Dave Carr is a guy who makes gamblers green with envy. He’s like the millionaire who hits the lottery jackpot, or the man who walks into a bingo parlor for the first time in his life and wins the $50,000 grand prize. Carr, in fact, shrugs off lotteries and contests. So he was surprised to learn that he’d won a new Peterbilt 387 Premier Edition, and that he’d be flown to the Mid-America Trucking Show in Louisville, Ky., last March to pick it up.

Carr didn’t even enter the draw himself. The owner-operator who hauls tanks for Harmac Transportation out of North Bay, Ont., ignored the ballot box at his local Peterbilt dealership and was talked into signing an entry card only after one of the salesmen had filled it out for him. “I walk by a lot of those things,” says the 53-year-old with the slightest of grins.

A few months later, while Carr was at home with his girlfriend and business partner, Joanne McDonald, the phone rang. “I thought it was a scam,” Carr says from the cab of the truck as he waits for decals and plates at Harmac’s yard in Toronto.

After Carr was presented with the keys, Peterbilt handled the logistics of the delivery to North Bay, at which point he was asked to take care of only the GST and PST. “A small price to pay,” he says.

Then what? Carr never planned to add to his two-truck fleet. He had to decide what to do with his two other Petes (a ’99 he’s financing and a ’96 that’s leased). Could he handle, or even want, the extra business?

Chris Bennett of TFS Group, a Waterloo, Ont.-based accounting firm that specializes in owner-operators and small fleets, recalls a client who won a Western Star truck in 1987. He suggests that cash flow — specifically, how to manage the abundance of it — should be Carr’s first concern.

“Without a truck payment, this guy is going to have tremendous cash flow,” Bennett says. “What does he do with that excess cash? Does he set it aside in his personal or corporate name? To get the value of your winnings, to get the return you need, I’d take, let’s just say, $2500 a month, and lock in on a guaranteed payment strategy as if a truck payment really existed.”

When you grow your business by 50% and your net worth jumps by $140,000, Bennett also says you should make sure all your personal assets are protected.

“You now have twice as much opportunity for things to go wrong,” he says. “You need to look at three areas to protect yourself: estate planning, tax planning, and liability planning.”

Carr is likely a step ahead in these areas, says Bennett, since he’s been through the experience of adding one truck already.

Carr says it was an easy choice this time. He has hired a third driver, picked up more business, and spent some pocket cash on appliances for the sleeper. The biggest challenges Carr faces nowadays is getting used to the larger, quieter cab and taking the brunt of a little razzing from co-workers. Is it worth it? You bet. Will he now take more time to fill out a ballot or two?

“Well,” he says, “I think I pretty much used up all my luck on this one.”