On with Kara Swisher - Makeup Mogul Bobbi Brown on reinventing herself in her 60s

Episode Date: October 6, 2025

In the late 80s and early 90s, makeup artist Bobbi Brown made a name for herself by pioneering a more natural look long before it became the dominant trend. She eventually turned her side hustle selling lipstick out of her house in suburban New Jersey into a billion-dollar eponymous makeup brand that changed the beauty industry. But her unceremonious exit from parent company Esteé Lauder, with approximately four years left on a 25-year noncompete clause, stripped her of the company she had built over decades and sidelined her from the industry.  Now in her 60s, Brown has started over with a new makeup line called Jones Road, and she’s telling her story in a memoir, “Still Bobbi: A Master Class in Resilience and Reinvention.”  Kara and Brown talk about how she changed the makeup industry and founded a second successful company, plus where she sees the beauty industry headed in the era of influencers and social media.  Questions? Comments? Email us at [e-mail] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hey, is she here? I'm here. She is. Oh, there you are, Bobby. How you doing? Hi, everyone. Hi, everyone, from New York Magazine and the Vox Media Podcast Network. 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 look long before it became the dominant trend in makeup, and she eventually started selling her own line of lipstick from her house in Montclair, New Jersey. She then grew it into a billion-dollar global brand, Bobby 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 Bobby, a masterclass in

resilience and reinvention. I actually use Bobby Brown products because I'm kind of her target audience because 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 Bomb. I think that's her best-selling product and some others, because it's really simple and very easy to use. and not fancy. I'm more interested as an entrepreneur in how she built her business. I often focus on tech people or media people, but cosmetics is a really interesting industry because 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 Bobby 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 Bobby Brown. Stick around. Support for On with Carousisher comes from Sacks Fifth Avenue. Sacks makes easiest shop for your personal style. Falls here, so it's time to invest in new arrivals you want to wear again and again, like a relaxed Prada Blazer and Gucci Lovers, which you can take from work to the weekend.

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Learn more at amex.ca.ca slash Y-Amex. It is all. Bobby, thanks for coming on on. Well, thank you for having me on. 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 Stillbobby. It's your tenth, but your first memoir. And according to New Times' interview you did, this isn't a tell-all. And you say you were strategic with your words. 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 told here. 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. 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. Sure. 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-dispargement, 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. 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. 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 four 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 do you, what, I mean, honestly, what would you do if all of a sudden and you couldn't work. Would you play tennis? I don't know what I would do. Right, right. So 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, he's 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 and

leaving direct-to-consumer brands. YouTube and social media are the perfect vehicle for this kind of organic contact 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. Well, first of all, when I first started Bobby Brown Cosmetics in 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 signing 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. Oh. And so I, 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. Right. So you were taking advantage of the media of the day. the most popular. 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 and 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. Which you couldn't do for several years, correct? 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. And what was the methodology of once you sold to SD Lauder to sell? What

was happening there? It's amazing when I look back. We sold Bobby Brown Cosmetics to Estee Lauder after four and a half years. And, you know, I signed. After growing it by doing all of these. After growing it. Right. Yeah. No, but after having it for four and a half years, I stayed at SD Laudder 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. That's 22 years. So there was something corporate about you, obviously. No, no, look, I'm not someone that breaks 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 I can add, and they supported me until things changed, and there was different people, and the industry was changing, right?

It was contour pallets and all of these things, and here is a department store brand that couldn't get out of their own way, think the traditional companies really struggled for a while. Talk about the department store brand. Explain that for people who don't know. You know, a lot of people are in department stores. A lot of cosmetics companies are in department stores because that's where people shop. And that's where they shop for makeup or that's where they shopped. And that's how SD Lauder. That's, that is definitely

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 DDC. You know, even if I want something from a department store, I go D to C. So you, when you sold to S.E. 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, right? 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. Well, we also had a buy-out, by the way. So, I mean, you know, there was a lot of reason for me to say 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 brand, which was really difficult. difficult when I left. Right. So 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? Well, we sold because, first of all, it was Leonard Lauder who made the contact. And, you know, 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 made, 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 a really not easy relationships. 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 um you know he also promised that i'd have total autonomy and it works really well when i had this autonomy when i didn't have it anymore it didn't work very well what changed the people or the well people started to change and then little things happen i mean look i i 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 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 skews, 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 pallets because I don't believe in contour, and I wouldn't do it. I didn't care. What do you have against contour?

