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 trucks face more obstacles than most people realize

— ELD regulations and how they've reshaped daily operations

— Practical advice: pre-trip habits, parking strategy, and navigating big cities— What intermodal drayage actually involves day-to-day

👉 SUBSCRIBE for weekly conversations about careers in the trades.

🔗 LINKS

Midwest Truck Driving School: https://midwesttruckdrivingschool.com

North Country Electrical Line & Heavy Equipment School: https://ncheschool.com

Listen on your favorite podcast app: https://built-in-the-midwest.captivate.fm/listen

📧 marketing@midwesttruckdrivingschool.com

📱 Follow us: @midwesttruckdrivingschool

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 actually demand. This one's a direct conversation about personal responsibility, what schools stopped doing, and why the next generation of tradespeople is going to have to prepare themselves.

Listen wherever your get your podcasts: https://built-in-the-midwest.captivate.fm/listen

Midwest Truck Driving School: midwesttruckdrivingschool.com

North Country Heavy Equipment & Electrical Line School: https://ncheschool.com/

Submit your Questions: https://webforms.pipedrive.com/f/6WfGT9X1zlYC6WvssJqfWxOOkvVa1AjzqgnAIIHOq70WWiNo5czEWXpBMqxVTW7UST

Email: marketing@midwesttruckdrivingschool.com

Facebook: https://www.facebook.com/CDLMidwest

Instagram: https://www.instagram.com/midwesttruckdrivingschool/

TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

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 for cameras on their 2026 trucks — and what it actually changes about the job
• The "reality check" that hits every new driver around day 19, and the small group who don't make it past it
• What David tells students who've got a speeding ticket or a DUI in their past
• The question David says separates the drivers who succeed from the ones who wash out
• Why the worst thing a new driver can do is walk in thinking they already know

ABOUT DAVID

David spent five years with the 82nd Airborne — three deployments, two to Iraq, one to Afghanistan — before transitioning into Army recruiting for a decade. He retired from the military in 2017 and has been recruiting drivers ever since. Today he's the military field recruiter for Roehl Transport, covering CDL schools and military bases across the Midwest. Roehl has been family-owned since 1962 and runs roughly 1,900 trucks across all 48 states.

Listen wherever your get your podcasts: https://built-in-the-midwest.captivate.fm/listen

Midwest Truck Driving School: midwesttruckdrivingschool.com

North Country Heavy Equipment & Electrical Line School: https://ncheschool.com/

Submit your Questions: https://webforms.pipedrive.com/f/6WfGT9X1zlYC6WvssJqfWxOOkvVa1AjzqgnAIIHOq70WWiNo5czEWXpBMqxVTW7UST

Email: marketing@midwesttruckdrivingschool.com

Facebook: https://www.facebook.com/CDLMidwest

Instagram: https://www.instagram.com/midwesttruckdrivingschool/

TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

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 about diesel tech. He ended up making a case that it might be the most underrated career in the trades.

If you have an electrical background, you're as good as gold in the modern heavy duty industry. Master technicians are rare, and those with these specialized skills can command good paying jobs. This conversation highlights the critical role of these trade jobs as a lifeline when mechanical issues arise, emphasizing how vital skilled mechanics are.

AJ started turning wrenches and worked his way up to managing operations at 10-4 Truck & Trailer Repair in the UP. His shop handles everything from routine maintenance to emergency road calls — tractor trailers, log trucks, heavy equipment, and anything else that runs diesel and needs help. He's one of those guys who keeps every other trade moving, and most people will never know his name.

Listen wherever your get your podcasts: https://built-in-the-midwest.captivate.fm/listen

Midwest Truck Driving School: midwesttruckdrivingschool.com

North Country Heavy Equipment & Electrical Line School: https://ncheschool.com/

Submit your Questions: https://webforms.pipedrive.com/f/6WfGT9X1zlYC6WvssJqfWxOOkvVa1AjzqgnAIIHOq70WWiNo5czEWXpBMqxVTW7UST

Email: marketing@midwesttruckdrivingschool.com

Facebook: https://www.facebook.com/CDLMidwest

Instagram: https://www.instagram.com/midwesttruckdrivingschool/

TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

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 existed
• Proximity software that locks machine controls when a person gets within eight feet — even in the operator's blind spot
• Why the "five years of experience" hire is a unicorn now — and what employers are asking for instead
• The NCCER credentials that are putting graduates a year ahead in apprenticeship programs before they even start
• Why having a CDL as an operator makes you a one-person crew — and why employers are starting to require it
• Donnie's take on women in heavy equipment: "Some of the best operators I've ever seen are women"
• The student age range that proves it's never too late — from 16 to 66

ABOUT DONNIE

Donnie is the lead heavy equipment instructor at Midwest Truck Driving School. He just came back from ConExpo 2026 — the largest heavy equipment show in North America — and what he saw is changing how he trains the next generation of operators.

We get into the technology that's coming, the credentials that are giving graduates a head start, why women are some of the best operators he's ever trained, and why the "five years of experience" hire is officially a mythical creature.

Listen wherever your get your podcasts: Listen to Built in the Midwest

Midwest Truck Driving School: midwesttruckdrivingschool.com

North Country Heavy Equipment & Electrical Line School: https://ncheschool.com/

Submit your Questions: https://webforms.pipedrive.com/f/6WfGT9X1zlYC6WvssJqfWxOOkvVa1AjzqgnAIIHOq70WWiNo5czEWXpBMqxVTW7UST

Email: marketing@midwesttruckdrivingschool.com

Facebook: https://www.facebook.com/CDLMidwest

Instagram: https://www.instagram.com/midwesttruckdrivingschool/

TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

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.

