Totally Booked with Zibby — Bobbi Brown, STILL BOBBI
Original Air Date: September 23, 2025
Host: Zibby Owens
Guest: Bobbi Brown, author of Still Bobbi: A Memoir
Episode Overview
This episode features an in-depth, candid conversation between Zibby Owens and beauty industry icon Bobbi Brown, centering on Bobbi’s new memoir Still Bobbi. The discussion moves fluidly across Bobbi’s evolution as an entrepreneur, mentor, mother, and creative. Bobbi shares lessons learned over decades at the helm of two major beauty brands, the challenges of balancing ambition with family, and her unfiltered personal perspective on body image, business, aging, and authenticity.
Key Discussion Points & Insights
1. Why Write a Memoir Now?
[04:02–05:14]
- Bobbi talks about being approached unexpectedly by a literary agent who petitioned her to share her journey in a memoir.
- Initially resistant ("I'm not ready for a memoir. I mean, I'm not done." [04:30]), but convinced of the power of her story to help others.
- The writing process involved finding the right collaborator and weaving together her personal and professional lineage—from her grandparents to her own grandmotherhood.
2. On Confidence, Vulnerability & Naivete
[05:44–06:31]
- Zibby notes how Bobbi authentically shares both her areas of deep confidence and moments of self-doubt.
- Bobbi reflects:
"I have this quality that I wish I could pass on to people, and that's just being naive. I'm just really naive. And don't think something's not going to work. And then when it doesn't work, all right, that didn't work. Let me move on now." [05:58]
3. Business Innovation: Accidental Origins of Her First Product
[06:31–07:44]
- Story behind the first Bobbi Brown lipstick—born from her needs as a working makeup artist, mixing her own concoctions ("cream blush and ... Vaseline and ... taupe pencil").
- Meeting a chemist by chance who turned that blend into her original product:
"That's how I started." [07:44]
4. Mentorship and Navigating Corporate Growth
[07:44–09:13]
- Leonard Lauder played a crucial role as an early mentor, along with other pivotal figures.
- They demystified corporate language and empowered her unique approach:
“I didn’t have to feel bad because I didn’t have the same understanding... when I understood exactly what they were talking about, I'm like, 'Oh yeah, you know what you should do? This is what you gotta do to fix it.'" [08:40]
5. The High Cost of Success & Burnout
[09:13–11:15]
- Bobbi is frank about the toll of leading a brand through massive growth, debunking external assumptions about her "perfect" life.
- The last year with her first company was particularly difficult:
“I was on autopilot... Did I like doing it? ... I enjoyed moments of it. But, you know, overall it was, it was pretty grueling.” [10:05]
- She emphasizes perspective and gratitude for being able to reconnect with positive memories after moving on.
6. Jones Road: Launching a Second Act
[11:15–12:51]
- Contrasts starting her first brand in department stores to leveraging social media for Jones Road: “Now you put something on social media and you've reached a couple hundred thousand people in two minutes.” [11:47]
- This time, she’s more efficient, avoids unnecessary bureaucracy, and values being “the boss again.”
7. Motherhood & Work: Defining Her Own Balance
[12:51–15:44]
- Bobbi describes her intent focus on family—even when the system didn’t encourage it.
- Turned work-life friction (like long commutes) into time to get organized, and unapologetically prioritized being present for her kids.
"Raising kids, to me is the best job in the world. But I was not equipped to be a stay at home mom, not for a nanosecond.” [13:47] “There were times where I said no to a big, fancy, ... corporate dinner because I wanted to do those things with my kids. I just realized it made me happier.” [15:40]
8. Body Image & Talking About Aging
[15:44–18:09]
- Open about the pressures and realness of body image—her own and the unspoken struggles of women, including celebrities.
- Cherishes functionality and strength (“I’m able to pick up my grandkids... sit on the floor and get up without my hands... put [my suitcase] up on the airplane.” [16:44])
- Finds freedom in no longer aspiring to impossible beauty standards:
“I’ll never look like a supermodel. And guess what? I don’t care anymore.” [17:18]
9. Authenticity & What Real Beauty Means
[20:29–26:56]
- Bobbi stresses bringing out the best in each person, not projecting an ideal.
