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Trucking insurance agent to hotshot trucker — the curious case of Steve Libertore

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Updated Jan 12, 2021

It’s not exactly the greatest of times for the most seasoned, long-in-business of hotshot haulers, as my colleague Tom Quimby wrote some weeks back. Freight in a variety of sectors had fallen off the cliff, direct clients in some instances had shut down entirely, and some were relying on spot loads that everybody and his brother were also relying on — or at least hoping to rely on.

Now imagine your three-truck business (and its equipment) is just 15 months old, truck and trailer payments continue, and you’re relying on the services of an independent dispatcher working load boards and other contacts to keep your 40-foot flatbeds filled. That’s been the situation of the three-truck S2 Transport fleet, headquartered in Ohio. It’s run from the operations side by President Scott Sabatini, a military veteran with prior trucking experience, and Steve Libertore, a man whose name you may well recognize.

No, Libertore’s not one of my owner-op or small-fleet-owner sources from years past, but rather an insurance agent who’s long specialized in insurance for the smallest of trucking companies operating with authority. He’s still in that business, now with Kincaid Insurance Group, with offices in Indiana and Ohio and specializing in part in transportation. His motivation for joining up with Sabatini (while both continue with other basically full-time jobs) to manage a three-truck fleet?

Both men were driven to go out on their own in some fashion, generally speaking, but Libertore noted the complementary past experience of the two. Sabatini’s “background is safety, compliance and driver recruiting,” says Libertore. “I’m risk management.” While Sabatini handles the day-to-day logistics, “I’m looking at the back end.”

Also, though, what he’s learned in the short time they’ve navigated the wide world of hotshot flatbed — a lot of their loads end up being LTL in nature — gives him a leg up, he feels, over competing insurance agents. “I don’t know how many agents can say that ‘I understand what you’re going through’ to a client with this or that,” he says, “the ELD issues and everything. I’m experiencing this firsthand myself.”

Problems he has a new appreciation for range from an ELD malfunction and/or user error that cost one of his drivers an out of service violation that’s now dinging their insurance, to the high cost of plates in IRP — “$4,800 for three 2018 Ram 3500 pickups” plated for 43,000 pounds, powered by Cummins diesels — to, gulp, insurance.

Libertore says they had exactly one option for an insurer given their new authority: Progressive. Shopping around for better rates wasn’t in the cards. They’ve done everything they can to minimize costs and take advantage of discounted services for better efficiency, and risk management, when they can. For instance, the fleet uses the dashcam option of its ELD provider, KeepTruckin, obtained with a discount add-on to the logs service via a partnership with Progressive.