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 about my nose.

You know, I don't understand why people need to turn themselves into something that they're not. 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 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? No, I won't do it. Talk about this, how you resist that. And you can't. Most people don't, correct? Right. Well, I resist it because it just doesn't make any sense. I'm very easy going 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 got to 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 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.

And you said too many times you had to do that, presumably. Is that what, is something, did something send you over the end? Was it contour pallets? No, it would, 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

going to 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. Right. Now, you're one of the number, 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, Betsy Johnson, and makeup there's Tony Coe, who founded NYX. Talk about this. Did you see yourself in context of these other women? And what are the parallels and differences? Well, I think it's very, very similar. And honestly, when I left, I thought, well, I'm done. You know, I'm done. No one's going to 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 things started to change. And I, you know, 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, you know, 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, you know, 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 Aboud who lost

control of his brand in 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, it's what you do with the shit that defines it. 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. Okay, that's okay. What else am I going to do? Right. So in every episode, this sort of dovetails that question. We get a question from an outside expert. Let's hear yours. Hi, I'm Lauren Sherman, fashion correspondent at Puck. Hi, Bobby. Congrats on the book. It's been a long time coming. My question for you is, you know, 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. I mean, you sold in the 90s, 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 Shuggets, and it's not an easy business, even when it was doing well.

You know, it's a family-run company. There was a lot of succession drama with the family versus outside executives, that sort of thing. What made you stick around? Because you could have gotten out of it somehow. Maybe your non-compete was complicated, but you stayed. And I'm just curious, were there certain people in that company that made it worthwhile? Was it the infrastructure? 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. lie 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 work together, you know, in PR, in 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 Dallas 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 going to fix it. I don't think even you could fix this. Right. Right. And that's when I realized. But the truth is, when I went in for the final meeting, I really thought they were

going to 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. 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 going to get to what you're doing now in a second,

you talk about a conversation you have with Leonard Lauder, who 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 in the brand and I wasn't able to do that. Talk about that and what was your response? Well, we had this three, almost three hour lunch. It was supposed to be an hour. We stayed for three hours. It was 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, 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. Yeah. What did you say to him? I said, Leonard, I wouldn't have changed the 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 mess. So it would have been a very different thing now. 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? Could you? And, you know, the aunt, I'm sure I could. Do I want to? It's a different story. We'll be back in a minute. Support for the show comes from Indeed. At your company, you're a 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

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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 Grooons. 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 Grooen's daily snack pack, you get more than 20 vitamins and minerals, six grams of prebiotic fiber, and more than 60 ingredients. They include nutrient

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relatively saturated with brands and growth may be slowing. Some, have folded. The former employee, 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 in the beauty industry in a larger sense over the next five to 10 years as you look at it. Well, first of all, I was really worried when we were going to launch a new brand. Like, you know, am I a one-hit wonder? Am I going to fail at this? Yeah, I was worried about that, but I 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 a work on, we're still growing. We're just not growing like we were in the first couple of years. And so, you know, five years has turned it into a real business. But I'm not in a rush. I'm not, 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, you know, it seems to be working again. 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?

Yes, we needed it, 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 come up with the name. You know what? I don't remember her names. She had a whole bunch, but, you know, one of these days I got to go find it.

What one was the second to Jones Road? You know, just enough. Oh, no. But if I would have said Jones Road, you would have said no, too. 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. Yeah, no, I named Pivot. I named Pivot. Everyone didn't like it. 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 look good. Which you had done before, correct? 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. That's what 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.

I mean, you don't have to use them all. They're here if you need them for different things. And that was the concept behind Jones Road. 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.

