The Exchanges

Q So here, here's my question. I mean, what does it, like, how were you Like, a better makeup artist than someone else. Like, what is it that you were able to offer?

A Well, alright, so let's go back to, um, the seventies and the eighties. The makeup back then was the epitome of unnatural. Foundation was pink, it stopped at the, at the jawline, it was contour, eyes were, eyeshadow was yellow and purple and blue. It was all of those things. I was always doing more of a, now it's called a bobby face, and now it's called nude makeup, but back then, It was just, I always made people look healthier. I wanted people to not look like they were wearing makeup, and I even had one very, very famous makeup artist, you know, who I asked his opinion on stuff, said, you will never work because people don't want to look like that. And I don't want to look like that. People want to look made up, and you know, I just couldn't do it. So even when I was doing makeup, I On TV, I had these really simple things I, I looked for. I wanted to make the foundation to actually be the color of the skin.

AI assessment note: “I wanted people to not look like they were wearing makeup”

Q This is the summer after your first year of college?

A Right. It was literally two weeks before I was supposed to go back to Arizona, and my car was actually, you know, packed when I made the decision to go to Emerson. So it was, it was like a, it was like days before. I flew up with my dad, went to Emerson, and they, and I asked if they had a makeup program, and they said no, but we have something called An interdisciplinary program, and you can create your own major. And sure, you can study makeup. I said, I'm in. I'm going. And honestly, when I got to Emerson, I found myself. Because it was a school full of kids like me. Creative, fiery, entrepreneurial, and you're creating films, and you're creating, you know, all different art projects. And I remember even doing Films, and you know, they pair you with someone, and instead of doing things the normal way, which is like, oh, what kind of film should we do? I remember thinking about what kind of makeup I wanted to do, and writing the film around the makeup.

AI assessment note: “Right. It was literally two weeks before I was supposed to go back to Arizona”

Q like There were expectations that you weren't fulfilling. I don't know. I mean, you know, you came from this sort of middle-class home in Chicago, and your dad was a lawyer, and so were you ever thinking, like, oh, man, you know, like, my parents have these expectations of me, and I need to, I don't know. I mean, were you ever thinking like that or worried about that? No.

A Can I tell you why? One, I have this really weird gift, and, you know, you don't know it's a gift until you're, you know, of a certain age and look back. I am so naive. So I never think something's not going to work out, and I never did. So I was not worried. You know, yes, I was always anxious about how I was going to pay the rent or if I had enough money for this. And my, I remember calling my dad one day, and I said, Dad, I just can't stick to this budget. I had a credit card with a limit. I think I had 250 dollars a month limit. And I kept, you know, incurring all these fees. And I said, Dad, I can't stick to this. And he said, all right, stop for a minute. Put it down. I said, okay. He said, stop trying to stick to a budget or create a budget. Why don't you figure out how you're going to make more money? I said, hmm, okay. And I remember telling myself, Monday morning, you get up and you fill your date book with appointments. So I go sees as they call it. So I went, I started making appointments. And as long as I, Monday was my day to fill it. And then I had the whole week to go see people. So I started calling, um, magazines, and I'd look on the masthead, and I would see the booking agent. I booked with them. Hi, I'm Bobby Brown. I'm a freelance makeup artist. I'd love to come in and show you my book. I had a, you know.

AI assessment note: “I am so naive. So I never think something's not going to work out”

Q This is the summer after your first year of college?

A Right. It was literally two weeks before I was supposed to go back to Arizona, and my car was actually, you know, packed when I made the decision to go to Emerson. So it was, it was like a, it was like days before. I flew up with my dad, went to Emerson, and they, and I asked if they had a makeup program, and they said no, but we have something called An interdisciplinary program, and you can create your own major. And sure, you can study makeup. I said, I'm in. I'm going. And honestly, when I got to Emerson, I found myself. Because it was a school full of kids like me. Creative, fiery, entrepreneurial, and you're creating films, and you're creating, you know, all different art projects. And I remember even doing Films, and you know, they pair you with someone, and instead of doing things the normal way, which is like, oh, what kind of film should we do? I remember thinking about what kind of makeup I wanted to do, and writing the film around the makeup.

AI assessment note: “Right. It was literally two weeks before I was supposed to go back”

Q were expectations that you weren't fulfilling? I don't know. I mean, you know, you came from this sort of middle class home in Chicago, and your dad was a lawyer, and so were you ever thinking like, oh, man, you know, like, My parents have these expectations of me and, and I need to, I don't know. I mean, were you ever thinking like that or worried about that? No.

