Bobbi Brown on Reinvention, Resilience, and the Power of Starting Over

Summary

Podcast Summary: Making Space with Hoda Kotb

Episode: Bobbi Brown on Reinvention, Resilience, and the Power of Starting Over

Date: October 22, 2025

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Overview of Main Theme

In this episode, Hoda Kotb sits down with beauty industry icon Bobbi Brown for a candid conversation about resilience, reinvention, and the journey of starting anew—personally and professionally. Bobbi shares her story of building a billion-dollar beauty brand, facing seismic life changes after leaving her namesake company, and ultimately rediscovering her passion and purpose with her new venture, Jones Road Beauty. The conversation is full of insights about family, fortitude, the nuances of letting go, and the surprising joys that come from embracing change at any age.

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Key Discussion Points & Insights

1. Writing the Memoir: "Still Bobby"

[03:16 - 04:52]

• Bobbi describes feeling “a little exposed” putting her story out into the world, but emphasizes the importance of authenticity and kindness, even when sharing hard truths.
  • “Not hurting people’s feelings...it does matter to me. Sometimes when you speak the truth, it doesn’t come off nice. And it’s really important that it comes off nice to me.” — Bobbi Brown [03:44]
• Her husband played a key role in ensuring the memoir sounded authentic and considerate.

2. Childhood and Family

[04:09 - 07:22]

• Bobbi opens up about her mother’s mental illness, emphasizing both the challenges and warmth of her childhood.
  • Her mother’s suicide attempts and the resulting responsibilities Bobbi took on as the eldest child are discussed with honesty, but she stresses her focus on the good memories:
  • “Somehow I’m wired to get rid of the bad things and think of the good things.” — Bobbi Brown [04:24]
• Bobbi’s mother was glamorous and her influence shaped Bobbi’s interest in beauty and makeup.

3. Discovering Her Path in Makeup

[07:22 - 11:17]

• Bobbi’s mother encouraged her to pursue what made her happy—which led to makeup artistry.
  • “If today’s your birthday, you could do anything you want...I said I want to go to Marshall Fields and play with makeup. She said, why don’t you be a makeup artist?” — Bobbi Brown [09:36]
• Attended Emerson College, where she designed her own major, laying the groundwork for her entrepreneurial spirit.

4. Coping and Moving Forward

[10:00 - 12:21]

• Discusses her tendency to move past trauma, preferring to focus on solutions and positivity.
  • “It’s very easy for me to let go of the things that are upsetting...I’m always someone chasing the light.” — Bobbi Brown [10:31]
• Found healing and stability in her relationship with her husband and his family.

5. Breaking Into the Beauty Industry

[12:54 - 17:33]

• Started with a waitressing job, then moved to New York and hustled for work as a makeup artist through persistence and ingenuity (Yellow Pages, union contacts).
• Innovated the “no makeup makeup look” by focusing on natural beauty, even when told it wouldn’t succeed.
  • “What do you think? He said, you’re never gonna work if you do makeup like this. But I kept doing it because it just felt right to me.” — Bobbi Brown [14:46]
• Built a reputation in fashion and media, leading to a Vogue cover with Naomi Campbell.

6. Building and Eventually Leaving Bobbi Brown Cosmetics

[21:06 - 26:30]

• The creation of her original lipstick began as a grassroots, side project—eventually catapulting her into major retailers, like Bergdorf Goodman.
  • First-month goal of 100 units sold, but sold out in a single day.
• The business exploded over four years, drawing the attention of Estée Lauder. Bobbi sold her company, stayed on for 22 years, but eventually chafed against the increasing corporate constraints.
• Her departure was sudden and difficult, but ultimately freeing:
  • “All I remember is this giant relief leaving me because I’d been trying to fix things...It just got too big.” — Bobbi Brown [26:49]

7. Reinvention and the Birth of Jones Road Beauty

[29:39 - 36:17]

• Post-corporate chapter involved emotional processing and leaning on her support system.
• With four years left on a 25-year non-compete, she explored other ventures (hotels, collaborations), but was ultimately drawn back to beauty.
• Interest in clean beauty inspired Jones Road, which launched the day her non-compete expired:
  • “Everyone said, don’t do it...I didn’t listen and I just launched, I just pressed the button.” — Bobbi Brown [33:02]

8. Embracing Second Acts and Not Overthinking

[36:17 - 37:43]

• Hoda and Bobbi discuss the importance of staying open and adaptable to change, even after early successes.
  • “Don’t overthink. Just do…You never know. I don’t believe in failure.” — Bobbi Brown [36:53, 37:22]

9. Family, Balance, and “Making Space”

[37:43 - 41:33]

• Describes her “time pie” and priority for family, balancing a busy professional life with raising three sons.
• Developed creative ways to stay present as a parent, like hacking the school calendar to avoid missing important events.
• On managing guilt and expectations as a working mom:
  • “I did the best I could do. I’m not perfect…” — Bobbi Brown [40:59]

10. “Making Space” – What Would Bobbi Do with a Day to Herself?

[41:33 - 43:45]

• Describes her ideal day: exercise, coffee, no work, leisurely shopping trips—just “being a person.”
• Finds joy in normalcy and small pleasures, with a little creative work as a hobby.
• Nighttime wind-down routine includes skincare, supplements, and quality time with her husband.

