Show notes
Bobbi Brown has spent her life helping people embrace who they are. Embracing herself—strengths and weaknesses—has also proven to be a powerful career strategy.
The veteran makeup artist and founder of the eponymous cosmetics line built her empire on the belief that people are most beautiful when they love who they are. This natural approach to makeup went against the over-the-top aesthetic of the 1980s—which, at the time, critics said would be her undoing—and people couldn’t get enough of her.
“My hope is to help women everywhere understand that being who you are is the secret to lasting beauty,” she writes in her book Pretty Powerful.
Powered by that philosophy, Brown became known as a makeup artist to the stars, touching up the faces of Carla Bruni, Katie Holmes, and Michelle Obama, to name a few. With characteristic warmth, she treats even the biggest of celebrities like old friends. A video for HELLO! Canada shows Brown in the back seat of an Uber with actress Meghan Markle, dishing out makeup tips and jamming to Biggie Smalls. As they part ways, Brown tells the now-Duchess of Sussex, “Text me later.”
Whether she’s getting celebrities ready for their close-ups or hobnobbing with the rich and famous in the Hamptons, Brown remains refreshingly down to earth. “One of my best attributes in life…is I'm incredibly naive,” she tells Foundr. “I think everything is going to work out.”
And for Brown, a lot of it has. She scored big with her first job out of college as a freelance makeup artist, catching the eye of Vogue, which hired her for a cover shoot with Naomi Campbell. In 1991, with just 10 lipstick shades, Brown launched a cosmetics line that she would sell to Estée Lauder four years later, and continue to work at for more than 20 years after that. When Brown stepped away in 2016, she left behind a billion-dollar company. And in the midst of all that, she met the man of her dreams, Steven Plofker, to whom she has been married for 30 years.
Yes, she has had an illustrious life and career. But one look at her latest projects makes it clear—Bobbi Brown is just getting started.
On Being Boss Again When she left Bobbi Brown Cosmetics (which she calls her “first baby”), the beauty world was stunned. But the company was no longer in her direct control, and she was eager to be back at the helm.
“I realized that it was time for me to be the boss again because that's really what makes me happy,” she explains. “I like to be in charge, and I like to work with really fun, cool people to create things.”
And that’s exactly what she’s been doing. Her first project after leaving the company was to write and promote a book, Beauty From the Inside Out, a lifestyle guide that details recipes, nutrition recommendations, and confidence-boosting tips. This was a nod to Brown’s aspirations to broaden her scope from cosmetics to general health and wellness.
“I don't like a lot of makeup,” says Brown, who is an outspoken opponent of contouring, using darker shades to “reshape” parts of your face. “I don't believe women need a lot of makeup. And I think the healthier you are, the better you feel and the better you look.”
In 2017, Brown opened Just Bobbi lifestyle concept shops inside of Lord & Taylor department stores, where she curated her favorite wellness and beauty products for the public to peruse.
Earlier this year, she launched a line of wellness products, Evolution_18, on TV shopping network QVC. She also runs a film and TV studio, 18 Label Street, and her own line of eyewear, Bobbi Brown Eyewear.
And in an unexpected move, she partnered with her husband to breathe new life into a 1902 historic landmark and launch The George, a boutique hotel in their hometown of Montclair, New Jersey.
As if that weren’t enough, she’s got a podcast in the works.
With so many projects, how does she maintain her focus and a sense of cohesion? “It all works together for me,” Brown says, “because it's pretty much authentic, and it's marrying, finally, really what I believe in.”
Why She Never Wants to Build Another Billion-Dollar Brand With Brown’s hard-earned success and elite status comes perhaps the greatest privilege any entrepreneur can obtain: the power to say no to otherwise enticing opportunities. She says many of her friends in venture capital have asked her, “How many millions do you want?” in an eager bid to invest in her projects—regardless of what those projects are.
“Look, it's very tempting,” Brown says of the investment offers. “But I don't want it.”
For entrepreneurs who have pounded down the doors of VCs hoping to snag just one investor, that outlook may be difficult to understand. But for Brown, it’s all about freedom.
“I don't want to have to report to anyone,” she says. “I don’t want to sit in meetings.”
While many tout the venture model of forgoing profitability now in order to borrow money, spend it on growth, and sell the company later, that’s not Brown’s style. If she were to sell 500 bottles of vitamins, for example, she says she would reinvest the profits by ordering 1,000 more bottles and keep growing incrementally from there.
