Diana Lee is the founder of Constellation Agency, which produces hypertargeted digital advertising for more than 700 auto franchises across the country, for brands including BMW, Audi, Jaguar, and Volks­wagen. Today, much of the work is automated: The company's software generates thousands of ads a month that make highly tailored offers, in multiple languages, based on a target market's ethnic and labor mix and other demographic data. But it wasn't always so hands-free. Lee describes how, with no outside funding or debt, she built an $18 million advertising agency by hitting the pavement and pitching car guys in their own showrooms. Little did they know, she had a secret weapon.

Constellation Agency
No. 65
2020 Rank
Three-Year Growth
New York City

In the beginning, I would just drive from dealership to dealership myself, nine to 12 hours every day, pitching my business door-to-door. A lot of times, the guys there would make me wait--they've been pitched 50 times that week; they don't want to hear another one, and especially not from me. To them, I'm this no-name 5-foot 4-inch Asian lady.

But within the first three months, I closed deals with 16 Volkswagen franchises. Soon enough, I get a call from Volkswagen corporate asking, who the hell are you? And why are you everywhere?

Well, I'm a pretty good closer. But there's another thing the dealership guys never guess about me: When I step into a car showroom, I'm on my home turf.

I've never been much of an auto enthusiast. By nature, I used to be pretty shy and quiet. When, the summer after my freshman year in college, I got a job at a car dealership, my parents were like, are you crazy? This is not what we want from you. You have to go to law school. They came here in 1975 from South Korea and worked 15-hour days to support my older sister and me. But after watching my parents suffer like that--they even got robbed at gunpoint at their convenience store, stuff like that--I decided I didn't want to ask them for money ever again. I wanted to support myself. And in those days, 1989, selling cars meant
making money.

It was a dealership in Worcester, Massachusetts, less than three miles from the Clark University campus. I was 18 years old, one of two women at the dealership, probably the only Asian woman salesperson in New England. That place was crazy--a lot of drugs, a sales manager who was sleeping with a sales associate. There was one employee there, this 60-year-old guy, who had girls coming in and out all day long. We all just called him Don the Pimp.

This was the school of hard knocks: Salespeople weren't allowed in the showroom unless they were accompanied by a customer. It didn't matter if it was snowing outside or pouring rain--no customer, you wait outside. A car would drive into the lot and you had to be the first one to that car, beating out men 20 or 30 years older than I was: "Oh, hello. You only want to look around? How about you follow me inside instead? Let me get you my card."

For whatever reason, I could sell cars--maybe because I was a woman, maybe because I was different. But people felt like they could trust me. When summer was over, the dealership had me constantly working. I was there from 2 p.m. until 9 p.m. every weeknight, and I worked full days on weekends, too--weekday mornings were the only time for classes. But I paid my rent. I paid off my college tuition. I got a demo car, this hot red number that I drove all the rest of college. And I never took money from my parents again.

After graduation, I moved back home to New Jersey to be closer to my parents, and I got a job at a dealership in New York City. By 22, I was a dealership finance manager, and, let me tell you, a lot of the older guys hated that. I got called Viper, and Nightmare. The practical jokes were constant--once they tied a dead bird to my car so it looked like it was flying next to my window. At a young age, I really stopped caring whether or not I was liked.

By 22, I was a dealership finance manager, and, let me tell you, a lot of the older guys hated that.

It certainly changed me as a person. That's what I understand about the car business when I walk into those dealerships--I have this fire inside me that says I've got to win. I know they have that super competitive streak, too. But I'm also compassionate. I know how hard the job is. They're always looking for the next trinket--that technology that gives them an edge--but they're not going to believe you unless you make them.

When I go in, I don't sell myself. I challenge them. I say I have a demographic study of their area: You know you have a demo that's 46 percent Hispanic, and a high density of Koreans. You are producing digital ads in those languages, right? No? What about the local hospital--certainly you're targeting ads to their doctors and nurses. Oh, really? I offer to start small. Then I respond that I didn't mean that small. You run a huge dealership--you must have had some guts to get all that you have. Give me something I can work with. My job is to ask for the moon. Because that's how they negotiate too.

These days, I don't walk into dealerships very often--mostly I meet with marketers at the manufacturers--although I stay in touch with dealership managers a lot. But all those days in the showroom made me really tough. What better preparation for launching a startup? Because I've never fit into a good-old-boys network, I've always had to fight to survive. And so you know if you are surviving in an environment like that, it's because you're doing something right.