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Notable Quotes and Memorable Moments

• “Somehow I’m wired to get rid of the bad things and think of the good things.” — Bobbi Brown [04:24]
• “It’s kind of the secret of life: finding your posse. The people that are around you that you trust, that have your back, that understand you.” — Bobbi Brown [15:45]
• “You never know. I don’t believe in failure...It’s good when things don’t work out because you’re like, why didn’t they work out? Oh, that’s why. I’m gonna do it differently next time.” — Bobbi Brown [37:22]
• “Thank God for Instacart. But I mean, like, how many times have you gotten fruit and you’re like, I know I should have gone.” — Bobbi Brown [42:26]
• “I’m on the way, because it does, it requires a lot of stuff.” — Bobbi Brown (on her evening routine) [43:42]

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Important Segments & Timestamps

• Bobbi’s experience writing her memoir [03:16 – 04:52]
• Discussing her mother’s mental illness and childhood [04:09 – 07:22]
• Path to becoming a makeup artist and early hustle [12:54 – 14:46]
• Innovating beauty and responding to industry doubt [14:46 – 15:39]
• Landing Vogue cover and building her reputation [17:03 – 17:43]
• Creation and rapid rise of her cosmetics brand [21:06 – 22:52]
• Selling to Estée Lauder and navigating corporate life [22:52 – 26:30]
• Leaving the company and emotional fallout [26:30 – 29:39]
• Reinvention and starting Jones Road Beauty [29:39 – 33:38]
• Facing fear of second acts and family balance [35:22 – 41:33]
• What Bobbi does to “make space” for herself [41:33 – 43:45]

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Tone and Final Thoughts

The episode is uplifting, honest, and deeply personal, reflecting Bobbi Brown’s straightforward yet optimistic approach to life. Her stories capture both vulnerability and strength, offering practical inspiration for anyone at a crossroads or seeking new beginnings.

“You can always begin again…The best chapters can come later in life.” — [Intro, 01:34]

Bobbi’s life illustrates that authenticity, courage to start over, and keeping a strong support network are key ingredients for success and fulfillment—no matter how many “acts” life holds.

Transcript

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[Bobbi Brown]

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Have.

[Podcast Host/Producer]

You ever worked so hard at something only for it to end in a way you least expect it? My guest today knows that feeling all too well. Her story is about success on the highest level and the courage it takes to start over. Bobbi Brown is a pioneer in the world of beauty who changed the industry forever with her no makeup makeup look. After years of not taking no for an answer, she built a billion dollar brand and became one of the most recognizable entrepreneurs in the world. After starting her own Bobbi Brown cosmetics brand, selling to Estee Lauder and spending 22 years at the helm, she found herself at a crossroads. The company she created and the brand that bore her name no longer felt like home. She had to face the reality that her next chapter was quickly approaching. And yet, what could have been the end became a new beginning. At 60 years old, Bobbi reinvented herself with Jones Road Beauty, proving it's never too late to start over. Well, now she's chronicling her journey in her first memoir, Still Bobby, a story of resilience, reinvention, and the strength to let go of the past in order to create something new. In our conversation, Bobbi opens up about why she decided to write a memoir, the power of trusting your gut, and why she believes the best chapters can come later in life. She's living proof that you can always begin again. I'm Hoda Kotb, and this is my podcast, Making.

[Hoda Kotb]

So, Bobby, when you put your life on the page and you hand it out to the world to see, it's gotta feel. Well, how does it feel?

[Bobbi Brown]

Well, it feels a little exposed, you know, it feels good. I mean, when I finished the book and handed it in, I was like, all right, I got this. You know, there was a lot of rewrites and, you know, shout out to my husband that went over word by word, making sure that it sounded like me and that I didn't hurt people's feelings.

[Hoda Kotb]

That matters to you?

[Bobbi Brown]

Not hurting people's feelings. It does matter to me. You know, sometimes when you speak the truth, it doesn't come off nice. And it's really important that it comes off nice to me.

[Hoda Kotb]

You're a straight shooter, which I like. And you feel that in this book, one of the things I knew nothing about was your childhood. I feel like I've known you for. I feel like we all know you. And when I read about your childhood.

[Podcast Host/Producer]

I guess I was a little surprised.

[Hoda Kotb]

I didn't know the backstory. I didn't know about your mom. I didn't know about your dad was writing about your mom. There are many facets to her, but I would imagine a part that was difficult to write about was her struggles with mental illness.

[Bobbi Brown]

You know, it's so interesting because growing up, I didn't really think that I had a complicated childhood. I just had a loving childhood. My mom had her issues and her struggles and had these bouts of mental illness before people even talked about mental illness. But I just remember everything lovingly. So somehow I'm wired to get rid of the bad things and think of the good things. But then when writing the book, it brings it all up again, and I'm like, ah, okay.

[Hoda Kotb]

So when you looked back and I'm not gonna be someone who harps on what's the underbelly? Cause life is a huge tapestry.

[Bobbi Brown]

It is.

[Hoda Kotb]

But when you did write about the part where your mom jumped out of a moving car.

[Bobbi Brown]

Oh, she tried to commit suicide many times. You know, my sister found her in the Bathroom, slitting her wrists. You know, she wasn't good at it, luckily, but for her, it was a cry for help. And it was, you know, definitely a scary time.

[Hoda Kotb]

And how did you cope as a kid? I know you say you kind of tucked it away.

[Bobbi Brown]

Yeah.

[Hoda Kotb]

And went about your business, but how does a little kid. Because you're looking for stability. You're looking for that.

[Bobbi Brown]

Well, I was in seventh grade. I was the oldest of the three kids. And, you know, my dad just really, you know, brushed himself off, and he was there, and him and I got really close during that time. And mom was in the hospital. I don't know if it was three weeks, a month. And then she came home, and then things were better for a while. She was finally diagnosed and was on medicine, so she was better. And then she had a couple different, you know, times, like relapses. My parents got divorced, and my mom met the next man who was the love of her life. And everything was calm and great until. Until he passed away and she had another episode.

[Hoda Kotb]

They say when you know the truth, your body relaxes. When you guys got the diagnosis that your mom was bipolar, was it like, oh, there it is. No. No.

