In short
Bobbi Brown discusses selling her namesake beauty brand to Estée Lauder, being fired after 22 years, and relaunching in her early 60s with Jones Road using a small, product-first approach and heavy direct-to-consumer feedback (including TikTok).
Guest background
Bobbi Brown is a beauty mogul and founder of Bobbi Brown Cosmetics (sold to Estée Lauder in 1995). She stayed at Estée Lauder for 22 years under a 25-year non-compete, then was removed from day-to-day control. She later launched Jones Road around age 62–63 and built it into a highly profitable, privately funded brand.
Key claims
She regrets nothing about the original deal; the firing was emotionally hard but ultimately a “clean slate.” She believes confidence comes from being comfortable in your skin, and leadership requires surrounding yourself with people who tell you what you don’t know. Jones Road succeeded by focusing on the product, launching with limited SKUs, and using real-time customer feedback.
Notable examples
Her “break the seal” campaign for Miracle Balm; her engraved “non-compete expiry” charm; being told to accept a new role after being fired; launching Jones Road with a website and TikTok rather than big events; launching a foundation called WTF (“What the foundation?”).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOEarly Ambitions and Career Beginnings
0:51 to 2:06
Bobbi shares her early entrepreneurial experiences and her family's influence.
“I feel like this has just been a really long time coming.”
Redefining Ambition at 68
2:06 to 3:27
Bobbi discusses her perspective on ambition and age, emphasizing her continuous drive.
“I think that you were 63 when you launched Jones Road.”
Launching Jones Road: A New Chapter
3:27 to 4:50
Bobbi describes her decision to launch Jones Road and her thoughts on starting over.
“I don't think of myself of a woman of a certain age.”
The Transition from Bobby Brown Cosmetics
4:50 to 6:20
Bobbi reflects on selling her brand and the impact of the non-compete agreement.
“So tell me, why would you go again in your early 60s?”
The Emotional Toll of Being Fired
6:20 to 7:40
Bobbi recounts the moment she was fired and the emotions that followed.
“I loved reading your story, where you came from.”
Understanding Success and Regrets
7:40 to 9:00
Bobbi shares her views on success, regrets, and the journey of her career.
“We would go back and forth to New York events and happy to come home to our home in New Jersey.”
The Journey Beyond Bobby Brown
9:00 to 12:00
Bobbi discusses the lessons learned from her experiences post-Bobby Brown.
“Can you just take me in that room and explain to me what that felt like?”
Reflections on Brand Legacy
14:02 to 15:01
Bobbi shares her mixed feelings about her past brand experience and personal growth.
“All of a sudden I had nothing except my own brain.”
The Impact of Selling a Brand
15:01 to 15:54
Discussing the complexities of selling a brand and the emotional detachment required.
“badly handled, but it's like, you did have this incredible thing and you built this amazing brand.”
The Birth of Jones Road
15:54 to 16:47
Bobbi explains the journey of launching her new brand, Jones Road.
“First of all, if I didn't get fired, I'd still be there miserable.”
Show all 35 chapters
Transition from Corporate to Independent
16:47 to 17:46
Exploring the differences between her previous corporate role and independent entrepreneurship.
“They went in different directions and that's, and honestly, it's fine.”
Navigating Non-Compete Challenges
17:46 to 19:09
Bobbi discusses the challenges faced during her non-compete period and her transition back to beauty.
“But honestly, I just, I don't need to say something not nice about anyone.”
Creating New Beauty Products
19:09 to 20:28
Bobbi shares insights on developing her Miracle Balm and the product creation process.
“with these 24 year old kids and they looked at me like, you know, I'm like, okay, I'm not going to go back to be a makeup artist at 60.”
Understanding Customer Needs
20:28 to 22:40
The importance of customer feedback and data in shaping beauty products.
“actually made you better or better prepared for the moment that you found yourself in when you launched Jones Road.”
Embracing Social Media
22:40 to 24:07
Bobbi discusses her approach to social media and engaging with customers on platforms like TikTok.
“was there any trepidation about you going on social in that way?”
Launching with Simplicity
24:07 to 25:48
Bobbi explains her strategy of starting small and focusing on product quality.
“Because when you've come from the safety of this kind of like giant company, right?”
Lessons Learned in Entrepreneurship
25:48 to 27:08
Bobbi reflects on the key lessons from her journey in building successful brands.
“You didn't hire like, you know, a big fancy schmancy CEO.”
Building a Supportive Team
28:00 to 29:39
Learn about the importance of surrounding yourself with honest, supportive people in business.
“He's the chairman of the board, but he's always been there next to me.”
Lessons from Corporate Experience
29:40 to 30:58
Discover what Bobby Brown learned from her corporate days that shaped her current business approach.
“And I would like figure out how things looked on different people.”
Embracing Change in Business
30:59 to 31:51
Understand the dynamics of adapting to market needs while managing a growing business.
“I mean, our first year, I was hoping to do a million dollars.”
Bobby's Vision for Jones Road
33:26 to 35:14
Explore Bobby Brown's vision for her beauty brand and her approach to product creation.
“So tell me, when you think about this brand, what did you want?”
The Importance of Authenticity
35:15 to 37:15
Discuss how staying true to oneself can drive confidence and success in business.
“It doesn't make me, it doesn't like scare me.”
Learning through Experience
37:16 to 39:20
Understand how personal experiences shape leadership and business growth.
“I tried to be other people and it did not work.”
Navigating Leadership Challenges
39:21 to 42:00
Gain insights into the challenges of leadership and the importance of team dynamics.
“Because this is one of my big things that I think plagues specifically women, that if we don't feel like we have all of the answers, we don't feel like we belong.”
The Evolution of Leadership Style
42:00 to 43:31
Bobby discusses her ongoing journey to develop her leadership style in the face of changing business dynamics.
“Creating the conditions for everybody to feed.”
Building Jones Road: The Family Dynamic
43:31 to 45:09
Bobby shares insights on building her company, Jones Road, and the unique challenges and benefits of involving family.
“But the building just makes me want to cry.”
Navigating Work and Motherhood
45:09 to 47:16
Bobby reflects on balancing motherhood with her career and the strategies she used to manage both successfully.
“Two couples in I mean, listen, I work with my husband, so I understand that dynamic, which is also a really complex one.”
Creative Solutions to Parenting Challenges
47:16 to 49:23
Bobby discusses her creative approaches to parenting and how she managed her children's needs while pursuing her career.
“You know, it's amazing that I didn't have a playbook when I had these kids.”
Decisions, Sacrifices, and Career Balancing
49:23 to 51:48
Bobby elaborates on her decision-making process regarding career sacrifices and the importance of prioritizing family commitments.
“And he just, you know, he took the kids.”
Staying Grounded Amidst Success
51:48 to 54:08
Bobby shares how she has remained grounded and true to herself despite her success and recognition in the beauty industry.
“You had a way that you wanted to raise your kids and be around as a mom.”
Resilience vs. Reinvention
54:08 to 54:38
Bobby emphasizes the importance of resilience over reinvention in her life and career journey.
“I wonder which of the two has served you more, resilience or reinvention.”
Legacy and Future Aspirations
54:38 to 56:01
Bobby reflects on her legacy in empowering people and remains open to future opportunities without defined goals.
“realize, what am I wasting this energy for?”
Legacy and Aspirations
56:01 to 57:30
Bobbi Brown discusses her legacy and current aspirations, emphasizing self-acceptance and open-mindedness towards new opportunities.
