Overdrive's 2025 Trucker of the Year contenders

A round-up of Overdrive Radio's business-focused podcasts since 2013, including exclusive interviews, presentations and more geared to owner-operator and small fleet owner businesses among listeners.

Trucking business

The voice you'll hear at the top of this Overdrive Radio edition is that of Overdrive's February Trucker of the Month Kenny Wingate. Clearly, he knows of what he speaks when he invokes the feeling -- "nothing like it," he said -- that he associates with best of trucking as an owner-operator, running your own game when times are good. It's part of what drove him to take the leap back from company work he was doing to launch his Southpoint Exchange businss with one truck and his own authority in 2019. He’s up to two trucks today, headquartered in Auburndale, Florida: https://www.overdriveonline.com/trucker-of-the-year/article/15738560/how-truckings-supposed-to-be-done-meet-kenny-wingate

He's the proud owner of two sharp Peterbilt 579s and stainless reefers, and he's been focused throughout the company's relatively short six-year history on business brass tacks, building a team around him for freight with regular brokers, many of whom he’s known going back decades. Likewise on the accounting, bookkeeping and general business management side of Southpoint Exchange, and he's set up for further growth after a lifetime spent trucking, as you’ll hear in the podcast. 

He's 55 years young today and relishes that long history in the business, though many of the men he learned from, and some of those he came up with in trucking, have passed on. 

Magnanimous in manner, clearly on top of his game as a business owner, Wingate is also nothing if not grateful for all the help of those who came before him. He told the story of a recent encounter of an old friend at a dock. "Our generation is starting to be few and far between ... The other day I run across a gentleman I probably hadn't seen in 25 years, and we trucked together," Wingate said. "We sat down on an old wooden bench at the back of our trailers while we were getting loaded" remembering all those who came before but also "we just laughed, man, and just cut the fool, and it felt good. It felt good to see somebody that you trucked with years ago, you know, when when things were a little different."

At once, most of the folks the two men asked each other about were gone, he said, or at the very least off the road for good for health or other reasons. Wingate, 55, stays grateful for his own longevity, and looks ahead to the future and opportunities to build better business with Southpoint Exchange. 

In the podcast, hear that perspective but also just how two-truck Southpoint Exchange is getting the work done with dedicated freight on lanes between Florida and Northern Ohio. After being nominated by one of his customers, he’s officially in the running for our 2025 Trucker of the Year award, which you can enter yourself or nominate another owner via https://overdriveonline.com/toptrucker

Trucker of the Month Kenny Wingate leans into the pride, and brass tacks, of owner-op trucking

"If it continues like it's going, it'll probably be our best year. ... The way it started out and the way it's going so far, it'll be our best year."  --Flatbed owner-operator Ollie "Rufus" Morris reflecting on the year thus far

May Trucker of the Month Rufus Morris of Youngsville, North Carolina, was sounding a lot like April's honoree and fellow flatbed owner-op George Kincaid reflecting on the year thus far: https://www.overdriveonline.com/overdrive-radio/15745657

Morris is leased today to Material Logisitcs Management out of Pennsylvania, operating from that home base in North Carolina, and was nominated for Overdrive’s 2025 Trucker of the Year award by his wife and business partner in the one-truck, two-flatbed-trailer outfit Midnight Rider Transport. We featured Morris late last month in Overdrive Senior Editor Matt Cole’s story about the decades of trucking experience behind Morris: https://www.overdriveonline.com/trucker-of-the-year/article/15747142/back-in-biz-owneroperator-rufus-morris-trucker-of-the-month

In this week's Overdrive Radio, hear Morris directly in conversation with Cole, walking through his current operation and long history -- this is his second stint as a trucking business owner, after hauling logs in the late 1990s into this century as an owner-operator. 

