Bobbi Brown

0:02When you are pioneering anything or introducing new ideas to the culture, you get criticized. You do? Yeah. Did you hear about that? I didn't find the one. I found someone I respected and we made it the one. In a sort of longing kind of view of love, people understand each other as if by magic. Nothing in itself is addictive on the one hand. On the other hand, everything could be addictive if there's an emptiness in that person that needs to be filled. I now know that nobody changes until they change their energy. And when you change your energy, you change your life. I'm Gwyneth Paltrow. This is the Goop Podcast, bringing together thought leaders, culture changers, creatives, founders, and CEOs, scientists, doctors, healers, and seekers, here to start conversations, because simply asking questions and listening has the power to change the way we see the world.

0:58Here we go. Welcome to the Goop Podcast. I'm Kelsey from Goop. If you listened to Gwyneth's recent AMA episode, you know she's taking a little holiday break, but we'll be back in the new year with an incredible lineup of guests. Until then, we'll be revisiting some of your favorite conversations from the archive, along with a few new guest-hosted episodes we're excited to share. Thanks for listening.

1:25Hi guys, welcome to the Goop podcast. I'm Emily Hickey, and I run a digital ad agency called Chief Detective, and I'm co-hosting a new sub-series within the Goop podcast that we're calling the Pursuit Series. This is all about exploring the various ways that we as women try to accomplish the fullest versions of ourselves and our most meaningful lives. And today I'm talking to Bobbi Brown, the legendary founder of Bobbi Brown Cosmetics and now the explosively growing Jones Road Beauty. She is the OG inventor of the no makeup makeup movement and the push for women to realize how beautiful their real faces are.

2:00We talk about the lifelong battle for self self-esteem and unconditional self-love, finding your personal why, and most of all, the power of saying, why the hell not? There's just so much to learn from Bobbi and from her perspective on life. And I hope that you guys find this as interesting and as helpful as I did.

2:21Hi, Bobbi. Welcome to the Goop podcast. Hi. So nice to meet you and thanks for having me on. Oh, it's so great to me. I've been looking super, super forward to this. And I want to say, So first of all, Bobby, congrats. You've built two really successful businesses. The first, of course, being Bobby Brown, which you sold to Estee Lauder and single-handedly created the no makeup makeup movement. And all of us women, I think, are very indebted to you for that. So thank you. And now you're building Jones Road, of course, which is also just off to an incredible start. And then you've written a lot of books, but this is a really special one because it's your personal memoir.

2:59And I burned through it and I have a million notes and underlined things. It really meant a lot to me, actually. And so I'm so excited to talk to you about exploring the pursuit of your fullest self and of your most productive and meaningful life. To me is what your book was all about, was kind of personal why and finding and accepting yourself. So truly welcome. I can't wait to talk to you about all this. Okay, so the first thing I wanted to ask you, like I've been like sort of obsessing over this lately, is just the concept of contentment. And when I got to the end of your book, it made me feel the same way as when I got to the end of that Ralph Lauren documentary, where he says, as you get older, you don't need all the things you thought you needed.

3:40Sometimes you have to fulfill your dreams to know what your real dream is all about. And it's about family and children and peace. And I was wondering, you know, I felt like when I got to the end of your book, I was like, she's done it. She's actually content. And so I'd love to hear your thoughts on that, if that is where you've reached and kind of your kind of Ralph Lauren conclusion about all this. No, I'm not there yet. I am not there yet. Should I be? Yes. Do I do I constantly question myself? Like, you know, I'm I'm right now in Florida, one of our you know, one of our homes. I'm this is my second podcast of the day.

4:19I've got meetings all afternoon. I couldn't be happier. I couldn't be happier. But then I'm like, why is my husband and my son playing golf for five hours and having lunch with their friends? And I'm so happy that I'm doing all these work things. But I'm like, what is wrong with me? I mean, I should be walking at the beach. I should be out, you know, by myself sitting there reading a book. I am not that person. And so I struggle with what I think I should be and what I actually am. Right. I'm not someone that plays cards or, you know, gardens. I just, I'm curious and I like action. So am I happy?

