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Kara Swisher
Hey, is she here?
Bobbi Brown
I'm here she is.
Kara Swisher
Oh, there you are, Bobby. How you doing? Hi everyone. From New York magazine and the Vox Media podcast network, this is on with Kara Swisher. And I'm Kara Swisher. My guest today is makeup mogul Bobby Brown. Brown first made a name for herself as a makeup artist in New York city in the 1980s and 1990s. She favored a natural, natural look long before it became the dominant trend in makeup. And she eventually started selling her own line of lipsticks from her house in Montclair, New Jersey. She then grew it into a billion dollar global brand, Bobbi Brown cosmetics. But in 2016, after 20 years of building her namesake company under the beauty conglomerate Estee Lauder, she left under less than ideal terms. And because of her existing non compete agreement with the company, she had to avoid the industry for four years. But now, at 68, Brown is heading another successful makeup company she started called Jones Road. She also has a new memoir that just came out called Still Bobbi A masterclass in resilience and reinvention. I actually use Bobbi Brown products cause I'm kind of her target audience cause they're really simple and easy to use. I don't use that much makeup to be honest with you, but my wife loves it, especially the main product, Miracle Balm. I think that's her best selling product and some others cause it's really simple and very easy to use and not fancy. I'm more interested entrepreneur and how she built her business. I often focus on tech people or media people, but cosmetics is a really interesting industry cause it's been sort of rocked by social media and other changes, ends of department stores and everything. So to hear from a cosmetic entrepreneur like Bobbi Brown is really interesting in what lessons she's learned. Our expert question comes from Lauren Sherman, the fashion correspondent at Puck News. All right, let's get into my conversation with Bobbi Brown. Stick around. Support for this show comes from Smartsheet. Your team is innovative. Your team is ready to achieve the impossible. Innovative teams use Smartsheet to defy expectations, spur growth, and make the impossible possible. Smartsheet is the work management platform that allows teams to automate workflows and seamlessly adapt as their work evolves. Whether you're managing projects or scaling operations, Smartsheet gives you the tools to cut through chaos and reach your team's full potential. With Smartsheet, the extraordinary is just another day at work. Smartsheet work with flow. See how Smartsheet can transform the way you work@smartsheet.com that's smartsheet.com.
Bobbi Brown
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Kara Swisher
It is on Bobby, thanks for coming on on.
Bobbi Brown
Well, thank you for having me on.
Kara Swisher
You know, you're well known for obviously your brands, your makeup brands, but this is a book about your journey as an entrepreneur, right? The idea of what it's like to be an entrepreneur and how you become one. And even though a lot of the focus on entrepreneurship tends to be on tech, you were really innovative early on in this space. Your new book is called still bobby. It's your 10th but your first memoir. And according to the new interview you did, this isn't a tell all. And you say you were strategic with your words, right? That said, the Times also noted candor is her calling card. Relatability is her stock in trade. You're 68 now. You found two successful makeup brands. You and your husband own a boutique hotel and you say you didn't sign a non disparagement agreement with Estee Lauder. Curious why it wasn't a tell all. I bet you know a lot more stuff than you do told here.
Bobbi Brown
You know, I'm from Chicago. I'm, you know, a nice midwestern girl. And you know what I was taught, you don't need to hurt people's feelings. You just don't. And yeah, you know, I also didn't want to come across like I was anger and bitter because I'm not. You know, in the beginning when I left, I was all those things and I had to really work hard to get the emotions out of my system. And you know, it took me a good year or two and nothing like another success to kind of get you over the first. You know, I looked at it as failure. They canceled my work contract and to me that was being fired. You know, I didn't want to stay the face of the brand without having anything to do with the brand. So you know, I was not going to sign a non disparagement but I don't need to disparage them and there were so many good things. So you know, I'll be happy to tell you any of the disparaging things when we're off camera.
Kara Swisher
So you were going here not to do a. Here's what happened to me and here's a lesson because sometimes one of the great lessons of entrepreneurship is failure, obviously.
Bobbi Brown
Yeah. Yes, well, I've had failures, you know, I mean I started a wellness brand after I left Bobby Brown called Evolution 18. We brilliantly launched at Walmart. It was not a success, you know, but it was a great learning opportunity. How to have a digital brand before I started Jones Road, you know, I had a 4 and a half years left on a 25 year non compete when I, when I left the company. So I had to fill myself with things to do because my kids were out of the house and you know what I mean? Honestly, what would you do if all of a sudden you couldn't work? Would you play tennis? I don't know what I would do.
Kara Swisher
Right, right. So, but let's talk about a big picture view of the beauty industry. Obviously that's where you've made your bones essentially and it's gone through a lot of change in the past decade. The global market is worth approximately $450 billion and it's experienced rapid growth. But the pandemic changed the relationship people had with cosmetics. In the past decade. We've also seen the rise of celebrity driven brands like Kylie cosmetics and Fenty from Rihanna and a focus on inclusivity. And of course the Internet has played a big role in the industry's evolution in leaving direct to consumer brands. YouTube and social media are the perfect vehicle for this kind of organic content around makeup. It's one of the most popular areas of those things. Talk about that evolution of where the industry was and where it is right now because you've jumped really two feet into it essentially from being part of one that was sort of went to department stores. Talk about the evolution a little bit of beauty.
Bobbi Brown
Well, first of all, when I first started Bobbi Brown Cosmetics in the beginning, the way it even got on the map is a friend of mine was an editor at Glamour magazine and she said, can I write about these lipsticks you're doing? And I was like, why would you want to do that? Now I know that was PR and then I was doing a lot of magazines because that's how my name got out there and people heard about me. And then one day I met this wonderful woman at a book who told me that she thought I was great when she saw me on the Today show. And she said, is there anything else you want to do? And it popped into my head, I want to be a regular on the Today show. And she said, honey, Jeff Zucker is my grandson.
Kara Swisher
Oh.
Bobbi Brown
And so, yeah, so I got on the Today show. I was the beauty editor for 14 years. And that was the first way to reach people and to really grow consumers. And I never talked about my brand.
Kara Swisher
Right, so you were taking advantage of the media of the day the most.