Morris hauls flatbed steel, a good bit of it oversize, in a 2004 model Peterbilt 379 he purchased several years back. It's in tiptop shape, shined up and outfitted with plenty in the way of bright parts and lights and just generally well-maintained, delivering all manner of benefits from the pocketbook on down to the scale houses. He takes pride in safety, clearly, the truck too.

"Get out there and stay consistent," he advised others on the safety front. "You just can't be in a hurry." Also: "Be proud of what you're doing. Keep maintenance up on your truck. I know they say, 'Chrome don't get you home,' but it does. Believe me." 

Most of the time crossing scales, Morris said, he's bypassed, the immaculate appearance of the rig he feels playing a big part in that. If your dog bites the inspector, though, all bets are off. (Catch an account of just such an incident in a recent-memory inspection in Matt Cole’s story about the Morrises.) 

Morris and Midnight Rider you can for sure call a little old-school in approach, in some ways, yet he keeps an eye on new ways and new people, too. In today’s episode of Overdrive Radio you’ll hear from him a clear priority placed on business relationships invested in, cemented over time, a key characteristic of so many a successful trucking business owner. Morris offered this word of encouragement for the next generation coming up behind him:

"A lot of people say, 'I wouldn't get into trucking for nothing in the world.' Don't get me wrong, it's dfiferent than it used to be. ... but I won't tell nobody don't get into it. If they want to do it? Trucking's done me good all these years. I can't complain one bit about it. If they've got a dream and want to do it, I'd say do it." 

Dive into Morris’s history trucking: an early business, long experience driving, and the reboot that was inspired in part by Patricia Morris herself after 25 years in real estate. 

Enter your own business or that of another owner-operator you admire (up to three trucks) for Overdrive's 2025 Trucker of the Year award here: https://overdriveonline.com/toptrucker

Relationship-value priority: Rufus Morris's old-school ways delivering new success trucking

Overdrive's June Trucker of the Month Scott Smith, owner-operator of Sapphire Cartage out of Searcy, Arkansas, has a couple of secret weapons when it comes to bookkeeping, tax accounting and business analysis. The first is his wife, Stephanie, who after time in the health care field and then with Scott rearing four young children, found new work Scott Smith describes in this week's edition of Overdrive Radio. Stephanie's built accounting expertise as support for a small-biz accounting software system, and her expert handling of the Sapphire Cartage back office has taken that load off of the independent.  

The second of those secret weapons regular readers encountered in the June 30 feature detailing Smith’s history trucking: https://www.overdriveonline.com/trucker-of-the-year/article/15749527/trucker-of-the-month-bets-on-equipment-diversity-as-failsafe 

Namely, it’s a custom spreadsheet the owner-operator built himself to effectively analyze per-ton rates in the hopper-bottom freight business when it comes to load offers. But not only that -- it's his go-to tool for week-to-week business performance as well. As was detailed in the story, Smith uses the spreadsheet to set revenues against not only hard costs like those for fuel but his weekly home needs, his own personal driver salary, if you will. What he needs to contribute to household take-home figures as an expense there, on a weekly basis. What he describes in the podcast brings to mind in some ways Overdrive’s own Load Profit Analyzer tool you can access at any time to game out rate scenarios or compare load offers: https://overdriveonline.com/load-analyzer 

With that tool, using your own fixed cost per day, variable cost per mile and that self-pay salary figure per day to then compare as many loads as you like for profit potential, you too can set those driver-pay needs to be calculated on the expense side of the profit analysis.

For June Trucker of the Month Scott Smith, though, it’s his own system that accounts for all of it -- indeed a now not-so-secret weapon we'd wager many owners out there might do well to emulate in whatever form works best for the operation. In the podcast, hear more about Smith's operation and history trucking from the start, back in the early 2010s when like many out there he just happened into a love for the road via work in a different sector than the hopper- and flatbed-hauling work he does today.

