Meet John Penn: Passion for the Road, Pride in the Details

Hey, everyone. This is John Penn, and I’m proud to be joining the Team Run Smart community as the newest Pro. Years ago, I was the guy listening to podcasts on night shifts, learning everything I could about owning a trucking business. To be invited in as a voice for the same community that helped me get here is a full-circle moment I’m incredibly grateful for.

I started driving at 19 years old, and this past October marked 24 years behind the wheel. I’ve had my own operating authority since 2014 and run my business, JP Transport, out of a small Indiana town of about 2,000 people. These days, I keep a steady routine on the road and back home on my small farm. It’s a busy life, but it’s a good one.

From Passenger Seat to Professional Driver

My connection to trucking started young. My dad was a company driver who started in 1998 when I was 16. I’d ride along in the passenger seat every chance I got. Even back then, I knew I wanted to be a driver, too. My first job was hauling propane and gasoline for a local outfit just a few miles from my house. It was a high-stakes job for someone with very little experience, and I had to learn fast. That job pushed me right into the deep end, and I’ve been running ever since.

Before going independent, I spent a few years with Air Liquide hauling carbon dioxide. It was during those late-night shifts that I really started digging into the business side of trucking. I’d listen to Kevin Rutherford’s Trucking Business & Beyond podcast while I drove, learning about accounting, fuel tracking, and business structure.

I then made the leap in 2014 to run under my own authority. Since then, I’ve built a setup that works: two trucks, two trailers, and a weekly rotation that keeps freight moving with little downtime. I haul office furniture, and the factory is only four miles from my house, so while I’m delivering one trailer, the next week’s load is already getting packed and ready to go.

The office furniture business takes a lot of planning, with around 15 customers I call every week to coordinate stops, weights, and delivery windows. If one thing runs late, it throws off the rest of the day. It’s a logistical puzzle every week, but I enjoy the challenge. My routes usually run through the Midwest, and I head down to Texas often, too. I’ve even made a few California runs over the years. I try to stay booked about two weeks out, always keeping the schedule tight but manageable.

When I’m back home in Indiana, I like spending time with my wife and our four kids, whether it’s at the house or taking the boat out. We also have a 20-acre farm, with a few cows and some antique Oliver tractors that still do the job. My 18-year-old son helps keep things running on the farm when I’m away. With trucking as my profession and farming as my hobby, there’s never a dull moment.

Looking Ahead

Throughout my years on the road, I’ve learned how important it is to trust your equipment and the people behind it. I drove Freightliner^® Trucks during my time at Air Liquide and I was getting 8.2 mpg when the fleet average was 6.2. I was comfortable with the product and knew I’d stick with it once I went independent. That’s why I bought the same year model when I got my own authority.

My first Cascadia^®, a 2014 model, ran strong for five years and hit a million miles without burning a drop of oil. I only traded it because I made a promise to myself: a new truck every five years or after a million miles, whichever comes first. When I went to replace it, I bought my 2019 Cascadia sight unseen. I got it from the same dealer, from the same fleet, and from the same salesperson. I trusted the relationship and the product so much that I just flew out and drove it home.

That kind of consistency and relationship building is what I hope to bring to the Team Run Smart community. I’m looking forward to sharing content and YouTube videos on topics like time management, business ownership, and making the move from company driver to independent. There are a lot of helpful learning tools out there, but there’s a lot of noise that comes with it, and not all advice is beginner-friendly. I want to be a steady voice for those just getting started, without scaring them off with all the “it’s a hassle and a headache” talk I used to hear.

I'm also excited about the future of the equipment itself. Optimized axle ratios, digital dashboards, and features like the heated LED headlights and the optional MirrorCam System are what stand out to me. I think it’s great to see Team Run Smart highlighting these innovations, especially for small operations like mine. I don’t run a fleet. I operate just one or two trucks, but I run them efficiently. And I know there are a lot of folks out there trying to do the same thing.

Wrapping Up

Thanks for taking the time to get to know me a little. I’m excited to be part of the Team Run Smart family. To anyone out there dreaming about running your own truck or starting your own business, I’ve been there, and I’m looking forward to sharing what I’ve learned along the way.

Stay tuned for more, and don’t forget to check out my welcome video below!

Meet John Penn: The Newest Freightliner Team Run Smart Pro

Freightliner Trucks YouTube Channel

John Penn
Team Run Smart Pro