“women feel good about who they are and in their skin and, and men too, you know, it's not just women.”
Pride and Self-Reflection
57:31 to 58:58
Exploring the importance of pride in one’s achievements and how Bobbi exceeded her childhood dreams.
“I mean, I, I thought I was going to be a teacher and, you know, be a suburban mom, which I am both of those things, but I never thought I would be any of the other things.”
Life Lessons and Inspirations
58:59 to 1:00:28
Bobbi shares pivotal life lessons and the importance of resilience, illustrated by a powerful book that impacted her life.
“But I still do it, but I probably shouldn't.”
Transcript
Automatic transcript. May contain errors.0:09So today I'm interviewing beauty mogul Bobbi Brown and she has such a story to tell. This is a woman that sold her brand to Estee Lauder, worked there for 22 years before she was unceremoniously fired. She's then launched again in her 60s, another brand which let me tell you is about to have a billion dollar exit, even if she says that's not what she's looking for. There is so much to learn from this woman. You are going to love the honesty. You're going to love the wisdom that she brings. But most of all, you are literally going to get a masterclass in how to launch a brand with real meaning.
0:46You're going to love this episode. I promise you. The Start With Yourself tour kicks off on April 15th in New York City. Tickets are on sale now at emagree.com.
1:00Bobby Brown, welcome to Aspire. Oh, I am so happy to be here. I am so happy to have you. I feel like this has just been a really long time coming. Yes, we've been courting a long time. Actually, you walked out of an elevator at some Forbes or Fortune thing where we both got awards and I was trying so hard to get your attention. You were just so busy. I was just like, let's go, let's get in and get out. Well, I honestly, I'm so excited to speak to you because when I think about the arc of a career, someone who has been successful, like you are just, I mean, first of all, you're the pinnacle. And I really want to make sure that we can have a brilliant and honest conversation today, because I really feel like you have lived it in so many ways.
1:43And what's so extraordinary about you is obviously you built Bobby Brown into a billion dollar brand. Not by myself, but yes. Not by yourself. I love that you say that, but you did. I mean, it's your namesake brand, right? It was a billion dollar brand. You sold it to Estee Lauder, 25 years in a non-compete. And on the day that your non-compete expires, you launch Jones Road. Yes. Congratulations, by the way. Thank you. I think that you were 63 when you launched Jones Road. 62, 63. 62, 63, which is the age that most people are thinking about retiring, but you've called it a new beginning. And so I wanted to start there because I wonder so much, and it's something I think about all the time, like where my ambition starts and where it ends.
2:25Have you always been ambitious? I don't know if I've always been ambitious. I mean, I was the kid that had the lemonade stand. I sold jewelry in my basement when I was a kid. So I've always been like that. And I come from a family of entrepreneurs. My Papa Sam, who came from another country and then built up a car dealership, I saw the way he worked. And, you know, I wasn't great in school, so I wasn't interested in normal things like being an accountant or, you know, money manager. And I just found what my passion was and I followed it. I mean, I'm going to label you ambitious because I feel like it's something that specifically for women, there can often be negative connotations.
3:04And I wonder if being called and labeled ambitious at the age of 68, which you are now, is the same way. And does it show up the same way from 28 to when you're 68? Well, the truth of the matter is I don't see age. I really don't see age. There's some very young people that are super smart and accomplished. And there's some older people that are not. So I don't see age. I don't think of myself of a woman of a certain age. I don't think of myself as a female founder. I'm a founder and I am a woman and I have figured things out. I'm also a wife, a mother and a grandmother. And it's like how I'm figuring out how to do it all at the same time.
3:45Still figuring it out. I feel like so many people look at your journey now, the fact that you have had this second coming and they really think of it as so inspiring. I know I certainly do, but is there something that is almost condescending in that, given that you're having all of this success, you've clearly engineered it that way. Is it the same as a young founder being called smart and inspiring, or are you just doing what you're doing? I just do what I do and I don't think about it a lot. And I don't even read the articles that are written about me or my journey. None of them? Some of them I do when they're really, really good because, you know, it's been how many years?
4:20There's so many of them. So when someone says, well, that was good, you should listen to it. And then I do. But, you know, I'm always on to the next thing. I just have so many things I'm interested in. I'm incredibly curious and I'm not afraid. So I guess, you know, you put the two things together. Well, that's the big one. I mean, curiosity and a lack of fear, that'll really, that'll really get you somewhere. So what was it all about launching Jones Road? Because at the end of the day, you don't need the money and you certainly don't need the accolades. You're not proving yourself. So tell me, why would you go again in your early 60s?
4:56Well, when I left Bobby Brown Cosmetics, I was 59 years old. My kids were out of the house and I either quit or got fired. It's all in the memoir. I got fired, which is a good thing. And I didn't know what I was going to do. It was the first time in so many years when we sold Bobby Brown cosmetics to Estee Lauder, my husband and I were 35 years old, had two kids. Now we have three. We didn't know anything. And when they asked us to sign a 25 year non-compete, I was like, I'm not going to work in my sixties. I mean, come on. Well, guess what? I didn't know what I was going to do. And I thought I'm done.
5:34I'm done with makeup. I'm done with beauty. I did that. And I started doing a lot of different things. We built a hotel together, my husband and I, a wellness brand, a line of glasses. Like I just kept doing things. And then I just didn't feel done. I just didn't feel done. And more important, I had an idea. I had an idea. I mean, I had an opportunity to go in and fix a very large brand, which was Avon. And luckily it didn't work out because I would have been miserable, right? I cannot, I cannot work in corporate anymore. No. And I also don't see you as like, because you so go against the grain in everything that you're doing.
6:11That feels really different from who you are. Except what excited me is to go in and shake it all up. Like I love the stories of the women because everyone has stories. I loved reading your story, where you came from. You just kind of put the pieces together and the Avon ladies have a lot of stories. And I thought that would have been - Well, the Avon ladies, they were the original. You know, I mean, probably the first entrepreneurs, legally working entrepreneurs that I knew. Yeah, no, it's true. Because everyone had an Avon lady in their street. But you didn't choose to do that. You chose to start again and go on your own.
6:41So just to contextualize this for people, in 1995, you sold Bobby Brown to estate audit. You were 37. You signed a 25-year non-compete at that time because you're like, I definitely don't want to work in my 60s. what would you tell yourself now if you could go back about what you were actually signing away? I would do things exactly the same way. I really, I don't have any regrets. And by the way, I stayed with Estee Lauder 22 years. How many people sell a business and stay? I mean, not for 22 years. 22 years. It's a long time. So it was great until it wasn't. But then when I was finally had a, you know, a clean slate, I had a piece of paper.
7:23I'm like, well, I don't know. So what did you think about the deal when you were signing it? Did you just look at the money and the opportunity and say, this is Estee Lauder and there's 70 odd million dollars here. And those two things make sense. What was it? And, you know, one of the reasons that we wanted to sell the company is, you know, we had two kids, my husband and I had a, you know, lived in the suburbs. We had this great life. We would go back and forth to New York events and happy to come home to our home in New Jersey. And we just wanted like to, to continue having this great life while growing the business.
7:54We didn't know how to grow a business back then. I mean, being at Estee Lauder for 22 years is quite an education. I learned so much you can't even imagine. So you don't have any regrets. I don't. I don't have any regrets. But you were fired and there was a moment where obviously it stopped being fun. You stopped learning and there must have been something where you were like, I've got to get out of here. Well, the two years before were pretty miserable. Up until then, you know, there's, look, nothing's easy. Business isn't easy. Relationships aren't easy. When Leonard Lauder was in charge, I always had him.
