John Penn
“I've always known I wanted to run my own business. Trucking just happened to be the road that got me there.”
John Penn’s journey to becoming a Freightliner® Team Run Smart Pro wasn’t built overnight. With nearly 24 years behind the wheel, over a million miles driven, and a decade as an owner-operator, John has shaped a career rooted in constant learning. In 2025, he joined Freightliner’s Team Run Smart as a brand ambassador to share his story and hard-earned knowledge with others interested in the trucking industry and entrepreneurship.
Meet John Penn
The Making of an Owner-Operator
John grew up in a small Indiana town, drawn to hands-on work and mechanical systems. Early jobs in construction and part-time driving helped him understand how things worked and how to eventually run something of his own. When the 2008 recession hit, he turned to trucking full-time and joined Air Liquide, hauling natural gas and liquids. It was there that he began refining his skills in loading and unloading, managing freight, and navigating logistics.
On the road, John made the most of his downtime. He tuned in to trucking and entrepreneurial podcasts to learn about fuel efficiency, business strategy, and long-term planning. In 2014, he earned his own operating authority and began carving out a niche hauling office furniture. It’s a line of freight that requires precision and proactive scheduling.
“When you’ve got five or six stops a day, you’ve got to be ahead of it. One delay can snowball everything.”
Over a decade later, John is running the entire operation, JP Transport, with the same hands-on approach he’s had since day one.
Behind the Wheel and Beyond
John’s weekly schedule is a careful balance of logistics, business operations, and family life. He currently has two Freightliner Cascadia® trucks, model years 2014 and 2019, both powered by Detroit® DD15® engines. His hauls often take him across Texas, Indiana, and Ohio with multiple daily stops. As he’s unloading one shipment, he’s already calling ahead to line up the next.
”It’s a never-ending cycle, but that’s what keeps the business running.”
When he’s home, John returns to his wife, son, and three daughters on their 20-acre farm in Indiana. There, he raises about 20 cows and maintains a small fleet of antique Oliver tractors, including a 1949 model he still uses. He balances quality time with his family, planning upcoming hauls, and keeping up with the farm, which his son helps manage while John is on the road.
Why Team Run Smart?
John’s connection to Freightliner started at Air Liquide, where he first got behind the wheel of a Cascadia. He was immediately drawn to the brand’s reliability, ease of service, and driver-focused performance. When it came time to buy his own trucks, there was no question he would choose Freightliner. His 2014 Cascadia had over a million miles on it and still never burned oil.
“I only had a day and a half of downtime in five years with that truck. How could you not like that?”
Today, he’s looking ahead to Freightliner’s Fifth Generation Cascadia and the new features it brings, like the heated LED headlights, a 2.16 axle ratio that aligns with his focus on long-term fuel efficiency, and the optional MirrorCam System for enhanced visibility.
Beyond the specs, John earned his place as a Team Run Smart Pro for the way he runs his business with focus and integrity and for his willingness to share his experiences to help others succeed. This mindset perfectly reflects what Freightliner’s ambassadors stand for.
“There were a lot of things I had to learn the hard way. If I can make it a little easier for the next drivers coming up, that’s worth it.”
Advice to the Next Generation
For drivers considering ownership, John stresses the value of self-education. With more resources than ever, he encourages company drivers to learn the business by listening to podcasts during long drives and watching videos during downtime.
His second piece of advice? Get your finances in order.
“If your money’s not right, don’t even think about owning a truck. You’ll feel like everyone’s got a hand in your pocket in the beginning.”
Lastly, he says that the best drivers are patient drivers. Between long hours on the road and tight logistics, it’s important to stay composed and mentally steady throughout each haul. And when it comes time to hire or partner up, look for that same quality in others.
Follow Along
From the cab of his Cascadia to his family farm in Indiana, John Penn represents what it means to be a Team Run Smart Pro: experienced, driven, and committed to helping others do it smarter. Follow along as he shares real-world advice, business strategies, and what’s next with Freightliner.