Want to build a small trucking company with a home base in the often lopsided load-to-truck freight market that is the state of Florida? You couldn't do much better than Kenny Wingate as your mentor. Wingate's owner of two-truck Southpoint Exchange, headquartered there in Auburndale. He himself learned a lot of what he knows about running a business over the years from small fleet owner Fred Johnson. .
Wingate certainly considered Johnson, since passed on, a principal mentor. "He was very successful," Wingate said of the owner, and taught him the tried-and-true maxim that "if you’ll take care of the pennies," keep a laser focus on improving all the small things you can, the big things, the dollars, "will take care of themselves."
Wingate's lived by that maxim over the five years he's been in business with authority, pulling LTL reefer freight often dedicated on north-south lanes. A lot of that work is done with the Patterson Companies fleet's brokerage side of the house. "We haul produce north and haul dairy products back to Florida," Wingate said.
Owner-operator Kenny Wingate,with his 2020 Peterbilt 579. Wingate notes Southpoint Exchange has supported the local community in and around Auburndale in various ways, including by contributing to the Future Farmers of America organization.
While Wingate's called Perez with problems to discuss, "I've never had an argument with him," Perez said. "I've never heard the gentleman curse."
The apple doesn't fall far from the mentorship tree, in this case. Perez could say the same about Wingate's mentor, too, he said.
Kenny Wingate's in measured growth mode today, with plans to put on a third truck after adding a second to his operation and hiring a driver in October last year. For these and plenty other reasons, he's Overdrive's Trucker of the Month for February, putting him in the running for the 2025 Trucker of the Year award.
Overdrive's 2025 Trucker of the Year program, sponsored by Commercial Vehicle Group and Bostrom Seating, recognizes clear business acumen and unique or time-honored recipes for success among owner-operators. Nominations are open for exceptional owner-operators, whether leased or independent. Nominate your business or that of a fellow owner (up to three trucks) via this link for a chance to win a custom replica of your tractor and prizes and perks from Bostrom and CVG.
Early mechanic experience, a life steeped in trucking: Pointing the way forward
As in anyone's personal life, as in business -- relationships are a two-way street. Perez's praise for Kenny Wingate comes straight back from the owner-operator. Wingate notes Perez has "always been in my corner if I need him for anything. Once he calls you back, everything is resolved."
When home, Wingate and company park their trucks, a 2020 Peterbilt 579 he drives and the 2022 model he purchased in October, at Patterson's terminal facility, where he's able to use the fleet's shop for routine maintenance work, he said. "Anytime I need the shop I just let him know, and the doors are open."
Kenny Wingate, 55, got where he is today after a lifetime trucking in some form or another. "I'm third generation" in the business, he said. "I grew up around it. My grandfather was a logger and a farmer -- my father was an OTR truck driver, running from Florida to California" and back.
Growing up, Wingate always told himself he'd never drive. As a young man, though, close proximity to trucking earned him plenty in the way of mechanical prowess. He ran a diesel-repair shop in Haines City, Florida, 35 years ago now, he said, where all too often he got offers he couldn't refuse from truckers coming back into town to his shop. "It got to the point where they'd come in, and they'd be like, 'If you deliver my load, I'll give you a $100, $150,'" just to take it to its destination in town.
"That's good money" for quick work, he told himself. One thing led to another, "and here I am today."
Wingate's owned trucks in the past, including early in his career, when he sought to stay local but "could never make ends meet" as an owner-operator that way. Work all day, "drive home, mow the grass" and otherwise take care of things around the house. "Eat dinner with the family and go to bed. You might get five hours of sleep if you're lucky."
He drove for a company over-the-road, worked for Sherwin-Williams then, too, "delivering paint, picking up and delivering their raw materials," he said. "You’d go out for a night and be back home," then out over the road for the next week. Everybody in the operation "was home every week."
