Aspire with Emma Grede

Episode: Bobbi Brown on Selling Your Name, Getting Fired, and Starting Over
Host: Emma Grede
Guest: Bobbi Brown
Date: April 9, 2026

Episode Overview

This engaging episode goes deep into the remarkable story of Bobbi Brown—the iconic makeup artist, brand founder, and entrepreneur—who built her namesake brand into a global phenomenon, sold it to Estée Lauder, was later fired from the company that bore her name, and then, in her 60s, launched the highly successful Jones Road Beauty. Emma and Bobbi share a candid conversation about ambition, resilience, reinvention, family, leadership, and what it takes to build not just a business, but a life of impact and integrity.

Key Discussion Points & Insights

1. Ambition, Age, and Identity

• Early Ambition: Bobbi grew up entrepreneurial, running lemonade stands and making jewelry:

  "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." (02:35)

• On Age and Labels:

  “I don’t see age. I really don’t see 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.” (03:22)

• Continued Drive: Launching Jones Road at 62/63, Bobbi describes it as a “new beginning”:

2. The Lauder Deal and Its Lessons

• Selling the Brand: In 1995, at age 37, she sold Bobbi Brown Cosmetics to Estée Lauder, signing a 25-year non-compete:

  "We sold everything." (11:56)
  "I stayed with Estee Lauder 22 years. How many people sell a business?" (07:17)

• No Regrets:

  "I would do things exactly the same way. Really. I don't have any regrets." (07:08)

• Learning from Legacy:

  “Being at Estée Lauder for 22 years is quite an education. I learned so much you can’t even imagine.” (07:42)

• Mentorship from Leonard Lauder:

  "He was really my mentor. And that stopped happening... The most important thing to understand, things change... You have to be able to kind of go with the flow. And I like change. I think it’s exciting." (08:55)

3. Getting Fired & the Aftermath

• Describes the Firing:

  "We are canceling your work contract... You're firing me?... When I walked into that elevator and pressed the button... I've never felt so much relief... until I got to the bottom and I was like, oh, now what?" (09:14)

• First Thoughts:

  "My first two thoughts were, my driver Fred's gonna be out of a job... and the second thing was, oh, my God, what am I gonna give to all for Halloween?" (10:45)

• Emotional Fallout:

  "I had to work really hard at my self esteem because you feel like a failure... This business was older than my oldest son." (12:27) “I was triggered every time I saw the logo.” (13:04)

• Grieving the Brand:

  "My friends came over... we drank a bunch of tequila and I cried and they listened." (13:33)

4. Starting Over: The Birth of Jones Road

• What Drove Her:

  "I just didn’t feel done. And more important, I had an idea." (05:03)

• Transitioning Era and Tactics:

  “You started Bobbi 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.” (21:39)

• Family Business:

  "Right now, a lot of it is our son, who's a CEO, his wife who's head of brand. It didn’t set out to be. It’s just the way it is." (29:00)

• Why Not Avon or Corporate:

  “Luckily it didn’t work out [Avon]. Cause I would have been miserable. Right. I cannot work in corporate anymore.” (06:13)

5. Mindset, Innovation, and Customer Insight

• Learning from Direct Feedback:

  "With the Internet, you could just write on ask, and you know... we have instant feedback." (22:07) “I love data, but I also have this creative brain.” (22:51)

• Simplicity and Core Product Focus:

  “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." (26:25)

• Lean Launch Approach:

  “We launched with a few products... Didn't have a big party... We just got the product to all the Editors, to my FOBs, my friends of Bobby, and we just started the process.” (30:25)

6. Leadership, Team Building & Family Dynamics

• Surrounding Yourself with the Right People:

  "Breathe, go slow, be thoughtful, and surround yourself with the right people, which is the hardest thing..." (27:55) “I always had my partner next to me, which is my husband... That’s part of my posse.” (28:08)

• Letting Go & Learning:

  "Sometimes you think they’re great and it doesn’t work out... If you wake up in the morning annoyed by someone every single day, you got to get rid of them." (40:45)

• Family as Business Partners:

  “It wasn't a decision... My son knew more, simpler how to do things. So he became the CEO. And his wife is the head of brand. So that's a little complicated.” (44:47) “We’re best friends. We’re partners on everything... he's practical. I need someone practical around me.” (45:53)