Bobbi Brown
Right. I've always loved media and I've always loved teaching. Like what I do is to teach people, you don't have to look like that, you don't have to wear your makeup like that, you don't have to shoot shit in your face. Like there's alternatives to everything. Because I really do think the reason people wear makeup is to not look tired, to not look stressed, and to just look prettier. And then, yes, in order to promote the brand, I would have to travel all over the globe because it was a big giant company and I would go into stores. How many people could you see? 100, 120. And so I worked my butt and it cost a lot of money by the way, flying me and my team from one place to another. And then when things started to change and you know, some of the newer brands came on the market, like Glossier, which was the first kind of direct to consumer messy hair makeup brand that inspired me to try to do things differently. I couldn't get any groundswell at my old company. So when I left, I had visions of what I wanted to do with the new company.
Kara Swisher
Which you couldn't do for several years, correct? Right.
Bobbi Brown
No, not till I launched. We launched Jones Road the day my 25 year non compete was up. One week before the presidential elections, right in the middle of the pandemic and we just turned on the lights and you know, everything was different.
Kara Swisher
And what was the methodology of once you sold to Estee Lauder to sell what was happening there?
Bobbi Brown
It's amazing when I look back, we sold Bobbi Brown cosmetics to Estee Lauder after four and a half years. And you know, I signed after growing.
Kara Swisher
It by doing all this. After growing it, right?
Bobbi Brown
Yeah. No, but after, after having it for four and a half years, I stayed at Estee Lauder as a corporate employee for 22 years. And there is nothing corporate about me. So it was, you know, it was great. I learned a lot. And then it got really.
Kara Swisher
That's 22 years. So there was something corporate about you, obviously.
Bobbi Brown
No, no, no. Look, I'm not someone that break rules. I like to make up my own. But I had people there who knew who I was, knew what my value was, knew what my, you know, what I can add. And they supported me until things changed and there was different people and the industry was changing. Right. It was contour palettes and all of these things. And here is a department store brand that couldn't get out of their own way. And I think the traditional companies really struggled for a while.
Kara Swisher
Talk about the department store brand. Explain that for people who don't know.
Bobbi Brown
You know, a lot of people are in department stores. A lot of cosmetics companies are department stores because that's where people shop and that's where they shop for makeup or that's where they shopped.
Kara Swisher
And that's how Estee Lauder.
Bobbi Brown
That is definitely the SD Lauder, and that's how they do it. But things were changing and people don't go to department stores anymore. I mean, I don't remember the last time I went into a department store and tried on clothes and bought clothes. I do everything D2C. You know, even if I want something from a department store, I go D.
Kara Swisher
To C. So when you sold to Essie Letter, though they were, that was the paradigm. This was in 1995. They bought your company, Bobby Brown Essentials, which had started off by selling a lipstick deal at Bergdorf Goodman too.
Bobbi Brown
Right.
Kara Swisher
Which another famous and fantastic department store still. But you were an indie brand. They bought. They couldn't do what you did. And so they bought you, paid you $75 million and put you on this 25 year agreement, which seems incomprehensible today.
Bobbi Brown
Well, we also had a buyout, by the way. So, I mean, you know, there was a lot of reason for me to stay. It was financial, but also I used to go to work like it was my company. I never really separated myself from my company. It was my baby and my. And, you know, my brand, which was really difficult when I left.
Kara Swisher
Right. So what. What factored into your decision to sell first and then talk a little bit about your decision to leave? Besides people changing again 22 years, a long time. But why did you sell in the first place?
Bobbi Brown
Well, we sold because, first of all, it was Leonard Lauder who made the contact. And Lauder was a much smaller corporation back then. They didn't have all the brands they have now. And it was really a family business and it was such a great fit. And my husband and I had partners that we started the company when we got into Bergdorf with. And it was of really not easy relationships. You know, we did really well together, but it was really personality tough. And I did not want to continue working with them. And that was a perfect way for us to grow the company. And Leonard Lauder said to me, he said, look, I know you want to be a mother and you want to spend time with your family, and we can help you grow your company while you do what you love and the things you don't love, we will take care of. And you know, that was the promise he made. And you know, he also promised that I'd have total autonomy. And it worked really well. When I had this autonomy, when I didn't have it anymore, it didn't work very well.
Kara Swisher
What changed? The people or the.
Bobbi Brown
Well, people started to change and then little things happened. I mean, look, I could handle being encouraged or pressured into creating products I didn't believe in because I would always try to figure out how to make them right for the brand. For example, there was a lot of angst about me doing a whitening skin product. I mean, anyone that knows me, I will not do tell people to lighten their skin. But I realized what they really wanted was brightening. So we interpreted and made it very on brand. And I always had a fight for things like not getting rid of the lowest selling skus, which were, you know, colors for dark skin. I'm like, guys, I'm not getting rid of them. When a woman comes to the counter, she needs to find her colors. So, you know, there was struggle, but then the industry started to change, and I wouldn't do contour palettes because I don't believe in contour. And I wouldn't do it. I didn't care.
Kara Swisher
What do you have against contour?
Bobbi Brown
Why do you need to tell someone that they have to change the shape of their face? I don't. First of all, when most people do contour on themselves, it looks like they have dirt. It just doesn't look right. So. And it just. What do you need to change? Like, to me, it's the same. My mother told me I was beautiful, but I needed my nose fixed. And I remember looking at her and like, mom, I've never complained. Complained about my nose. You know, I don't understand why people need to turn themselves into something that they're not.
Kara Swisher
Well, that's a bigger issue. We'll get to later. This idea of things that are happening now. But I have been in the same position. Someone said, why do you leave? Places I go. I don't like mama telling me what to do, essentially, you know, And I don't. And at one point, when I left somewhere else, they said, why are you leaving? I'm like, I don't want to talk to you anymore. I just. I don't know what else to say. As an entrepreneur, you're not doing what I like. When you go along with people as an entrepreneur, can you talk about this? Doing things that are sort of unnatural to you, like a contour palette or whitening stuff?
Bobbi Brown
Yeah. No, I won't do it.
Kara Swisher
Talk about this how you resist that. And you can't. Most people don't. Correct.
