This week’s edition of the Overdrive Radio podcast features C.W. Express small fleet owner Steve Wilson, reigning Small Fleet Champ in the 11-30-truck division, after a bit of a growth spurt for the fleet followed Wilson’s brush with death in 2022.
The team he’d built around the dry van fleet sustained while he was in the hospital for the better part of that entire year, and in the aftermath has only continued to not just sustain, but excel, on dedicated lanes for a central broker in Avenger Logistics.
Wilson (left) and one among C.W. Express's operators are pictured after a big catered lunch offered to all the staff and drivers the day I visited headquarters.
Wilson’s up to near 20 trucks and drivers today, and doesn’t have all his freight eggs in that single basket, as you’ll hear in today’s podcast, with customers in his area helping build lanes loaded both ways -- in one case out to Arkansas and back to the Louisville, Kentucky, area, where he’s headquartered in Sellersburg, Indiana.
The podcast amounts to a tour around C.W. Express headquarters on Avco Boulevard in Sellersburg, right off I-65 and purchased and moved into in 2023, marking a significant upgrade to the former location.

Wilson, a wear-all-the-hats small fleet owner for decades, continues to build out support structures for C.W.’s trucks and drivers with deft delegation, too, particularly on the time-consuming maintenance side of the business. He's added an expert lead mechanic you’ll hear who oversees the operation and a younger diesel tech, Clayton Higdon, to provide an assist and a well for education and growth, no doubt.
If your business, like C.W. Express and Steve Wilson here, has thrived even amid so many of the challenges of the last several years, you’re no doubt a contender worthy of competing in the 2025 Small Fleet Championship. Enter your fleet at the link:
Overdrive's Small Fleet Champ entry period is open through July
The program is sponsored by the National Association of Small Trucking Companies, and four finalists in two divisions between 3 and 30 trucks will square off for a final awarding of two winning fleets in late October.
I met Steve Wilson in person during the NASTC conference last Fall, yet I’d not had a chance to see the headquarters in person, nor meet a variety of personnel, including C.W.’s longest-tenured driver, Tommy Meredith. Meredith’s 79 years young, with 58 years of trucking experience of various kinds.
C.W. Express driver Tommy Meredith
Overdrive Radio's sponsor is Howes, longtime provider of fuel treatments like its Howes Diesel Defender all-weather mileage booster and winter anti-gel treatments to get you through the coldest temps, the Howes Multipurpose penetrating oil, and other products.
Lead shop man Andy Newbolds here is pictured working on owner-operator Dale Sutberry's truck, purchased by Wilson and company from his widow after the news of his Sutberry's passing. Wilson planned to keep the Tennessee Vols T on the side of the rig just as it is.
C.W.-leased owner-operator Kendall Ray
Steve Wilson the second, increasingly taking an operations and safety role in the business, is pictured here with the office mascot, one Tilley, smiling for the camera.
[Related: Entries open! Overdrive's 2024 Small Fleet Championship]