Count down to the new year with this playlist featuring the most-listened-to editions of the Overdrive Radio podcast, from No. 17 to No. 1, covering trucking businesses and on-highway issues, music by and for highway haulers, and so much more.

2021 in review: The top Overdrive Radio podcasts of the year

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

Wisconsin-based owner-operator Jason Hurley, a former Schneider- leased owner-operator, made a move earlier this year to the young operation of CloudTrucks. The Texas-based company, with some operations in California, pitches to owner-operators as a "virtual carrier," operating less like a traditional asset-based carrier and more like a support company, basically. Cloud puts emphasis on its technology and systems in place to support otherwise independent businesses.

Yet they're no broker or dispatch service -- it's CloudTrucks’ motor carrier authority under which an owner leased there runs.

And though its model generally is tech-assisted self-dispatch for how owner-operators run there, it does field a functional support staff on the back end to smooth out the rough edges of any carrier-broker transaction. The brokered freight market comprises the large majority of its freight universe. Since founding within the last years, they’ve grown quickly. They were up to more than 70 owner-ops leased as of the company’s most-recent MCS-150 federal update earlier this year.  

Hurley was attracted initially for a percentage contract for compensation much lower than is traditional for asset-based companies taking care of leased owners' liability insurance. CloudTrucks allots 5 points of its 15%-per-load fee to the owner-operator's liability insurance, Hurley said, leaving a 10 percent fee otherwise for access to the company's freight platform and support networks. What he's found so far there? Find out in this podcast. 

Read about CloudTrucks' "Road to Independence" partnership with third-party leasing companies to offer a path to truck ownership for company drivers through fair lease-purchase programs: https://www.overdriveonline.com/business/article/15065768/alabama-truckers-fight-truckonly-toll-proposal-in-mobile

More from Overdrive Radio: http://overdriveonline.com/overdrive-radio

Real success leased to a 'virtual' carrier: Owner-operator Jason Hurley and CloudTrucks

The context for the conversation you'll hear in today's 60th-anniversary special edition of Overdrive Radio, conducted at the Great American Trucking Show in 2019, was twofold, centered around both driver training and history. 

Over the course of the 20th century, as you'll hear, the licensing required for a driver to operate interstate tightened. In the early days of motorized transport, an 18-year-old had no problem being licensed for interstate operation of what passed for the big trucks of the day. 

They weren't, of course, very big at all by today's standards. The picture here is one of of Walter Thompson of Shelburn, Indiana, grandfather of Jay Thompson, now an independent consultant to various trucking and natural gas interests through his Transportation Business Associates company.

As I wrote at the time of this conversation's original airing two years ago, Thompson’s been quite a resource for me when it comes to owner-operator and trucking history in general. He grew up in rural Indiana and starting his working career driving big trucks, a route taken by the generations of men in his family as well, all the way back to his grandfather.

Walter Thompson had a chauffer’s license enabling him to move freight as early as age 18, in 1917. And given debate continues around training and potentially opening up interstate operations, perhaps in a limited fashion, to some drivers younger than 21, Thompson's thoughts do more than just gives us a window on trucking's history through the lens of one family's experience.

We were also talking at the time about the potential potential for a pilot program for under-21 CDL drivers, then under intense debate, as we sat down to ferret out a little bit of the history there.

As Thompson says, history often repeats itself in various ways … 

Find more installments in Overdrive's 60th-anniversary series of lookbacks on history via http://overdriveonline.com/trucking-history

What came before the CDL? 18 years old and hauling interstate in 1917

The thumbnail image with today's podcast was the product of the 2019 groundswell of grassroots advocacy that rose leading into the ultimate passage of the AB 5 law in California, which codified a controversial court decision that applied the ABC contractor test in the state. That test, to say the least, is problematic for owner-operator lease arrangements with motor carriers as they've traditionally been drawn up -- and federally recognized now for decades in the Truth in Leasing regulations. 

In this week's edition of Overdrive Radio, we’re going to drop into the annual Symposium event hosted by Overdrive sister fleet publication CCJ. This past Wednesday in Birmingham, Alabama, at the event, CTA CEO Shawn Yadon described what he saw with his own eyes on the ground in 2019 as that groundswell of advocacy rose. The result of that advocacy – a myriad of carveouts in the law by the legislature aimed at a laundry list of professions, but not for trucking, not for owner-operators.