Bobbi Brown
Right. Well, I resist it because it just doesn't make any sense. I'm very easygoing until you're making me be something that I don't believe in. I get it. I know we have to increase our business. I know we have to grow our audience. I know we need competitive products. I know all of that. But it's gotta be what's right. It always has to be what's right for the brand. And so, you know, look, I'm not afraid of guys in suits. I'm just not afraid, you know? So I have to, you know, be nice, but I have to just say it. It doesn't make any sense. It's not who this brand is. And I would have to, you know, stick to my guns.
Kara Swisher
And you said too many times you had to do that, presumably. Is that what. Is something. Did something send you over the edge? Was it contour palettes with.
Bobbi Brown
No. What? No, because I wouldn't. I didn't do a contour palette. They did. I know they put one on the market when I left, but. No, it's when they. When people. Like, I used to interview every single person. You know, not every person, but most of the people I would interview. And when all of a sudden these people started showing up and like, hi, I'm your new head of International. Hi, I'm this. And I'm like, excuse me. I didn't meet them. Well, we think they're gonna be the best for the brand. We think this. We think this. So I wasn't included in what, to me, was important, which, you know, was running and growing the brand. And when I left, it was a billion dollars. It was a growing, growing brand.
Kara Swisher
Right now you're one of the number of. Small number of women who's lost control of their namesake brand around this time, especially because either they left or were pushed out. I'm thinking of women like Kate Spade, Jill Sander, Donna Karen, Betsey Johnson in makeup, there's Tony Ko, who founded Nyx. Talk about this. Did you see yourself in context of these other women, and what are the parallels and differences?
Bobbi Brown
Well, I think very, very similar. And when I. Honestly, when I left, I thought, well, I'm done. You know, I'm done. No one's gonna ever call me up and ask me the hard breaking questions. You know, the journalist. What do you like to eat for breakfast? Where do you go on vacation? I'm like, it's done. You know, those are the questions that I get asked. But. But things started to change, and I realized at some point that I was a brand, not just the company, that there was two sides of me. But it was a really, really hard time in my life. And looking back, I wouldn't trade it for the world, because how do you grow and how do you learn to get better? You have to kind of go through that. I mean, there was so many emotions. And, yes, I definitely saw similarities with a lot of these women founders. And, you know, it happens to men, too, that have brands. There was like a. I forget. I'm trying to remember the name of the guy. Was it Joseph Abboud, who lost control of his brand and his name, and then he tried to start again, and they did everything to stop them, to stop him. My husband and I were following his case for a while after I left. So, you know, it happens. Like, shit happens, and then it's what you do with the shit that defines you. Like, some people don't go back to work. Some people don't start something new. And, you know, my age was also a factor. I never thought about it. I'm like, all right, I'm in my 60s.
Kara Swisher
Okay.
Bobbi Brown
That's okay. What else am I gonna do, right?
Kara Swisher
So in every episode, this sort of dovetails that question. We get a question from an outside expert. Let's hear yours.
Bobbi Brown
Hi, I'm Lauren Sherman, fashion correspondent at Puck.
Kara Swisher
Hi, Bobbi. Congrats on the book. It's been a long. My question for you is, you know.
Bobbi Brown
When creative entrepreneurs sell their companies, they usually have some sort of exit. You have to stay for three to five years, that type of thing.
Kara Swisher
I mean, you sold in the 90s.
Bobbi Brown
So maybe it was a little different back then, but you stayed for, what, two decades at Estee Lauder, which, as you know, we cover that company very closely at Puck. Rachel Strugatz.
Kara Swisher
And it's not an easy business.
Bobbi Brown
Even when it was doing well, you.
Kara Swisher
Know, it's a family run company, there.
Bobbi Brown
Was a lot of succession drama with the family versus outside executives, that sort of thing.
Kara Swisher
What made you stick around?
Bobbi Brown
Because you could have gotten out of it somehow. Maybe your non compete was complicated, but you stayed.
Kara Swisher
And I'm just curious, were there certain.
Bobbi Brown
People in that company that made it worthwhile? Was it the infrastructure? Like, why did you stick it out for all that time? Because so many people who were in your position wouldn't have. I stayed for 22 years because I was really happy and I was fulfilled and I was part of this process of growing the brands and trying new things and doing things differently. I had so much support. Those were the glory years. And every time I see some of my lieutenants from the old country, as I call it, we just talk about the magic that we had. You know, we really had this posse creative brains that worked together, you know, in PR and marketing and finance. I, you know, our CFO is the one that taught me everything I needed to know about business. And it was glorious. It really was. And then when it wasn't, I thought I could turn it around to go back, that I would. And I thought I would have control again. And it really took my 94 year old aunt Alice to tell me, bobby, it's time. It's time. I've been hearing you complain and I've been hearing you complain every time I talk to you. And you keep saying you're gonna fix it. I don't think even you could fix this. And that's when I realized. But the truth is, when I went in for the final meeting, I really thought they were gonna come to me and say, here are all these great candidates we found to run your brand. And that's not what happened when I walked into the meeting. So I was again naive.
Kara Swisher
Yeah, it's interesting, the idea of complaining. Whenever I start to complain too much, my family's like, stop it. And I have made that a policy. Now the minute I start griping about people, it's my problem, which is hard now toward the end of the book. And we're gonna get to what you're doing now in a second. You talk about a conversation you had with Leonard Lauder, who you just spoke about after his 90th birthday. I should note he died just a few months ago at 92. You write that during that conversation you said, he told you, I promised I would take care of you and the brand. And I wasn't able to do that, talk about that. And what was your response?
Bobbi Brown
Well, we had this three, almost three hour lunch. It was supposed to be an hour. We stayed for three hours. I hadn't talked to him since that day where I left, quote, got fired. But it was an amazing meeting of these two people that really loved each other and worked hard. And when I went to leave and say goodbye, he said, I have to apologize to you. And I said, for what? And he said, because I promised you I would always take care of you and your brand. And I couldn't do it. Which made me realize he probably said, don't do this. But they did it anyways.
Kara Swisher
Yeah. What did you say to him?
