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 [email protected]

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: [email protected]

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

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

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

New episodes every Friday!

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 feel right—like when he realized that working behind a desk just wasn’t his jam. We also tackle the challenges veterans face when transitioning to civilian life, and Mason's insights could be a game-changer for anyone feeling a bit lost after leaving the military. So, whether you’re contemplating a career shift or just curious about the trades, this episode is packed with relatable stories and valuable advice.

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 Midwest. Hosts Josh and RJ both made career decisions they'd handle differently — and that's a big reason this show exists. They get into what goes wrong when people choose a path based on emotion instead of information, the careers that were never even presented as options, and why a classroom full of people ranging from 18 to 65 might tell you more about the trades than any brochure ever could.

WHAT WE GET INTO

1. Why it's crazy to make a life-altering decision based on almost no real information
2. A 26-year-old veteran was terrified of being the oldest person in a classroom — and what he found out when he got there
3. The career paths that were never even presented as options — and what that costs people
4. How emotion drives most career decisions, and what happens when you try to reverse-engineer the facts afterward
5. What this show is here to do about all of it

ABOUT THE HOSTS

Two guys who believe people should have the opportunity to work meaningful, well-paying careers that allow you to live well and provide for your family.

1. Josh Barron serves as the School Director for Midwest Truck Driving School as well as North Country Heavy Equipment & Electrical Line School.
2. RJ Parrish manages the schools' marketing and media, helping to drive awareness and understanding of trades career opportunities.

TIMESTAMPS

00:00 — Cold open

00:42 — What this show is and who it's for

01:13 — The 18-to-80 classroom

02:36 — "If I don't do this, I'm going to regret it"

03:27 — The veteran who thought 26 was too old

08:35 — The question most high schoolers can't answer

11:40 — "I had a very different image in my head"

13:48 — The decision that started with a Starbucks

16:01 — Emotional decisions vs. informed ones

18:30 — The guests you'll hear from in this show

21:45 — "That decision will affect you your entire life"

CONNECT

1. Website: midwesttruckdrivingschool.com/podcast
2. Facebook: https://www.facebook.com/CDLMidwest
3. Instagram: https://www.instagram.com/midwesttruckdrivingschool/
4. TikTok: https://www.tiktok.com/@midwesttruckdrivingskool

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

Learn more about the training we offer at midwesttruckdrivingschool.com

New episodes drop every Friday.