4:55A hundred percent. Am I content? Yeah. But do I have that itch and that angst that I want to do more or want to do other things? A hundred percent. That's so interesting. It really is. Like I've been, this is really, I've been thinking about this really acutely lately, actually. Like, is there some second life that you're supposed to live. And if you put a shot clock on your life, what would you regret not having cut over to doing? You know, but, and I keep thinking, I don't know, like I'm a real worker too. This is what you want to be. You could do anything. I could do anything. And this is what I want to do.

5:32And the only good thing I'm going to tell you about getting older and, you know, being able to look back, especially, you know, when you write a book, cause it's very cathartic, you realize, okay, I'm, I still have the same angst and struggles, but I'm okay with that. Like, it's like, I'm less upset that I have those angst and struggles. And, you know, now I have two grandkids and I find myself when Lily, my oldest one, who's three, leaves my house and, you know, she's my first girl. So she's got a whole kitchen, a wooden kitchen. It's so beautiful. I find myself sitting there for 40 minutes, organizing all her food and all her things the same way I did with her father, who's Cody.

6:14And I'm like, but you know what? It makes me feel good when it's organized. So I don't make myself crazy anymore. Right. Like to get it like, OK, it's fine. Yeah. No, but I mean, it's interesting because you something very unique happened to you as a woman, which is that you presumably hit your financial goals in your 30s, you know, and your life changed very drastically in your 30s when you sold your company. And I feel like so many of us have this terrible trick we play on ourselves of this receding horizon of milestones and that we'll let ourselves actually live in a present version of our lives once we make X amount of money or lose X amount of weight or whatever the milestone is.

6:55And you actually hit that milestone in your 30s. You know, I just like what did you see that as a positive or negative? I didn't have a milestone to hit because I never thought about it that way. You know, I just I'm the most naive person you've ever met. So I just kept working and doing things and, you know, met met someone that I knew I wanted to marry. I knew I didn't want to live in the city. I wanted to live in the suburbs. You know, I wanted to have this normal life in addition to being the fabulous Bobby in New York and doing all those, you know, high heel moments that, you know, were not always my favorite, but they were fun.

7:35I never thought, wow, I've got to make certain kind of money. Like, you know, I thought when I was young, if I only could make$100 ,000 a year, I would be fine. And I'm like, all right, well, you know, I did that. So, you know, now it's like, what am I in pursuit of? You know, I'm in pursuit of, you know, scratching the itch. I'm in pursuit of the unknown. I'm in pursuit of learning more. Do you think that's the point, the point of life? For me, it is. You know, for me, it is. I have people that say to me all the time, why are you doing this? You don't have to do this. I'm like, no, I don't have to, but I want to.

8:16You know, why did you say yes to this thing that you're going to? You're not getting paid. I said, because it sounds really interesting. And you know, what's the worst that happens? It's not, you know, I'm like, no big deal. Yep. Yep. One of the things I wanted to try to do with you, even though I think I have a good sense of it from your book, but I do these brand exercises of trying to figure out the why of a brand and how that would map out to product strategy and everything else. And then I think you can put it on a person too. You know, you know, your why, you know, it's clear you operate with a high degree of self-awareness.

8:47But I wanted to try asking you a series of questions to try to ladder out to that, to a guess on you. But I mean, the first one I think is just your parents and your childhood. And when I read about your mom, my heart really sank because it seemed like you went from having this great relationship to all of a sudden she was deeply mentally ill and you really like kind of lost her, you know? And so I was curious, like your childhood and your parents, how do you think that that shaped this itch or whatever you're after here? Well, I'm really lucky because my mom really was amazing until, you know, college.

9:24So I, you know, the most important years, I was the oldest kid. I got this incredibly, you know, present mom who just thought I was the greatest thing and said, you could do anything. And, you know, she was the most like encouraging person when she had her first nervous breakdown, she recovered. And then she didn't, you know, it didn't kind of become like, she didn't really recover after I was in college. Like, you know, I got married, she was there. She wasn't the same person. She, you know, I had kids, she kind of was there, but not really. So I didn't have her. But, you know, I was really lucky because I had my mother in law.