Bobbi Brown
I said, leonard, I wouldn't have changed a thing. First of all, I couldn't imagine being there now or when I left and having to fight to really fix things because the entire industry kind of turned into a message.
Kara Swisher
So it would have been a very different thing now.
Bobbi Brown
Oh my God, it would have been very different. And people are still coming to me saying, what if we buy Bobby and Jones? What would you do? You know, could you fix it?
Kara Swisher
Could you?
Bobbi Brown
And you know the answer I'm sure I could do I want to is a different story.
Kara Swisher
We'll be back in a minute. Support for the show comes from Indeed. At your company, you're across a lot of things and everyone on your team is a multi hyphenate and stretching their bandwidth, which is all great but can also lead to burnout fast. And it might be time to consider hiring more people. And when you need to hire folks fast, turn to Indeed. Indeed Sponsored Jobs helps you stand out and hire fast. With Sponsored Jobs, your post jumps to the top of the page for your relevant candidates so you can reach the people you want faster and it makes a huge difference. According to Indeed data, Sponsored Jobs posted directly on indeed have 45% more applications than non sponsored jobs. There's no need to wait any longer. Speed up your hiring right now with Indeed and listeners of the show will get a $75 sponsored job credit. To get your jobs more visibility@ Indeed.com on just go to Indeed.com on right now and support our show by saying you heard about Indeed on this podcast. Indeed.com on terms and conditions apply. Hiring Indeed is all you need. Support for this show comes from Framer. When the Internet was still novel, even the most basic websites were impressive. But it's been like 40 years and countless Internet generations since then and it'll take more than basic pixel art to stand out for that, you might want to try Framer. Framer is the design first. No code website builder that lets anyone ship a production ready site in minutes. You can get inspiration from hundreds of templates or strike out on your own from a totally blank canvas. Multiplayer collaboration means your writer, designer and marketer can all tweak the same page at once with no risk of corrupting version control. And under the hood you'll get responsive breakpoints built in, hosting a flexible CSM and privacy friendly analytics so that you know what's working and what needs fixing. And at every step, Framer's AI powered Dev Assistant helps you generate banners, pricing tables, navigation bars and more, all specified to your palette and branding. Ready to build a site that looks hand coded without hiring a developer? Launch your site for free@framer.com and use the code Kara to get your first month of pro on the house. That's framer.com promo code Kara framer.com promo code Kara rules and restrictions may apply. Support for on with Kara Swisher comes from Groons. Your body is your home. Of course that's not your actual home, but it's a good metaphor because like the home you live in, you can tell when something is off. Diet and exercise are of course a great way to realign yourself. But what if you wanted something more? Something that can improve your skin, gut, health and immunity? It might be time to try Grunes. Grunes are a convenient, comprehensive formula packed into a daily pack of gummies. It's not a multivitamin, a greens, gummy or a prebiotic. It's all those things and then some at a fraction of the price. In Groons Daily Snack Pack you get more than 20 vitamins and minerals, 6 grams of prebiotic fiber and more than 60 ingredients. They include nutrient dense and whole foods, all of which help you out in different ways. And now Gruens has long launched a limited edition Gruni Smith Apple flavor for fall. You get the same full body benefits you know and love, but this time they taste like you're walking through an apple orchard. Stackable and packable and a flavor that tastes just like sweet tart green apple candy. On top of it all, Groons are vegan and free of nuts, dairy and gluten. Grab your limited edition Groonie Smith Apple Groons, available only through October. Stock up because they will sell out. Get up to 52% off. Use the Code Cara so there is also reckoning of sorts happening right now. Obviously the beauty industry is relatively saturated with brands and growth May be slowing. Some have folded. The former employer, Estee Lauder, as you noted, cut more than 3,000 jobs this year and says it close to 4,000 more. Other major cosmetic companies are making similarly big cuts. Talk a little bit about the beauty industry in a larger sense over the next five to 10 years, as you look at it.
Bobbi Brown
Well, first of all, I was really worried when we were gonna launch a new brand. Like, you know, am I a one hit wonder? Am I gonna fail at this? Yeah, I was worried about that, but didn't stop me from doing it. The industry has changed so much and there are, you know, so it's easy to start a brand. It's not difficult. There's so many ways to do it and people are doing it. Some are successful, some are not. You know, a lot are struggling, trying to figure it out. And being in business, it's not easy. And it's always problems. I don't care what business you're in. That's part of being in business. And you know, our success and our growth has been amazing. You know, at some point it was meteoric and it has slowed. So now we are like, you know, have had to work on. We're still growing. We're just not growing like we were in the first couple years. And so, you know, five years has turned it into a real business. But I'm, I'm not in a rush. I don't worry when things get a little slower because it's time to sit back and say, okay, what's working? What's not working? How could we do something a little better, differently? And it seems to be working again.
Kara Swisher
As you mentioned, the day your non compete ended, you launched your new makeup line, Jones road. It was October 2020, as you said, in the middle of the pandemic. And you did it without any outside investors. What was the thinking behind it at that moment and what were you trying to go for? You named it after a road in the Hamptons, is that correct?
Bobbi Brown
Yes. We needed, I mean, in order for me to launch it on the day I wanted to, I needed a name that weekend because no matter how many people we hired and friends that were helped, naming couldn't come up. I mean, Gloria Steinem was helping me name this company. We couldn't.
Kara Swisher
What's one of the names?
Bobbi Brown
Come up with a name. You know what, I don't remember her name. She had a whole bunch. But you know, one of these days I gotta go find it.
Kara Swisher
What one was the second to Jones Room?
Bobbi Brown
You know, just enough.
Kara Swisher
Oh no.
Bobbi Brown
But If I would have said Jones Road, you would have said no, too, because it doesn't make any sense. You know, my father said, oh, it's a terrible name. And now he loves the name, so you get used to it. It's like naming a kid.
Kara Swisher
Yeah, no, I named Pivot. I named Pivot. Everyone didn't like it, so.
Bobbi Brown
Oh, I love that name. How do you. You know, that's the best thing? So, you know, we really thought, you know, why not just do this? And I thought, well, I'm not done teaching. And I had something new to teach. I wanted to teach women and men, but mostly women, that you don't need all that stuff to learn.