8:28I could always just call Leonard and he would say, okay, we'll figure this out. We got it. So he was really my mentor. And that stopped happening. And it stopped happening. And you know, the most important thing to understand, things change. Even the way things are now are going to be totally different in six or eight months. You have to be able to kind of go with the flow. And I like change. I I think it's exciting. There's a part in your memoir, which I kind of remember reading. You said that you were called upstairs and unceremoniously just told you were no longer in charge of the brand that you built.
9:02Can you just take me in that room and explain to me what that felt like? Sure. So I had just gotten back from the UK celebrating 25 years of Bobby Brown. timing. Right. And came back and I thought I was called to the principal's office to say, we found a couple of candidates that's going to help you lead the brand because we didn't have anyone. And we went to search and I never heard anything. So you were the acting CEO? Well, no, I've never been a CEO in my life, but no, there was someone that was there who was in between. He ran the business, but he wanted to leave as soon as we found someone.
9:41And I went up there, I thought they were going to hand me all these beautiful, you know, resumes and basically sit down. And I said, what's going on here? And she said, we are canceling your work contract. And I said, you're firing me. She said, no, we're not firing you. We have a new offer for you. And she handed it to me. And I said, I'm not opening it. She goes, you have to. I said, no, I don't. You're firing me. And I walked out. When I walked into that elevator and press the button. It was the 42nd floor. I've never felt so much relief because all the things I was angsty and worried about, because I felt the brand falling apart for different reasons, went away until I got to the bottom.
10:24And I was like, uh-oh, now what? Uh-oh, what just happened? And my first two thoughts were my driver, Fred's going to be out of a job because I'm too cheap to pay. And the second thing was, he was part of your package. Yeah. And the second thing was, oh my God, what am I going to give to all the girls for Halloween? Cause I always had thousands of girls come to my house for lip gloss. So those are my two first worries. And then I called my husband and he came in and he said, I'm so glad I've been waiting a long time to get you back. I don't know if I want to knock on your door at Halloween, if I need to go and get your husband out and have the separate conversation with him, or I need to understand what was in the envelope.
11:06Did you open the envelope? My husband opened the envelope and the offer was for the same or more money that I would be on call and I'd be the face of the brand, but not in the day-to-day. The face. And everybody tried the face and everyone tried to talk me into taking this large amount of money. And I just wouldn't. I just wouldn't. Can I ask you a bit about the money? Because of course you got a bunch of money when you first sold the brand, right? When you were in your thirties. I think it's like 70-ish million. Then I'm assuming you would have had a contract that kept you in that brand for the next 22 years.
11:43We had a percentage buyout. You had a percentage buyout. So you sold the majority or you sold everything? We sold everything. You sold the lot. So your compensation annually was linked to how well the business was doing. Well, there was a salary and plus. And plus. Okay, so that kept you there for the 22 years. No, that didn't keep me there for the 22 years. What kept me there was I loved what I did. And it was my brand, even though it wasn't. Even though it wasn't. And the deal that they offered you on what essentially became your exit was not something that you wanted to do. That wasn't the company you wanted to be part of.
12:20Not even like a nanosecond. And when they told my husband, we would like Bobby to be available, but if the teams call her and ask her what she thinks of a certain launch, she can't tell them she doesn't like it. So, you know, so it was rough. It was emotionally hard. And I had to work really hard at my self-esteem, you know, cause you feel like a failure. I don't care who you are. You feel like a failure. You're embarrassed. And you know, I didn't know what I was going to do. And it wasn't about the money. It was just like, who was I? This was, you know, this business was older than my oldest son.
12:55Wow. And you were embarrassed. I was embarrassed. sure. And I, and I was triggered every time I saw the logo. Oh, I was triggered. Because that's, this is what people don't really understand. You know, you owned that company. That was your logo. That was your graphic designer friends that made that logo that belonged to you before you sold the business, the brand and all that that is to Estee Lauder. So there is an emotional process. Did you, did you have to grieve? Was there like a grieving process? I did. My friends came over for two, like literally the first two days, we drank a bunch of tequila and I cried and they listened.
13:33And then I just started making phone calls and going out and I didn't have a car in my driveway. Like I had to take an Uber. Fred was gone. Fred was gone. And, you know, I think I tried to take the train once and I said, forget that. Like, I really wanted to be normal again. Like, I can't describe it. I wanted to be normal. I felt like I was on a treadmill for 20 something years. I knew exactly what I was doing every day for six months, eight months. I knew where I was traveling. I knew that hundreds of people, makeup artists were coming in. I knew all that. All of a sudden I had nothing except my own brain.
14:06Did you feel like you had got what you deserved from that brand? Yes. A hundred percent. A hundred percent. Well, that's wonderful. I got so much from it. Honestly, my experiences, everyone likes to talk about the last couple of years because they like, you know, there's not really dirt. It's just the truth. But for most of it was magic. I mean, it was magic. Leonard Lauder used to invite us to all of his events. We'd sit at his table and sit with, you know, Elizabeth Hurley and Hugh Grant and Helen Gurley Brown. It was just, it was unbelievable. Glory days of New York and that, you know, that company.
14:41And I actually love that you say that because I think that sometimes, you know, it's a bit like a relationship, like the end goes bad and you can think of it like a failure, but you had all of these like amazing years and arguably built something and did something that you needed in order for. So it's like a double-edged sword. And I get that the end was unceremoniously and badly handled, but it's like, you did have this incredible thing and you built this amazing brand. And I was so lucky that I got to see Leonard before he passed away. Oh, I'm happy about that. So we had a, we had a three hour lunch and you know, it was the most incredible conversation.
15:17and I'm just really, really lucky that I got to do that. I mean, it's interesting how you speak about that time because I certainly know a lot of people that have sold their companies and could never get on the side of the decision that they make. There was a piece of them that they never really sold it, right? Like they never sold it in their heart. They took the money, but they believed that the brand was still there. Oh, I thought it was still mine. You did? Sure. And were you in a position, like were you calling the shots for the majority of that 22 years? Talk to me about what that relationship really looked like.
15:48For the majority of the time I was in charge, you know, until it became definitely more corporate and there was a new leader and things just were not about supporting individual brands and founders. And, you know, that's what they wanted. And that's fine. First of all, if I didn't get fired, I'd still be there miserable. So it's really good that it happened. And, you know, it wasn't easy. I didn't just walk out and say, oh, I'm going to start another brand. You know, I had a literally emotionally detach. Detach. It was hard. It was really hard. So what does it feel like now when you see your name on those products like everywhere?
16:30I don't have an affinity at all. It's not the brand it was. It's not what I would have wanted to make it into when I was leaving. Before I left, I wanted to turn it into something, which kind of is Jones Road. I kind of wanted to just turn it clean and be a little cooler and, you know, less makeup and, you know, didn't happen. They went in different directions and that's, and honestly, it's fine. I don't spend a lot of time talking about the brand. You know, I don't wish any ill on them. It is what it is. And I'm, you know, mostly so, so elated and excited that I have Jones Road, which is my passion project.
17:09But you don't regret having sold your name. I don't, I don't. Wherever I go in the world, you walk into the best places, right? The best beauty halls, the best department stores. You will see a Bobby Brown counter. There must be something that that trick, I mean, it's your name. I kind of go the other way. I don't like to deal with it. I mean, it was a time and it was an amazing time. My memories and my posse and the people I met, you know, we still talk to each other. Like, do you remember? You know, it's not the same. You know, people send me things like, you know, like, have you seen this? But honestly, I just, I don't need to say something not nice about anyone.