- Advises women to seek help from experts, try things, and follow what makes them feel comfortable (“I like to look less dressed up than anyone in the room. Like, I'm comfortable that way and I think I look the best.” [22:38])
- Shares how seeing actress Lorraine Bracco show up to an event makeup-free and comfortable inspired her.
“It was the first time I saw someone show up looking like that. And it kind of helped me realize... I could be like that, too.” [24:37]
10. Retirement is Not in Bobbi’s Vocabulary
[26:56–29:58]
- She laughs off the notion of retirement:
“Retirement sounds like you’re tired...I can’t imagine myself ever not doing something that I can’t wait to do when I wake up in the morning.” [26:56]
- Besides Jones Road, she’s balancing multiple projects—including co-owning and Instagramming for a boutique hotel, The George.
11. The George Hotel: A Family Business
[27:40–29:58]
- Describes how she and her husband developed the boutique hotel from a derelict building, designing every detail hands-on and creating meaningful partnerships.
Notable Quotes & Memorable Moments
-
On Naivete as a Superpower:
“I always say that I have this quality that I wish I could pass on to people, and that's just being naive. I'm just really naive. And don't think something's not going to work. And then when it doesn't work, all right, that didn't work. Let me move on now.”
— Bobbi Brown [05:58] -
On Corporate Imposter Syndrome:
“You could feel like, ‘Oh, I must not be smart enough or I don't have the experience to be sitting in this table.’ But when I understood exactly what they were talking about, I'm like, ‘Oh, yeah, you know what you should do? This is what you gotta do to fix it.’”
— Bobbi Brown [08:40] -
On Motherhood and Prioritizing Family:
“There was times where I said no to a big, fancy, ... dress up corporate dinner or some fabulous dinner because I wanted to do those things with my kids. I just realized it made me happier.”
— Bobbi Brown [15:40] -
On Body Acceptance:
“I'll never look like a supermodel. And guess what? I don't care anymore.”
— Bobbi Brown [17:18] -
On Authenticity in Beauty:
“I like to look less dressed up than anyone in the room. Like, I'm comfortable that way and I think I look the best.”
— Bobbi Brown [22:38] -
On Never Retiring:
“Retirement sounds like you’re tired...I can’t imagine myself ever not doing something that I can’t wait to do when I wake up in the morning.”
— Bobbi Brown [26:56]
Segment Timestamps
- 00:00–03:48: Ads, show intro, guest bio
- 03:48–05:14: Bobbi’s initial hesitation and process of writing her memoir
- 05:14–06:31: Discussion of confidence vs. vulnerability and its origins
- 06:31–07:44: Story of creating her first signature lipstick
- 07:44–09:13: Value of mentors and navigating male-dominated business
- 09:13–11:15: The personal cost of business growth, burnout, shifting perspective
- 11:15–12:51: Founding Jones Road, lessons learned, and new freedoms
- 12:51–15:44: Balancing motherhood and work, sense of identity
- 15:44–18:09: Body image, aging, and honest conversations
- 20:29–26:56: Beauty authenticity, simplicity, daily routines, and makeup
- 26:56–29:58: Dismissing retirement, multi-project life, building The George hotel
- 29:58–32:12: Talking retreats, reading, and collaboration ideas
Tone & Takeaways
The tone is honest, warm, and humorous, marked by Bobbi’s “what you see is what you get" personality. She and Zibby connect over shared experiences as working mothers. Bobbi’s story is less about a linear path of ambition and more about adaptability, resilience, and staying true to oneself. Authenticity, simplicity, and real connections—whether through makeup, work, or family—are central.
For listeners:
This episode is packed with gems on balancing career and family, why it’s never too late for a reinvention, and the importance of owning your story. Bobbi’s relatable wisdom and Zibby’s thoughtful questions make this essential listening, whether you’re interested in beauty, business, or just living with a bit more confidence and self-kindness.
For more information about Bobbi Brown's memoir, Jones Road Beauty, or Zibby’s retreats and literary projects, visit zibbymedia.com.