Kara Swisher
Which you had done before, Correct?
Bobbi Brown
I had done before in the beginning, but by the time I left, we were teaching 10 step makeup routines and all. You know, of course, you need a starter and a finisher, and that's what. But the pressure to grow the company is new products that maybe are not necessary. So I wanted to kind of clean the slate, start all over again, and just, like, teach women how. All you need is the minimum. Of course, as we're growing, we're coming up with new, amazing products, but I'm teaching women you don't have to use them all. They're here if you need them for different things.
Kara Swisher
And that was the concept behind Joad's Road.
Bobbi Brown
It's. The concept is how you could look like yourself and how to have. I love a glow in the skin like my aesthetic. The models always have positivity coming out of their eyes. Then they have good skin. And they're not all models.
Kara Swisher
Right. So one of the other things you've done is target a certain area that others weren't targeting. A lot of things are targeted just to youth. For example, now Jones Rhodes does well with women over 50. Gen X elder Millennials. It's sort of at a forefront of this trend. There's been a big, obviously, awakening about perimenopause with women like Oprah, Pamela Anderson, and Julia Louis Dreyfus leaning into. But there aren't a lot of makeup companies actively targeting the demographic. Was it a conscious decision on your part to take advantage of the trend or just born out of your own experience?
Bobbi Brown
I mean, I think it was more born out of my own experience. At the beginning, I wanted to make sure that I had all skin colors covered. I wanted to have age covered. And I'll never forget, because I walked around the Hamptons looking for a woman. I had this vision, a woman of a certain age with, like, Grayish hair and no work done in her face. Not an easy thing. Not an easy thing. Especially in the Hamptons.
Kara Swisher
Yeah, I don't know why you thought you could find that there, but I did.
Bobbi Brown
I found her at a farm stand. She had this long gray hair, this beautiful face. She's a mother of five kids. She's got like, you know, a tattoo on her finger. Like, I also wanted to show interesting, cool looking people and honestly show the difference. This is no makeup. And look at, look at this. And it's not like a big makeover. Like you see all this makeup, they just look so much better. So it's, it started that way.
Kara Swisher
So what did you say to this woman at the farm stand?
Bobbi Brown
I said, could you take your mask off? And she looked at me and I said, I'm Bobby Brown. And I was still under a non compete, so I said, I'm Bobby Brown. And I said, I sometimes do shoots. Would you be interested in coming to model for me? And she said, well, people usually say something about my hair. And we tried it and I loved her. And then I brought her into our studio in New Jersey during the pandemic. We did our first big shoot and then she ended up getting Wilhelmina to represent her. So it was a big career change for her. She's not at the farm stand anymore.
Kara Swisher
But what you were, the idea was that you were going for different looks that weren't being. Because most of targeting is young people. Glossier kind of fell on that sword in a lot of ways.
Bobbi Brown
Right. I mean, I don't see age. I really don't. I see people wanting to look good and I know I'm of a certain age, but I know my daughter in laws who are in their, you know, early to mid-30s. They're also. That age group is also customer. I think that's. Is that an older millennial or a millennial? Yes, older millennial. Yeah. So, you know, and yes, I'm not targeting 18 year olds. And I think the book is going to reach a lot of women in there who are just entering the workforce and are trying to figure out their life and their work balance, which there isn't such a thing as, you know, but, but to me, any woman is a customer. And yes, the women my age really shops big in the beginning for sure.
Kara Swisher
We'll be back in a minute.
Bobbi Brown
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Kara Swisher
Mutine adjective used.
Bobbi Brown
To describe an individual whose spirit is.
Kara Swisher
Unyielding, unconstrained, one who navigates life on.
Bobbi Brown
Their own terms, effortlessly.
Kara Swisher
They do not always show up on time, but when they arrive you notice an individual confident in their contradictions. They know the rules but behave as.
Bobbi Brown
If they do not exist.
Kara Swisher
New Teen the new fragrance by Miu.
Bobbi Brown
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Kara Swisher
Now you're also great at social media, and your personal accounts have over 1.4 million followers on Instagram and TikTok. And you're on Substack and YouTube. And a few years ago you went viral when an influencer with millions of followers left a negative view on one of your foundation projects. She was using it wrong and you responded with your own video parroting her and quadrupled your sales. Talk about the creator economy. Built by makeup artists and beauty influencers. YouTube and social media have transformed cosmetics in a way that would have been impossible to predict when you were starting Bobbi Brown Cosmetics.
Bobbi Brown
Oh, I think it's so much fun. Like, this is not. I don't do this because it helps the brand. I know it does. Of course it does. I find it fascinating and interesting.
Kara Swisher
Tell me why.
Bobbi Brown
Because you get to connect with people that you wouldn't normally connect with. And I tend to make friends on Instagram. It's really I admire someone. I say something and they're like oh my God, I admire you back. And you just start this. Like I'm hop on the phone with someone and they can't believe they're talking to me. I can't believe I'm talking to them. And it wouldn't have happened. You know, I'm not gonna call and say do you wanna have lunch date? Like, I don't go out to coffee, I don't go out to tea. I don't meet people for drinks, but I could connect with people on my.
Kara Swisher
Social media and talk about it as a business plan. Because, like, there's all these new makeup brands. Right? Right. And they're mostly small. Let's be clear. Most of these things are pretty small. Talk a little bit about how it affects. Cause you have all the makeup influencers. You have people testing you yourself were answering questions from. From users constantly.
Bobbi Brown
Right. Well, it's.
Kara Swisher
It's.
Bobbi Brown
It's honestly everything. So you know right away, when people are struggling with one of your new products. You know, we first launched Miracle Balm, and people are like, there's no color.
Kara Swisher
Explain what Miracle Balm is for people. This is my wife's favorite thing you make.