[Bobbi Brown]

Because honestly, I never saw a lot of weird activity. So I didn't know. I don't know why. I mean, you know, I was there. I was busy with my friends, you know, here in fifth, sixth, seventh grade. You know, I'm My independence. And we lived in a nice suburb of Chicago. We had pidelic life. And then this thing happened. And I don't remember being embarrassed by it. And I remember my father explaining it to me. And I felt very grown up because I knew it was my responsibility to come home and be someone there for my brother and sister. And he also hired a woman to come in and take care of us. I'll never forget. Her name was Frances Fisher, and she was a very strong German woman. And she used to make us hamburgers, put mayonnaise on the. And french fries. My mother never served us that food, so there's always a good side to bad things. And I remember the french fries and the mayonnaise on a hamburger, which I would never eat again.

[Hoda Kotb]

But you know what I love? When you describe your mom, you talk about her as the epitome of beauty. And for you, who fell in love with that part of life, that industry, to have her as your very first teacher without knowing it, tell me about that part of her that drew you in that way.

[Bobbi Brown]

Well, she was a very beautiful young woman, and she you know, she was young. She was 20 or 21 when I was born. So, you know, I would stare at her and she'd wear her high heels. She either had her Jackie Kennedy period or, you know, when she got older, she looked like Joan Collins. You know, she kind of went. She loved glamour.

[Hoda Kotb]

Yeah.

[Bobbi Brown]

And she used to watch me on the Today show and say, huh, Was that a suit you were wearing? I'm like, why? She goes, well, one was navy, one was black. I'm like, she just. She couldn't focus on anything. Except it's not about how I did on the show, by the way, you know, But Diane Sawyer told me the same story of her mother. She called her to ask her about some interview she did with Castro, and she goes, diane, you looked so tired. You needed more makeup. So, you know, be kind to your girls.

[Hoda Kotb]

Be kind to your girls.

[Podcast Host/Producer]

You're right.

[Hoda Kotb]

So when you knew that makeup was a thing, a lot of parents want their kid to kind of follow a practical path that has a clear goal at the end. What you were in love with with wasn't practical. It was risky.

[Podcast Host/Producer]

It was scary.

[Hoda Kotb]

Were your parents cheering you on or were they like, Bobby, let's, You know.

[Bobbi Brown]

Well, actually, my mother is the one that led me in that way because I had gone to two colleges. I was never a good student in school. You know, I didn't know early on that I was a visual learner and not a traditional learner. So a creative kid. You know, there's a million people like me. And I said, mom, I want to drop out of school. I had gone to two colleges. She said, you can't. She didn't graduate. She wanted me to graduate. And I said, but, mom, it's so boring. She said, you need a degree. And she goes, what do you want to do? I said, I have no idea. She said, forget what you want to do with your life or how you're going to make money. If today's your birthday, you could do anything you want. And I thought I could have said, go clothes shopping, go to a bakery. I said, I want to go to Marshall Fields and play with makeup. She said, why don't you be a makeup artist? I said, I don't wanna go to beauty school. She said, I'm sure there's a college somewhere that you could get a degree in.

[Hoda Kotb]

Wow. Wow, that is awesome.

[Bobbi Brown]

And there wasn't, but I found Emerson College that let me design my own major.

[Hoda Kotb]

Oh, they let you carve out what you wanted?

[Bobbi Brown]

I did bad.

[Hoda Kotb]

That's cool.

[Bobbi Brown]

Back then and now I know that's kind of started me being an entrepreneur.

[Hoda Kotb]

Right. You knew what you wanted, so you said, this is what my major's gonna be.

[Bobbi Brown]

Yes. God, yeah. Moxie.

[Hoda Kotb]

You know what I like about you? Well, I like a lot of things. But a lot of people find their pain, their Achilles heel, their childhood trauma, and become defined by it. And that's kind of the way it is. Like, what is it? Oh, my parents were X, and so that's therefore I'm Y. You were sitting here, wildly successful in your life, largely because you didn't do that. What did you do with the trauma? Like, where was it? Do you just carry it along and say, I'll deal with it later?

[Bobbi Brown]

Or, you know, I honestly don't know. But when I. It's very easy for me to let go of the things that are upsetting. Even when I fight with my husband, I forget why we're in a fight. And I'm over it. As soon as we have the fight, it takes him a little bit longer. But with what happened with my family, I don't know. There was constantly something between my mother, my brother. They both had their struggles. I don't know. I just kind of went on. And even in my work life, when things were challenging and I just went on, I went around things, right? Like, okay, that's not good. That doesn't make me feel good. Let me try it this way. And I just. I'm always someone chasing the light, I guess. I don't know.

[Hoda Kotb]

I think there's a thread there. Cause I was thinking of Maria Shriver. She's kind of the same way. She had a lot of childhood stuff, but continued on, unpacked it later. But after she had already, like, done all of the great things and still many, many more to come.

[Bobbi Brown]

Okay, so maybe I haven't unpacked it yet, but writing this book and reading my book, I would think it would, you know, trigger something. And it hasn't yet.

[Hoda Kotb]

I do think some people. I mean, this is an extreme example, but I was talking to a man who was a Holocaust survivor, and he was watching a tennis match, and he had joyful grandkids and was playing. And I was watching this whole scene in his house, and I go, I have to ask, like, how is that? And he said something to the effect of, some trauma's so big, you carry it. Now. This is. Obviously, I don't wanna not have a beautiful, fun, fulfilling life because of. So it lives here. And then I go on and hug my grandkids of Course, that's the extreme example, but we all have little bits and pieces we probably lug around, right?

[Bobbi Brown]

And I'm also really lucky. Cause when I found my husband, I got his parents who, like, you know, I mean, I mentioned Ozzie and Harriet to someone in my car and no one knew who it was. But, you know, it was my Ozzie and Harriet moment. Like, these people were normal, down to earth and nice. I got to kind of build my family in a new way.

