Thirty years of business, a hard chapter, and every lane of trucking there is — here’s how The Cigar Boss Trucking Academy got built.
It’s May 12th, 2009. I’m standing in a federal halfway house in Charlotte, North Carolina with a CATS bus pass, a job application, and $62.39 to my name — but I’m free. Behind me are twenty years in a myriad of businesses: OTR trucker in 1987, the automobile business in ’89, sports management in ’92, mortgage consulting in ’96, an independent auto dealer in 2002. I’d made real money and lost it, and I stood there thinking, there has to be a better way.
In 2012 a truck driver put me onto the expedite and hotshot side of the business and how good the income had been for him. I jumped in head first — owner-operator, running the lower 48 doing less-than-truckload and last-mile work — and the thought kept coming back: this business could help other people with a challenged history earn a good living, the same way it was helping me.
By 2015 I was back in big-truck, full-truckload freight. In 2016 the FMCSA rewrote the training requirements for new CDL drivers and set a real curriculum — Entry Level Driver Training — along with rules for who could teach it. That’s where The Cigar Boss Trucking Academy comes in: teaching the information every ELDT student needs, from someone who has actually lived every mile of it.
Trucking is one of the few businesses that will still pay you what you’re worth after a hard chapter. Fitzgerald lived that — and the Academy exists so the next person doesn’t have to learn it the slow, expensive way.
Real experience, taught plainly: the road from company driver to owner-operator, the numbers that keep you profitable, and the ELDT training the FMCSA now requires before your CDL-A permit test.
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