Yet he kept high in mind through all the years a distinct feeling. "There’s no feeling like being an owner-operator," he said, being "your own boss," captain of the ship "when things are good."
“Good luck!” --Patterson Companies VP Ruben Perez to the owner he nominated to compete for Overdrive's 2025 Trucker of the Year honor
In 2019, he decided to make the jump and get back into it with a truck, and for the first time his authority, as Southpoint Exchange. The decision followed time spent talking to brokers he'd known well through the years in his area, and owners like Fred Johnson of course. Of the brokers, he said, "They all told me that if I wanted to do it they'd welcome me back with open arms."
He found a Peterbilt 389 that he bought, but once up and running felt the fuel mileage was "like dumping a gallon of fuel on the ground" every time he got into it. He located the then-new 2020 Peterbilt 579 on a lot out West in Fontana, California, Cummins-powered (Wingate's a self-described "big Cummins guy"). "I picked it up and am driving it to this day." It's now sitting at half a million miles and averaging around 7 mpg. Given the truck's a mid-roof, he's getting beat by his employed driver by a few tenths of a mile per-gallon. That second truck purchased last year is a 2022 579 with an UltraLoft sleeper.
Wingate's minded the pennies on fuel economy, too. He added a Talladega Fiberglass whale tail to the roof of his 2020 to better direct air up and over the top of the stainless reefer. The move brought an extra 0.7 mpg to his own economy. He's got both trucks governed at "72 on the foot, 70 on the cruise," and took each into "economy mode, trying to create better fuel mileage to keep more money in the trailer," fundamentally.
Wingate's 2020 579 (3.25 rears, low-pro 24.5s) is shown here cutting a sharp picture with its Thermo King unit (with chrome and light package) and stainless 2024 Utility reefer, with a seven-light package. His other 2022 579 also pulls a stainless Utility reefer, 2025 model, but with a Carrier reefer unit.
On the business management side he's leveraged those longtime broker relationships, and newer ones, too, with service providers like his accountant for payroll services and his taxes, which he files as a S Corp, he said. Another longtime permits-handling local he works with for his IFTA filings and other permitting. Maintenance-wise, he does most preventive work himself. "When we're on the road, I use SpeedCo, convenient for greasing the truck," he said.
Wheel seals, lights, water pump and more he'll do himself "when the truck gets home, provided I have the time," he said. "Labor cost is certainly more than the parts," though he knows sometimes it's money well spent. Nonetheless, "we try to do the most we can ourselves."
What's it like running a small trucking business in the national hotspot for the well-known dynamic of just too many truckers looking for too few loads? "I feel like I’m blessed in that aspect of things," Wingate said. It comes back to team-building, in the end. With "my handful of people I have" feeding freight to Southpoint Exchange, he added, "we don't get gravy all the time. But for the most part, it's a very consistent thing that we have." He's got regular customers on both ends of his LTL runs North to Ohio and back into Florida. "The rates are the rates, and we revisit it once a year."
Dedicated freight is certainly refuge from the difficult seasonal dynamics in Florida, times when competitive pressures really heat up. "A hundred trucks and 16 loads," he said, and "everybody’s fighting over something to get out of here. That load board -- man, it’s scary. I don’t know how people can truck for a dollar a mile. ... If I have to truck for that I need to set back and think about things, change things up, or step away."
[Related: More 'cheap freight' curves ahead: Better ways to assess costs, rates and revenues, emotions]
Perfecting the owner-operator craft
"Every now and then you find that person who handles themselves as a professional in their field. This is someone who has been taught the old adage, 'Any job worth doing is worth doing right.'" --Jim Dye, Lanning Foods General Manager, about Kenny Wingate
Anyone who thinks they can run for $1/mile for very long might take a page from Wingate, as was suggested by one among dedicated customers Southpoint serves, General Manager Jim Dye of the Lannings Foods grocery, headquartered near the upper northern reaches of Southpoint's dedicated lanes in Ohio. Wingate made a memorable first impression on him several years ago with a pretty basic but not easily achievable quality. Everything about his truck was 100% tip-top.