Nominate your own or another business to contend, like Smith, for Overdrive's 2025 Trucker of the Year award: https://overdriveonline.com/toptrucker 

Read about all of our 2025 Truckers of the Month via https://overdriveonline.com/trucker-of-the-year

Secret weapons for bookkeeping, biz analysis: Trucker of the Month Scott Smith

This week on the Overdrive Radio podcast, another entry in our 2025 Trucker of the Year competition: https://overdriveonline.com/trucker-of-the-year 

You may have seen Matt Cole’s feature a couple weeks back now about longtime independent Ron Kelsey, who’s achieved something of an "owner-operator holy grail," as it were, trucking for decades now in a 1981 Peterbilt 359 and hauling direct freight for customers that date back three decades for the owner: https://overdriveonline.com/15751895 

Kelsey’s recent-history experience, too, stands as testament to the bedrock value of direct-freight relationships when the proverbial you-know-what hits the fan. With a "freight recession" ballyhooed by prognosticators time and again over the last three years, and spot rates down over the same period, Matt Cole asked Kelsey how he’d fared through tough times of these recent years.

"I really don't notice a change," Kelsey said, on the ground with his two principal customers. "I'm not No. 1 anymore" among independents hauling for them, given as he's progressed in his career he's not quite as consistently over-the-road as he was in past years. Yet general freight slowdowns he hasn't noticed. "I work when I want to work," and the loads are plentiful, always something availble, loading pipe outbound from the Phoenix and most often steel on the return. Invoiced, customers pay within days, too. 

"I'm very fortunate," he added, but there's more to his business prowess than just following the tides of fate, as you'll hear in the podcast. He’s well set-up to weather anything that comes, ultimately, and has come a long way himself from the young man who would end up inking a deal for his 1981 Pete after two-stepping with the owner way back in 1984. He’s hauled with it ever since, getting his authority 10 years later and building what the Kelsey's Trucking business remains to this day. 

Hear his story in his words in today's episode, starting like many an owner-operator in a straight truck in vocational operations before a trial by fire over the road in the late 1970s. 

Nominate your own or another deserving owner-operator business for the 2025 Trucker of the Year award via this link: https://overdriveonline.com/toptrucker

Freight recession? Trucker of the Month Ron Kelsey just hasn't seen it with two direct customers

This week's Overdrive Radio podcast is a re-air for owner-operators and other truckers on the occasion of the 2025 Commercial Vehicle Safety Alliance Brake Safety Week inspection blitz. Get over to OverdriveOnline.com for an updated list of our Top 10 toughest states for brakes violations, to get a bit of a clue into where you might expect inspectors’ scrutiny of braking systems to be most intense this coming week: https://www.overdriveonline.com/csas-data-trail/article/15753592/10-toughest-states-for-truck-brake-inspections-as-blitz-arrives

Brake Safety Week runs August 24-31, and along with reporting around brake-system inspections there for this episode we revisit a talk with Fleet Safety Services’ Jeff Davis delivered at the 2023 annual conference of the National Association of Small Trucking Companies. Davis offered time-honored ways fleets and owner-operators can avoid the inspection to start with. Even in an inspection-blitz week like this one, fundamentals still apply. And keeping on top of maintenance -- particularly with regard to lights -- is a big part of it, but there’s more to it than that. So we’ll just let the tape roll on the past episode this week. Keep in mind it was released ahead of the Spring 2024 Roadcheck event, initially. There are plenty references to that now-bygone inspection blitz event throughout, but nonetheless plenty to chew on from Davis. 

