Podcast Summary: On with Kara Swisher
Episode: Makeup Mogul Bobbi Brown on Reinventing Herself in Her 60s
Host: Kara Swisher (Vox Media)
Guest: Bobbi Brown
Date: October 6, 2025
Overview
This episode centers on Bobbi Brown, the trailblazing makeup artist and entrepreneur, who discusses her journey from launching Bobbi Brown Cosmetics to reinventing herself with a new beauty brand, Jones Road, in her late 60s. Kara Swisher explores Brown’s business philosophy, resilience after corporate setbacks, and her candid perspectives on the evolving beauty industry—including the impact of social media, inclusivity, and the modern challenges of beauty standards.
Key Discussion Points & Insights
1. Bobbi Brown’s Beginnings and Entrepreneurial Rise
[03:30–06:02]
- Brown started as a makeup artist in the 1980s, championing the natural look before it became mainstream.
- Her original brand, Bobbi Brown Cosmetics, grew from handmade lipsticks sold at home to a billion-dollar company.
- Sold her company to Estée Lauder, stayed on as a corporate employee for 22 years under unusually long agreements.
“You don’t need to hurt people’s feelings. You just don’t... I also didn’t want to come across like I was angry and bitter, because I’m not.”
— Bobbi Brown, [04:23]
2. Handling Failure & Reinvention
[05:17–09:17]
- After leaving Estée Lauder, Brown faced a four-year non-compete, which forced her to find new avenues.
- Launched an unsuccessful wellness brand (Evolution 18) but considers each setback a learning opportunity.
- Reinvention came with Jones Road—launched the exact day her non-compete expired, amid the pandemic.
“How do you grow and how do you learn to get better? You have to kind of go through that.”
— Bobbi Brown, [17:02]
3. Evolution of the Beauty Industry
[06:02–10:24]
- The rise of celebrity and DTC brands, the influence of YouTube/social media, and changes in retail (decline of department stores).
- Early PR came through traditional media—TV appearances like Today Show helped her teach rather than just promote products.
- Difficulty for big conglomerates like Estée Lauder to adapt to fast-changing consumer habits.
“All of a sudden, these people started showing up and like, hi, I’m your new head of International... I wasn’t included in... running and growing the brand.”
— Bobbi Brown, [15:57]
4. Life Inside the Corporate Beauty Machine
[09:23–17:02]
- Brown describes her difficulties fitting into corporate culture (“nothing corporate about me”) but valued the learning and support received in earlier years.
- Tensions increased amid industry changes (the rise of contour palettes, pressure to create unwanted products), ultimately prompting her exit.
- Losing her namesake brand rights parallels other famous female founders (Kate Spade, Donna Karan).
“I used to go to work like it was my company. I never really separated myself... which was really difficult when I left.”
— Bobbi Brown, [11:29]
5. Staying & Leaving: A Deep Dive
[18:40–22:46]
- Fashion correspondent Lauren Sherman asks Brown why she stayed at Estée Lauder for two decades, far longer than most founders.
- Brown stayed for “the glory years,” close creative teams, and real fulfillment—until the magic faded and she realized it was time to leave.
- Emotional closure and reconciliation with Leonard Lauder.
“I had so much support. Those were the glory years. And every time I see some of my lieutenants... we just talk about the magic that we had.”
— Bobbi Brown, [19:32]
6. The Modern Industry: Oversaturation, Social Media, & Realness
[27:07–30:16, 35:07–42:15]
- Beauty industry is saturated; it’s easier than ever to start a brand, but many struggle to endure.
- Social media’s immediacy and reach have changed everything—Brown engages directly with critics and fans, leveraging virality to quadruple sales.
- Brown leans into realness and authenticity online rather than chasing celebrity competition.
“The game is realness. The game is how do you get people engaged?... At least people that are going to love Jones Road.”
— Bobbi Brown, [38:42]
- Jones Road is DTC; avoids most retailers, focuses on owning the customer relationship and avoiding traditional retail complications.
“Direct to consumer, we own our customer. When you’re part of another retailer, they own the customer.”