10:05So, you know, I didn't feel bad that I don't have something. I felt really grateful that I had her. And my father at the time kind of became, my parents were divorced by then. He kind of took the role of my mom. Like he would come once a month and we would have the best time and he'd be the most involved grandpa. And so I, you know, I got to fill that hole of not having my mom there. And I think I've always been that person, you know, that I've, I understand like, okay, so I didn't get that, but I have this. So, you know, I mean, look, I wasn't a smart kid. I felt really insecure that I was not, you know, as smart as anyone.

10:47And then I discovered how frigging smart I am in a different way when I was older. So I got to kind of fill, you know, fill that up. That's interesting. So because I guess I thought it happened when you were younger. And then you also talk a lot about your mom being pretty hard on you. Yeah, she was. I mean, you know, look, I still have self esteem things. And it's ironic because what I do in life is I help women with confidence, being comfortable in their skin. And a lot of that comes from my childhood, where I was never quite pretty enough, at least in my mind for my parents, and I never dressed the right way.

11:27And I, I've always been a little bit of a, of a dork. You know, even when I get all dressed up, I just, you know, I'm most comfortable in my bathrobe, by the way, and my tights, like, you know, I, you know, and look, and what I do, I'm in the public eye. So I always have to put on whatever the right face is, you know, and I've learned that I can only do what I'm comfortable being. So I am my most comfortable, you know, when I'm wearing jeans, when I'm wearing plain Navy pants, when I'm, you know, I just, I, I, when I get invited to these parties in the Hamptons and I know everyone's wearing flower dresses and they're going to be twirling around, I'm like, oh my God, like, do I really want to go?

12:08And that's when I just find white jeans and a white shirt and I tie it, you know, and I've met other women that kind of dress like me. And I'm like, shoo, you know, so I don't feel that out of place. Now, that was one of my favorite parts of your book. I mean, it seems like a big part of your journey was these little rebellions of self, you know, self-defense and self-esteem where you just were going to kind of zag against what you were supposed to be doing and do what you wanted to do. Only because it wasn't working the other way. Like I didn't like to feel bad, right? I felt bad because other, you know, I couldn't do a cartwheel.

12:45Like I felt bad. And then I'm like, I'll be fine without doing a cartwheel. Okay. I mean, I'm not a cheerleader. And then when I would, you know, what, what do I do? I go to New York city and I jump into this, you know, high-end fashion industry where, you know, Linda, Cindy, Naomi, Christy. And I remember one day there was a fashion show and I was probably eight months pregnant and I was 30 years old. And I felt so much older than these 21 year old, you know, glamazons. And I remember looking up at them right before the show started and said to myself, all right, don't go there. Don't compare yourself to them because you're going to lose, first of all.

13:23And you're, you know, it's okay. You're five foot and married and pregnant and 30, right? I can't be that anyway. So I'm not going to waste my energy on feeling insecure because they look like that. Yeah. Self-esteem is a hard one. But your mom and dad, you can always mirror image the parents' fears with the adult's complexes. So I just, your mom being critical, your dad, were there aspects of his life that were unlived? I mean, what do you think you carried as complexes from how you were raised? I mean, really, it was just about my looks, you know, and my parents stopped punishing me for getting D's in, you know, subjects I didn't care about because they had punished me a couple of times.

14:13And I, you know, I got a D in spelling. They punished me. I couldn't go take cooking classes with my friends. Well, you know, I apologize to my husband. I still can't cook. You know, I didn't take the class. And then I somehow managed to get a B plus the next semester. So, you know, I'm like, all right, well, I just got to put a little more energy into it. And so I never got good grades in algebra or, you know, biology or chemistry, but who cares? Right. In retrospect, so what, you know, but I felt bad because I didn't understand concepts. And to this day, I mean, like if, if someone hands me, you know, an instruction guide, how to do something, I can't do it.

14:52I can only do it. Like when someone shows me because I'm a visual learner and it took me a while to kind of, you know, know that. Yeah. It's so great to get out of school and realize what, yeah, who you actually are. So there was nothing, I mean, as a parent, do you think that you tried to break the chain of that criticism from your mom or how did you translate that to being a parent? You know, I 100 percent. I was always very aware. And the good news about becoming a parent and having, you know, my husband and I have always been incredibly aligned and tight. And he's got the most wonderful family that I got to almost recreate the family dynamic that I wanted.

