On the way out to John Penn's house in Orleans, Indiana, you pass through farms on county roads where you share the blacktop with, variously, dump trucks and passenger cars, pickups and horse and buggy. The hilly terrain might have you thinking you took a wrong turn, that surely this couldn't be Indiana, but crest the last hill on the run and you see it.
The farmhouse where owner-operator Penn has lived for a couple of decades now once belonged to his grandparents -- he bought the place after they passed. And it's more than 100 years older than the 2019 Freightliner Cascadia you see parked up ahead of the hay barn for his cattle, and another, similarly-spec'd Cascadia not visible in the image he keeps as a spare.
It's there he's built a family with his wife, Pam, and a son in the early stages of adulthood who works for the furniture manufacturer, scarcely a couple miles from the spot, that Penn most often hauls outbound freight from.
It's there he's built the J.P. Transport business Overdrive's been proud to host this week in Louisville, Kentucky, at the Mid-America Trucking Show to honor Penn finally as 2025 Trucker of the Year.
Friday, March 27, Penn joined trucking radio host Steve Sommers' live broadcast of Overnight Drive from the show floor, along with Overdrive Editor Todd Dills.
Sommers keyed in on many of the aspects that contributed to Penn being named Trucker of the Year -- his special attention to fuel mileage and what contributes to that, his journey to becoming an independent owner-operator.
He's averaging greater than 10 miles per gallon operating in his 2019 Freightliner Cascadia, coupled one or the other van trailers he owns, both now outfitted with aerodynamic upgrades, lift axles for each ont he way. That combination, along with Penn keeping speed top of mind, help keep fuel expense in check in a way far and above most of the competition.
Penn encouraged owner-operators with the ability to build a trailer with aero upgrades -- no doubt for box trailers it leads to fuel savings. The truck's to pull with less resistance, meaning there's not as much wear and tear on the engine.
His 2019 Cascadia's spec'd optimally, though he bought it on a dealer lot after an intentional search for a 2.41 gear ratio and Detroit DT12 automated transmission with the e-Coast feature. The latter's certainly beneficial, giving the transmission capability to determine when the truck gains uphill momentum sufficient to enable coast mode over and on the downslope -- you "get rolling downhill for free," Penn said.
When it comes to speed, "go as slow as possible, but as fast as necessary," Penn said. He told Sommers of a time he got stopped by a trooper in Tennessee going 58 mph because it was "unusual behavior," the officer told him. After explaining his mindset on fuel mileage (and getting a Level 2 inspection for his courtesy), he was on his way.
Penn refuses to idle his truck, which he believes is the "real killer" for modern emissions systems.
During the broadcast, livestreamed to Sommers' social networks and broadcast over the air, Dills presented the Trucker of the Year with the contest "trophy," a 1/42nd scale model replica of Penn's J.P. Transport 2019 Freightliner Cascadia, built by Pennsylvania's Eston Hoffman of Hoffman Mechanical Design.
With the tractor, spec'd and modified for maximum fuel efficiency, Penn's prepped for the current cost environment with perhaps the best cushion an owner-operator could have against the hammer of spiking diesel prices: His time with the tractor has yielded an average fuel mileage approaching 11 mpg.
Penn was impressed with the replica. "The only thing better than a big Cascadia is a small Cascadia," he said.
Despite the recent run-up in fuel, Penn said he's noticed some positive changes in the freight markets so far in 2026 -- some in rates, but more notably in volume and the desire by brokers to build relationships. He works with several to fill the trailer hauling back east for his bread-and-butter runs outbound from Orleans.
He recommended owners work hard on those relationships, building over time five to ten brokers you can rely on for freight when needed.
At MATS, Overdrive also debuted preps for the annual update of the Partners in Business manual, coproduced with owner-operator business services firm ATBS and since last year in a dynamic online library format. Browse the playbook for an owner-operator career via this link.
Penn's Youtube channel is a repository for documentation of his own maintenance and other work, much of it performed in and around the shop at the home place in Orleans shown here.
Big congrats to the owner-operator from all of us here at Overdrive.