[Hoda Kotb]

So you carve out your own little major. And there are a lot of women who love girls who loved makeup. So what was your path? Or did you have a mini plan or what was going on?

[Bobbi Brown]

I graduated and I did the most important thing. I got a waitressing job. Cause I was so worried about supporting myself. And I did that for a year and tried to get hired as a makeup artist in Boston. And there was really no work. I did one film on teenage alcoholism. It was so boring. I said, I don't wanna be in the film business. And I moved to New York, didn't know anyone. And I opened up the Yellow Pages. You know, there was no Internet.

[Hoda Kotb]

Yeah, exactly.

[Bobbi Brown]

I opened up the Yellow Pages and I looked up makeup. Oh, makeup union. What's that?

[Hoda Kotb]

I called a makeup union.

[Bobbi Brown]

Okay. And I made an appointment. I went there and I said, I'm here to sign up for the union. And the guy laughed at me. And he said, who do you know? I said, nobody. He said, well, it takes about seven years. And I'm like. To get in the union. To get in the union, but I'm gonna help you and throw you some things. So he would call me with a. I got to assist a makeup artist on Saturday Night Live. I did, you know, NBC News. I did all these things, okay? So I got experience. And then I started, you know, dealing with fashion and going to see modeling agencies. And then I got totally, like, you know, in love with the fashion world. So I became a freelance makeup artist.

[Hoda Kotb]

Fashion makeup is funky. I mean, anyone who's watched New York Fashion Week, sometimes it's wild. Is that the kind of makeup you were doing back then?

[Bobbi Brown]

You know, I was trying to do the makeup that was popular at the time. I was trying, and I was really not good at it. I didn't like it. I didn't think anyone looked good. And I couldn't get the girls to look good. So I started just using makeup the way I would make myself up, just to make the girls look prett. And, you know, one day it became a cover of an Italian magazine.

[Hoda Kotb]

How? How?

[Bobbi Brown]

Because someone hired me, and I did the makeup. I made her really bronzy and tan. I remember I took the bronzer, put it on her eyelids, on her lips. I was just always making things up.

[Hoda Kotb]

Yeah.

[Bobbi Brown]

And it made the COVID and I showed it to this top makeup artist. What do you think? He said, you're never gonna work. You're never gonna work if you do makeup like this. But I kept doing it because it just felt right to me.

[Hoda Kotb]

So when you get a no like that from somebody who you respect, why did your small voice beat his?

[Bobbi Brown]

Well, I'm. Look, I felt it in my stomach when he first told me, and then I just kept on. I mean, when I told someone I was launching a makeup line, you know, the first time he said, oh, no, no one needs another makeup line. There's not a chance that this is gonna work.

[Podcast Host/Producer]

Geez.

[Bobbi Brown]

I mean, we get a lot of rejections. Yeah, yeah.

[Hoda Kotb]

And how do you weather. I know you have the voice inside, but how do you like it?

[Bobbi Brown]

I feel it, and then I let it go. Okay, that's your thing. I mean, I do.

[Hoda Kotb]

That is your superpower. That must be it, right?

[Bobbi Brown]

I let it go because it doesn't serve me.

[Hoda Kotb]

Okay, so you want a makeup line, and your whole thing was you like natural. You like women to look like who they are.

[Bobbi Brown]

Right. No one else was doing it, and I just kept doing it, and I found people that liked it slowly, and they started hiring me more. And the people that I struggled when I worked with, that I never felt I was good enough, I stopped working with them, or they stopped hiring me, whatever it was. And I just found my people, found my posse. It's kind of the secret of life, finding your posse. Right. The people that are around you that you trust, that have your back, that understand you.

[Hoda Kotb]

Yeah. How did you find them?

[Bobbi Brown]

Slowly.

[Hoda Kotb]

Slowly.

[Bobbi Brown]

You know, slowly. I mean, I found a photographer that liked my work and said, this is amazing. And then I found another one, and then editors started calling me for a certain look, and, you know, it kind of spiraled.

[Podcast Host/Producer]

Yeah.

[Hoda Kotb]

It sounds like a slow build, but there's usually a moment where you go, oh, my God, like, I got something here. Was there one?

[Bobbi Brown]

There was a zillion moments. The first moment was when I got hired for Glamour magazine to do. It was a dancer. I lied and said I did hair too, and I don't. So I did her hair and makeup, and it was, you know, a lot of pictures on a double page spread, so you couldn't really see the Face, but it said makeup by Bobby Brown inside. And that was like, oh, my God.

[Hoda Kotb]

Wow. Wow.

[Bobbi Brown]

Right, right. And it was a photographer, Brigitte Lancome, who has become a very famous celebrity photographer. And she just kept hiring me. Cause she liked me. And then I started working with Bruce Weber, and he loved what I did, and he actually taught me to do less, even less makeup than I was doing. So that worked out well. Found another couple photographers, and after seven years, I got a Vogue cover. Seven years. Who was the COVID Naomi Campbell.

[Hoda Kotb]

Oh, wow.

[Bobbi Brown]

Yeah.

[Hoda Kotb]

Wow.

[Bobbi Brown]

On the COVID Vogue.

[Hoda Kotb]

Is that when people started to know your name outside of kind of the inner circle?

[Bobbi Brown]

Pretty much, you know. And then what happens when you're a freelance makeup artist? They would call you for, Bobby, what's the trends of the season? Bobby, how do people keep your makeup on? And so I became the expert. And I think because I was such a simple person, straight shooter, the editors loved my tips. So that became a part of, you know, I would do the makeup, but then be quoted in it. And then all of a sudden, they'd want to photograph me for the things, and I'd be like, doing all that stuff. So I've always had a couple. And then I wrote a book and then another book, and then I was on a book tour, and I answered this really nice, like, old lady's question. She was like, you know, shorter than me even. And she said, I've seen you on the Today show. I had been on once. She said, is there anything else you want to do in your life? You've done so well. I. I'd love to be a regular on the Today show. She said, honey, my grandson is Jeff Zucker.