15:40So I've been very lucky with that. And, you know, God was great to me. I have three boys and no girls because honestly, I don't know if I would have been a good girl mom because my mom didn't mean to make me feel bad. You know, both my parents were chubby kids. And so when they lost their weight, they realized they were very attractive. And, you know, here they raised I mean, I wasn't fat, but I was chubby. So here they were like, you know, probably looking at their selves, you know, in me. So they tried to help me. I mean, they really wanted me to be better. And when I finally kind of broke out of the ugly duckling thing, you know, my dad, you know, he didn't mean it, but he said, wow, I'm so proud to say you're my daughter for a few years.

16:26I'm not sure I, you know, I don't remember. I'm not sure I would have been so proud to introduce. He said something like that. And I remember being like, what the who says that? Like, you know, it didn't really trigger me. Yeah. But, you know, I my mother told me I was really pretty, but I'd be gorgeous if I had my nose fixed. And I remember the same reaction. I'm like, who says things like that? Right. And it didn't like, honestly, it could have made me in a you know, but I just didn't let it. And I think that's one of the things I'm most proud of in my book, that all the things that I kind of was up against, both that part of my life and also working in a corporation with a bunch of men that thought they were smarter than me.

17:09I'm like, who says these things? And I just realized I don't need to waste my time and energy and angst on people that are putting such negativity out there. mm-hmm but and and you just naturally were able to do that or you worked on that no I think I was just naturally I never worked on it I guess I just realized this is stupid I've always been someone like my mother used to insist that my room was clean every Monday morning and she would fight with my brother like bloody murder and he'd be punished and I just realized it is so much easier to keep the room clean and she would leave me alone like to me it's common sense.

17:49I mean, why would I, you know, and even, you know, working with corporate, yes, I took a lot of those skills and working with my son now, you know, and being happily married 37 years, I use a lot of those things. It's like, it's not worth my time and energy, you know, to fight about certain things, even if I know I'm right.

18:11So, see, it's so interesting. You're just a very high functioning person. Like, Like, but you say in the book, I thought you said in the book that you'd worked on a lot in therapy. No, I've my, I was in therapy when I was a kid. My mother put all of us kids in therapy. So I never did it as a, you know, a grownup. When I first met my husband, he was into alternative therapy. So we saw these two people and I just remember like, you know, hitting pillows and I just remember, it was like very odd, but you know, I was with my new, a new guy. So we did that a couple of sessions and I'm like, I don't need to hit this frigging pillow, you know, to get whatever happened to me when I was a kid.

18:52So I'm more into working with life coaches because life coaches kind of help you deal with, you know, some of the things that I'm struggling with, with like action plans. Like I am someone, if I have an action plan, I'm fine. I can move forward. If I, if I'm like stuck in the weeds or, you know, whatever, I, I don't do really well. You know, I need to go forward. I am high functioning. That is correct. It's so interesting because you haven't really, it sounds like you don't really have any glass ceilings that you've set for yourself in terms of bad self narrative. I mean, once you got through the appearance stuff, that was kind of the, your gotcha.

19:29Yeah. And it's, I mean, it's still something I deal with every day. I'm, you know, I'm not going to lie. It's doesn't get easier as you get older because I can't just throw on my little skirt anymore. And my sleeveless, cause you get to be a certain age and I'm like, I don't want to be, I don't want my arms photographed. There's nothing wrong with my thin arms, but I just don't like, you know, I'm such a visual person. I'm like, no, no, no, no, not happening. So I, you know, I've never seen a glass ceiling. I just don't get it. You know, I mean, yes, I don't have an MBA, you know, I don't have the intellect that other people have, but it doesn't have anything to do with me being successful.

20:08You know, I'm completely like ADD and a little OCD. Those are just my gifts instead of seeing that they're a curse. You know, I'm like, I'm so curious. I'm so open. Everyone's like, well, now what are you going to do? I'm like, I don't know, but I know I'm going to be doing it, you know? And I think that's kind of interesting and cool. I agree.