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 Roads 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 Dreyfuss leaning into it. But there aren't a lot of makeup company actively targeting the demographic. Was it a conscious decision on your part to take advantage of the trend, or it's just borne out of your own experience? 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. I don't know why you thought you could find that there. But I did. 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. I also wanted to show interesting, cool-looking people. And honestly, show the difference. This is no makeup. And 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 started that way. So what did you say to this woman at the farm stand? I said, could you take your mask off? And she looked at me. And I said, I'm Bobby Brown. And I was, you know, 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 Willamina to represent her.

So it was a big career change for her. She's not at the farm standing. But 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. 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? 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 to me, any woman is a customer. And yes, the women, my age, really shopped big in the beginning, for sure. We'll be back in a minute. Hey, listeners. I want to tell you about a new podcast from a box media podcast network called Access with Alex Heath and Ellis Hamburger. It's a show about the inside conversation happening across the tech industry. You may know Alex Heath from shows like Decoder and The Vergecast, and he's a founder of sources, a new publication about the tech industry and a contributing writer for The Verge. And you'll probably only know Ellis if you worked in Silicon Valley yourself. He's the former tech reporter turned tech industry insider working closely with today's hottest startups. Their first episode features an interview with, Mark Zuckerberg about Meta's latest smart glasses, the AI race, and what's next for the social media giant. You can find the Access podcast with Alex Heath and Ellis Hamburger on YouTube or wherever

you listen to podcasts. The smart home has been a good idea for decades, just that you can control your windows and your doors and your floors and your appliances and everything and just have everything. work together. It's a good idea. It's just never been possible. But now, this week, we got some new gadgets and some new software from both Amazon and Google that suggest that if we're not getting there, we're at least getting close. This week on the Vergecast, we talk about all of that, plus what it's like to have a TV that won't stop showing you ads. All that on the Vergecast, wherever you get podcasts.

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 others left a negative view on one of your foundation projects, she was using it wrong and you responded with your own video parodering her and quadrupled your sales. Talk about the creator economy built by makeup artists and beauty influencers, YouTube and social media transform cosmetics in a way that would have been impossible predict when you were starting Bobby Brown cosmetics. 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. Tell me why. 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. They're like, oh, my God, I admire you back. And you just start this, like, I'm up, 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 going to call and say, do you want to 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 social media. Talk about it as a business plan. Because, like, there's all these new makeup brands, right? And they're closely small.

Let's be clear. Most of these things are pretty small. Talk a little bit about how it affects, because you have all the makeup influencers, you have people testing. You yourself were answering questions from users constantly. Right. Well, 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. Explain what Miracle Bomb is for people. This is my wife's favorite thing you make. All right. Miracle Balm is one of the products that we launched with, and it's this little

tub of makeup that is a skin care, its color, it could either be a tinge. It could be a blush. And this is so good for women of a certain age because when you just look dry 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 Bomb. So some people, like, for example, and you pushed up against people, love it, like my wife, and other people do not. Hate it. Yeah.

Right, right. Other people hate it. You kind of leaned into the hate, too, correct? Well, you know what? It's about being honest and communicative. So not everyone's going to like this. If you have oily skin, it's not going to 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 want to 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 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. And when you think about the power of social media in terms of where cosmetics is, what's the game now online from your perspective? What has changed?

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 they get people engaged. At least people that are going to love Jones Road. Not everyone's going to love Jones Road. I mean, you know, my aesthetic is my aesthetic, and Jones Road really shows that. But some people still like different kind of makeup. And how do you then compete in sort of the celebrity-driven culture, you know, Rihanna, Kim Cardass, whoever it happens to be is selling makeup or et cetera? 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. 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. Right, right.

Who are you impressed with right now, especially online in the makeup game besides yourself? I don't know her, but Haley Bieber has done a phenomenal job at Road. Explain why. 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 Haley Bieber. But I think she's done a phenomenal job. Of course, she's just sold part, you know, which is, how do you think that? What do you think of deals like that? 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.