[Podcast Host/Producer]

Oh, my God. Are you serious?

[Bobbi Brown]

That was on a Friday and Monday. I became.

[Hoda Kotb]

I can't.

[Bobbi Brown]

Jeff came down. He came down, and he always called me Barbara. We're still friends to this day. And he said, barbara, Grandma Fran said she wanted you on the show. I said, yeah, this is awesome. He said, how often do you want to come on? I said, once a month. He said, okay, you're on once a month. I came down the next month. He came down to say hello. He said, all right, Barbara, now what do you want? I said, can I have a title? He said, what kind of title? Everyone had, like, something. So I said, can I be the beauty editor of the Today Show? Okay. He never came down a third month. So I never asked him for money, But I was on the show for 14 years.

[Hoda Kotb]

Holy moly.

[Podcast Host/Producer]

More with Bobby Brown after the break.

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[Hoda Kotb]

So when did you decide to do the cosmetic line in this time frame?

[Bobbi Brown]

Well, I never really decided to do anything. It just things happen. I was doing a shoot and I went into Kiehl's, whatever, whatever it's called and I met a chemist behind the counter and I told him I always wanted to make a lipstick that looked like lips, that wasn't greasy, didn't smell bad. He said, oh, I'll make it for you. So we worked together on a formula and a color and then he said, I'll give them to you, you sell them and we'll split the $15. I said, great. So I started this little thing out of. I didn't know it was a side hustle. We didn't have words like that then. I didn't know that I was an indie beauty person. We didn't have those terms yet, and I started selling them out of my house. And all these stories are in the book. But one day I went to a party, and whoever invited me, I said, thank you for inviting me. She goes, oh, I'm a big fan. And I said, oh, what do you do? She said, I'm a cosmetics buyer at Bergdorf Goodman. I said, oh, I have a line of lipsticks. And that's how I got into Bergdorf.

[Hoda Kotb]

And did it sell? Because in Bergdorf, first of all, that's monumental and crazy, and that's the gateway.

[Bobbi Brown]

But did it?

[Hoda Kotb]

Cause a lot of times people do get things in a big department store and it gets lost in the sauce. How did anybody find it?

[Bobbi Brown]

Well, there was no room on any counter, so they said, we have a table in the middle of the floor with a couple cosmetic bags. I said, great, I'll take that. So they put it there. And it turned out to be a great thing. Cause people saw it, and we thought we'd sell 100 the first month, and we sold 100 the first day. So it became, you know, a makeup artist doing lipsticks who people have read about in a magazine. It became a thing.

[Hoda Kotb]

All the building blocks were there for it to be, like, wildly successful. So wildly successful, in fact, that when you get as good as you are, you get the attention of the Estee Lauders of the world. How far along in your business were you when Estee Lauder came knocking and said, hey, we're interested.

[Bobbi Brown]

Four years. Okay, Four years. You know, we had become the number one line in both Bergdorf and Neiman Marcus.

[Hoda Kotb]

Wow.

[Bobbi Brown]

Trust me. They were looking.

[Hoda Kotb]

They were like, let us. So tell me about the debate in your head when an Estee Lauder comes and says, we would like to have you.

[Bobbi Brown]

Well, first of all, there was no debate. There was no debate. I never thought in my wildest dreams that would happen. And, you know, my husband and I had business partners, and we were having a tough go of it. A lot of personality issues, and I was glad to have it someone else's problem. And Leonard Lauder, if you ever had, you know, you met the man, he's just the most incredible human being. And when he looks you in the eye and says, I want you to be part of the family, you know, I want to nurture and take care of everything, and I want to teach you. And I just said, of course. And so we sold it. I stayed on 22 years as an employee, and when we sold the company, I had a 25 year non compete.

[Hoda Kotb]

So they really knew your potential. So before you signed, they said, great, we'll do this, but you can't have another makeup line for 25 years or.

[Bobbi Brown]

Be in beauty or anything.

[Hoda Kotb]

Quarter century.

[Bobbi Brown]

Right. You know, I mean, look, there was a buyout connected to it. Meaning, you know, how much I got every year depended on how we sold. Like, they wanted me to be in it, and I was in it. Cause even when I was there, I thought I still owned it. I acted like I still owned it.

[Hoda Kotb]

It was still yours.

[Bobbi Brown]

It was mine.

[Hoda Kotb]

Yeah. So being acquired by a big company like that is amazing. Cause you make a ton of money and you got to be able to keep your hands on the steering wheel. But like a lot of these big companies, they're the ones who are in charge ultimately. And they get to decide. You were used to calling your own shots, doing your own thing, you know what you want, you've done it your whole career. And then suddenly, later on during this thing, they were telling they were putting things through without. You're okay.

[Bobbi Brown]

Right. But in the beginning, I. I would say, I mean, a good 18 years were easy and fun. And I mean hard. Not easy, but. But really great. And, you know, I. I was totally in charge. Any. Any whim I had, anything I had, I had the support I had. You know, I learned so much. And then, you know, things change in companies, and it was definitely harder and harder, and the last two years were pretty unbearable. But I kept thinking I was gonna fix things.

[Hoda Kotb]

You did. You're an optimist.

[Bobbi Brown]

Oh, yeah, totally. I was like, no, I got this.

[Hoda Kotb]

I'm gonna turn it around. Yeah, you talk in detail in your book, and I'll let people read it. Cause it's very interesting. For anyone who's been in. You don't have to be in this situation to know these feelings. But it is the feeling of you're in charge, and then suddenly everything gets chipped away. And suddenly before you know it, they're telling you that they're, in essence, firing you. You were face to face in an office, and they handed you a letter.