Bobbi Brown
All right. Miracle Balm is one of the products that we launched with, and it's this little tub of makeup that is a skincare. It's color. It could either be a tint, it could be a blush. And this is so good for women of a certain age, because when you just look and you put makeup on and just something doesn't look good, and you don't know why, you're probably tired. But you take this Miracle Balm, and you have to dig your finger through the top of it, which we call break the seal. Then you put it on your fingers, put it on your skin, and all of a sudden, you look so much better. I put it on my neck, sometimes on my hands. Gets the flyaways. And it became one of our biggest products early on. So that's Miracle Balm. But I love.
Kara Swisher
Because some people like, for example, and you pushed up against love it like my wife.
Bobbi Brown
And other people do not hate it. Yeah, right, right. Other people hate it.
Kara Swisher
But I leaned into the hate too. Correct.
Bobbi Brown
Well, you know what? It's about being honest and communicative. So not everyone's gonna like this. If you have oily skin, it's not gonna be good for you. So then we came out with a face powder, and I said, all right, guys, if you have oily skin and wanna use Miracle Balm, after you do your foundation, put powder on. Then take Miracle Balm only on the tops of your cheek for a little highlighter. That's how you use it. So, you know, I use my education, my educational ability to teach women how to use the makeup. And Jones Road is made not for makeup artists. It's made for women to be able to do their makeup in a car, in a pinch, you know, whatever it is.
Kara Swisher
And when you think about at the power of social media in Terms of where cosmetics is, what's the game now online? From your perspective, what has changed?
Bobbi Brown
I mean, honestly, just realness. The game is realness. The game is how do you get people engaged? Right. It's not anymore the fabulous things. It's the real things, I think, that get people engaged. At least people that are gonna love Jones Road. Not everyone's gonna love Jones Road. I mean, you know, my aesthetic is my aesthetic and Jones Road really shows. But some people still like different kind.
Kara Swisher
Of makeup and how you can compete in sort of the celebrity driven culture, you know, of Rihanna, Kim Kardashian, whoever it happens to be, is selling makeup or et cetera.
Bobbi Brown
I don't try to compete. You can't. You can't. I cannot compete with a Rihanna or a Kardashian. I can't. Their audience, their platform is way different. And you know, Selena Gomez, she has a great brand. Like a lot of these, you know, successful celebrities have done it, but a lot of them have not done it, have tried and it hasn't worked.
Kara Swisher
Right, right. Who are you impressed with right now, especially online in the makeup game? Besides yourself?
Bobbi Brown
I don't know her, but Hailey Bieber has done a phenomenal job at Rhode.
Kara Swisher
Explain why.
Bobbi Brown
I don't know why. I think because she's so beautiful. Her products are very simple and she has a giant platform and, you know, she's got these beautiful big lips and when she goes and draws them in, you know, I can't stop staring at her. I know a lot of young girls are obsessed with her. Women my age are not looking at Hailey Bieber, but I think she's done a phenomenal job.
Kara Swisher
Of course, she's just sold part, you know, which is. How do you think that, what do you think of deals like that?
Bobbi Brown
I mean, I think it's, you know, good on her. I think it's, you know, I know from my experience it's not going to be all magic. It's going to be tough. I mean, I have so many friends that have started brands, you know, sunscreen brands and, you know, skincare brands, undergarment brands, and one by one, they sell it and it just doesn't work out.
Kara Swisher
Yeah, it often doesn't. It often doesn't.
Bobbi Brown
Yeah.
Kara Swisher
So Jones Road has a few physical stores, but sales are mostly online, correct?
Bobbi Brown
Yes, we're about 10 to 15% our stores. We have 12 stores right now, and we're opening them quicker than I'm comfortable with.
Kara Swisher
But why?
Bobbi Brown
I don't know. Because I like to nurture every little thing but now I have someone that people that will nurture those things. And my son, I don't know who raised this kid but he's like.
Kara Swisher
He'S quick, he's quick. But you mostly bet on direct to consumer and you avoid places like Sephora, Ulta and other big departments and departments.
Bobbi Brown
We have one retail account and that's Liberty in the uk.
Kara Swisher
And why is that? Why did you avoid the Sephoras and everything else?
Bobbi Brown
I've been there, done that.
Kara Swisher
Explain what that means.
Bobbi Brown
It means it's a whole different business model when you are in retail and there's deliverables and there is costs and fees that we don't have. Direct to consumer, we own our customer. When you're part of another retailer, they own the customer. So there's so many things and you know, you don't have to share the profit with people so we don't have to. I'm sure someday Jones Road will be maybe one day if and when it gets acquired it would be on the table for whoever bought us. But we're not even thinking about that right now.
Kara Swisher
Is that your goal to sell again?
Bobbi Brown
No, no, it is not my goal. But I know who, you know, I know who doesn't think about the possibilities, you know, and who would it be? And I know there's not a third makeup brand in me. So this is my love. And if we did sell it honestly, it would have to go to someone who's a really strategic partner and would understand and give me another 20 something years.
Kara Swisher
Right. You're also one of the things that's the through line in the book Away from Business. You're very candid in the ways you always felt insecure about your appearance. It's something a lot of women can relate to. But young people today have a lot to condemn with. There's pressure to look perfect from social media and celebrities like the Kardashians have ultra normalized plastic surgery. Dermatologists report they're seeing more teens and tweens using anti aging skin care projects like Retinol. There's also AI and Ozempic. As someone who's built a career around the natural look, who fought against pressure to create products like skin whiteners like we talked about, talk about these trends and talk a little bit about your own journey. Cause it's a through line in the book, right?
Bobbi Brown
Well, it's a through line in everything I do. You know, growing up in the suburbs in Chicago with my tall friends who, you know, a one, you're not a Barbie. I'm not. I'm five foot tall. I'm not a Barbie. And you know, well, you're Skipper.
Kara Swisher
You are Skipper.
Bobbi Brown
Okay, I could be Skipper. Or maybe, I don't know, maybe I'm Marianne. I don't know. But you know, I was always insecure about the way I looked. And now I look back and I'm like, I was so frigging cute in seventh grade. What was wrong with me? But you know, it's a typical thing that people go through. And I think it helped me understand what confidence is. And I've always been someone that teaches confidence, which to me is just people that are comfortable in their skin and who they are. That's confidence. It's really just being comfortable. But you know, a big moment for me growing up and I talk about her all the time was sing Love story with Allie McGraw. Because she was the first like brunette, beautiful, outdoorsy, natural looking girl. And you know, she was a big role model for me.
