Bobbi Brown may be the most famous entrepreneur in her family, but she wasn't the first. Decades before she launched her cosmetics empire in 1991, she spent weekends helping her grandfather Sam Shatten at his car dealership. His favorite lesson: Good things come to those who keep their eyes peeled.

Every business decision I ever made I learned from my grandfather Papa Sam. He moved here from Russia when he was a boy. He worked his way up selling newspapers and ladies' handbags, and eventually, he became Cadillac Sam, one of the biggest car dealers in Chicago. When you come here from another country by yourself, you're naturally entrepreneurial. You're used to figuring it out as you go.

There was one story that always stayed with me. One day, a guy who looked like he lived on the street came into the dealership carrying a big shopping bag. None of Papa Sam's sales guys would go talk to him. But Papa put his arm around the guy and said, "How ya doing, boss?" Turns out the shopping bag was full of cash. The guy bought two cars. My grandfather taught me how important it is to have your eyes open, because you never know what's going to come your way.

When I first proposed my lipsticks to Bergdorf Goodman, they said yes and then changed their minds. I had been working with Saks Fifth Avenue on a catalog shoot. I told Bergdorf's, "It's OK that you're not taking me, because Saks is." They said, "Let me call you back." That's how I launched at Bergdorf's.

It's not bluffing. It's thinking on your feet, and it's helped me a million times. One time, I was doing makeup for the Rachel Roy fashion show, and Rachel said she wanted lipstick the color of Hershey's Kisses and espresso. But when I asked my assistant for my lip palette, she whispered, "I forgot to pack it." I said, "OK, hand me the eye shadow and some lip balm." After the show, Rachel said, "I couldn't have imagined it better." Vogue wrote about it. Now, I have a lipstick named Mahogany, all because I didn't panic.

College major: Theatrical makeup
Total start-up funding: $5,000
Products sold per day worldwide: 60,000