A Can I tell you why? One, I have this really weird gift. And, you know, you don't know it's a gift until you're, you know, of a certain age and look back. I am so naive. So I never think something's not going to work out, and I never did. So I was not worried. You know, yes, I was always anxious about how I was going to pay the rent or if I had enough money for this. And my, I remember calling my dad one day, and I said, Dad, I just can't stick to this budget. I had a credit card with a limit. I think I had 250 dollars a month limit, and I kept, you know, incurring all these fees. And I said, Dad, I can't stick to this. And he said, all right, stop for a minute. Put it down. I said, okay. He said, stop trying to stick to a budget or create a budget. Why don't you figure out how you're going to make more money? I said, hmm, okay. And I remember telling myself, Monday morning you get up and you fill your date book with appointments, so I, go-sees as they call it, so I went, I started making appointments, and as long as I, Monday was my day to fill it, and then I had the whole week to go see people, so I started calling, um, magazines, and I'd look on the masthead, and I would see the booking agent. I booked with them. Hi, I'm Bobbi Brown. I'm a freelance makeup artist. I'd love to come in and show you my book. I had a, you know.

AI assessment note: “I am so naive. So I never think something's not going to work out”

Q What was it about makeup that you liked, or that spoke to you?

A Well, it wasn't even just the makeup. It was everything that goes along with it, so I've always been someone that knew how to use makeup differently than other people did, so, and, and doing theatrical makeup, making someone look old, or like a character, was amazing for me, because in order to do makeup for a play, for a film, you have to read the script, You have to talk to the director. You have to create what the, what the person is going to look like. Did they have a hard life? How do you make them look tired? How do you make them look old? I'd have to go figure it out and understand it and then make the girls look like that.

AI assessment note: “doing theatrical makeup, making someone look old, or like a character, was amazing for me”

Q You are, and maybe I'll be a mentor and an investor and, you know, kind of dabble here and there. But to, to, to muster all your energy, because a startup, as you know better than anyone else, it is a full-time, twenty-four-seven job. It is all-encompassing. And did you feel like you just had to do it? Like, you just couldn't contain the energy that was inside of you?

A I, it was not an option of doing it or non, or not doing it. When I, when I started to make these products, I just thought these are so simple and they're so much better. People are going to love these. I thought I would maybe start the company on Etsy. Just put like the best brown eyeshadow and start there. And, and then I realized, okay, there's a different way to do this. So no, I, I could not wait to launch and I did everything completely different the second time that I did the first time. But I didn't look at it as hard. I looked at it as, this is so cool. I felt, I felt renewed. First of all, I was 62 years old when I started this brand.

AI assessment note: “it was not an option of doing it or non, or not doing it”

Q So what happened? You went, you brought your lipsticks to, to, to show her that a couple days later?

A She brought them in. I mean, I had no press release. I had nothing. She called me back, and she said, they're really interested. We'd love to take them. And that's when I realized I had really changed the way we were doing things. And, you know, I had to find a different way to scale up than the chemist, because that was the only way he knew. So I parted ways with the chemist, and I had to find A lab to recreate the lipsticks the way I wanted, and we needed to find someone to do it. I remember making all these calls, but then one day, I was in an elevator, and I said hi to the girl in the elevator, and she said hi. I think we were on the 11th floor, so we had a few minutes.

AI assessment note: “She brought them in. I mean, I had no press release. I had nothing.”

Q What was it about makeup that you liked or that spoke to you?

A Well, it wasn't even just the makeup. It was everything that goes along with it. So I've always been someone that knew how to use makeup differently than other people did. So, and, and doing theatrical makeup, making someone look old or like a character was amazing for me because in order to do makeup for a play, for a film, you have to read the script. You have to talk to the director. You have to create what the, what the person is going to look like. Did they have a hard life? How do you make them look tired? How do you make them look old? I'd have to go figure it out and understand it and then make the girls look like that.

AI assessment note: “making someone look old or like a character was amazing for me”

Q You're trying to scale to a five, hopefully greater million dollar business. Bobby Brown. Yeah. What do you think?

A Well, first of all, what you're doing is working and not everything. Why does everyone think every business has to be like a rocket ship? It's got, it's got to grow, but, but it's also sometimes if things are so explosive and big, like, you know, we've, we've had tick tock moments that are like, you know, like, We could not keep up with it. It happened. And then you look a year later and you're like, how are we going to anniversary that? So that's, I'm not going to worry and figure out what else can I do to, you know, to go viral? No, let's look at the business. What's working? What's not working? What, what do I not need to be spending as much money on or time on? You have a big success on social. And I mean, have you done a sub stack? Have you done YouTube? You know, there's other things you could do. Are you doing like other company, um, giveaways and collabs? Like that's a good thing.

AI assessment note: “Why does everyone think every business has to be like a rocket ship?”

Q a question for you. Mark is a very busy guy, okay? He is an orthopedic surgeon. There's got to be a lot of demand for his time, and this is a side project. You were a makeup artist. You were very busy. How, how would you recommend he starts to balance these things out? Because look, let's be honest, most of his income is coming from being a, A surgeon.