[Bobbi Brown]

And basically said, we're canceling your work contract.

[Hoda Kotb]

And you said, so I'm fired?

[Bobbi Brown]

And they said, no, we have a new deal for you. And she handed it to me, and I said, I don't have to read it. She goes, yes, you do. I said, you fired me. I don't. And I turned around and walked out and left.

[Hoda Kotb]

Wow. Wow, that's so you.

[Bobbi Brown]

I was like, I'm not. I don't have to stay here anymore.

[Hoda Kotb]

I don't have to stay. I know for you things last fleetingly, but.

[Bobbi Brown]

But no, that was not fleeting.

[Hoda Kotb]

That was real.

[Bobbi Brown]

Oh, yeah, that was real.

[Hoda Kotb]

Something you built, that all your years went into. And all of a sudden it comes down to this. How did you process what was happening?

[Bobbi Brown]

Well, the most interesting thing, when I got in the elevator from the 42nd floor going down, all I remember is this giant relief leaving me because I've been trying to fix things. Every time I'd walk into a counter, I'd be like, this looks terrible. Look at the lighting. Look at this. Like, it was, you know, it just got too big. And there was. I always thought the right people were not dealing with the brand. And I was always, you know, complaining. I'm sure I was a pain in the neck to everyone, but I'm like, this is not right, guys. It's so easy to fix. Just get different light bulbs, you know, I mean, to me, like, that's the way. Very basic, really basic. But I just had this relief. But then I had like. Like, oh, now what?

[Hoda Kotb]

Yeah.

[Bobbi Brown]

And I called my husband, who came in. We sat down at a, you know, restaurant downtown, and, you know, I had been signing two year contracts at that point because I didn't know how long I wanted to stay. And he just said, finally, I have you back. He said, I've wanted to travel. And he says, I have a new project I want you to work with me on. He said, I bought a building and I thought we should do a hotel. I'm like, oh, okay, why not? Sure, let's do a hotel.

[Hoda Kotb]

Can I ask you a question about the ending part? And this is not a parallel to Sarah Blakely, but I interviewed her, and she describes the moment that she sold Spanx. Different things, but still, it's like your baby's not your baby anymore.

[Bobbi Brown]

Right. But she sold to a financial. I sold to a company that's different, that wanted, you know, more strategic.

[Hoda Kotb]

More strategic. But she did say once it wasn't hers, which happened at the end for you. And she said she went into this spirally kind of depression. Of course. Of course. I built this thing, I made this thing, and now this thing doesn't belong to me anymore. What was that time like for you?

[Bobbi Brown]

I never felt that. No, I never felt that. I mean, first of all, it wasn't nearly as big, and it was only four and a half years. And it was optimistic because these people were gonna help us grow it. And, you know, I was. You know, I was a kid From Chicago, living in the suburbs and, you know, mom of two kids, and all of a sudden I'm showing up at all these fabulous, you know, dinners and parties and meetings and, you know, it was an incredible experience for many, many years.

[Hoda Kotb]

And at the end, how did you reconcile? Somehow when you talk about the firing and the rest of it in your book, that you could tell it's full of like, how could this have happened at the end? Have you reconciled that?

[Bobbi Brown]

You know, it took a long time. I mean, it's been seven years already, so. The first year was rough. I mean, it was tough. You know, I've never used the old brand's cosmetics since the day I left.

[Hoda Kotb]

Really?

[Bobbi Brown]

Never? Yeah, never. I just didn't wanna touch it. And I, you know, look, what happens is you feel like a failure. You're angry, you're sad, you're mad. Then you get euphoric, like, okay, what's next? And then you have the, you know, you still deal with these emotions. So I didn't go to a shrink because I'm not a therapy guy, but I did go to my chiropractor who does emotional releases. And I would go there a couple times a week. And he really helped me get the angst out of me and my support team, my husband, my besties, they listened and they listened and they listened and they encouraged me. And Bobby, there's a million things you could do. There's life after this. Cause I thought it was over.

[Hoda Kotb]

Over?

[Bobbi Brown]

Yeah, I thought, I'm done. You know, no one's gonna ask me, bobby, where do you. What do you like to eat in the morning? You know, all the, all the things that used to drive me crazy. I'm like, well, that's done. Trust me. It was the opposite.

[Hoda Kotb]

Well, what's interesting is you had the shackles on you because you weren't allowed to start another company for several more years.

[Bobbi Brown]

I had four and a half years on a 25 year non compete.

[Hoda Kotb]

That to me, I mean, just getting that in my head, it's like, not only do you not want me, but I can't do something else. That seems so unfair.

[Bobbi Brown]

And I'm sure you know, I am not a person that does well when people say you can't do something.

[Hoda Kotb]

So what did you do?

[Bobbi Brown]

Well, first of all, I had ideas. I'm like, you know what, I'm gonna just open a line of cosmetics and call it no Name. I still own that, by the way. And my husband was like, no, you're not. But I said, yes, I am. But I didn't. And I started doing other things. I worked on the hotel, then I went out to lunches and breakfast with a lot of people. One of those people owned Lord and Taylor and he said, hey, hey, let's do a just bobby shop in like four of the stores and see if we could create excitement. I said, okay. So I did that for a year, and then Lord and Taylor sold. So then I brought it in house and I started just doing different things and I realized how much I missed makeup. I went back being a makeup artist, started doing shoots in a photo studio that we have in Montclair. And, you know, I was. Was kind of off to the races. And then I said, you know what? I wonder what's going on with this new makeup world, meaning the clean makeup world, because not that there's anything wrong with traditional products that I used my whole life, but things were changing, so people wanted cleaner formulas. And I just said, let's try it. And so I hired one girl and we started formulating things. And then it's like, like, oh my God, this is so good and fun. You got that and fun.

[Hoda Kotb]

You. That's what you love, right?

