A Life and Industry of Opportunities: Winston Pittman Creates an Empire

Winston Pittman

When Winston Pittman decided to open a Chrysler dealership in Louisville, KY in 1988, he walked into several stores in the black neighborhood where his dealership was to be located and started up conversations. “Now Louisville back then was 13 percent black and the whole state was four percent. So I went into the black community and just started talking to people about whether they were excited about an African-American opening a dealership.”

They weren’t.

“They all thought that whoever the black guy was opening that dealership was crazy. Turns out the dealership was where the KKK headquarters used to be.”

Pittman laughs at the memory but it also is telling. He beat the odds of, not only getting a dealership, but succeeding and he did it with determination, hard work and being able to connect with people.

Minority Programs

“I blend in wherever I am because people have formed opinions about people for the simple fact of the color of their skin. It’s always ‘just because’. People don’t like you just because you’re black, white, Hispanic,” he says. “But, given the opportunity you can convert people over. Someone has to take the high road and the attitude that if we don’t try, we’ll never fix this. Hatred is taught; no one is born that way. I’ve sold cars to people who have called me bad names.”

Since his first dealership, Pittman Enterprises has grown to seven dealerships, nine brands in four states, and is one of the largest African-American auto dealers in the nation. It posts revenues north of $1 billion. He has 381 employees and last year sold about 8,000 vehicles with the goal of selling them in less than 90 days.

He has served on the National Dodge Dealer Council, the DaimlerChrysler Minority Dealer Association, the National Association of Minority Automobile Dealers, the Toyota National Dealer Council, The Lexus National Dealer Council and the Toyota Lexus Minority Dealer Association.

“Getting into the Dodge National Minority program was very instrumental to me but there’s been a lot of people who have been very influential in my life. Parents, school teachers, bosses and the folks at Chrysler, Toyota and Lexus,” he says. “All the people in the my life helped develop me and helped me get to where I am today. My wife, my mama.”

Pittman is a strong believer in minority programs, although he realizes that in today’s world of large dealerships it’s getting harder. “They used to give minorities a leg up for the simple reason that the industry itself didn’t create minority GMs, sales managers or used car salesmen. There weren’t enough of those where they could have gone out, come up with the money and open a dealership,” he says.

Adding, “When I started back in the 1980s, there were 40,000 dealers; today it’s 19,000 and most of those are multi-owned. We don’t have as many mom and pop shops in itty bitty towns. They used to put minorities in their itty bitty towns and they didn’t blend well into that market. Those small towns like to cater to their own. They’re not big on outsiders — black or white. We’ve got to get to the point where these programs are not important.”

Jack of All Trades

Pittman, who was born in 1950 in Grenada, MS., spent his formative years working in a variety of jobs, plowing fields, tending to cattle, picking cotton and doing construction. “My father was a contractor and helped build churches so I was a plumber, electrician, carpentry, concrete work. He also had me supervise people much older than me — folks who were working in the fields. I was just a well-rounded kid who could do everything.”

Not only was he tasked with a variety of jobs, he says he was naturally curious, which eventually served him well in the car business. “As a child I was always watching people and listening to every word that was said. In the South, we observed and black people, back in the day, had to observe more and talk less. In my family my father did all the talking and I just listened. And, that’s what I did when I got to a dealership.”

Pittman didn’t plan on being in the car business. He graduated from Jackson State University with a degree in accounting and went to work for UPS. But in 1975 he saw an ad in the paper that said a car salesman could earn $60,000 “and I thought ‘Wow’ I could use some of that.’”

He applied at Capital Dodge in Jackson and was told to come back the next day — a scene that repeated itself for three days. Eventually he was hired. He later was told that the manager, seeing that he worked for UPS, though he was a plant from the federal government. “I don’t understand that but that’s what they told me,” he says. “Of course, back then they weren’t hiring a lot of blacks in the car business in Jackson, MS.”

Once he was hired he hit the ground running and discovered he had quite a knack for it. “It’s not an hourly job and you get out what you put into it. You can make a lot of money in this business or you can make no money. It’s all performance driven. If you’re good, you’re gonna get paid.”

