a year earlier. “I was elated and quite impressed to get a store of [that] size in a market of [that] size,” he recalls. But it was tough for Pittman’s new business, which suffered from a bad reputation.
Then, in early 1991, while attending a Chrysler forecast meeting, a Chrysler branch manager grabbed a dollar bill out of his pocket, tossed it at Pittman, and told him that would be the value of his stock in six months. He reflects: “That made me very, very angry. I thought, ‘Man, I could go out of business…my family, business, and everything down the tubes.'”
The sales manager motivated the tough, feisty Pittman — who plays four to five Pro-Am golf tournaments a year — to develop an aggressive marketing and sales campaign. He wouldn’t let any customer leave his lot without purchasing a vehicle. The result: Pittman was recognized as Chrysler’s most profitable dealer in the nation that year. By 1992 he was able to pay off his loan in full and buy the dealership from Chrysler three years early. To this day he still has that dollar bill, encased in a gold frame behind his cherry-wood desk. “It was a kick-start,” says the five-star Chrysler dealer. “It reminds me to never get sales down to a dollar.”
He hasn’t slowed down since.
BUILDING FOR THE NEXT GENERATION
Part of Pittman’s drive is to create a legacy for the next generation. Though he did not force his wife, Alma, or children — sons, Winston Jr., 27, and Jabari, 18, and daughter Misty, 234to become auto dealers, they are all part of the business.
Alma, a former nurse, is vice president of the Mercedes-Benz-BMW operation, overseeing customer relations. “It would be a shame if something happened to me and she didn’t know about what sh
e owns,” he says. “She would have a lot of dealerships and not know what makes them click.”
Pittman began prepping the children when he acquired a Dollar Rent A Car franchise in 1994, both as an industry learning tool and as a way to teach the children — who did everything from rent cars to wash vehicles — about hard work. Now Winston Jr., a Union College graduate who has worked in all areas of his father’s business, has recently become the assistant to the general manager of the Toyota-Lexus dealers in Savannah. All three children have successfully completed the Jim Moran southeast Toyota school. Misty is currently working at the Mercedes-BMW franchise in Bowling Green, and her husband, Marcus Withers, 27, is business manager there. As for Jabari, the University of Louisville student works in the parts department at Cardinal Dodge, where Pittman’s older brother, Clyde, 63, serves as vice president of operations.
Winston Jr. maintains that he would like to get the keys to the business one day. “Becoming a second-generation dealer is not easy. You have to work as hard, if not harder than everybody else,” says the CEO-in-training. “[My father has] taught me to be very competitive and not make excuses for any mistakes.”
Such talk has