17:53Fair. I mean, because you've well and truly moved on. I did. I really did. Congratulations for that, because I think it is such a difficult thing to do. Success, baby. When you have success, it's easy to move on. Well, here's, that's the thing. Success will figure out all your problems, right? If you had a little fledgling brand that none of us cared about, that might be a little bit different, but you don't, you have Jones Road. And that's what I want to talk to you about. So you had this charm necklace that was engraved with the date of your, that your non-compete expired. It's an ampersand, which means and, and I put the day the non-compete was up because four and a half years to someone that has no patience and gets bored really easily.
18:33I get bored constantly, which makes no sense because I'm so busy. But I waited four and a half years and I did a whole bunch of projects in between and then just started questioning what the clean makeup market was. So tell me when did the thinking start in terms of, because you're doing all of these other projects that are outside the beauty space. When did you make that decision? I'm going back into beauty. I realized I missed it. Like one day I put together a portfolio. This is what a, you know, a nerd I am. I put a portfolio together and called agents in New York. And no one, and I went in and I walked into these offices with these 24 year old kids and they looked at me like, you know, I'm like, okay, I'm not going to go back to be a makeup artist at 60.
19:17It's not going to happen. You really did that? 100%. Shut up, you did that. I did with my jeans and my sneakers. No way. Why wouldn't you just call all your famous mates and be like, I want to start doing your makeup? I just, I wanted to, I just kind of wanted. She's humble. I am, I'm humble and I'm not. So I did it and, you know, it was not a, didn't feel right. So then I came home and started thinking and I'm like, I really miss makeup. I miss beauty. I have a photo and a TV studio in my town that my husband built. And so I just started doing shoots. And then I met someone who I thought we could like make a couple products together.
19:54And I just wanted to see what was possible. and we played around in the lab and we came up with this crazy little balm, which is called Miracle Balm. And it is a miracle. I'm telling you that I am addicted to that stuff. Like you just gave me a lovely bag and I went through it all, even though I own like maybe 20 of those around the place. I was like, is there a Miracle Balm in there? I want to understand a bit more about your mindset as you were in this non-compete, because I think you said you were frustrated during the non-compete, But frustration and readiness are two totally different things.
20:28And I wonder if the wait actually made you better or better prepared for the moment that you found yourself in when you launched Jones Road. I'm someone, if someone says it can't be done, I say, yeah, right. And I figure it out. So I knew I couldn't launch anything. So I'm like, all right, I'm just going to make a really good brown eyeshadow or pencil and I'm going to sell it on Etsy and no one's going to know. Okay. That didn't happen. And then I got the name nameless. I said, why don't I launch a brand and let no one know what's behind it? I got the name, but my husband is like, that's ridiculous.
21:04He stopped me. And then, you know, he said, just wait, just wait, just wait. He's an attorney also developed a real estate developer. Literally just wait. And he's a developer. So, you know, he likes doing new things, but he's very sensible. And so I, um, said, okay, I'm going to wait. And then I had this idea and did the math, figured out, you know, what I would need to get it done. And we launched with a few products. I mean, this is what I love about you because you started Bobby Brown in the good old days with a lipstick, Bergdorf Goodman, makeup counters. And then you started Jones Road with a website and a TikTok account.
21:44And it's just like the two things are just so far away from each other. What does each approach really tell you or teach you about where the customer is at? And what have you learned about the customer that you couldn't have understood like almost the first time around? Well, it's amazing because I used to sit in meetings and my, you know, marketing people would come to me with consumer insight. Right. And I was like, right. And who are these people sitting in a room getting paid$10, you know, to tell you what they like or don't like. But with the internet, you could just write on ask and you know everything.
22:20When we launched Miracle Balm, people were saying, oh, there's not a lot of color payoff. And I realized you have to break the seal. So we did a whole campaign, hashtag break the seal. You push your finger through and people were putting their palms through. And we had to say, no, no, no, just your fingers. And so I have instant feedback. I love data, but I also have this creative brain that I like putting the two things together. I know what women want. was there any trepidation about you going on social in that way? Like I have still not found my feet in TikTok and I'm 43. You were doing this at 63.
22:56So like what, what was in you that just was like, I'm going to go on and sit there and start because you went against the grain. You actually didn't join in with what was happening in the beauty and the makeup space. You were like, I'm going to be Bobby. You like did the same thing that you did back in the eighties because everyone was doing full face, like big Mac, crazy, like, you know, fully glammed, fully contoured faces. And you were like, I'm going to do an actual nude lip. I'm going to work with the face that's there. What you don't know about me is when I sit in a room and all these brilliant people tell me what they think, I just get so bored and my eyes glass over.
23:33But then I think about, oh, we should just do this. Like, that's how I operate. So even, you know, yes. Oh my God, How are we going to do a TikTok? We have to get, you know, an agency of this. I'm like, no. My son took a phone. He said, here, mom, go. I said, hi, it's Bobby. I'm new here. What do you want? I, you know, I'm not the TikTok person. Who's watching and what do you want to know from me? And people went bananas. Oh my God, I feel, you know, so tired. How do I not look tired? They just went crazy asking me questions. Like, I like people and I like communicating with people, whether it's my Substack, my ShopMy I just started.
24:07I'm like, I just lean in. And when I get bored, I stop doing it. And was there any fear at all? Because when you've come from the safety of this kind of like giant company, right? Estee Lauder, you've got all the kind of protection, the good, the bad, the ugly, but you have this sort of moat and this competitive moat. Was there anything that for you, you felt, I'm really vulnerable. I'm like me, I'm out on my own. I'm in this big new world of like social media. Was there no fear that crept into you? Well, right before we pressed the button and launched Jones Road, I had this weird feeling. I'm like, uh-oh, what if I'm a one-hit wonder?
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24:47Uh-oh. But it was too late. I was about to press the button for it to go live. So I get really excited. I get overexcited on things where I'm like, oh my God, this would be so great. Why don't I do this? And I do a lot of it. And so I never think about, uh-oh, what if it doesn't work? I don't think about it. No, I didn't think about it. And, you know, what if people think, you know, I'm a one hit wonder. What if there's no payoff? And you know what? I liked it. I liked the logo. I thought it was cool. I liked all these things. So you were really betting on yourself. My gut, myself. No, myself, by the way, means my team.
25:23So I've written 10 books. I don't know how to type. All right. So I have figured out how to get things done. I am now all into Claude. And I'm like trying to figure out how to get photos. So I just call my assistant and say, here, there's 12 photos. can you please put them and make this deck so I could explain to the marketing team what I really want to do here. And you kept the brand really simple, right? Because you launched with such a limited number of SKUs. You didn't launch with investors. You didn't go out and raise capital. You didn't hire like, you know, a big fancy schmancy CEO. You didn't go for a flashy announcement.
25:53Why did you start small? Because it just makes sense. And it's easier. It's digestible. I think a lot of people want to start when they don't know what they're doing. And they just, they don't, they just, they mess up so much. They, they invest too much money. They raise too much money. They don't know what they're doing and they don't even know what the most important thing is. You know what the most important thing in a makeup company? It's so simple. Is it the makeup? The product. Yes. But people forget about the product. It's not the packaging. It's not the market. It's the product. If people like the stuff, it doesn't matter if it's in a Ziploc bag or a fancy jar.
