Welcome to Beauty Boss, a reoccurring series in which we spotlight the power players driving the beauty world forward. Consider this your chance to steal their get-ahead secrets, and grow from the real-life lessons they’ve learned on the job.

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Credit: Ben Ritter

Long before no-makeup makeup was even a blip on our collective beauty radar, makeup artist Bobbi Brown was keeping it real. A natural, you-but-better approach became her calling card in the editorial world, and not long after, on the beauty floors of department stores across America. She recently chose to step down from the brand that made her a household name, but rest assured the word "break" isn't in Brown's vocabulary: Her new book, Beauty from the Inside Out ($16; amazon.com), hit shelves last week. Here, the makeup mogul talks us through the makings of her multi-faceted career.

Where did you grow up?

The suburbs of Chicago. It was pretty normal. Young parents who had kids and moved to the suburbs. Parents got divorced. Parents got remarried. I was the oldest of three kids.

Did being the oldest teach you anything about leadership?

Not as much as the time I spent with my grandfather. He came to this country from Russia and worked really, really hard on many different things and ended up owning one of the biggest car dealerships in Chicago. I use to hang with him at the office. I helped send out brochures to clients and customers. It really taught me how you just never can stop. You’ve got to keep going, no matter what.

Did you know then that you wanted to become an entrepreneur?

Looking back now, yes. But I didn’t know much about real entrepreneurship at the time. I didn’t know that could be an option for me. I thought about being a teacher. I went to college. I was really fortunate because my mother—after my first year in college when I announced that I was dropping out—sent me in the right direction by saying to me, “Forget about what you want to do with your life. It’s your birthday and you can do anything you want. What would you want to do?” Unbeknownst to me, because I didn’t even realize it, I said I’d love to go to the makeup counter and play with makeup and she said, “Why don’t you become a makeup artist?”

I enrolled back into college, this time at Emerson. It’s a very small school that allowed me to design my own major. Now I know it’s called entrepreneurship.

What was that experience like?

In senior year, I studied theatrical makeup. I just thought I would do fashion on the side. But during that time I read an article in a magazine about a well-known makeup artist named Bonnie Maller, who was doing makeup for all the Bruce Weber shoots and Ralph Lauren ads. I didn’t even know that career existed. So what did I do? I wrote her a letter that said I’d love to assist her. She did not write back, but I then knew about the career. When I moved to New York, I called her up. She did not call me back, but on her answering machine it said that if you wanted to book her to call Bryan Bantry, her agent. So I did! I called Bryan and he started my career—and I did eventually assist Bonnie.

That was fast! What do you think made you stand out amongst the thousands of hopefuls that call that agency?

I think one of my biggest strengths, which cannot be learned, was naiveté. I probably still am the most naïve person. I never think that something can’t work. So I am sure if you asked Bryan, it was that I walked in there with my portfolio—which was, you know, not what people were looking for in New York City—and I was incredibly wide-eyed and eager and available and willing to do anything that they asked. I offered my services without getting paid and they started helping me and that’s really how I got started in New York.

What were those early days like?

I was pretty amazing. When you are assisting someone, just even walking into a shoot or a fashion show that you’ve never seen before is just incredible. So you know sometimes you’re standing there. Other times, you get to do makeup. Sometimes you’re just carrying bags and cleaning up. So it just really depended. But I asked a lot of questions of people and then I started getting hired. My first magazine job was with Glamour. The photogrpaher was Brigitte Lacombe, and it was a dancer. I had to wash the ballet dancer’s feet. It took me seven years, and then I got a Vogue cover. Along the way I did catalogs and other jobs to pay the bills, and I even had other covers at other magazines, but the Vogue cover with Naomi Campbell—her first—was definitely a big deal.

What happened next?

Well, what I’ve always been good at is not just focusing on my career but actually focusing on my life and my relationships and having a balanced life. So I fell in love, got married, I moved from the city to the suburbs and had a baby. I realized that I didn’t want to be travelling anymore and going on these location trips. Around that time, I had an idea for a lipstick. I was doing a shoot and I met a chemist. I told him about my idea, which was to make a lipstick that didn’t smell bad, wasn’t greasy, wasn’t dry, and looked like lips—and he made one for me. That’s how the brand started.

How did you go about bringing your product to the masses?

I thought about color. I wanted a collection that looked like lips. Not everyone has the same color lips so I made every kind of tone that I could imagine as lip tones. Then I realized that some people don’t even like those kind of colors, and some people would rather have an orange or a red. So I just came up with ten colors that you can mix or blend like a makeup. I thought women would really love it because I thought it was the best thing I ever used. I started selling it out of my house.

Within a year or so, it happened that I met a cosmetics buyer for Bergdorf Goodman at a party. I didn’t even shop at Bergdorf Goodman at the time. But they launched us. It was a big success. I mean the opening day we sold 100 lipsticks and we had thought we were going to do 100 in a month. We knew we had something. Then we just started adding products—the pencils were next. Then it went on. We were on a table on the floor at Bergdorf Goodman. We didn’t even have a space at the time. So that was new and it was interesting. Then Neiman Marcus was calling along with the other big stores, and after fours years, Estée Lauder came calling.

And I know the story goes that though they purchased your brand, you remained very much involved until recently...

I mean I never thought in a million years that I’d be part of a billion-dollar brand. So you can imagine that it was ginormous and not exactly the brand I’d started. I’m someone who is very entrepreneurial. I love to do things really quickly. I don't like to do things by committee. I was just ready for another challenge. I am looking at this part of my life as my third phase. The first phase was freelance. The second phase was this cosmetics company that grew. So here I am again!

Speaking of, you have a new book…

Beauty from the Inside Out is mostly focused on my belief that what you put into your body is even more important than what you put on your face. I don’t call myself a health expert or a wellness expert—but I am someone that’s incredibly interested in it. I was lucky enough to bring in all these really cool women who are pros. I’m curious, and my curiosity is something larger than I am. And I think the book is so timely because people are really starting to pay close attention to what they are eating. The better you eat ,the less makeup you need. But there is makeup in the book. My publisher insisted!