That set up the Supreme Court case Yadon and CTA filed Monday, and here we get more on potential outcomes from both Yadon and transportation attorney Greg Feary of the Scopelitis, Garvin, Light, Hanson & Feary law firm. Both men had much more to say about the history of how we got to this point, with owner-operators and their contracting motor carriers still playing the high-stakes waiting game on the outcome. 

Read more about the session in this report from the scene Wednesday: https://www.overdriveonline.com/regulations/article/15113768/the-california-conundrum-independent-contractor-state-of-play

And more about the 2019 advocacy efforts here: https://www.overdriveonline.com/channel-19/article/14897067/rumblings-of-protest-out-west-in-wake-of-california-contractor-law

Owner-ops' big role out West as AB 5 wound toward this week's Supreme Court filing

In this edition of Overdrive Radio, hear the musical entries of, and interviews with, the three songwriters who are finalists in this year’s Overdrive Red Eye Radio Trucker Talent Search. It's something of a preview of the big finale, set for September 16, at 5 p.m. Eastern time, and streaming from OverdriveOnline.com. 

Find out just how to tune in live that date and sign up for email reminders just before the broadcast via this link: https://www.overdriveonline.com/trucker-talent-search/article/15066153/trucker-talent-search-final-competition-set-for-september-16

In the podcast, we'll hear from trucker Mike Sheffield of Kentucky coal country, from Michigan-based Grassmid driver Rich Scripps, and Dayton, Ohio-based Guy Archer. All are featured in conversation, too, with the great Eric Harley, host of Red Eye Radio, Overdrive's partners in the program, now in its 8th year.

This year's event's proved to be a special one, no doubt, with these excellent songwriters with incredibly diverse styles.

Read more about Guy Archer via this link: https://www.overdriveonline.com/trucker-talent-search/article/15065701/trucker-talent-search-finalist-covers-chesneys-anything-but-mine

Mike Sheffield: https://www.overdriveonline.com/trucker-talent-search/article/15065572/mike-sheffield-performs-original-song-hammer-down-again

Rich Scripps: https://www.overdriveonline.com/trucker-talent-search/article/15065636/trucker-talent-search-competitor-covers-hawaiian-christmas-song

Trucker Talent Search preview: Sheffield, Scripps, Archer square off September 16

Helping carriers dealing with the 'fun' that can come with safety and compliance during federal or state audits is at least a good part of the life of Fleet Safety Services consultant Jeff Davis, the principal voice in this edition of Overdrive Radio. After starting in trucking as a driver, Davis eventually made a career helping mostly small motor carriers through those compliance reviews. 

At the annual conference of the National Association of Small Trucking Companies this past week in Nashville, Davis offered information into new audit activity related to the relatively new drug and alcohol testing results Clearinghouse maintained by the Federal Motor Carrier Safety Administration -- and common slip-ups carriers are making with required pre-employment and other checks there. 
Too many, he said, are getting dinged by auditors for violations that are ultimately easily prevented, as he tells it. There’s a lot happening in terms of the Clearinghouse, too, that Davis rounds up in what follows here, certainly germane to those of you in the audience who employ or lease with one or more drivers or owner-operators. 

Also in the podcast: We'll dive into the Small Fleet Champ awards presentation Thursday night to the record-setting group of NASTC attendees at its annual conference – according to President David Owen, attendance at the event nearly doubled prior years’ registrations, truly something to behold. 

Congrats again to finalists Hallahan Transport and Professional Transportation Services Inc. – and the ultimate Small Fleet Champ in Silver Creek Transportation. This isn't the last we'll hear from owners Rob Hallahan, Nick Hewitt and Jason Cowan, be assured. 

Read more about each of the finalist fleets:
Hallahan -- https://www.overdriveonline.com/small-fleet-champ/article/15280238/hallahan-transport-thriving-on-lessons-learned-from-the-past
PTSI: https://www.overdriveonline.com/small-fleet-champ/article/15280537/trucking-legacy-of-nick-hewitt-and-platform-hauler-ptsi
Silver Creek Transportation: https://www.overdriveonline.com/small-fleet-champ/article/15115043/diversification-silver-creek-transportations-growth-secret

'Fun' with safety/compliance: Low-hanging fruit to avoid drug/alcohol Clearinghouse violations

This week's Overdrive Radio edition puts a wrap up our series featuring 2025 Trucker of the Year contenders with the story of Orleans, Indiana-headquartered John Penn, his one-truck business operating with authority and hauling finished furniture on multistop runs West and/or South from his home base, other brokered freight back. 