More brakes-related resources at OverdriveOnline.com/15753592

Even during blitz week, fundamentals count: How to avoid inspection without dodging scales

"I spend a lot of time making deliveries around here, so I have my little spots I know I can park." --Owner-operator Jason Shelly, speaking to knowledge borne of more than two decades' experience serving customers in Amish markets on the East Coast   

Those words were among the first owner-op Jason Shelly spoke when he talked to Overdrive Editor Todd Dills in early August attendant to reporting on his longtime one-truck business, Overdrive's 2025 Trucker of the Month for August: https://www.overdriveonline.com/trucker-of-the-year/article/15753418/trucker-of-the-month-jason-shellys-multistop-reeferhaul-niche 

He'd gotten parked up for the call mid-run on his regular route through the Washington, D.C., area, among the many routine destinations for his multistop reefer-haul business. It sets the scene, as it were, but also demonstrates the expertise he's built through consistency through the years, through specialization in that now 20-plus-year run loaded with fresh meat bound for those Amish markets. In this week's Overdrive Radio edition, sit in with Shelly as he tells the story of how he proved his invaluable nature to the customers starting with a partner serving a premium pork producer, then following through with consistent customer service as demand grew and grew and grew for the product over those decades.

Headquartered in Pennsylvania in the town of Telford today, owner-operator Shelly's legacy is certainly a work in progress. He's got plenty of working years ahead of him, but he's been nothing if not outgoing in his efforts to lend the benefit of expertise to those coming up behind him. As experience has shown, those relationships then grow to the point of mutual business benefit, too, as the Trucker of the Month feature about Shelly last week illustrated. Owner-operator Kris Bair, a decade and more Shelly's junior, calls him a mentor, no doubt, a sounding board for ideas and questions. Bair also bought his first truck, a restored 1980 A model Kenworth, from Shelly, with private financing worked out between the both men. 

For the very brief moment Shelly thought he was going to be potentially getting entirely out of trucking when he and his business partner sold to a larger operation, Bair then traded that W900A back to Shelly for his longtime runner, a 2000 W900 outfitted with a custom Double Eagle big bunk. 

Does Shelly still have that W900A in his stable today? Dills asked the owner-operator.   

"I upgraded and financed it for another" young trucker looking to get his start in business. "I'm not looking to get in the finance business" by any stretch, said Shelly, "but I figure everybody needs to get started, and I had some really good guys in my life that helped me get started." 

He's been able to be that helping hand up the ladder, so to speak, for the generations of owners behind him "several times over the years," he added. Hear his story, in his own words, in this Part 1 of our talk with Shelly on the podcast today. 

Shelly's Trucker of the Month nod for August puts him in the running for the 2025 Trucker of the Year award, sponsored for the year by Bostrom Seating, who’s putting a new seat on the line for the ultimate winner. You can enter your own or nominate another deserving business for the award at https://OverdriveOnline.com/toptrucker.  

A helping hand up the ladder: The mentorship legacy of Trucker of the Month Jason Shelly

"I want to honor my wife and her being the 'woman behind the man behind the wheel,' which is a high calling. Our first date ... was the day I bought that 1997 W9, so she didn't know what she was getting into." --August Trucker of the Month Jason Shelly 

Jason Shelly starts this Part 2 of a series of Overdrive Radio episodes featuring the owner-operator with a tribute to Renita Shelly, who's been Shelly's "biggest fan," as she once told him, since the very start of his business. The truck he invokes in the quote up top and in the podcast is the very first one he purchased, when he was a company driver for Horseless Carriage Carriers in the 1990s and thinking he'd be able to lease on with the car hauler. The fact that he didn't, though, as he told in Part 1, set him off on a journey to a long-term customer and a business that has benefited from all manner of family support, including Renita's, through the years. He's striven to pay it forward in all sorts of ways, and does so here of a fashion with his emphasis on that support, key to many a truck owner-operator's success. 

His longtime owner-operator father, also pictured in the cover assemblage for this episode, is intimately involved in the accounting/bookkeeping and other aspects of Shelly's one-truck business, including recent work reburshing the 2017 53-foot Great Dane reefer trailer also pictured. 

But it's Renita he emphasizes most for all manner of sometimes intangible impacts that have nonetheless been a lynchpin of his long-term success. 