Kara Swisher
Beauty, beauty, role model. Because she was simple. Yeah. Cause she was natural, unusual looking. Not pretty. Well, she's beautiful but you know, a different kind of pretty. A different kind of pretty. So talk about young people today. Sort of how you look around at the way things are presented to young people. There is a lot of young people using these anti aging skin care products in a more intense and maybe desperate way. It feels like, I mean, I think.
Bobbi Brown
It'S pretty crazy, you know, what has happened in beauty society. You know, like try to find a young girl who has natural lips. It's really hard. Everyone thinks it's okay to get your lips done and it's not. And yes, young girls don't need retinol. I mean, I liked playing with my mother's makeup when I was a kid, but it wasn't my beauty routine. And it's unfortunate, but because of social media, it's so available to anyone. So I think it's tough. And you know, I'm just glad that I have three boys that I didn't have to raise a girl. Cause it would be tough.
Kara Swisher
Yeah, I have a daughter. Yeah, I have one daughter. I worry about it. But in terms of where it's going, who is leading beauty standards going forward, who do you think represents where it's going? Or is it just so dissipated like everything else? Like all media used to be. Glamour, Vogue, Cosmo. Right. Or four department stores. Now it's everywhere.
Bobbi Brown
Yeah, it's like a rain shower. It's really coming from everywhere. I try to be a voice. I've written two teenage beauty Books trying to help girls feel good about who they are and not comparing yourself. And again, both those books were written before social media. So, you know, I know another book is in me to write a young woman or a teenage book, but I think they're getting it from all different from their friends, but they're getting it from not the best places on social media. And I don't know how, you know, a mother or a parent is going to, you know, prevent that.
Kara Swisher
Yeah, but there is no Lauder. There's no. There doesn't seem to be anyone leading. Correct. From. From the old brands, certainly.
Bobbi Brown
No, I don't think so. There's. What was it like yeardley when I was a kid that was for young girls and I don't even remember what the other brands.
Kara Swisher
Clinique.
Bobbi Brown
Yeah, well, Clinique was not for young girls. It was for like college girls or going into the workforce. So there's a lot of teenage brands right now. There's a lot of brands that are marketing to seven year old girls. There was a skincare brand that was just had 80,000 fans show up at the Meadowlands from this one social media girl. 80,000. I saw the pictures. It's not even believable how mothers would take their 8 year old and 10 year old kids, 80,000 of them to show up to buy this skincare product.
Kara Swisher
How do you figure out what new products you should have? Obviously you're not gonna have 80,000 people in the Meadowlands would be my guess.
Bobbi Brown
Yes. Yeah, well, I listen to people. I mean, I listen both online and when I go into a store, what people are struggling with and what do they need? I never have a loss for ideas. I have a lot of products in the pipeline. You know, I see things out there and I'm like, oh my God, this color is amazing. But what if we did this? You know, being an entrepreneur, that's how I think about makeup. What if this was this and this had this. So, you know, I don't want to overload Jones Road assortment because I like to keep things simple. But I also love creating products. So, you know, we have a new lipstick. We just launched kind of a celebration Back to lipsticks. We launched a new lipstick. With the book, we launched a lipstick 12 colors and they're all like nude colors of the lips. So it was kind of a full circle moment for me. And we talk about how I even got these original lipsticks out in the marketplace. So, you know, you have to discontinue things. Like we had, you know, we had to discontinue a whole category of lipsticks because I don't want four of them, I want one or two of them.
Kara Swisher
Is there any product that you absolutely want to have for Jones Road?
Bobbi Brown
I'm very excited. We have two different, higher, fuller coverage concealers that work when you're really tired, that don't get in the lines. So that's kind of a lot of what I'm focusing on now is things that have a little bit more, a little bit more coverage, but they don't look bad, they actually look good. Because most things, most concealers, you go in a store, buy a concealer, you look terrible. Yeah, it doesn't look good. So I'm all about the feel and the texture.
Kara Swisher
Okay.
Bobbi Brown
And after all these years, I'm still excited about it. That's what's so weird.
Kara Swisher
Then you can stop when you're done being excited. So my last question, you obviously started a company from your house in suburban New Jersey. You scaled it, you sold it, left it, waited out, you're non compete, started a new company and found success again. It's hard to do it twice, that's for sure. For most people. I'd love you to give some people who are young entrepreneurs, or any entrepreneurs of any age actually, what you think the key lessons that you would impart to them are as an entrepreneur.
Bobbi Brown
First of all, to breathe. Like, no one tells entrepreneurs to breathe. You have to breathe.
Kara Swisher
No, you're supposed to hustle, my friend.
Bobbi Brown
No, you have to breathe. You have to breathe because everyone is such, I need a series A, I need a series B. I got no, calm down. You need to nurture this baby. You need to understand what your brand is. A, you need to understand what it means to work in an office, with people or out of your house. I tell many young entrepreneurs, go get a job. I don't care if it's for a year. Just understand what you don't want to do and how you don't want to do things. You will learn things, but also make sure whatever your brand is, that there's a reason for it. And you're not just doing it because you want a makeup line or you want a granola company. Look at what's out there and how is yours different? How are you going to differentiate it? And you know, you have to always.
Kara Swisher
Be thinking, what's the biggest mistake you think you've made?
Bobbi Brown
Not breathing. It's easy to give advice. You know, I definitely don't breathe. I don't calm down. Probably the biggest mistakes I've made are hires that I've done that are not good. Sometimes I worry that it's me and I try to do it, and then it's tough to fire people.
Kara Swisher
Yeah.
Bobbi Brown
It's not easy.
Kara Swisher
It's not. It's hard. It's very hard. Often people don't fire fast enough.
Bobbi Brown
Right. And by the way, most of those people that you want to fire, it's good for them to be fired because it's not the right fit.
Kara Swisher
When you say still Bobby, what does that mean?