He’s the owner of another power unit, too, that he keeps as a spare, both rigs Freightliner Cascadias he details in the podcast and in this in-depth feature about his business, where he was named the October 2025 Trucker of the Month: https://www.overdriveonline.com/trucker-of-the-year/article/15770500/trucker-of-the-month-reaps-10mpgplus-rewards-learning-growing

Both Cascadias feature specs that help him achieve maximum fuel mileage -- upward of nine miles per gallon in the older unit (10-speed manual transmission) and more than 10 mpg in his current 2019 model, with the DT12 automated manual transmission. 

We didn’t know it when he entered our Trucker of the Year competition, but he’s also the newest member of Freightliner’s Team Run Smart group of owner-operators sharing their own successes in various ways with their Freightliner equipment for the benefit of anyone interested. Team Run Smart hadn’t yet officially intro’d him as part of the crew there when we published the above story about him. Reps confirmed he was going to be a part of it for sure, but what they didn’t tell us was they’d post his official intro video to their Youtube networks that very same day: https://www.youtube.com/watch?v=gFyerQQX7lY

Find him now at his profile page on the Team Run Smart site: https://www.freightliner.com/team-run-smart/pros/john-penn/

I’d encourage you, too, to track back through all of our Truckers of the Month and Trucker of the Year contenders for 2025 at the main page for the competition: https://overdriveonline.com/trucker-of-the-year  Plenty business best practice examples there, plenty to learn from in the stories of 10 exemplary owners this year. Keep an eye out there for the 2026 competition's entry page, where you can get in the running yourself in the coming weeks. 

Though owner-operator Penn's modest about his success, it’s clear the owner’s doing quite a lot right with a very low operating ratio given his business’s efficiency, and with a home life that’s benefiting, too, as a result. Dive in with Penn from the very beginning, when he first got his CDL around the turn of the century, the start of a journey toward maximum trucking efficiency.

J.P. Transport: Building max trucking efficiency, with owner-operator John Penn

Off the top of the Overdrive Radio podcast this week is the voice of fuel-payments provider Wex's Vice President of Global Anti-Financial Crimes William Fitzgerald, laying out a 1 in 12,000 transaction rate for detection of fraud over the company's entire fuel-payments network. That is, 1 in every 12,000 purchases are flagged as suspiscious, potentially fraudulent, and blocked in automated fashion among its millions upon millions of fuel transactions facilitated annually. 

Translate that incidence to the roughly 350,000 fuel transactions National Association of Small Trucking Companies President David Owen knows move through the association’s own Quality Plus fuel network any given month, and that’s right at 30 transactions being held up by the system. William Fitzgerald was speaking at NASTC's annual conference to outline the evolving landscape of fuel fraud/theft for attendees and showcase tools within Wex's (and some other card providers') networks that are increasingly successful in helping carriers of all shapes and sizes eliminate fraud's impact. Along the way, too, the company's been able to reduce the rate of so-called "false positives," legimate fuel purchases held up by the card provider's systems. Fitzgerald's well aware such hold-ups can be particularly annoying, and unproductive. Illustrating the huge financial impact of stolen fuel, though, he asked this hypothetical question to a room of NASTC conference attendees: 

"What would be an acceptable false-positive rate in your minds?" he asked. "How many good transactions would you be OK with me stopping to prevent a bad one?"

The goal is zero false positves, of course, as Wex and other card providers calibrate a variety of techs operating in the network's background to get there, in addition to more human-focused efforts aimed at education to prevent account takeovers and the like that can bring the biggest hits to a fuel buyer’s bottom line. Results from ongoing efforts at Wex in particular have been good in recent months, he said. "We've got overall, over the last 10 months, a 25% reduction in losses, a 32% reduction in false positives," and a big increase in detection, too, he said.  

Those results he attributed largely to technical innovations in company’s network, some described in part in a recent paper authored by the company you'll find at this link: https://www.wexinc.com/wp-content/uploads/2025/09/WEX-Closed-Loop-Fleet-Card-White-Paper.pdf

But the human element in fraud prevention might be the biggest factor any size carrier can address to make the most gains in preventing losses, empowering themselves through self-education and passing that on to team members for those of you with more than just a single truck under your management. "We've seen the most yield" in fraud prevention, he said, "with education and empowerment." 