"It's not an easy life, schedule-wise, and just the ups and downs. And at a certain point, she knew I wasn't going to be home until she saw the whites in my eyes, because anything can happen between here and there," he said. And when it did, "she's just been so patient, so understanding."

Going into the "second half of my career," he said, he's making a conscious effort to be more accommodating, too, remedy for all those times that "something or other happens at home and I'm 400 or 700 miles down the road and headed the wrong direction," which the "woman behind the man behind the wheel" bears on her own. Shelly referenced the old trucking song there. (We had a podcast episode put together by Max Heine about that one back several years ago here: https://www.overdriveonline.com/15065078 )

So for this episode, a tribute, but also plenty more in the way of Shelly's advice for the next generation of owner-operators trucking. Jason and Renita Shelly are certainly making it work for their family, and diversifying investments as time goes on that ought to set them up long-term financially. Not that Jason’s got a particular eye on retirement, which we’ll also hear more about in today’s episode. 

As he says, "I don't look to retire, exactly. I may slow down. But biblically, there's no verse that I've ever found in the Bible that says you retire at this age" or that age. Rather, "it says to finish strong." Read more about Shelly: https://overdriveonline.com/15753418 

As mentioned in the podcast, the playlist of all the episodes featuring of our Truckers of the Month for 2025, contenders for the Overdrive Trucker of the Year award: https://soundcloud.com/overdriveradio/sets/overdrives-2025-trucker-of-the

Read about all of them: https://overdriveonline.com/trucker-of-the-year  


Trucking success, with a family assist -- the woman behind owner-operator Jason Shelly

This week on the podcast, the voices of two semi-finalists for Overdrive's 2025 Small Fleet Champ award: 

First, Robbie and Levi Turnage of Mississippi-headquartered tanker fleet Turnage and Sons, LLC. They're respectively fourth- and fifth-generation milk haulers who've made good on a business with a stable of dairymen in the region specializing in organic milk over two decades of so Robbie's grown the fleet from just a single truck, following in the footsteps his father, grandfather and great grandfather before him -- the hands-on nature of each successive generation’s training and involvement in the shop, behind the wheel, and everything else that goes along with running a trucking business have no doubt contributed to the family business' longevity, with 19-year-old Levi now fully entrenched as well. 
 
In the podcast, you'll hear the Turnages in conversation with Overdrive's own Long Haul Paul Marhoefer in the cab of Levi's 2005 Peterbilt 379 "Big Red" parked up in March at the Mid-America Trucking Show. Marhoefer wrote about the pair in a story published in July you can read here: https://www.overdriveonline.com/overdrive-extra/article/15751311/five-generations-trucking-the-turnage-familys-longevity-secret

Catch some pictures there of Big Red, too, which placed second in its class at the MATS show. Stay tuned for more reporting on the Small Fleet Champ contender in the coming weeks. 

Also in the podcast, fellow semi-finalist MRL Transport owner Mark Ledford, who founded and grew Red Baron Transportation to 35 trucks over 15 years starting in the early part of the decade before selling out and restarting with just one truck in 2019 as MRL. That story aired just last week at https://www.overdriveonline.com/small-fleet-champ/article/15753736/mark-ledfords-mrl-transport-master-class-in-trucking-rightsizing 

He’s up to five trucks now, with four drivers employed, and similarly gets his hands dirty behind the wheel himself, a fact key to both maintaining customer relationships spanning back decades now but also inking new business, as he tells in the podcast. Here, he takes even farther back to his origins in trucking working a dock in the 1980s, then his first OTR driving experience with a team operation. On his first run from North Carolina out to California his co-driver woke him up by turning the rig on its side in the middle of the night, memorably leaving Mark to climb out of a window and onto the cab's side, now upright, unable to find his glasses to sharpen the blurry lights all around him. Needless to say, as he notes in the podcast, he never would run team again. 