Bobbi Brown
Well, the book is called Still Bobby. First of all, it was a very cathartic experience writing it, and I started understanding how and why and how I maneuvered through a lot of these things. But no matter what I did. And I've had some really cool, interesting, you know, I mean, I was in a motorcade. Who gets to go in a presidential motorcade? A makeup artist. Like, it's just weird. And I love that I was able to tell this story because when I left and I went home, I was still Bobby. I didn't come home. Like, you know, my husband would not allowed me to come home. You know, being. Aren't I great? And it's my comfort place, honestly, is still being Bobby. Being around people that I don't need to get my hair done or wear high shoes. That's kind of my comfort zone right now.
Kara Swisher
All right, Bobbi, thank you so much for your time.
Bobbi Brown
Thank you for having me.
Kara Swisher
Today's show was produced by Christian Castro with Kateri Yocum, Michelle Aloy, Megan Burney, and Kalyn Lynch. Nishat Kirwa is Vox Media's executive producer of podcasts. Special thanks to Katherine Barner. Our engineers are Fernando Arruda and Rick Kwan, and our theme music is by Trackademics. If you're already following the show, you're Skipper. If not, keep letting mama tell you what to do. You'll be unhappy. Go wherever you listen to podcasts, search for on with Kara Swisher and hit follow. Thanks for listening to on with Kara Swisher from Podium Media, New York Magazine, the Vox Media podcast network, and us. We'll be back on Thursday with more.
Bobbi Brown
Limu Game and Doug Limu. And I always tell you to customize your car insurance and save hundreds with Liberty Mutual, but now we want you to feel it. Cue the emu music.
Kara Swisher
Limu, save yourself money today. Increase your wealth. Customize and save. We save.
Bobbi Brown
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Kara Swisher
Insurance Company and Affiliates excludes Massachusetts.
Bobbi Brown
It's okay not to be perfect with finances. Experian is your big financial friend and here to help. Did you know you can get matched with credit cards on the app? Some cards are labeled no Ding Decline line, which means if you're not approved.
Kara Swisher
They won't hurt your credit scores.
Bobbi Brown
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Episode: Makeup Mogul Bobbi Brown on Reinventing Herself in Her 60s
Host: Kara Swisher (Vox Media)
Guest: Bobbi Brown
Date: October 6, 2025
This episode centers on Bobbi Brown, the trailblazing makeup artist and entrepreneur, who discusses her journey from launching Bobbi Brown Cosmetics to reinventing herself with a new beauty brand, Jones Road, in her late 60s. Kara Swisher explores Brown’s business philosophy, resilience after corporate setbacks, and her candid perspectives on the evolving beauty industry—including the impact of social media, inclusivity, and the modern challenges of beauty standards.
[03:30–06:02]
“You don’t need to hurt people’s feelings. You just don’t... I also didn’t want to come across like I was angry and bitter, because I’m not.”
— Bobbi Brown, [04:23]
[05:17–09:17]
“How do you grow and how do you learn to get better? You have to kind of go through that.”
— Bobbi Brown, [17:02]
[06:02–10:24]
“All of a sudden, these people started showing up and like, hi, I’m your new head of International... I wasn’t included in... running and growing the brand.”
— Bobbi Brown, [15:57]
[09:23–17:02]
“I used to go to work like it was my company. I never really separated myself... which was really difficult when I left.”
— Bobbi Brown, [11:29]
[18:40–22:46]
“I had so much support. Those were the glory years. And every time I see some of my lieutenants... we just talk about the magic that we had.”
— Bobbi Brown, [19:32]
[27:07–30:16, 35:07–42:15]
“The game is realness. The game is how do you get people engaged?... At least people that are going to love Jones Road.”
— Bobbi Brown, [38:42]
“Direct to consumer, we own our customer. When you’re part of another retailer, they own the customer.”
— Bobbi Brown, [41:41]
[30:31–33:29, 43:17–47:18]
“You know, growing up in the suburbs in Chicago with my tall friends... I was always insecure about the way I looked. And now I look back and I’m like, I was so frigging cute in seventh grade... But it helped me understand what confidence is.”
— Bobbi Brown, [43:32]
[47:18–49:03]
“Jones Road is made not for makeup artists. It’s made for women to be able to do their makeup in a car, in a pinch, whatever it is.”
— Bobbi Brown, [38:33]
[49:07–51:03]
“First of all, to breathe. Like, no one tells entrepreneurs to breathe... You need to nurture this baby... look at what’s out there and how is yours different?”
— Bobbi Brown, [49:36]
“Not breathing. It’s easy to give advice. You know, I definitely don’t breathe. I don’t calm down. Probably the biggest mistakes I’ve made are hires that I’ve done that are not good.”
— Bobbi Brown, [50:31]
On not writing a tell-all:
“I didn’t want to come across like I was anger and bitter because I’m not… I looked at it as failure. They canceled my work contract and to me that was being fired.”
— Bobbi Brown [04:23]
On rejecting industry pressure:
“Why do you need to tell someone that they have to change the shape of their face?... When most people do contour on themselves, it looks like they have dirt.”
— Bobbi Brown [14:04]
On losing her brand:
“…there was so many emotions. And yes, I definitely saw similarities with a lot of these women founders… It happens. Like, shit happens, and then it’s what you do with the shit that defines you.”
— Bobbi Brown [17:02]
On authenticity in social media:
“It’s not anymore the fabulous things. It’s the real things, I think, that get people engaged.”
— Bobbi Brown [38:42]
On the purpose behind Jones Road:
“I wanted to kind of clean the slate, start all over again, and just, like, teach women how. All you need is the minimum.”
— Bobbi Brown [29:39]
On advice to entrepreneurs:
“First of all, to breathe. Like, no one tells entrepreneurs to breathe. You have to breathe. Everyone is such, I need a series A, I need a series B… Calm down.”
— Bobbi Brown [49:36]
Bobbi Brown’s story is one of resilience, clarity of purpose, and staying true to one’s values through seismic shifts—both personal and societal. Brown’s candor and strategic thinking offer practical wisdom for entrepreneurs across industries, as does her insistence on authenticity, simplicity, and listening to consumers. The episode is a masterclass not just in business reinvention but in navigating power, ego, and change with grace.