26:30I think that what's happened and largely owing to social media is that people think the marketing is the thing. They think the social, they think the influence strategy, the launch event is the thing. And I'm like, guys, that's not the thing. Like figure out, like make a product that people absolutely love. That solves your problems. And you can figure it all out afterwards. I mean, you know, our foundation that we launched, which I never could have launched this foundation at a big company. It's called WTF. What the foundation? Because when I was putting it on my face, I'm like, oh my God, I look like I'm not wearing anything.
27:04So WTF. I mean, that makes total sense. No, you could never have launched. Certainly not a border. Never. And all, you know, people said, okay. And that was how we, that's how we decided. There were no teams, you know. So, so tell me, what are the biggest lessons? Like when you look at what you had done, what you built over there with your team and what you've got now, what, like, as you kind of take a seat back, like, what do you say to yourself? because I think that what my audience has, right, is they've got dreams and hopes and ambitions, and they want to do their own version of what it is that you do.
27:38And so I'd love to know having the benefit of hindsight, because nobody's built$2 billion brands like this. What would you say to them that the big lessons are? Breathe, go slow, be thoughtful, and surround yourself with the right people, which is the hardest thing, for example. So, you know, I made sure that I always had my partner next to me, which is my husband, you know, not an involved person. He's the chairman of the board, but he's always been there next to me. And he's the one that says, so that's part of my posse. And then I always need someone to help fix my, you know, digitals and my, you know, my, my, uh, all the things that we're working on.
28:19The things you don't know. The things I don't know, you know, and then you need people around you that believe in you and that aren't afraid to tell you what they think. Like, I don't want people to say, oh yes, Bobby. No, I want people to say, I don't know. Are you sure people really need one more? Because I have so many ideas for products, but I need someone to say, okay, we can have five different things that does the same thing on your face. And who do you count on for that? Like, what does it look like? It's your husband. What type of people have you surrounded yourself with? Right now it's a lot of it is our son, who's a CEO, his wife, who's the head of brand.
28:52Oh, wow. This is a family business. It didn't set out to be. It's just the way it is. You know, I mean, I have people around me, my makeup, first of all, my makeup artists and all the Jones Road stores. I mean, they're number one. I go right to them and say, what do you think? And I have women of different ages, different skin colors. So I know like we have a new concealer that's coming out next year. It's not even named. it is like night and day, how not to look tired. But I, you know, there's 30 colors. They've got to be the right colors. So I'm using all the different people in my, you know, in my network.
29:25By the way, when I started the first line, you know who my people were? Nannies. I would go to the park with my kids and the nannies would be from all over the world. So I'd say, can you try this lipstick? Oh, you have, you know, your, your skin's dark, but your lips are pink. Well, you have dark lips. And I would like figure out how things looked on different people. That's why one lipstick never looks the same on any two people. It's so true. So when you were at Lauder, of course, when you're going through a product cycle, you've got layers of people, you have consultants and you've got months of planning.
29:57And obviously at Jones Road, I'm assuming it's very, very different. It is. I read that you're launching 14 products this year. We made a mistake. We really made a mistake. I feel so sorry for my team. I just, I feel sorry for my team just getting all the things. It's not, it's easy for me. So what did the old corporate processes perhaps teach you and what were they just in the way of? Right. Well, that's a really good question because I learned so much being there, but the most important thing I learned is what is not important to do. Like we launched Jones Road. We didn't have a big party. We didn't have little bags with, you know, ribbons on them.
30:32We didn't have a fabulous dinner where people walked in and twirled. We didn't do that. We just got the product to all the editors, to my FOBs, my friends of Bobby. And we just started the process of people, oh my God, I love this. Can I have more for my sister? Can I have another one? And then we knew we had something and we weren't in a rush. We didn't have anyone breathing on our necks to say, we need these numbers. But guess what? Everything blew up. I mean, our first year, I was hoping to do a million dollars. We did 18 our first year. We doubled that the next year and the next year and the next year.
31:09So crazy. And right now things are not doubling and it's okay. Right. I know, I know enough that in with five years, now I've got to look at everything. We are all looking at everything. Okay. What's working? What's not working. It's fun. It's like kind of rebuilding, you know, while you're building, I'm not afraid of it. You're not afraid of it? No. You know what I am afraid of? Tell me. Not having something fun to do. That's the only thing, you know, the only thing that I ever think about. Like, what would I do if I didn't do this? I don't know. I'd have to think of something else. I mean, I'm pretty sure at your rate, you would think of something else.
31:44Yeah, but I happen to love what I'm doing now.
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33:06So before we wrap, a quick reminder that Start With Yourself is available for pre-order and tickets for the live shows are available now. Starting April 15th, we're coming to New York, Los Angeles, San Francisco, Chicago, D.C., Boston, Atlanta, and London. Visit emagreed.com for tickets and full tour details. I cannot wait. So tell me, when you think about this brand, what did you want? Like what was in your mind that you were like, okay, what itch did you have left to scratch in the beauty world? I wanted to teach women that you could wake up, you know, after yoga and put on your hair in a ponytail, put a really nice sweater on, whether it's the row or whether it's, you know, you in a glow, doesn't matter.
33:52And you could put your makeup on. So you just look pulled together and feel good. So you can go on with your day. Like that's how I live my life. I want things simple. I don't like complicated. And what about your business aspiration? You must have had something in your mind that you saw. I still have it in me. And I believe that I can create better products. I really just, I mean, honestly, forget everything I am. I am, I am someone, I'm a makeup artist and I understand how makeup should and could look on the skin. Like that's to me is the ultimate of who I am. All these other, you know, creative things that are involved in business things.
34:33I, you know, I'm involved in both and I'm good at both, but I'm really good at formula. And you didn't think I am Bobby Brown who does billion dollar brands and I'm going to do another one. No, that's not who I am. Really? I don't think that way. And as a matter of fact, I said, I think to Financial Times that no, I do not want to build another billion dollar brand. Well, what are you going to do? You're going to have to close it. And a few of my finance friends said, don't ever say that again. And yes, we are. We're on our way. I mean, you really are. There is no arguing that. The math is what it is.
35:07You're going to build your second billion dollar beauty brand. Possibly. And by the way, along the way, everyone and their uncle is launching brands. And I'm like, that's okay. It doesn't make me, it doesn't like scare me. And yes, there's room for everyone. You know, Jones Road is my aesthetic. It's the way I think people look good, but other people have different aesthetics. Well, I love that you talk about aesthetic because I think for me, you know, before it was ever cool, before anyone was talking about embracing your skin and clean beauty and skin first, like that was always your aesthetic.
35:41That was your vibe. That's how you did makeup. You owned that. So where did that belief come from? Where did that intuition come from? It didn't come from anything inside. I just thought people looked better, right? I just thought people looked better. I remember, you know, we were shooting a big campaign for the old brand and this girl had all this makeup on and we were shooting it. You know, you had to do it for the lighting and to sell all the products. And then after the shoot, she washed her face, put her hair in her ponytail, came back and said, goodbye, thank you. And I I said, oh my God, sit down.