“I'm very simple-minded,” she says. “I know it makes no sense, but I really do believe in making a profit.”
So, for now, she’s content to bootstrap, even if that means slower growth or a smaller business. “I never want another billion-dollar brand. … I never want to go that big again because the headaches that come with it are not worth the rewards.”
Reflecting on the expansion of Bobbi Brown Cosmetics, she calls the first 15 to 17 years “amazing,” but says that as the company grew, her control over it diminished. “I'm not the boss anymore,” she says, “which is why I'm not there.”
Beauty, Glam, and Instagram So if Brown is hesitant to grow her new businesses too big or too fast, and still wants to be able to call the shots, what is her plan for growth? A lot of it revolves around working her connections—especially the connection to her audience.
Back when Brown launched her career as a professional makeup artist, and even later as a cosmetics line founder, there was no such thing as social media or ecommerce. To get her products off the ground, she started mailing out lipsticks until one day, a New York department store agreed to carry them. In the digital age, when brands have direct access to consumers online, Brown is thriving.
“The internet is an amazing place for people to go on and really look and find the community they need,” she says. “Whatever you're going through, there is a support group for that. There are people teaching and empowering.”
Brown is active on Instagram (in fact, she manages at least four accounts), where you can find anything from the announcement of her latest probiotic product to photos of her recent trip to Paris. On Facebook, she hosts a weekly live broadcast where she interviews everyone from Gary Vaynerchuk to her Aunt Alice. And the best part? These episodes don’t cost her a thing; they’re shot on her smartphone.
“There are so many ways for people to start their own brands,” she says. “There's a lot to teach and a lot to learn.”
Making It Up as She Goes By this point, Brown may seem unstoppable. But she’ll be the first to tell you that accepting her weaknesses has made her a stronger entrepreneur by forcing her to embrace her strengths, and get help with everything else. It’s similar to her approach to cosmetics. As a makeup artist, Brown refuses to hide clients’ “flaws,” preferring instead to accentuate their natural beauty.
“It's such a sign of strength for someone to know what they're not good at,” she says. “And I think a lot of…people starting to be entrepreneurs think they could do everything, and you can't.”
For instance, Brown doesn’t know how to type—but she’s written nine books. At times, she gave an assistant her handwritten notes and had them transfer them to digital; other times, she had writers interview her and take the information down for Brown to edit. “What you're not good at, find someone that is and tell them what to do.”
Her sharp sense of self-awareness was honed from a young age. Growing up, she struggled in school and didn’t have access to tutoring. “Either my parents punished me or they said, ‘Oh well, she'll never be a secretary.’ They were right…because I dropped out of typing because I couldn't figure it out.”
From those early experiences, she learned a valuable lesson. “I had to figure out, like, almost coping mechanisms. I don't know if I had learning disabilities. I wasn't good at something, but I knew I had to do this.”
When conforming to convention didn’t work for her, Brown would develop her own distinct approach. For example, the first time she wrote a book, she followed the rules: write the book, edit it, then source the photos. But it was extremely difficult for her. So with her last couple of books, she did photo shoots first, then put the book together based on the photos, then had the writers write. “I drove my publishers crazy,” she says. But for her, it worked better.
So if there’s something essential you don’t know how to do? “Figure it out,” Brown says. “That’s my only advice.”
Happiness Never Goes Out of Style In many ways, Brown has been a contrarian in an industry that is notoriously cookie-cutter. And maybe that’s been the key to her success. While she used to compare herself to the supermodels she worked with, she’s learned to be comfortable in her own skin. When people told her things had to be done in a certain way, she forged ahead with her own process and succeeded. But even with her many accomplishments, Brown doesn’t subscribe to any notion of perfection or “having it all.”
“I'm not tall and blond and athletic, which I always wanted to be,” she says. “I can't sing. I can't draw. But I have a sense of humor, and I have a lot of friends. I've been married 30 years…I have three amazing boys that I adore…and I've been able to be an entrepreneur.”
“Is that having it all?” Brown says. “No—there’s no all. But I'm happy with what I have.”
Key Takeaways Why Brown never wants to create another billion-dollar brand
Her philosophy on what makes entrepreneurs strong
What she believes is the ultimate secret to lasting beauty
How to accept your weaknesses as an entrepreneur and forge ahead in spite of them