Overdrive Radio

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


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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
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