36:11And we shot her after she washed her face that she could be in a Jones Road ad today. She looks so much better. You're like anti-makeup. Yes, kind of, kind of. I mean, I buy all this makeup on Instagram that looks so interesting. I get it. I'm like, it doesn't feel good. It looks terrible on my skin. So, you know, but again, that's just my aesthetic in my opinion. It's so interesting. I drink my own Kool-Aid. What can I say? I think what's really interesting is that you've clearly had a point of view your whole career. And that doesn't seem to have veered off. And while you and your style and your aesthetic really hasn't changed, but all the business mechanics and the way you bring it to customers and the way you've packaged it and the way you deliver it from a marketing point of view, all of that has shifted.
36:56But the core of what you do is the same. I am the same person. I was. My principles are the same. I'm the same person I was in middle school that I am today. I'm more confident. Do you know why? Because I figured out what confidence is. What is it? It just means you're comfortable in your skin with who you are. Because then you could walk in a room and be yourself. It's the only thing that works. I tried to be other people and it did not work. So why do you think so many of us struggle with confidence? You've been surrounded by women. Women are your customers. What have you seen? And why do you think that's such a huge struggle still now?
37:34Well, I think we're all human. And, you know, I don't, I've never seen a little teeny finger full of you not being completely confident and comfortable in your skin. And I'm sure you are because you are human. I am. Right? No. But I mean, you know, I've worked with some of the most successful women and, you know, politicians and movie stars and everyone has that. And, you know, what you bring to a room when you walk in, you don't just get there, right? We have to wake up in the morning and who knows if we slept or didn't sleep. Our kids, a fight with our husband, you know, we're going through something.
38:09We're menopause. Like there's, we just had a baby, divorce. We're human. So it's like, what do you do with that? I understand that. And makeup is a way to kind of put it all together so you do feel your best self and you can walk in the room and be your best. Could you have done Jones Road and have the success that you're having with it now had you not had the Lauder experience? Absolutely not. I learned so much. I really, I learned. So I had a CFO who's still one of my dearest friends who would come into my office and I'd say, that was a good launch. We sold all this. And he'd say, well, actually we did.
38:42But look at what happened to our regular business. It went down and now we have three or four million dollars we have to make up. And I'm like, what does that mean? And David would say, you know, one of your bronzers at the time sold for a million dollars. He said, we need to make up three or four million dollars. I said, then I'll give you four new colors of bronzers. We have the packaging. We could turnkey it. And we did it. But that's how I learned. Because you had somebody in the business explaining what was happening. Because not all launches are created equal and success isn't always success.
39:13If it's eaten in another part of the business. And by the way, I don't feel bad that I don't know things. I just like to ask questions so I can understand it. Bobby, say more about that. Yeah. Because this is one of my big things that I think plagues specifically women, that if we don't feel like we have all of the answers, we don't feel like we belong. So just talk to me about that. I still don't know what an EBIT is. I know we have a good one. I was going to say, you're good, girl. I know. And if my son was here, he'd roll his eyes and say, I've told you, mom, 10 times. It's the something before.
39:43I don't know. It means we're doing really well. And I ask all the time. So a lot of women are afraid to speak up. I mean, I have a dear friend who's a CMO of a giant bank and she got this job and she didn't know anything about money and finance. And she had to say, could you explain this to me? And they did. And she says, I never felt bad not knowing it. I feel better. To me, the truth is everything. So I feel better saying, you know, tell me because I don't know this. Explain to me. And learning. And there's no shame in that. There's a lot of different attributes to leadership and to being able to build something, but nobody has everything.
40:27Like I am yet to meet a founder, somebody that started a business, a leader in a business that knows every single little piece of it. You've got to surround yourself with great people and you've got to know what you don't know. And you've got to get rid of the people that aren't great because sometimes you think they're great and it doesn't work out and you try to try to try. And, you know, someone told me this, if you wake up in the morning annoyed by someone every single day, you got to get rid of them. Right. You know, like your, your problems. Was that hard for you to, uh, to learn? Yes. Really hard.
41:02Especially if I really like someone. How long would you let them annoy you for? Well, when you were part of a corporation, and you had to write them up 32 times and turn around in that circle and do that and give them feedback. So that took a long time, but there were other people to do it. But were you decisive in making a decision that this is somebody that needs to exit the business or was that hard for you? In the beginning, it was hard. And now? And I blamed myself sometimes. Well, arguably, sometimes we're to blame. Right, yeah, right. I blame myself that I wasn't letting them do their job.
41:33And I realized I didn't like the job, what they were doing. They just weren't right. What type of leader are you? You should ask that to my team. I think I'm a very open leader. I'm definitely working on my skills, not just telling everyone what I think. I'm trying to get people to tell me what they think first. How do you do that? I've been scolded by my son many times because my natural reaction is say, oh, I can't stand all those things. Why don't you do that and do this? But that's not a team. Creating the conditions for everybody to feed. Yeah, right. But I also love - But it is your style.
42:09It is my style. So I'm, you know, I'm never too old to work on my personality. You're still working on it? Oh, 100%. You're still learning to be the type of leader you want to be? Yes. And it's hard now because I'm not physically in the office as much as I used to be. So Jones Road, this incredible company that you have now built, it's privately funded. It's very clearly profitable. Yes. I'm going to say approaching a billion dollar valuation because I've done the math and I'm like, it definitely is. If you thought about selling again and if somebody offered you, what would you say? It depends who it is.
42:48I would like, I mean, look, I want to still do it. I want to still be there. I want someone that would see my value. And then I, you know, then I'd be open to something, but I haven't met the person or the company yet. I mean, you can imagine we get a lot of calls. You know, we're not even in retail yet. We're in one retail store. That's why you're getting so many calls. You've got all the upside. No, I mean, seriously, we're opening freestanding stores. We have 12. We're opening another 12 to 15. Our D2C business is still growing. We're in one retail store, Liberty, because I have to be in London.
43:23Beautiful store. Yeah, it is. I mean, yeah, there's no... First of all, I love that beauty hall that they created there because it's just the most unexpected and it's heaven. But the building just makes me want to cry. I know, it's beautiful. It's the most beautiful. I walked in that store and I said to my team, I said, I want to be number one. We are. You're number one in Liberty? Yeah, we're number, well, in beauty, not in the whole store. Wow. That's, I mean, that's impressive. There are some, again, really big brands in that department. Yeah. Good for you. Yeah. So obviously you're building with no outside investors and that gives you an element of freedom, but it also costs you.
43:58And I wonder what it's cost you. What does it cost? Well, I always think about it as, first of all, I mean, it's on your shoulders, right? So it's like, there's the financial cost, there's the implications of the pressure from the outside. You've also got this family dynamic that's in there. Does that weigh anything on you? Well, I mean, it's not all upside, trust me. I mean, that's why they call it work. You know, just like raising kids, you know, trust me, it's not all upside. Kids go through things and, you know, but as far as the business, you know, having your family involved is amazing. There's a trust there.
44:28There's things that you could say to them and they could say to you that no one else says. It's amazing that you have this family dynamic. What was that decision like to put your son in as CEO? It wasn't a decision. That's what's so weird about it. it was, he started helping us because he was brilliant at digital marketing and growth. And it, and then he became the marketing and then he became the CMO. We had other COOs, we had other people and one by one, my son knew more simpler how to do things. So he became the CEO and you know, his wife is the head of brand. So that's a little complicated.
45:09Two couples in I mean, listen, I work with my husband, so I understand that dynamic, which is also a really complex one. You obviously have, you know, worked with your husband for a very long time. I mean, he even negotiated your deal and your non-compete with Lourdes back in the day. So why did you want to get back into business with him? And how have you managed to, like, weave even more family members in? When it comes to Stephen, we just were partners on everything. You know, his buildings, you know, he's like, what do you think about this tile? for what he's doing. So we're very, we're best friends.