Right. It's going to be tough. I mean, I have so many friends that have started brands, you know, sunscreen brands and, you know, skin care brands, undergarment brands. And one by one, they sell it and it just doesn't work out. Yeah, it often doesn't. Yeah. So Jones Road has a few physical stores, but sales are mostly online, correct?

Yes. We're about 10 to 15 percent are our stores. We have 12 stores. right now, and we're opening them quicker than I'm comfortable with. Why? I don't know, because my, you know, I just, I like to nurture every little thing, but now I have someone that, you know, people that will nurture those things. And, you know, my, my son, I don't know who raised this kid, but he's like, you know, he's, he's quick. He's quick. So what, but you mostly bet on direct-to-consumer, and you avoid places like Sephora, Alta, and other big department stores.

We have one retail account, and that's Liberty in the UK. And why is that? Why did you avoid the Sephora's and everything else? I've been there, done that. Explain what that means. 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 in 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. Is that your goal to sell again? 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, you know, I, I know, 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. Right. You're also one of the things that's the through

line 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. Dermatologist report there's seeing more teens and tweens using anti-aging skin care projects like Latinol. There's also AI and Ozzympic. As someone who's built a career around the natural look, who fought against pressure

to create products like skin whitensers like we talked about, talk about these trends and talk a little bit about your own journey because it's a through line in the book. Right. Well, it's a through line in everything I do, you know, growing up in, you know, the suburbs in Chicago with my tall friends who, you know, a world on a student. I'm not. I'm five foot tall.

I'm not a Barbie. And, you know, you're a skipper. You are skipper. 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 seeing 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, beauty role model.

because she was simple, yeah, because 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 what's, 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 product in a more intense and maybe desperate way, it feels like. I mean, I think 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 because it would be tough. 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. It used to be glamour-vo, Cosmo, right? Or four department stores. Now, it's everywhere. 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.

is going to, you know, prevent that. Yeah, but there is no lotter. There's no, there doesn't seem to be anyone leading, correct, from the old brands, certainly? No, I don't think so. There's, what was it, like, Yardley when I was a kid that was for young girls. And I don't even remember what the other brands. Clinique. Yeah.

Well, Clinique was not for young girls. It was for, like, college, college girls or, you know, going into the workforce. So I, you know, 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 like social media girl. 80,000. Like I saw the pictures. It's not even believable how mothers would take their, you know, eight-year-old and 10-year-old kids 80,000 of them to show up to buy this skincare product. How do you figure out what new products you should have? Obviously, you're not going to have 80,000 people in the metal lands would be my guess.

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? 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 lipstick? 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 a, 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. Is there any product that you absolutely want to have for Jones Road? 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 back. They actually look good because most things, most concealers, you go in a store by a

concealer, you look terrible. Yeah. It doesn't look good. So I'm all about the feel and the texture. Okay. And after all these years, I'm still excited about it. That's what's so weird. Well, then you could 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 that you sold it, left it, weighed it out, your 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 in part to them are as an entrepreneur?

First of all, to breathe, like no one tells entrepreneurs to breathe. No, you're supposed to hustle, my friend. No, you have to breathe. Like, 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 have to always be thinking. What's the biggest mistake you think you've made? 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. It's not easy. It's hard. It's very hard. Often people don't fire fast enough. 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. When you say still bobby, what does that mean? Well, the book is called Still Bobby. First of all, it's 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 I, when I was. left and I went home, I was still Bobby. I didn't come home like, you know, my husband would not have allowed me to come home, you know, being our, 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. All right, Bobby, thank you so much for your time. Thank you for having me. Today's show was produced by Christian Castro Roussel, Kateri Yocum, Michelle Alloy, Megan Bernie, and Kaelin Lynch.

Nishot Kirwa is Vox Media's executive producer of podcasts. Special thanks to Catherine Barner. Our engineers are Fernando Aruda and Rick Kwan, and our theme music is by Tracademics. 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 podcast, search for On with Kara Swisher, and hit follow. 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.