Bobbi Brown

28 Oct

The Pioneer

Season 001 / Episode 012 · October 6, 2026 · 1 hr 1 min

Beauty icon Bobbi Brown, the makeup artist behind the “no makeup” makeup revolution, takes us back to growing up outside Chicago, never quite feeling pretty, and the conversation with her mother that sent her to Emerson to build her own degree in theatrical makeup and photography. We trace her path from a 1980 move to New York and working alongside photographer Bruce Weber, to launching Bobbi Brown Cosmetics out of her house in 1991, and selling it four and a half years later with a 25-year non-compete attached. Bobbi shares how that non-compete quietly set the launch date for Jones Road, and how the pandemic made launching it even harder.

Tune in for a conversation about trusting your gut over the data, why “beg for forgiveness, not permission” might be the only business advice you need, and what it looks like to disrupt the beauty market twice without losing yourself in between.

Quote card: Things reveal themselves in time. Bobbi Brown on time as our teacher.

Literary layout card for Season 001, Episode 012 with Bobbi Brown

Radial moodboard for Episode 012 with Bobbi Brown

Fig. 01 — From the episode archive

Guest Questionnaire

The Questionnaire

Favorite work of art?: Anything by Donald Robertson
Favorite quote or mantra?: What if? Why not?
Favorite book of yours?: Breaking Night by Liz Murray
Favorite time of day?: Before bed, in bed at 11pm
Favorite movie?: Love Story
Album or musical artist you have on repeat?: Shaboozey
Favorite type of tree, plant, or flower?: Peony

Illustrated portrait of Bobbi Brown — Fig. 02 — Bobbi Brown, *The Pioneer*

Three Questions on Time

Take Your Time Back

If everything on your calendar tomorrow was canceled, what would you do?
Exercise, walk, and check in with friends and the important people in my life — then probably call someone to tell them about a new idea I had.
Time is the only thing you can’t fake. What’s something you could have only learned over time?
Never, ever ask for permission. Just beg for forgiveness.
When does time stand still for you?
Honestly, it doesn’t — it just keeps going. But it comes closest in the slow winters in Florida while my husband golfs, and I notice how fast it’s moving every time I see my grandkids, who were just lying in a bassinet and are now running and jumping.

From the Episode

Show Notes

Also on Spotify · YouTube

In This Episode

0:00Opening: I Always Wanted to Be Pretty
1:22Welcome to Take Your Time
6:06Growing Up Bobbi
10:26College, Emerson & Finding Makeup
15:08Moving to New York in the 1980s
19:21Thinking Like a Customer
25:49Building & Selling Bobbi Brown
29:3622 Years at Estée Lauder
33:14The Non-Compete & Planning Jones Road
34:49Launching Jones Road During the Pandemic
44:51Retail & the Jones Road Store Empire
49:25Building a Beauty Brand Today
56:45Take Your Time Back

In Her Words

“Things reveal themselves in time.”
“Anything can be a form of meditation.”
“Yes, there’s a million competitors doing a million things. I don’t care, I say let them.”
“I don’t know how to do things the traditional way. I just don’t. I can’t do things the way other people do, and it doesn’t make sense to me.”
“I have a sense of humor and I’m not afraid to try things.”
“You can’t be an asshole. It comes back to you. You shouldn’t be.”