45:45We're partners on everything. How long have you been together? We've been married 38 years. And we got engaged in three months. So it's been a long time. And we're both each other's biggest supporters. And he's rightly tough on me. He is. I don't know if I'm as tough on him. If he was sitting here, he might say, yes, I'm equally tough. Tell me about how is he tough on you? I always think that my husband's pretty tough on me when it comes to that. Well, if he ever walks in a room and hears me talking, he'll, you know, he'll make a comment about, why did you say it like that? How, you know, so I have to deal with that because we both work at home.
46:24Are you each other's critics? Yes. I think I'm less critical of him, but he's also the biggest supporter I have. I wouldn't have started the brand if it wasn't for him. He's like, come on, we could do this. We could do this. Here's a, you know, he gave me an office. It was a closet, my first office. It was a closet. It's still a space. But still, it was a space. It was a space. It was a signal that he believed in you. You could do it again. And he gave me the first Jones Road store. He had a building in our town. He said, I've got a perfect place for Jones Road. And, you know, it was a little small, but then he doubled it the next year because it grew so much.
46:58So he could say the writing was on the wall. He's practical. I need someone practical around me because, you know, sometimes I'm not so practical. Fair. Given the benefit of hindsight now, Now your kids are much older and obviously one of them involved in the business. What can you tell me about motherhood? Ready for the exhale. Yeah. And working how you did. Right. You know, it's amazing that I didn't have a playbook when I had these kids. People were not starting businesses with kids. And, you know, I commuted. I lived in the suburbs and I would come home and I would, you know, put my scrungie on and my clogs and go to the afterschool sports.
47:38I was at every single thing that mattered to me because you know what? I knew my happiness was not being, you know, a working woman, but was being like an involved mom. I just luckily had this passion, which was work. So I've been able to figure out how to do both. I'm very scrappy. I'm pretty organized. and I'm really good at figuring things out. Like I figured out I was going to buy birthday presents every single weekend for these parties and wrapping them. And finally I said, this is dumb. And my answer - I bulk buy them. What did you do? Please tell me. I went to the local bookstore and I bought five, this was back in the day, five and$10 gift certificates, you know, a couple hundred dollars worth of them, kept them in the drawer, you know, to Timmy, happy birthday, love Cody.
48:26Damn right. Right? Yeah, I have a toy shop in my house. I have Legos because Legos don't, you know, it's like it doesn't matter if it's for a girl or boy. Everyone loves a set of Lego. And then I have some gift vouchers and it's like depending on the person. But then you've got to be real close to me. No, I have a nanny. Oh, you do? 100%. Because who has the time? I've got four kids. It's like two birthday parties a week. I'm like, we don't have the time. And I never go. I never go to the birthday parties. Did you go to the birthday parties? What a woman you are. No, because I wanted to see the other moms.
48:56You did? I did. Well, first of all, What else was I going to do on a Saturday or a Sunday morning? Really? Yeah. You didn't want to work out or paint your nails? I worked out and I'm, you know, I always, I had babysitters. So tell me what that looks like, because I feel like, and I've read so much about you, Bobby, like you really had it figured out. So what, what gives? No, I was figuring it out. I didn't have it figured out. I was always figuring it out. You know, I used to hire teachers from my kid's school to be an afterschool nanny. you know, so they could play sports. I had a Manny for a while.
49:32I had three sons. I hired a Manny. So smart. He was so great. And he just, you know, he took the kids. He, I think he coached one of their, I think the third one's, you know, baseball team and he was in school to be a teacher. So he helped with the homework. I couldn't help my kids with the homework. So you didn't do that. Like, I want to know. I did not. I did not do that because I couldn't. How did you make the decisions of like what you would do and what you would have to sacrifice. Well, doctor's appointment, I wanted to go. You know, I wanted to go to all the school sing-alongs. I was the class mom, at least for one of the kids every single year.
50:08I wanted to go on the field trips. You're making me bad. No, but I chose that. You're making me feel, I want to know the trade-offs. I want to know what stuff. Well, because it means... How could you, you are Bobby Bloody Brown with your name everywhere, Estee Lauder. Surely they were like, you got to come to work, Bobby, like there's stuff to be done. You know what? I figured out certain things. Like I figured out I could do my job better if I work from home on a Monday or a Friday. And I just started doing it. No one stopped me. And then they would, you know, then I figured out on Wednesdays, I'd have all the creative people come out to New Jersey and, you know, meet with me and we got a lot done.
50:43And my Tuesdays and Thursdays were bump, bump, bump, back to back. You were organized, yeah? Yeah, yeah. But never really organized. I just kind of figured it out. And I would call from the car and, okay, I didn't have chefs. I didn't have those kind of people around me. I would go to Whole Foods. I would buy a cooked chicken. I would shred it as soon as I got home, put it in a glass thing. I would make pasta. My Italian friends hate when I say this. I would make pasta, drain it, put it in a glass container. I would do one thing of vegetables. and I would just literally start, when I come home, I can make dinner in 15 minutes.
51:19Just put it all in a pot, you know, smear it together and I fed everyone dinner. You found your way. I found my way. You found your shortcuts. You know, I always look for shortcuts. You know, like what makes sense? I talk about that in my book all the time. I can't wait for your book. Making shortcuts and accepting help and accepting the trade-offs and I feel like it's so important because none of us can do everything. You can't. And you got to, like for you, you had a set of principles. You had a way that you wanted to raise your kids and be around as a mom. Arguably, your deal with Lourdes allowed you to do that and enabled you, I should say.
51:57It enabled you to do it. But it's really impressive. And I let a lot of the working women on my like small team come in late because their kids had a doctor's appointment or it was, you know, teachers. Before that was acceptable in corporate. Trust me, I would have gotten in big trouble. Would have gotten in big trouble. What has stayed, you know, because I, again, just kind of looking at your career and reading your memoir, it's called Still Bobby. Still Bobby. Still Bobby. After the sale, after the non-complete, after losing your name, after rebuilding. I wonder what stayed the same about you that you're the most proud of.
52:33Everything stayed the same about me, who I am as a person. Like who I care about. You know, I'm from Chicago. I'm from a very good family. We're very close. I still pick up the phone and call my 95-year-old Aunt Alice, my cousin Barbara, my friend that went through some back surgery. I made sure on the way over I called her. Like those things, once I do those real-life things, I made sure I connected with the people just so I feel like my feet are on the ground and everything's fine. That's always been important to me. I mean, look, I've been in a motorcade at one of the presidential elections, two motorcades.
53:13I've been in the White House. I've, you know, just like you, I'm with people. I have dinner at Mick Jagger's house. I do all these cool, amazing things, but I still go home. And I still am exactly who I am. I'm still Bobby. How have you kept grounded? Because my comfort place is to be there. I'm someone that loves the word comfortable. I love to be comfortable. And I find that if I'm myself, I'm much more comfortable than if I am trying to be someone else. I tried. I did my high heels and my shoulder pads and I'd walk into places and I'd be like, oh, when do I get these shoes off? You know, this coat is so uncomfortable.
53:51Like, I just like being comfortable and being myself. You're you. I am me. You're literally still Bobby. I am still. See, that's why I called it Still Bobby. It's a great name. Yeah. It's a great name. I was looking at the book's subtitle. It's a masterclass in resilience and reinvention. Two of my favorite words, Bobby. I wonder which of the two has served you more, resilience or reinvention. You know, I think resilience. I think resilience is important because it's so easy for you to choose a different path because something happened to you. And, you know, it's kind of what you do with that information.