A I mean, come on. Dr. Oz was a heart surgeon. Okay. So, you know, you start somewhere and you go and you go whatever pace you're comfortable with. And how could you get things done while you're actually at work? You know, just whether it's a meeting in the morning with who's going to help you this kid that you're going to hire. And, and then at the end of the day, you check in with them. Things are working. The business is continuing because, you know, you have someone to do that. So it's, but, but there's no rush for, for this to kind of take off. It's going to happen, especially the more people that know about it.

AI assessment note: “whether it's a meeting in the morning with who's going to help you”

Q that their success, limited success or whatever it might be, might be a trend or fad or so. How do you, how do you think about the thing that you're building, right? That into something with more longevity, something that has more staying power? Because as I say, I mean, people, People at the time said, oh, this nude makeup thing is just a trend, and you know, it'll pass.

A Right. And people thought that, you know, I mean, I had comments from people that said, oh, you're just putting your name on some package. No, I'm not. That's not how we're doing it because we didn't have fancy packaging. But I think for anyone that is, you know, an entrepreneur and a founder, you look at what you're doing and yes, it's got to constantly not just like grow into something else. You've got to pay attention to what you have and make sure it's the best. And sometimes you have to make little fixes and sometimes you have to make big fixes. But you always have to make sure that it's the best thing on the market so people will come back for it, people will tell their friends about it, and people will rebuy the same thing over and over again, but you need new things so people are interested. So it's, you know, it's just kind of figuring out the whole ecosystem.

AI assessment note: “make sure that it's the best thing on the market so people will come back”

Q So Bobby, With all this, the success that you've had in your career, how much of it do you think is because of your, your intelligence, your hard work, and how much of it because of luck?

A I think that, um, my, my intelligence is mostly emotional intelligence, which is, you know, dealing with what's around me. I am incredibly lucky and, you know, fortuitous and grateful and all of those things. I'm not the only one that works hard. I am not the only one that seizes opportunities. I don't know why, you know, things I do are successful. Not everything I've done is successful, but I keep going, and I'm really good, what I'm really good at, and I hope there's other entrepreneurs out there that understand this, I am really good at hiring people that are good at things that I'm not. That's really important, because I'm not good at everything, and I'm not, I told my Aunt Alice, I'm not really good at anything, I'm just good at telling people what to do. I'm really good at telling people what to do.

AI assessment note: “my intelligence is mostly emotional intelligence... I am incredibly lucky”

Q So when you, uh, so when it's time for you to leave home and go to college, what did you, uh, what'd you study?

A Well, I went to, you know, with a lot of my friends, there were probably a dozen of us, that went freshman year of college to University of Arizona in Tucson, and I was so bored in school, you know, because you would sit in, you know, it's a huge university, and you'd sit in these big giant halls with 500, a thousand people, and see this little teeny professor at the, you know, lecture us with, you know, an overhead projector, And I certainly, it was not the way that I was meant to learn. So, you know, I went through the motions, and the end of the year, I came home, and I told my mom I wanted to drop out of school. And my mother says, you can't. And I said, but why, mom? It's so boring. I don't want to go to college. She says, I never graduated college. And she says, you have to. I said, but mom, I have no clue what I want to do. And my mother said, I remember the two chairs we were sitting at. I was sitting cross-legged, as I always do, and she said, okay, forget what you want to do with your life. If today was your birthday, you could do anything you want, what would you want to do? And I had no idea. And I remember, as I always do, quickly saying the first thing that popped into my head was, I want to go to Marshall Fields and play with makeup.

AI assessment note: “I said, but mom, I have no clue what I want to do.”

Q So when you, uh, so when it's time for you to leave home and go to college, what did you, uh, what'd you study?

A Well, I went to, you know, with a lot of my friends, there were probably a dozen of us, that went freshman year of college to University of Arizona in Tucson, and I was so bored in school, you know, because you would sit in, you know, it's a huge university, and you'd sit in these big giant halls with 500, a thousand people, and see this little teeny professor at the, you know, lecture us with, you know, an overhead projector, And I certainly, it was not the way that I was meant to learn. So, you know, I went through the motions, and the end of the year, I came home, and I told my mom I wanted to drop out of school. And my mother says, you can't. And I said, but why, mom? It's so boring. I don't want to go to college. She says, I never graduated college. And she says, you have to. I said, but mom, I have no clue what I want to do. And my mother said, I remember the two chairs we were sitting at. I was sitting cross-legged as I always do, and she said, okay, forget what you want to do with your life. If today was your birthday, you could do anything you want, what would you want to do? And I had no idea. And I remember, as I always do, quickly saying the first thing that popped into my head was, I want to go to Marshall Fields and play with makeup.

AI assessment note: “I said, but mom, I have no clue what I want to do.”