottom. In this one we talk about the decision he made in a parking lot that set the next decade in motion, why he chose eight years in the Marines instead of...

The Most Dangerous Job in America (That No One Wants) 05.06.2026

He got his CDL nine years ago and went straight into one of the hardest, most dangerous corners of trucking there is. Kyle has hauled logs out of swamps, flipped a pup on its side, and trimmed loads with a chainsaw over his head — and he's still one of the youngest people left doing it. We sat down to talk about what the work actually takes, and why so few people his age are willing to do it. Kyle...

The Real Reason Trucking Companies Use Cameras 29.05.2026

Josh Rouse came up through trucking, stepped away for a stretch, and got pulled back in by a buddy with an opening in operations. Two years on the board later, he moved into human resources and safety — and now handles the hiring, the safety tech, and the IT that ties it all together. A.M. Express is a locally owned, Escanaba-based carrier running vans, tankers, flatbeds, lowboys, and reefers acro...

Opportunity Doesn't Wait for the Perfect Time 22.05.2026

This episode is for the kid being told he has one option. It's for the apprentice trying to figure out if going local is worth the pay cut. It's for the lineman wondering if the side hustle is real. Mike's career didn't follow a plan. It followed a series of decisions — and the ones that paid off weren't the ones anyone told him to make. WHAT WE GET INTO The guidance counselor conversation that in...

The Invisible Barrier Every Trade Student Faces | BTS episode 15.05.2026

Quick heads up before you press play: we recorded this one inside a moving training truck during an active class day, so the audio gets scratchy in spots. We cleaned up what we could — some of it just is what it is when you record on the road. Bear with us. The conversation makes it worth it. THE PREVIEW This one's a behind-the-scenes episode. No table, no studio, no script — just a mic in the cab...

Trade School Is The Door, Not The Destination 08.05.2026

A high school CTE director drives a busload of students two hours each way to spend a day at a CDL school. Why? Because somewhere along the way, he figured out something most people building career pathways for young people miss — and it changes how you should think about every trade school you've ever seen. Josh had a chat with Linus Parr, who runs the Career and Technical Education programs at N...

College Enrollment Is Collapsing for a Reason 01.05.2026

Nine years ago, the average truck driving school student was 50. Today, they're 18-20. Why are high schoolers and career changers walking away from college and choosing skilled trades careers — truck driving, lineman work, heavy equipment operation — instead? In Episode 11 of Built in the Midwest, we sit down with Kyle Barron, Director of Admissions at Midwest Truck Driving School and North Countr...

50 Years and a Few Million Miles Driving Heavy Haul 24.04.2026

Dan started hauling 140,000-pound chip trucks through the UP woods at 17. Fifty years and a few million miles later, he sits down with Josh to talk about what trucking was, what it is now, and what every new driver needs to know. 🔑 KEY TOPICS — 50 years of trucking experience across van lines, intermodal, heavy haul, and OTR — The financial realities of owner-operator trucking— Why autonomous tru...

The Real Cost of Being Unprepared After High School 17.04.2026

A math tutor who works with trade students says the bar for a high school diploma has never been lower — and he's watching the consequences walk into apprenticeship programs every week. Our guest this week, Kent King, has taught public school, run GED prep in a county jail, and now tutors math for our students. He sees what happens when students who "passed" high school meet the math the trades ac...

Why Most CDL Applicants Never Get Hired | Roehl Transport Recruiter 10.04.2026

David spent ten years recruiting for the U.S. Army before he ever recruited a single truck driver. Now he travels the Midwest sitting down with CDL students and soldiers transitioning out — and he's blunt about what most of them get wrong before they ever sign an application. WHAT WE GET INTO The thing every new driver assumes about hiring that's costing them offers Why Roehl swapped side mirrors...

The Trade That Keeps Every Other Trade Running 03.04.2026

Every truck on the road, every piece of heavy equipment on a job site, every log truck bouncing through the woods at 160,000 pounds — someone has to keep all of it running. That someone is AJ. He started as a diesel tech and worked his way to managing a shop that serves everyone from over-the-road drivers passing through the UP to log truck operators 30 miles deep in the woods. He came in to talk...

The Future of Heavy Equipment Operation Is Insane 27.03.2026

Donnie walked into the largest heavy equipment show in North America and watched someone operate a real excavator in Germany — from a console in Las Vegas. That moment changed how he thinks about what's coming for the industry. And what he's bringing back to his students. WHAT WE GET INTO The ConExpo experience — 2,200 vendors, five buildings, four parking lots, and technology Donnie didn't know e...

The True Cost of Being an Owner Operator in Trucking 20.03.2026

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. T...

The Real Reason Truck Drivers Fail (It's Not What You Think) 13.03.2026

A driver clears $90K his first year. Another one with the same CDL is stuck at $55K and frustrated about it. Bill Oglesby has watched hundreds of students come through Midwest Truck Driving School. He can spot the difference between those two drivers before they ever leave the building. This week, he breaks down what that difference actually is — and most of it has nothing to do with driving. WHAT...

What a Schneider Recruiter Learned from Talking to Thousands of Drivers 06.03.2026

Jillian Garcia never planned on a career in trucking. She was a self-described introvert who'd spent years in childcare and the restaurant industry before a temp agency placed her at Schneider. Ten years later, she's a Senior Territory Recruiter covering Wisconsin and Upper Michigan — and she's talked to more drivers than most people will meet in a lifetime. In this conversation, she opens up abou...

From the Marines to MO Valley: Mason's Veteran Story 06.03.2026

Join us as we dive into an engaging chat with Mason, who reveals his unexpected journey from military life to pursuing a career in the trades. He candidly shares how his decision to join the Marines at a young age sparked a series of life events, leading him to discover his true passion for hands-on work. Mason's story is all about finding your niche and not being afraid to pivot when things don't...

Your Career Decision Defines Your Entire Life 04.03.2026

How much did you actually know before you made your career decision? Not what you thought you knew. What did you really understand about the work, the pay, the day-to-day — before you committed years of your life and thousands of dollars to it? Most people don't have a good answer. And the ones who do usually wish they'd asked better questions first. This is the first episode of Built in the Midwe...

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