[Bobbi Brown]

I feel like I went back to when I was a kid starting it the first time. I mean, I was 31, but, you know, I felt very, very refreshed and very excited and people loved what I was doing. And I got to film a masterclass on makeup and I used all the testers because it was just better than anything else I used.

[Hoda Kotb]

Oh, that's brilliant. That's brilliant.

[Bobbi Brown]

Yeah. So that was my way. I tested.

[Hoda Kotb]

So Jones Road was born.

[Bobbi Brown]

Was born. The day my non compete was up. Oh, the day. By the way, everyone said, don't do it. Every PR person.

[Hoda Kotb]

Why?

[Bobbi Brown]

Because you can't do it. Because it was a week before the presidential election, in the middle of the pandemic, in the middle of all the social unrest, they said, just don't do it. Wait till January. Remember what happened in January 6th? Yes. So I didn't listen and I just launched, I just pressed the button. We launched it on the Today show. Joanne lamarca. Uh huh. Love that show. In the middle of the pandemic, my friend Elvis Duran and the business article in the Wall Street Journal.

[Hoda Kotb]

Boom.

[Bobbi Brown]

And Instagram flipped it on and it was live.

[Podcast Host/Producer]

More with Bobby Brown when we come back.

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[Bobbi Brown]

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[Bobbi Brown]

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[Bobbi Brown]

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[Hoda Kotb]

So Jones Road is born. Yes. And now, I mean, I see it everywhere now. It's just like when you touch something, that's what happens. Were you at all nervous? It's like a musician who's had so many hits, like, I'm going on the road again. Who's gonna show up? Did you wonder, are people gonna come?

[Bobbi Brown]

Are you kidding? Absolutely. When we first launched, I'm like, oh my God, what if I'm a one hit wonder? And what if people just say, oh, this is like the Emperor's new Clothes. There's nothing to it. Because I come from a world where fancy packaging, fancy boxes over marketed things, you know, which never were, never sat well with me because I didn't really believe they did the things that they were tested to do. So I did something completely opposite. I bought stock packaging, put, you know, stamped a big Jones Road on it and kept the price point down. Put it in a really cool, you know, plain box. And I didn't know if people were gonna like it or not.

[Hoda Kotb]

I mean the idea, what did you learn? And this isn't really a second Act. It's a continuation. But I feel like I'm in a similar situation to you where it's like repotting. Let's start again. Let's see what the new thing is. Let's see how the roots feel and some other ground. Oh, it feels cool.

[Bobbi Brown]

That's why you're successful. A lot of people can't get their head around things that are changing or things that have changed, and all of a sudden they're at home feeling bad that they're not doing anything. But you've got to lean in to the good stuff. It's all new. It's like, huh, all right, I'll open a substack. Huh? I'll go on TikTok. Huh? Oh, events. Of course. We'll do events like. Oh, yeah, that makes sense.

[Hoda Kotb]

I watched one of your commencement speeches. I think it was at FIT Maybe, but you were talking about first. Don't overthink. Just do. I like that. Because that's what's. I think, stopping people you'll think of once, you know the odds. Like, if someone would have told you the odds of being a wildly successful makeup artist when you were a kid trying to make that, getting math and science, getting Ds in math and science, the odds probably would have been a million to one.

[Bobbi Brown]

And here you sit.

[Podcast Host/Producer]

So I love that.

[Hoda Kotb]

That advice that's kind of served you throughout.

[Podcast Host/Producer]

Yes.

[Bobbi Brown]

Cause you know what? You never know. You never. And it's like, I don't believe in failure. And a lot of things I did didn't work out. I had a wellness brand that didn't work out. I had an eyeglass line that didn't work out. So it's not like everything I touch turns to gold. And it's good when things don't work out because you're like, why didn't they work out? Oh, that's why. I'm gonna do it differently next time.

[Hoda Kotb]

Your life is full of richness. You talk a lot about your husband and you mentioned your kids.

[Bobbi Brown]

Yes, my three sons.

[Hoda Kotb]

Your three sons who. And now you've got two grandkids. Describe what your time pie looks like. Like, how does that look?

[Bobbi Brown]

Well, I'm really lucky. You know, I come from Chicago, and us Chicago people are, you know, have our feet on the ground. I feel most comfortable when my feet are on the ground. I've got. You know, I spend every day of my life with my husband, and our three sons are in the area. You know, we see two of them more than we see the third. Cause he travels for work. But they're our posse. And I have a couple nephews that are also in our posse.

[Hoda Kotb]

And now everybody.

[Bobbi Brown]

Everyone's. I was always. My husband and I traveling with three sons, two nephews, and a couple foreign exchange students. So I'm used to having a lot of people around. All boys.

[Hoda Kotb]

All boys. You got a lot of that.

[Bobbi Brown]

Right? But now I got a granddaughter, so everything is pink in my life. Everything. I even bought a pink bra and pink socks that when I'm with Lily, I wear, you know? And now I just got another grandson. And you know what? I have friends. I do. I have a lot of friends that I really like that I, you know, that we go out to dinner. But my family is the center of my universe. It always has been.

[Hoda Kotb]

I was gonna say always has been when you were. Cause a lot of working moms, especially successful ones like you, feel that it's a struggle to, like, I'm gonna miss back to school night. Cause that's the way the cookie crumbles. How did you deal with.

[Bobbi Brown]

Are you missing back to school night?

[Hoda Kotb]

Yes.

[Bobbi Brown]

Why? What's my thought?

[Hoda Kotb]

Nothing's more important. But I have a speech that I signed a contract for before you knew.

[Bobbi Brown]

Right.

[Hoda Kotb]

Six months ago.

[Bobbi Brown]

Okay.

[Hoda Kotb]

Otherwise, who would have done that?

[Bobbi Brown]

I get it.