"Clean, neat and organized," Dye said. "I thought that he must have just purchased a new truck and trailer because it was so immaculate."
Wingate disarmed him in some ways with basic courtesy, too, offers of help of any kind he could provide "to make sure the load was processed correctly," Dye said. He assumed Wingate was going out of his way to make a "good first impression, but after three years of service to my company I began to realize that the immaculate standards that I witnessed the first delivery turn out to be Kenny’s everyday standards."
Running with his own authority may well be something of a new adventure for Wingate, yet five years in it feels like a logical extension of where his long experience behind the wheel has pointed him. The Southpoint Exchange company name is an extension of that long trucking history in Florida, in some ways. "Honestly, I just thought it was a cool name," Wingate said at first when asked about its origins. Yet with it he took a cue from a past business that was headquartered nearby doing dedicated work similar to what his own business does today.
"Southpoint Distributing had been around a very long time," hauling as a contract carrier for Publix grocers and others, he said. "They had very nice equipment, employed a lot of drivers, very successful." A buyout by another company, "years passed," the old company "building's gone." He always respected that business. And always liked the name. "So I changed up a bit" and ran with it.
He's living up to if not surpassing that company's standards equipment-wise, that's sure. In Tennessee a couple drivers walked up to him out in the truck stop lot "and they're like, 'Oh my God! Is Southpoint back in business!' And I just laughed."
Lanning Foods' Jim Dye sees in Kenny Wingate an idealized version of just what it means to be professional trucker. As he put it:
Have you ever watched a common task performed for years and then someone comes along and executes that task so perfectly that you are left shaking your head and saying to yourself, 'So that’s the way it is supposed to be done!' This is how I feel about Kenny Wingate.
Trucking's more than just work for him, yet the last years haven't been without the struggles many a small-business trucker has dealt with.
"The reduction in rates and the rise in fuel costs" have impacted profits somewhat, he said, yet the aforementioned adjustments to improve fuel economy, likewise minimizing idling, have helped soften that blow considerably. With a recommendation from Patterson's Ruben Perez, he's hoping to save 1,000s on the insurance front at renewal, too, even with plans for further growth.
In the end, it's those strong relationships with folks like Dye and Perez that sustain the company's success. As noted, there's expansion on the horizon -- in short order, too.
"I talked to my brokers," he said. "And they tell me 'get the truck, we have the freight, don’t worry about that.' ... I've already made arrangement on the trailer and started looking at the truck." The right professional driver for the role is the wild card as yet. "It's hard for a small company to find great drivers, it really is."
He feels, though, the right candidate can easily expect 2,800-3,200 weekly miles -- with additional pickup and drop pay, a safety bonus every 30 days and paid vacation after the first year.
He's hopeful on that front, yet getting to 3 trucks could represent something of an end point when it comes to growth. One of his customers "told me to buy two [trucks] this year," Wingate said. "If I want them, they've got the freight. And I'm like, 'Well, I don't know. I think I'm a three-truck guy, and I just want to stop right there.'"
Enter your own or another deserving owner's business (up to 3 trucks) in Overdrive's 2025 Trucker of the Year competition via this link.
For our 2024 winner, Trucker of the Year Alan Kitzhaber, Eston Hoffman of Hoffman Mechanical Design in Pennsylvania has been hard at work on the perennial "trophy" to honor the Eau Claire, Wisconsin-based owner-operator. As with the 2006 Western Star built last year for Jay Hosty, Hoffman's building a 1/42nd-scale replica of Kitzhaber's 4-million-mile-plus 1995 Kenworth T600. Check out a little bit of the progress made below, and keep tuned for an opportunity to meet the Trucker of the Year at the Mid-America Trucking Show in March.
[Related: Staying young, learning more: Trucker of the Year Alan Kitzhaber]
