Bobbi Brown On How To Build Your Own Empire, Start Over, & Why It's Never Too Late To Bet On Yourself

Lauryn Evarts Bosstick (0:00)

The one, the only, the Bobbi Brown is on the show, live from Dear Media, East Hampton. We had the opportunity to interview the renowned makeup artist, entrepreneur, best-selling author, beauty industry icon, mom and wife. She talks about her journey and how she has founded two successful cosmetic brands, Bobbi Brown Cosmetics, and most recently, the clean beauty brand, Jones Road. This conversation is a playbook for anyone building a company, developing a product, entering a second act, or trying to become more confident in their own instincts. Bobbi, welcome to The Bossticks.

Michael Bosstick (0:36)

We're with Bobbi Brown, for those that aren't watching, not Whitney Houston's Bobbi Brown, not the porn star Bobbi Brown, but the Bobbi Brown.

Lauryn Evarts Bosstick (0:42)

Not the baseball Bobbi Brown.

Michael Bosstick (0:43)

Yeah, the Bobbi Brown.

Lauryn Evarts Bosstick (0:45)

The one and only.

Bobbi Brown (0:46)

And my dad's name is James Brown. So yeah.

Michael Bosstick (0:49)

Well, that's even more complicated. Your dad just wanted to take all the space, the names. Well, thank you for doing this.

We're here in the studio in the Hamptons. We're in your neck of the woods. We're total rookies out here. So by the end of this, we're going to be total pros. For those that are unfamiliar with you, I think everybody's familiar with you. You've done so much. How do you describe yourself at this point of your career?

Bobbi Brown (1:11)

Can I call myself a multi hyphen? I have no idea.

Lauryn Evarts Bosstick (1:14)

I think you can.

Bobbi Brown (1:15)

But if someone's, you know, I'm a makeup artist. I'm a makeup artist. That's what I went to school for. That's what I am. That's what is a center. But I've kind of taken it far and wide.

Lauryn Evarts Bosstick (1:27)

Well, I feel like you're also an entrepreneur.

Bobbi Brown (1:29)

I'm definitely an entrepreneur. I can't spell it, but I'm an entrepreneur.

Lauryn Evarts Bosstick (1:32)

That's okay. I feel like I can't spell it either. But you are an entrepreneur. I think you are, in my opinion, the biggest entrepreneur when it comes to the glam space.

Bobbi Brown (1:41)

And I'm so not glam. I love that you say that. There's not a glam thing about me.

Lauryn Evarts Bosstick (1:45)

Is that annoying you that everyone is so heavy with the glam now?

Bobbi Brown (1:50)

No. I think everyone is allowed to be who they are. Because that makes you feel like you. It's just my style.

I am comfortable with my style.

Lauryn Evarts Bosstick (1:59)

So if you were doing my makeup, would you do a little less? No.

Bobbi Brown (2:04)

No, you don't have a lot of makeup on today.

Lauryn Evarts Bosstick (2:06)

I thought you might have said I have a little too much on.

Bobbi Brown (2:08)

No, you don't have a lot of makeup. I mean, I might try a different formula foundation. But it's good to know a couple different formulas. Some are good for lighting. Some are good for going out. So, you know.

Lauryn Evarts Bosstick (2:21)

Would you still do someone's makeup at this point?

Bobbi Brown (2:23)

I do makeup all the time. I, you know, we do our shoots every two months. We have a studio in our hometown of Montclair where our office is. And I do the makeup. I do the styling. I pick the photos. I pick the models.

Lauryn Evarts Bosstick (2:37)

Multi-hyphenate.

Bobbi Brown (2:38)

Yeah. I mean, it just makes sense. It's just simple.

Lauryn Evarts Bosstick (2:41)

Yeah. You have your hands in a ton of different things. At what point when you were little, did you know that you wanted to do makeup and be creative like that?

Bobbi Brown (2:50)

I was always creative, so I never knew I wanted to be, and I just assumed growing up. I mean, I was born in 57 You could do the math, I'm 69

I know people are like, I am. But no one ever thought that. It was just, you'll be a teacher, you'll go to law school, you'll be a mother. Those were the options. I went to college, three different colleges. And after my first college told my mom, I wanted to drop out and she said, you can't, but mom, it's so boring. She said, what do you want to do with your life? Mom, I have no idea. She says, forget what you want to do with your life. If today was your birthday, you could do anything you want to do. What would you want to do?

I said, I wanted to go to Marshall fields and play with makeup. She goes, that's it, be a makeup artist. I said, I don't want to go to beauty school. She said, I'm sure there's a college and a friend of my dad's told me about Emerson in Boston.