[Hoda Kotb]

But nothing's more important than. So I feel yuck.

[Bobbi Brown]

Right? Yes.

[Hoda Kotb]

So how did you deal when you had things like that?

[Bobbi Brown]

Well, I hacked my life. So I realized, because I also had to commit to travel for the company before I knew when the sing alongs were. So I used to go in the first day of school with a bag of makeup and knock on the principal's door. And we always had women principals mostly. And I would say, hi, I brought you something. Could you just please tell me when things are scheduled? So I got the entire list of when the teachers conference is. So then when I put my dates for travel, you worked around those. You know, things don't always go perfectly. I once missed one of the sing alongs at school, and, you know, only once. I don't remember what it was that was more important, but I had to miss it. And I look back now, I laugh because my kids are brilliant, fantastic, but they can't sing or dance. But I was there watching, so it's okay.

[Hoda Kotb]

Like, showing up is really the whole thing for me.

[Bobbi Brown]

Like, I wanted to be there. I wanted to see the other parents. I wanted to be part of it.

[Hoda Kotb]

Yeah.

[Bobbi Brown]

You know, I always struggled because, you know, a lot of the moms were not working, and they would get Together for book group. They'd get together for pickleball. Not pickleball. Tennis. All that stuff. I couldn't do it. Yeah, I couldn't do it. Yeah.

[Hoda Kotb]

Yeah. But you ended up when you. So it seems rare that you would miss something, so you prioritize.

[Bobbi Brown]

I tried. And if I couldn't do it, my.

[Hoda Kotb]

Husband wasn't able to. Your husband might be able to. Yeah. You worked it out. You worked it out.

[Bobbi Brown]

We worked it out. But it was. I did the best I could do. And, you know, I'm not perfect. I know it's not easy, you know, to anyone. I had it easier because I kind of thought I worked for myself. And I started doing things without asking permission. Like. Like working from home on a Monday and a Friday, and then I started then on Wednesdays having all the creative team come out to Montclair. Yeah, that's smart. So this was before the pandemic, when people were working at home and I just kind of did it and it made my life a little more balanced.

[Hoda Kotb]

Right, that makes sense. Okay, so this podcast is called Making Space. So if you had a full day, Bobby, that was for you, that you had no commitments, no nothing, clear calendar, do what you want, wake up when you want, sleep when you want. What would you do?

[Bobbi Brown]

Okay, I wake up and I drink my double water or AG1, have an espresso, read the paper on my iPad, put my exercise clothes on, go do an exercise class, something, come home, shower, put my wet hair in a ponytail, put a big sweater on, a clean pair of tights. And honestly, I would either go to the mall or I would go to Costco or I would.

[Hoda Kotb]

What are you doing? Just walking around.

[Bobbi Brown]

Yeah, just being a person. Just walking around, touching. You know, I order everything online because I'm so busy. I want to go in and try some things on and touch them.

[Hoda Kotb]

Yes. I like that.

[Bobbi Brown]

You know, so look, thank God for Instacart.

[Hoda Kotb]

Yeah.

[Bobbi Brown]

You know, but I mean, like, how many times have you gotten like, fruit.

[Hoda Kotb]

And you're like, I know I should have gone.

[Bobbi Brown]

I know, but it's hard, you know? But yes, I would. I like doing those things for myself and just having a moment to walk around and just look.

[Hoda Kotb]

Yeah. That's interesting because you like all that. Would there be any work related stuff in your day now?

[Bobbi Brown]

No, you're giving me a day to do whatever. Do whatever.

[Hoda Kotb]

You can fill it.

[Bobbi Brown]

You might know. Yeah, I mean, look, I'll hop on my creative call with my creative director, who gives me really cool visuals to approve or not approve. That's to me, that's my hobby.

[Hoda Kotb]

Yeah, that's fun one is it lights out for you?

[Bobbi Brown]

I'm not a late night person at all. So I, you know, I, I stay up till about nine and then I go upstairs and I put my jammies on and there is so much to do in the bathroom before I go to bed now. It's like you take your makeup off, you wash your face, you put maybe a serum on, maybe a moisturizer. You floss, you brush, you put the hormones on.

[Hoda Kotb]

Oh, you take.

[Bobbi Brown]

Yeah, I take bioidentical hormones. I take a couple things to help me sleep. Natural things. And my husband's always like, what are doing up there? You know, I thought we were gonna watch this show. I'm like, I'll be right down.

[Podcast Host/Producer]

I'm on the way.

[Bobbi Brown]

I'm on the way. Because it does, it requires a lot of stuff.

[Hoda Kotb]

All right, Bobby. Thank you guys. Get this book. It's called Bobby Brown Still Bobby. It's a great, great, great read. I dog eared a bunch of the pages. Bunch of life lessons, beautiful pictures and just a life well lived. And you're not even, you know, you're on a roll.

[Bobbi Brown]

So I'm living.

[Hoda Kotb]

Yeah, you are. Thank you, Bobby.

[Podcast Host/Producer]

Hey guys, thank you so much for listening and for coming on this journey with me. If you like what you heard, and I hope that you do, please give Making Space a five star rating and review on Apple Podcasts and make sure.

[Bobbi Brown]

You tell your friends.

[Podcast Host/Producer]

Follow us on Apple Podcasts, Spotify or.

[Hoda Kotb]

Wherever you're listening right now.

[Podcast Host/Producer]

Making Space with Hoda Kotb is produced.

[Hoda Kotb]

By Allison Berger and Mitch Rissmiller along with Kate Saunders.

[Podcast Host/Producer]

Our association associate audio engineer is Juliana Masterilli. Our audio engineer is Joe Plourd. Original music by John Estes. Bryson Barnes is our head of audio production. Missy Dunlop Parsons is our executive producer. Libby Leach is the executive vice president of Today and Lifestyle.

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