Meet all Overdrive's 2025 Small Fleet Champ semi-finalists and read more about them through this month via https://overdriveonline.com/small-fleet-champ 

Two Champs will be honored along with two fellow semi-finalists at Championship sponsor NASTC's annual conference October 23-25 in Nashville. More about NASTC: https://nastc.com

Small Fleet Champ semi-finalists not afraid to get their hands dirty in shop, behind the wheel

How might truckers get back a measure of flexibility in the hours of service rules, such as that enjoyed by so many owner-operators of past generations? That is, the ability to split the 10-hour required rest period into two periods of any length they want. That’s the option favored by a whopping 88% of readers who responded to Overdrive polling around the subject this time last year, with results published earlier in the year showing most readers wanted the ability just to split as they saw fit, fundamentally. 

Since the 14-hour duty window came into play more than two decades ago, well before the time of electronic logging device mandate's implementation in 2017, greater duty-window and/or rest period flexibility has been owner-operators' cardinal ask of regulators when it comes to the hours of service. 

After trucker appreciation week last week, we might see a path forward to it. In this Overdrive Radio edition, Chief Editor Todd Dills and Matt Cole break down the details of the DOT and FMCSA's announcement to start truck appreciation week last week of two proposed pilot programs to fully test two different options for split flexibility. 

It’s not often we start the annual appreciation week with something other than a free soda at a truck stop or other deal from a vendor or supplier to write about. Yet that was the case for Cole last week Monday, when DOT announced formal proposals to conduct those safety-efficacy studies. One's the split-as-you-see fit option of up to 5/5-hour sleeper splits, the other a daily up-to-three-hour pause button, spot to speak, for the 14-hour clock. 

The news wasn't entirely unexpected, nontheless. The formal proposals had been teased back in June as part of what the DOT called a “Pro Trucker” package of efforts. The formal proposals open up a comment period on how regulators might set up and conduct the programs, each of which will be open to more than 250 drivers to participate: https://www.overdriveonline.com/hours-of-service/article/15755537/what-fmcsas-hoursofservice-flexibility-pilot-programs-could-look-like

We’re certainly months out from interested participants being able to apply to take part, and given each test could take years to bring to fruition, it could be quite some time before any subsequent regulatory action is taken. That is, unless another federal body pushes the ball more quickly forward, as Cole puts it in the podcast, and "Congress were to get involved." 

Absent Congressional directive to take regulatory action, further hours flexibilities for all drivers aren’t likely in the cards before the next decade rolls around after these studies conclude -- depending on results, of course. That timeline takes us into whatever administration follows the current one.

"Personally I don't see this as necessarily a partisan issue," said Cole. "If a Democratic Administration were to come in" come 2029, he felt FMCSA wouldn't be likely to wholesale abandon work put into potential new flexibilities. After all, some of groundwork for the 2020 split-sleeper enhancements was put in under the Obama administration. 

If these two studies show positive or even neutral safety impacts for participating truckers, it might really get things moving toward change for the next administration's FMCSA.

Where to read and comment on the proposals, through mid-November: **Split-sleeper program: https://www.regulations.gov/document/FMCSA-2025-0193-0001 
**Split-duty program: https://www.regulations.gov/document/FMCSA-2025-0194-0001

More on the 2020 split-sleeper change, which itself offered a boost in duty-pause and split flexibility: https://www.overdriveonline.com/partners-in-business/safety-compliance/video/15737159/significant-hos-change-fmcsas-2020-splitsleeper-provisions

Sleeper berth: Will truckers be able to split as they see fit? FMCSA opens potential path forward

The Overdrive Radio podcast is produced by Overdrive magazine, the Voice of the American Trucker for 60-plus years. Host Todd Dills -- with a supporting cast among Overdrive editors, contributors and others -- presents owner-operator business leading lights, interviews with extraordinary independent truckers and small fleet owners, and plenty in the way of trucking business and regulatory news and views. Access an archive of all episodes of Overdrive Radio going back more than a decade via this link: http://overdriveonline.com/overdrive-radio