Fitzgerald described efforts of Wex to illustrate the kinds of schemes that might result in infiltration of its own backend, including simulated phishing attacks through targeted fake emails designed to get a user to provide access to their login data with a goal of compromising accounts. Wex sends such emails to its own employees on occasion to lure them in, thus serving an educational purpose in awareness. Their most "successful" such an effort? An offer of "free Taylor Swift tickets. Everybody clicked on that," Fitzgerald said. 

In the podcast, track through Fitzgerald's entire NASTC talk, tracking through those backend upgrades but also plenty more you can do to work with the company's team and tools in its system, like its SecureFuel solution, to prevent fuel theft. Likewise, should the worst, to work with law enforcement to apprehend the thieves. 

Mentioned in the podcast: 
**'Personal cyber hygiene' in age of social engineering hacks: https://www.overdriveonline.com/15755615 
**More from NASTC's conference on insurance, ELD data: https://overdriveonline.com/15770374

Trucking tools to prevent fuel fraud, from complex AI to simple cybersecurity self-education

December’s here, and it’s time for the big push through to 2026 and opportunity a new year always brings a business owner to set goals, to lay plans and start acting on them. Yet as you’ll hear in this edition of Overdrive Radio, it’s also true that in so many ways the time for all of that is now, for any small trucking business owner, at any given moment. Like a football coach responding to what the opposing team throws at his own, a quarterback changing the play at the line, successful owner-operators are nothing if not masters of the art of getting prepped for the unforeseen. It's an impossible ask of anyone in some ways, but also a reality you’ll hear through today’s talk with four Overdrive Trucker of the Year contenders for this year’s title. 

None less so than owner-operator John Treadway, our September Trucker of the Month. He delivered the shocking news of his pristine 1998 Peterbilt 379's October catastrophic engine failure. How might one prepare for that? Owner Treadway's long experience taught him, like others featured in this roundtable talk, the importance of the back-up plan, and not only could he afford what will ultimately be a reman Caterpillar crate engine powering the unit. The original Cat in the 1998 379 he's hopeful to rebuild with some close associates, furthermore, to in future repower his back-up power unit. 

That backup, a 2006 379, with plenty miles on the odometer itself, is yet another element of Treadways effective prep for the October catastrophe. It's enable him to continue serving his primary and other customers as Caterpillar works through issues with the engine replacement. 

His isn't the only update you'll get from owners in this podcast, where host and Overdrive Chief Editor Todd Dills put two principal questions to four owners: 

1. How's business looking as we head into 2026, and have any goals set early in year 2025 been brought to fruition? 
2.  Reflecting on your own history trucking, what's the single best piece of advice you might deliver to new and/or aspiring owner-operators to help on the long road to success? 

Featured, along with Indiana-headquartered Treadway: 
**John Penn, our most-recent Trucker of the Month in October, hauling LTL furniture principally: https://overdriveonline.com/15770500
**Similarly LTL-focused fresh meat reefer hauler Jason Shelly, based in Pennsylvania: https://overdriveonline.com/15753418 
**And two-truck dump fleet owner (with a third truck in more OTR work) Hunter Hubbard: https://overdriveonline.com/15741276

Overdrive's Trucker of the Year competition is sponsored for 2025 by Bostrom Seating -- there's a new seat on the line for the contenders. Consider this roundtable the "Exit interviews" with each ahead of announcements late this month of finalists, after the judging round. Stay tuned in the coming weeks for more featured contenders.   

Catastrophic engine failure delivers customer calamity: How one owner-operator prepped for the worst

As you'll hear off the top of this week's Overdrive Radio podcast, this “exit interviews” part 2 in our final run to conclude Overdrive's Trucker of the Year competition for 2025 features an all-flatbedders group. You’ll hear a bit of what some call "bygone" driver-to-driver camaraderie amongst the four owner-operators featured around -- what else -- the subject of tarping. 

Arkansas-headquartered Scott Smith, owner-operator of Sapphire Cartage, described some new work hauling outbound to Atlanta with overlength freight. The rates are great with permits required, and lightweight, delivering fuel savings. Yet also: tarps required: "Putting on three tarps, putting three tarps' worth of bungees, taking off three tarps, folding up, putting up three tarps," he said. "Anybody got any sympathy?" Much laughter followed, of course. 