— Bobbi Brown, [41:41]
- On celebrity-driven brands: applauds some (Hailey Bieber’s Rhode) but notes most do not succeed long-term.
7. Redefining Age, Demographics & Beauty Norms
[30:31–33:29, 43:17–47:18]
- Jones Road intentionally targets overlooked demographics, especially women over 50, but stays inclusive.
- Sought to represent a realistic, age-diverse range in brand marketing, rejecting industry’s youth obsession.
- Concerned by the pressure on young people, normalization of cosmetic procedures, and trends like tweens using anti-aging products.
“You know, growing up in the suburbs in Chicago with my tall friends... I was always insecure about the way I looked. And now I look back and I’m like, I was so frigging cute in seventh grade... But it helped me understand what confidence is.”
— Bobbi Brown, [43:32]
8. Product Philosophy & Creation
[47:18–49:03]
- Product development is driven by listening to consumers both online and in person.
- Focuses on simplicity; prefers to offer fewer, more versatile products (like Miracle Balm) rather than overwhelming customers with too many choices.
“Jones Road is made not for makeup artists. It’s made for women to be able to do their makeup in a car, in a pinch, whatever it is.”
— Bobbi Brown, [38:33]
9. Advice to Entrepreneurs
[49:07–51:03]
- Brown urges new entrepreneurs to “breathe” and nurture their brands deliberately—don’t rush into funding or scaling.
- Recommends having real reasons for new ventures and understanding what truly differentiates your business.
- Admits her own mistakes—moving too quickly, bad hires—and emphasizes honest self-reflection.
“First of all, to breathe. Like, no one tells entrepreneurs to breathe... You need to nurture this baby... look at what’s out there and how is yours different?”
— Bobbi Brown, [49:36]
“Not breathing. It’s easy to give advice. You know, I definitely don’t breathe. I don’t calm down. Probably the biggest mistakes I’ve made are hires that I’ve done that are not good.”
— Bobbi Brown, [50:31]
Memorable Moments & Quotes (with Timestamps)
-
On not writing a tell-all:
“I didn’t want to come across like I was anger and bitter because I’m not… I looked at it as failure. They canceled my work contract and to me that was being fired.”
— Bobbi Brown [04:23] -
On rejecting industry pressure:
“Why do you need to tell someone that they have to change the shape of their face?... When most people do contour on themselves, it looks like they have dirt.”
— Bobbi Brown [14:04] -
On losing her brand:
“…there was so many emotions. And yes, I definitely saw similarities with a lot of these women founders… It happens. Like, shit happens, and then it’s what you do with the shit that defines you.”
— Bobbi Brown [17:02] -
On authenticity in social media:
“It’s not anymore the fabulous things. It’s the real things, I think, that get people engaged.”
— Bobbi Brown [38:42] -
On the purpose behind Jones Road:
“I wanted to kind of clean the slate, start all over again, and just, like, teach women how. All you need is the minimum.”
— Bobbi Brown [29:39] -
On advice to entrepreneurs:
“First of all, to breathe. Like, no one tells entrepreneurs to breathe. You have to breathe. Everyone is such, I need a series A, I need a series B… Calm down.”
— Bobbi Brown [49:36]
Notable Segments (Timestamps)
- Estée Lauder Sale and Corporate Life: [09:23–13:08]
- Industry Changes & Rise of Social Media: [06:02–10:24], [35:07–39:43]
- Launching Jones Road & Target Demographics: [28:20–33:29]
- Expert Question (Lauren Sherman/Puck News): [18:40–22:46]
- On Modern Beauty Standards & Pressures for Youth: [43:17–47:18]
- Entrepreneurial Lessons: [49:07–51:03]
Conclusion
Bobbi Brown’s story is one of resilience, clarity of purpose, and staying true to one’s values through seismic shifts—both personal and societal. Brown’s candor and strategic thinking offer practical wisdom for entrepreneurs across industries, as does her insistence on authenticity, simplicity, and listening to consumers. The episode is a masterclass not just in business reinvention but in navigating power, ego, and change with grace.