Clifford Hay II grew up in and around the trucking business. His father started the family business in 1972, and the junior Hay rode in his dad’s truck as young as two years old. He got his CDL in 1985 and has been trucking steadily ever since.
In 1999, Hay's initial foray into business ownership duly came when he bought the family business, Clifford C. Hay Inc., from his father. At the time it was but a one-truck, one-trailer outfit. Today, Hay owns six trucks and 30 trailers, hauling hay, lumber and dry van freight, mostly operating in the Northeast and up into Canada out of his Cobleskill, New York, home base.
He grew the fleet in the early years of ownership, by 2010 up to four trucks, humming right along as a business. In February of that year, though, his garage caught fire and burned to the ground, along with his four trucks, all of his tools, everything.
“That was quite a setback,” he said. “You know, found out how underinsured I was. It was a huge wake-up call.”
Hay didn’t let the setback define him, however. In the 15 years since, he’s rebuilt the business beyond where it was at the time.
“If it wasn’t for my wife and daughter, with their support of telling me I wasn’t going to give up," he said, encouraging him to rebuild the shop and get the business rolling again, Hay might not be where he is today. "My wife and daughter just kept pushing me like, ‘that’s not you’” to quit. “’We know who you are.’”
He went to his local bank. “No matter what I wanted, they supported me. No questions, nothing asked," he said. "They said, ‘we know you can do it, your credit’s great.’ And whatever I needed to buy, to purchase, they have me the loan for it without any questions.”
Hay's fleet hauls a lot of hay. Lumber and wood shavings, too, all of that for direct customers -- that's been the case since he bought the business and took on his father's customers. The son has continued to grow during his quarter-century-plus of ownership.
“Cliff and his team have been hauling lumber and shavings out of here for years,” said Alex Darrah, sales manager with Durgin and Crowell Lumber Co. “I cannot imagine a more professional outfit. His trucks and equipment all look like show pieces; they are immaculate at all times. I don’t know how he does it.”
Hay’s personal 2007 Peterbilt 379 Legacy shows what Darrah means, no doubt, crowned Overdrive’s Pride & Polish Limited Mileage champ last year. While that truck doesn’t work anymore -- he pulled it off the road in 2020 after working it for about a decade -- it’s an example of the pride Hay and his drivers take in the company’s equipment.
Cliff Hay is shown here with that 2007 379 Legacy, in the midst of the only work it does in its retirement -- hauling the the mobile Vietnam Wall that Heals memorial.
This is one of several Small Fleet Champ semi-finalist profiles that will air throughout this month. (Access all of the published stories via this link.) Two finalists in each category (3-10 trucks, 11-30 trucks) will be announced in October.
Clifford Hay II and team are among semi-finalists for Overdrive's 2025 Small Fleet Champ award, competing in the 3-10-trucks division.
Rolling with the punches of trucking's ebbs and flows
Hay said he’s happy with the size of his fleet at six trucks, four of which run daily. He turns 58 in September and isn’t looking to grow anymore at this point in his career. As also noted fellow Small Fleet Champ competitor Mark Ledford about MRL Transport, “this is my sweet spot,” Hay said.
With the ups and downs of trucking in the last half-decade, Hay's well familiar with the cycles, "your slow times and your busy times," he said. "And when it’s the busy times, you got to go no matter what." A successful business doesn't "turn customers down. You got to go, even if you’ve got plans, dinner plans. No matter what, you got to go to keep the customer happy.”
According to Darrah with Durgin and Crowell Lumber, that’s just what Hay and his team do.
“It’s like the man has 12 more hours in a day than the rest of us,” Darrah said. “Cliff is the type of guy you can talk to and make a handshake deal and it’s as good as gold, which is far too rare these days.”
When business does slow down, “you try to ride it out as much as you can,” Hay said. He helps out a local wrecker company during dead periods, who may “call you in the middle of the night and you’ve been working all day, but you still go out and help them, you know, because you never know where your next dollar is going to come in."
The National Association of Small Trucking Companies sponsors the Small Fleet Championship. Finalists receive a year's worth of membership in the association, with access to a myriad of benefits from NASTC's well-known fuel program to drug and alcohol testing services and much more. All will be recognized at the association's annual conference, where the winner will be announced in late October in Nashville, Tennessee. Find more about the association via their website.
[Related: Right-sizing for management: MRL Transport owner Mark Ledford hits five trucks]
Darrah has observed that, too: “One of his guys, Mike, brings all my forklift drivers breakfast sandwiches like once a month out of his own pocket. That’s just the kind of above and beyond character Cliff attracts to his operation.”
With the economic challenges trucking has faced in the post-COVID years, Hay said he has raised his rates “a little bit” to “stay competitive,” while trying “not to price himself out.”
He’s also focused on safety with his drivers and has installed forward-facing cameras “to help take the liability away from us when we’re not at fault.”
Maintaining equipment, managing employee relations
In addition to Hay’s retired Legacy-edition 379, the fleet features two other 379s, a 2015 579, a 2024 Peterbilt 389 and 2025 589.
Hay's 2007 379 Legacy is shown here (right) with a 2024 Peterbilt 389X, No. 697 of 1,389 of the limited-edition run.
Of his three 379s, Hay said “they’ll stay forever” in the fleet as his all-time favorite truck model. Otherwise, Hay generally tends to hold onto other equipment for about five years before trading for newer units under warranty.
He performs a lot of the fleet’s smaller maintenance work in-house -- tires, oil filters, greasing. For large jobs, he works with a local shop, Palmer Service Center in Howes Cave, New York.
Oil changes happen every 50,000 miles, with filters changed every 10K. The trucks all get greased every other week. At each oil change, he samples and sends it to a lab to make sure there's nothing in the oil that shouldn't be there.
To help control maintenance and repair costs further, Hay's outfitted each truck with a Herd moose bumper to absorb impact and prevent damage from deer strikes. Insurance costs, too. "We’ve had to try to keep the insurance costs down from making claims of hitting deer,” he said.
Hay pays his drivers by the hour, an average of $30-$33 an hour. If they have to stay out overnight, they get an additional $70 flat. “And if they wash the truck, they get paid for washing the trucks because I’ve got a wash bay in my shop,” Hay said.
The company also pays half of the drivers’ health insurance.
[Related: Meet Overdrive's 2025 Small Fleet Champ semi-finalists]