20:39so I asked Cody, your middle son, a few things. And among them, I said, what do you think motivates your mom? And that's basically what you just, he said, you know, I think she has a chip on her shoulder from her mom being hard on her, but that she, it's all, it's, it's a, it's not a curse for her. It's a blessing because it motivates her. And that's really clear from everything you're saying that you're when you have a an obstacle that's a blessing for you I love obstacles and I love when people call me you know with problems because it's such common sense like I use my Chicago common sense in my business life in my personal life you know with my friends and I think that has been my superpower like I'm really into people have superpowers what they have.

21:26And once you realize what yours are and, and, and the things that you don't feel you have superpowers, you got to, I always bring people around me that have those superpowers. That makes me a better person. I'm not, I don't feel less of a person because I have someone that's more capable than me. So what, what do you think you're trying to resolve outside of the ongoing, you know, self-esteem and appearance and like, but what about things like vulnerability and letting go of control and on being unstructured in ways. I mean, is that hard for you? Well, let's see. One at a time. You know, I like I don't like structure, but I like process.

22:08Right. And I, you know, I come from a lot of structure and a lot of process. And, you know, Jones Road, the startup, doesn't have as much process as I think we should, you know, and doesn't have the structure, which I think we maybe could use a little bit of, but we, you know, we're working, we're working on that. You know, it's been such meteoric growth for five years that now is the time like, okay, hold on. How do we kind of recalibrate to make sure the team is, you know, really has what they need and has, and it's the right team. So that's what we're kind of in right now. So, you know, I like, or I like organization.

22:47I, I just, I, I, I have mastered it because now I hire organizers to come in and help me because, you know, by the end of a, you know, a summer at the beach or the end of, you know, my season in Florida, my, my, my OCD is out the window. My ADD has taken over. So I need someone to kind of, there's nothing that makes me feel better than to open a drawer or a cabinet or a garage when someone else visually organized it. So, you know, so that was one point. And what was the other vulnerable thing you asked? Well, vulnerability. So I looked at your birth chart for two seconds before we jumped on this.

23:25And I don't even know if I believe in astrology, but there are a couple of things I think are always really metaphorically interesting in someone's chart. One is where is Saturn? Because that's where the fears and insecurities are. And then the other one is this north-south axis that's sort of the hero's journey of someone's life. And yours goes from structure and control and personal success. It goes to things that aren't as defined and controlled and that it would say that your growth would be to let go. So I'm just curious. Yeah. So, you know, when you're a freelance artist and you're so angst that no one's calling you, you know, you're busy, busy, busy.

23:58And all of a sudden, like the phone stops ringing and you're like, oh, how am I going to pay my bills. It's over. I learned to let go because it seemed like as soon as I was able to let go, the phone started ringing again. It was just one of those weird things. And then I'm like busy again. And I'm like, darn, I could have been, you know, doing all these fun things. And I was so busy worrying. So, you know, so that I, that I've been able to let go. When it comes to working with my team, I let go when I have confidence that the person could make the right decisions if I'm not around. But as a manager, I like to be involved in the decision making of what we're doing.

24:41And then I'd like to know how we're doing. And, you know, and look, I'm happy for people to do things without me, as long as they don't mind, if they do something I don't like, I can call them and tell them. You were born to be in charge. Yes, but I'm also born to have other people doing things because, you know, like it took us 15 minutes to get on this podcast. I only use my iPad. I couldn't figure out my son's, you know, my youngest son's computer. It's brand new. He already warned me to get and don't get fingerprints anywhere, you know. So I'm like, all right, so I don't know how to use a computer, but I figured out the answer.

25:21I have my two amazing assistants and they FaceTime me. So we figure it out and I don't, I don't get stressed or panic because I know we'll figure it out. So, you know, yeah, I like to be in charge, but I'm, I like to let go because I, I have, I want to have confidence that it's all going to work out fine. Yeah. Letting go is a real trick. Yeah. Yeah. So you've kind of, I mean, a big theme of your life has been helping women. And I'm curious with your experiences with women, you know, what advice would you give women trying to build meaning into the second half of their lives if they don't work for one thing, or if they work, like what if your life hadn't been successful?