1. What it actually costs to become an owner-operator — and the $4,000 bet that started everything
2. The stuff CDL schools don't teach you — blown airlines, brake adjustments, and the road etiquette nobody mentions
3. Why most owner-operators will tell you not to do it — and why Andrew did it anyway
4. 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
5. Electric trucks, autonomous semis, and where Andrew thinks the industry is headed in five years

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.

Listen wherever your get your podcasts: Listen to Built in the Midwest

Midwest Truck Driving School: midwesttruckdrivingschool.com

North Country Heavy Equipment & Electrical Line School: https://ncheschool.com/

Submit your Questions: https://webforms.pipedrive.com/f/6WfGT9X1zlYC6WvssJqfWxOOkvVa1AjzqgnAIIHOq70WWiNo5czEWXpBMqxVTW7UST

Email: marketing@midwesttruckdrivingschool.com

Facebook: https://www.facebook.com/CDLMidwest

Instagram: https://www.instagram.com/midwesttruckdrivingschool/

TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

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 WE GET INTO

1. Why Bill chose pneumatic tanker — and how he really made his money
2. The exact habits Bill sees in students who go on to earn $80–100K+ vs. those who plateau
3. What "reducing liability" means from the employer's side — and why it's the fastest way to get noticed
4. How your reputation spreads faster than any billboard — for better or worse
5. Why pre-trips aren't boring busywork — they're how you prove you're worth the better truck
6. The one mindset shift that separates people who burn out from people who build careers

ABOUT BILL OGLESBY

Bill is the lead instructor at Midwest Truck Driving School in Escanaba, Michigan. Before teaching, he hauled dry bulk pneumatic tanker. He got recruited to teach while hauling a load of lime, and he's been watching students go from nervous to hired ever since.

TIMESTAMPS

00:00 — "We all have the same 24 hours." Bill on what most people get wrong.

01:10 — The earning gap nobody talks about: why two drivers with the same CDL can end up $30K apart

05:13 — How Bill increased his income hauling pneumatic tanker

08:33 — Endorsements and the freight that pays more — what doors they actually open 10:54 — The phone call that pulled Bill off the road and into the classroom

13:07 — The loneliest part of trucking — and how drivers build real connections on the road

17:06 — "It's just trucking. It's going to be easy." Why that mindset kills careers.

18:20 — 200+ divisions in trucking — if you hate what you're doing, you haven't found your niche yet

22:48 — The guy who shows up 20 minutes early vs. the guy who's 10 minutes late.

24:47 — Pre-trips, dirty boots, and why the determine your career

26:02 — You want the fancy truck? Here's how you earn it.

27:32 — You're not just an employee. You're a liability. How to flip that.

29:50 — The McDonald's French fry fryer broke. It'll be okay. (Seriously — this is about more than fries.)

33:40 — Bill's advice to his younger self: one word that changes everything

LINKS

Episode 3 with Jillian Garcia (Schneider National): https://built-in-the-midwest.captivate.fm/episode/what-a-schneider-recruiter-learned-from-talking-to-thousands-of-drivers/

Midwest Truck Driving School: midwesttruckdrivingschool.com

CONNECT

Got a story? Know someone who should be on the show? Reach out at marketing@midwesttruckdrivingschool.com

See what we're building at midwesttruckdrivingschool.com

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 about overcoming social anxiety, what she actually looks for when she's evaluating candidates, why the first year breaks some drivers and builds others, and the career paths in trucking that most people don't know exist.

WHAT WE GET INTO

— How a girl who was "terribly shy" with social anxiety ended up doing presentations and connecting with people for a living - and why pushing past that fear changed everything

— The traits that separate drivers who build long careers from the ones who don't make it past year one (hint: it's not driving skill)

— Why "being teachable" is the single most important piece of advice she gives every new driver

— What the day-to-day actually looks like at a company like Schneider — home time, truck setup, dedicated vs. OTR, and the options most people don't realize exist

— Schneider's mirrorless truck technology and why they're always first to test what everyone else eventually adopts

— The real talk on safety: cameras that protect drivers, tech that prevents accidents, and why "you're the captain of your ship" isn't just a slogan

ABOUT JILLIAN GARCIA

Jillian is a Senior Territory Recruiter at Schneider National, covering Wisconsin, Upper Michigan, and Northern Illinois. She's been with Schneider for ten years, starting as a temp in customer service before moving into recruiting. Her grandfather drove for Schneider in the late '70s.

She travels to CDL schools, hiring events, and job fairs across her territory, connecting with students and career changers who are figuring out their next move.

📩 GOT A QUESTION ABOUT THE TRADES?

Leave a comment or send us a message — we'll get into it on a future episode.

LINKS

Connect with Jillian: https://www.facebook.com/JillianGarciaSNI

Midwest Truck Driving School Lineman Program: midwesttruckdrivingschool.com

North Country Heavy Equipment & Electrical Line School: https://ncheschool.com/

🔗 CONNECT

Website: midwesttruckdrivingschool.com

Email: marketing@midwesttruckdrivingschool.com

Facebook: https://www.facebook.com/CDLMidwest

Instagram: https://www.instagram.com/midwesttruckdrivingschool/

TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

New episodes every Friday!