Pittman, in addition to his sales duties, started to learn all the other aspects of the business. “I wasn’t getting paid to do it but I was preparing myself,” he says. In 1979 he became the used car manager; 1980, the new car manager; 1981 F&I manager and in 1983 the general manager.

In 1986 he entered the Chrysler Dealer Development Program in Detroit. Most of those in the program had come from outside the car business so they were learning from the ground up; not Pittman. “I had been in the business 13 years and it rehashed a lot of things for me and refined the things I had learned over the years. I had spent most of my career in the front end of the business so the program gave me the opportunity to work in the service department, parks, accounting — to focus on all the areas that  I hadn’t really worked in before.”

One Store and Then More

In 1988 he got his first store, Cardinal Dodge in Louisville. He quickly became successful and started adding dealerships. In 1994 he opened Cardinal Dodge Acceptance Corp., a used car dealership in Louisville, then Winston Pittman Pontiac GMC, which he sold in 1986. In 1995 he became owner of Dollar Rent A Car; 1997 Chatham Parkway Toyota in Savannah, GA., 2000 Kings Nissan in Cincinnati, Bowling Green Imports (a Mercedes Benz and BMW dealership) in Bowling Green, KY, Chatham Parkway Lexus in Savannah; in 2005 Colerain Ford and Lebanon Ford, Lincoln, Mercury in Lebanon, OH and in 2013 Hilton Head Lexus in Hartville, SC.

He’s not looking to sell any of his dealerships but he’s open to other dealerships in the Savannah to Hilton Head and Cincinnati to Springfield, Ohio markets. “I’m not interested in spreading beyond those areas” he says.

With expansion comes new challenges, he says. “The day you decide to buy a second outlet, that’s the day you have to learn how to delegate. It takes all your energy to run one; everything you’ve got,” he says. “I have great people and the general managers run the day-to-day in the stores but I see every report every month. I visit each dealership every month and I know the employees. I’m involved in the day-to-day but not the nuts and bolts. I want to know what’s going on.”

His son, Winston Pittman Jr., is the executive vice president of Chatham Parkway Subaru. “I didn’t hand him the business. He’s been working here since college and he’s done a stellar job with the Subaru store. I think he’s matured to the level where he can start getting to know the other manufacturers and I think he’ll do well.”

An Industry of Opportunities

His other big challenge is finding people. “In the past we’ve gotten people by robbing other industries but we need as an industry to get our own people. Nobody goes to college wanting to go into the car business. They want to go to Apple, Google and other major brands. But no one know how great our industry is! We’re the people movers. Everything comes under our industry,” he says. “And, no one knows how much you can make. A technician can make astronomical money. You can make great money being a title clerk in the office.”

He preaches hitting numbers as the key to his success. “It’s important to meeting the manufacturer’s expectations and keeping your CSIs at a level that is above the national average. That’s critical,” he says. “You only have stores awarded to you if they know you’ll keep them at a certain level and you’re not awarded them unless you’re doing well with someone else’s brand.”

He says his rewards his teams for hitting and exceeding their goals. “If you focus on them, amazing things happen,” he says. “You get it done.”

He’s also learned some lessons, such as sticking to his prime business and expertise and not venture off into offshoot businesses. He once was in the rental car business and real estate. “I don’t get involved in anything other than cars. I do like to own the real estate that my dealerships are on.”

Changes in Marketing

He also is involved in Lexus’ national marketing and remembers the ay when it was simply a matter of advertising on the local radio and TV stations and in the newspaper. “You knew what you were going to do,” he says. “Now it’s the internet and you’re always having to change and look for new ways of doing things. I used to visit the stations, now there’s hundreds of channels and you’re never certain of what people are watching.”

Even though he calls himself a general marketer that aims at a broad market, he does support the minority community in terms of advertising in minority papers and radio stations.

Pittman has overcome much and loves the auto industry that has given him and his family much. It’s part of his legacy that he’s offered opportunities to hundreds of people.

“If I ruled the world, the first thing I would want to do is to be fair to everyone.” he says. “I don’t want to flip it. I just want it to be fair.”