Also in the podcast: 
**West Virginia-headquartered independent George Kincaid: https://overdriveonline.com/15743659
**Longtime Kelsey’s Trucking owner-operator Ron Kelsey, who hauls in a beautiful 1981 Peterbilt 359 repowered in the 1990s with a C15 Cat and working with two principal direct customers upwards of three decades: https://overdriveonline.com/15751895 
**And Rufus Morris, out of North Carolina, leased to Material Logstics Management and for whom it’s been an eventful year for his equipment: https://overdriveonline.com/15747142

Much like the story you heard from John Treadway last week, an eariler-than-expected in-frame reared its head with a cracked head for his 2004 Peterbilt 379. Then: more troubles rose in the following weeks and months. His advice to any aspiring owner-operator: Be ready for anything, at any moment. 

Tough moments at roadside can be enough to make even a seasoned veteran like Morris question himself. 

"I've had plenty times this year when I was like, 'Man, is it worth it?'" Morris said. But taking stock further, staring at that beautiful 2004 379, and despite all of its problems, "it's a good life," he added. "Yeah, it's worth it." 

Just be prepared for anything. 

With that something of a “final thought,” as it were, from Morris, the end is in the beginning for this edition of Overdrive Radio, full speed ahead to 2026 for these four Trucker of the Year contenders, this year’s competition sponsored by Bostrom Seating, who will deliver a new seat to the winner, ultimately. 

Enter the Trucker of the Year competition at this link: https://overdriveonline.com/toptrucker -- we're in the process of updating the form page there for 2026, but know that all entries received before the end of 2025 will be considered for the new year's program. 

All of the Trucker of the Year 2025 profiles you can find at this link: https://overdriveonline.com/trucker-of-the-year 


Trucker of the Year 'exit interviews,' Part 2: Flatbedders edition

"Every day had an episode like that along the way. It was just the high, and the low." --XPO driver David May, reflecting on the roller coaster of emotion hauling in the Maine-to-Arlington Naitonal Cemetery run of Wreaths Across America

Off the top of the podcast, we dive right into the experience of military veteran and longtime professional driver David May, trucking out of the Buffalo, New York, area and speaking the range of emotion delivered by his 2024 participation in what is the annual effort of Wreaths Across America. That's the Maine-headquartered organization that for many years now has been built momentum across the nation, every December honoring fallen U.S. military members by laying wreaths on graves in ceremonies at military cemeteries. Trucking plays a big volunteer role in it, for certain, with wreath deliveries from Maine to points far afield, this year reaching nearly 5,600 sites, according to Wreaths Across America organizers: https://www.wreathsacrossamerica.org/Home/News/1495 

The big day for the 2025 effort was this past Saturday, December 13, and for this Overdrive Radio podcast, we’re marking another big haul for participating truckers and trucking companies by revisiting David May’s experience as part of the 2024 convoy moving out from Maine toward Arlington National Cemetery for the big event held there annually. To give you an idea of the scale of that one, this year at Arlington, organizers noted, wreaths were placed on 265,000 individual headstones there through the work of 30,000 volunteers. 

That haul alone is a massive undertaking, no doubt. 

Honoring the memory of the fallen isn’t the only aim of the Wreaths organization. Here’s the goal in full: "Remember the fallen, Honor those who serve, and Teach the next generation the value of freedom."

Through our conversation with David May you'll hear quite a bit of all of that -- Remember, honor, teach -- yet also a window on just what his experience of the 2024 convoy toward Arlington was like. May’s hauled day-to day for XPO going back decades to when he was with Con-way Freight before the XPO buyout,. He’s a past America’s Road Team captain, where he first learned about Wreaths Across America in its early days. In 2024, he hauled wreaths in the convoy piloting the camouflage-wrapped “workforce heroes” truck of the road team, but it’s his individual experience, the veterans met and the fallen remembered, that most stand out. 

That includes memorable time spent with a Vietnam veteran in-cab, and much more besides. 

Just a few pieces of past coverage of the Maine-Arlington convoy, and other wreaths events around the country: 
**2023 interview with Don Queeney, Director of Transportation for the organization: https://www.overdriveonline.com/15304674
**2022 convoy stop in Connecticut: https://overdriveonline.com/15304350
**2021 in the San Joacquin Valley, California: https://overdriveonline.com/https://www.overdriveonline.com/15286668
**2014: Trucker Vince Strupp recalls prior-years' participation in the convoy: https://www.overdriveonline.com/14887458
**2013 in Nashville, Tennessee: https://www.overdriveonline.com/14885399

Wreaths Across America: Professional trucker David May's emotional highs, lows on mission to Arlington

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