7. Motherhood & The Working Woman’s Juggle

• Balancing Work and Family:

  "I knew my happiness was not being a working woman, but was being like an involved mom. I just luckily had this passion which was work... I'm pretty organized and I'm really good at figuring things out." (47:27)

• Practical Tips:

  "I bought $5 and $10 gift certificates, you know, a couple hundred dollars worth of them. Kept them in the drawer... Two. Timmy. Happy birthday. Love, Cody." (48:19)

• On Accepting Help and Shortcuts:

  "I always look for shortcuts. You know, like what makes sense." (51:34)

8. On Confidence & True Leadership

• What Confidence Means:

  "It just means you're comfortable in your skin with who you are. Cause then... you could walk in a room and be yourself. It's the only thing that works." (37:18)

• The Importance of Asking Questions:

  "I don't feel bad that I don't know things. I just like to ask questions so I can understand it." (39:21)

• Inclusivity & Honesty:

  “I have worked with some of the most successful women... and everyone has that [a lack of confidence].” (37:41)

9. Legacy, Resilience, and Staying Grounded

• Staying True:

  "Everything stayed the same about me. Who I am as a person, like who I care about... 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." (52:40)

• On Resilience vs. Reinvention:

  "I think resilience is important because it's so easy for you to choose a different path because something happened to you. It's kind of what you do with that information." (54:20)

• Living Above Her Dreams:

  "I am way above my dreams. I mean, I thought I was gonna be a teacher and be a suburban mom... I never thought I would be any of the other things. So it's, like, kind of cool, kind of crazy." (57:40)

• On Pride and Self-Belief:

  “I'm really proud of myself because I really didn't think I was gonna amount to much growing up.” (58:02)

Notable Quotes & Memorable Moments

• On Starting Over at 63:
  "Guess what? I didn’t know what I was gonna do. And I thought, I'm done. I'm done with makeup, I'm done with beauty. I did that... and then I just didn't feel done." (05:03)
• On Walking Out After Being Fired:
  "I've never felt so much relief because all the things I was angsty and worried about... went away until I got to the bottom and I was like, oh, now what?... I was embarrassed, sure. And I was triggered every time I saw the logo." (09:14–13:04)
• On Building Something New:
  "You started Bobbi 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... What does each approach really tell you about where the customer is?" (21:39)
• On Simplicity in Product:
  "If people like the stuff, it doesn't matter if it's in a Ziploc bag or a fancy jar." (26:25)
• On Leadership & Firing People:
  “If you wake up in the morning annoyed by someone every single day, you got to get rid of them.” (40:45)
• Best Advice from Leonard Lauder:
  "Never ask for permission. Beg for forgiveness." (58:49)
• On Confidence:
  “Confidence just means you’re comfortable in your skin, with who you are.” (37:18)
• On Living Beyond Her Dreams:
  "I am way above my dreams... I thought I was gonna 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." (57:40)

Timestamps for Key Segments

• Selling Bobbi Brown/Early Ambition: 02:12–04:44
• Deal with Estée Lauder: 06:54–08:13
• Getting Fired and Grieving: 09:14–13:33
• Building Jones Road & Launching in the New Era: 18:29–22:51
• Simplicity and Product Focus: 26:02–27:13
• Family, Team-building & Leadership Lessons: 28:48–34:09, 39:40–41:44
• Motherhood & Life Balance: 47:27–52:07
• On Confidence and Leadership: 37:18–40:23
• Resilience, Principles, Pride: 52:40–54:20, 57:40–58:09
• Rapid Fire (Beauty, Advice, Life): 58:10–60:40

Takeaways & Closing Thoughts

Bobbi Brown's story is a masterclass in resilience, entrepreneurship, and authenticity. She emphasizes the power of following your curiosity, the necessity of surrounding yourself with honest and supportive people (family included!), and always prioritizing the product over trends or marketing fads. Her journey shows that there are no age limits on ambition or reinvention, and that staying true to yourself—personally and professionally—is the most sustainable form of success.

For anyone aspiring to carve their own path, Brown’s humility, openness to learning, practical approaches, and refusal to be boxed in by age or convention are nothing short of inspiring.