54:25So I think that's, I mean, because I didn't really reinvent myself. I was kind of the same, but I'm just, I'm very resilient. I'm like, all right, that didn't work. You know, even when I have a fight with someone, you know, you feel bad for a second, but then I realize, what am I wasting this energy for? What am I wasting angst and anger on people that don't matter? Like that's, there is some good things about getting older. I will tell you that. And that is one of them. That was going to be my question because I was going to ask, were you always like that? I mean, I think I've always been like that, but I've always, you know, been able to run home to my husband or my best girlfriends and say, do you believe, you know.
55:03So, you know, I look, I, I, I'm angsty. There's, I'm not just all smooth. Like I come across, I'm angsty and I just have learned what to do with angst. So unbelievable. I mean, I think you're so wonderful. It's no, you really are because it's so seldom that you meet someone and they're exactly what you thought they were. Like you are exactly what I thought you were. like a really down to earth, normal woman. Like no bullshit. Maybe that's not good. I don't know. I think it is really good. Like to me, I think it's really, really good. Do you ever think about your legacy? Like, do you think about yourself, maybe the way other people see you and like what that projection of you might be?
55:52Like, you know, that you're this like beauty mogul. Well, I know my legacy because people have told me and people have asked me forever and ever and ever on it. And so my legacy is that, you know, is I'm proud of what I think it is, you know, that I have helped women feel good about who they are and in their skin and, and men too, you know, it's not just women. I'm, you know, I'm surrounded by men in my life. So I know everyone's about the woman, but I'm about the men too. So I think my legacy is that I helped people a, you know, feel good about themselves and realize that they are capable of anything they want to be capable of.
56:26What are you still aspiring to do? I don't know. And that's, what's so exciting. I'm still, I'm still open to things that would make absolutely no sense. I get calls all the time. What do you think of this? And I'm like, sounds interesting. Like I, I, I answer people that I probably shouldn't, you know, whether it's DMing or, or on LinkedIn, I don't really answer people on LinkedIn, but mostly on DMs. And, you know, I have quick conversations because you just never know when something is going to, you know, get my interest. You never know. I mean, I dropped a bombshell on you when I first met you and you might call me back and say, I think it's a really good idea.
57:04You never know. Are you afraid of anything? The only thing I'm ever afraid of is safety of the people I love, you know, people's health. Like, you know, I know nothing stays the same. You know, my aunt Alice is 95. My dad's 91. You know, you think about those things. And I, you know, I don't think about getting older until I realize everyone around me is getting older. Like, I guess I am too. Bobby, are you living the life of your dreams? Oh no, I am not. I am way above my dreams. I mean, I, I thought I was going to be a teacher and, you know, be a suburban mom, which I am both of those things, but I never thought I would be any of the other things.
57:46So it's like kind of cool, kind of crazy. And you know, my, I know my parents and my husband and my kids are proud of me and that's what matters. Are you proud of you? I'm really proud of myself because I really didn't think I was going to amount to much growing up. So I'm really proud of myself. And here you are. And here I am. It's just the best. Like you're the best. I'm going to take you to some rapid fire before we finish. One beauty product that you take to a desert island. Is there a mirror? um no then it would be miracle bomb because you could do five things with one product what if there what if there was a mirror maybe i would need concealer i don't know fair fair i still don't know how to use concealer do you know that it's the one thing that's like not in my then you probably don't need it no i mean i've really bad dark circles like i really do i have other people that know how to use concealer what's the best piece of business advice you've ever gotten?
58:42It was from Leonard Lauder. He said, never ask for permission, beg for forgiveness. That's a good one. I mean, Leonard Lauder really had some lines, didn't he? What a joy to be surrounded by somebody like that. Something you changed your mind about after 60? Just that I couldn't do something. There's nothing I can't do. I love your answer. Except high impact aerobics. Oh, fuck that. But I still do it, but I probably shouldn't. You do do it? I do it, yeah. I love that you say aerobics, by the way. That's just like the best. Like as soon as somebody says that to me, I go like totally Jane Fonda.
59:21I was in a class in New York City when I first moved there with Madonna. Shut up. She was in the back of the class. I'm like, God, that girl dances amazing. And you're like, oh, it's Madonna. We didn't know Madonna then. That's pretty amazing. And what are your top guilty pleasures? Caviar, potato chips, and french fries and a martini. I mean, literally, you're my best friend. I could be best friends with you. Nothing. If I could just sit and ask you a hundred more questions with those four things, I could be here for, done. That's a good, that was four, perfect. What is a book that changed your life?
59:54Liz Murray wrote a book called Breaking Night and it was called From Homelessness to Harvard. She wrote a book about her life. Everyone should read it because she'll never complain about anything. She was drug addicted parents. She was homeless for years. She had a dollar left. She could either have a piece of pizza or take a subway. She took a subway for a dollar to a school, met a teacher, helped her. She lived on people's couches and ended up going to Harvard. And she's my friend. And she's your friend? Yeah, and I know her. Did you meet her before or after the book? After the book, yeah. You went after her?
1:00:27Yeah, I've been a very... You went after people. I've been a very bad friend, though, to her. So if you see this, I really do miss you. Well, you've got plenty of time. Plenty of time for catching up. And you just called out her books. that's super lovely. Bobby, thank you so much. I loved meeting you. Me too. Same here. Really did. Thank you. Thank you.
1:00:48If you're loving this podcast, be sure to click follow on your favorite listening platform. While you're there, give us a review and a five-star rating and share an episode you loved with a friend. You'll be so grateful. Aspire with Emma Greed is presented by Odyssey. I'm your host, Emma Greed. Executive producer, Ashley McShan, Derek Brown, and me. Our executive producers from Odyssey, Leah Reese Dennis, Asha Saluja, Lauren Lagrasso, producer KK Sublime, Stephen Key is our senior producer, sound design and engineering by Bill Shultz, Angela Peluso is our booker, original music by Charles Black, video production by Evan Cox, Kurt Courtney, Andrew Steele, and Carlos Delgado, social media by Olivia Homan, Catherine Bale.
1:01:32Special thanks to Brittany Smith, Sydney Ford, my teams at The Lead Company and WME. Maura Curran, Josephina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson-Rose, Tim Meekle, Sean Cherry and Lauren Vieira. If you have questions for me, you can DM me at Aspire with Emma Greed. Greed is spelled G-R-E-D-E. That's Aspire, A-S-P-I-R-E with Emma Greed. Or you can submit a question to me on my website, emagreed.me. Thank you.
From the publisher
What does it mean to build something so successful that it outgrows you, and then start again from nothing with your name legally off the table? Bobbi Brown built one of the most iconic beauty companies in the world. She was 37 when she sold it, stayed for 22 years, then eventually pushed out of the business that carried her name. She waited out a 25-year non-compete, and on the day the clock ran out, she launched Jones Road—at 63, with six products, no outside investors, and a completely different playbook.
Bobbi shares:
What it really costs to sell your name (and whether she’d do it again)
Why getting fired from the brand she built was the best thing that ever happened to her
The difference between building something massive and building something that’s yours
The social media strategy behind Jones Road and why it works
The leadership lesson she’s still learning at 68 and what confidence means after decades of trying to be someone she’s not
Have you ever built something—a business, a career, an identity—and had to walk away from it? What did starting over teach you? Tell us in the comments.
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