Bobbi Brown moved to New York with a love for makeup and zero connections. She cold-called agencies from the Yellow Pages, landed her first gig, and quickly saw a gap in the industry: everything looked artificial. She believed makeup should make women look like the best version of themselves—not like they’re wearing a mask. That belief turned into a $75M brand sold in 70 countries.

In today’s Storytelling for Entrepreneurs newsletter, I’ll share her cosmetics journey along with:

• 3 storytelling lessons from Bobbi you can emulate today

• Why emotionally connected customers are 52% more valuable

• A mvideo on building a brand with authenticity

Enjoy this all natural journey down the makeup aisle…LG

Founder Tip: Bobbi Brown, Bobbi Brown Cosmetics

When she was a young girl growing up in the Chicago suburbs, Bobbi Brown loved makeup. She would sneak into her mother’s stash and apply blush to her dolls, her siblings, and—when no one else was around—even the family dog. 🐕

She was mesmerized watching her glamorous mother get ready, whether for a night out or just a trip to the grocery store. 

Even then, Bobbi sensed that makeup wasn’t just about looking good—it was about expressing something real, something beautiful, from the inside out.

After bouncing around colleges and struggling to find her purpose, Bobbi hit a crossroads. When she told her mother she wanted to drop out, her mom gave her a gift that changed everything: 

That suggestion led Bobbi to Emerson College in Boston, where she earned her degree in theatrical makeup photography. 

Armed with a new degree, a beginner’s portfolio, and a dream to be a makeup artist, she moved to New York without knowing a soul. When she arrived, she started cold calling photographers and modeling agencies in the Yellow Pages. 

It took time. The first six months were full of rejection and empty promises. Then came her break: assisting a makeup artist on a GLAMOUR Magazine shoot. When the lead artist fell ill, Bobbi stepped in. That one opportunity opened doors to working with top photographers and publications.

Along the way, she discovered something was missing. The industry was saturated with lipsticks that were dry, greasy, or too artificial. Bobbi’s style—natural, understated beauty—clashed with the products available. 

She wanted shades that made women look like the best version of themselves, not like they were wearing a mask.

On a shoot in the late ’80s, she met a chemist at Kiehl’s and pitched him her idea: a lipstick that didn’t smell, stayed on, wasn’t greasy or dry, and looked like lips—only better. He agreed to make it. Bobbi sent him a mix of eye pencil and blush as a swatch. Together, with $10,000, they developed 10 wearable shades and called it Bobbi Brown Essentials.

The early days were grassroots. She sold her lipsticks from home by mail order. A friend at Glamour Magazine wrote a few lines about the new line and included Bobbi’s phone number. The article ran. The phone didn’t stop ringing.

At dinner one night with a group that included her husband (a business attorney), a PR firm owner who once hired her, and a cosmetics industry veteran, the conversation turned into a business plan. In one of those moments that sounds like fiction, Bobbi learned the cosmetics veteran had recently bought a house in Florida—from her mother. Fate, it seemed, was on her side.

Next came the kind of chance encounter most entrepreneurs dream of. At a party, she met the cosmetics buyer from Bergdorf Goodman. Bobbi pitched her on the spot. 

A few days later, Bergdorf agreed to carry the line. Then they backed out. But Bobbi, now learning the art of the bluff, told them Saks was interested (which was kinda true). Bergdorf changed their minds and Bobbi Brown Essentials launched there weeks later.

She hoped to sell 100 lipsticks that first month. She sold that many on the first day.

Within two years, the brand landed at Neiman Marcus. Four years later, Estée Lauder came calling with an offer. The acquisition was reportedly around $75 million. Today, Bobbi Brown Cosmetics is one of Estée Lauder’s most successful brands, sold in over 70 countries.

Storytelling Lessons: Beauty & Belief Comes from the inside

Bobbi Brown’s set out to solve a problem and help women feel more confident in their own skin. Her focus on authenticity, belief, and creating something that enhanced rather than masked became central to her business. That clarity shaped her brand—and her story. Here are three storytelling lessons founders can take from her journey:

1. Speak Their Language, Not Yours - The Power of Relatable Connection

   Bobbi created a story that spoke directly to women who were tired of the heavy, artificial makeup trends of the 1980s. She framed her brand around the person, not the product. Her message was clear: “You’re already beautiful. Her real-world tone made women feel like she ‘got them’, and that connection is what fueled loyalty.

   
   Reframe your origin story. Focus less on the specs of your product or service, and more on the people you serve. Ask yourself: What frustration did I solve for my customer? Speak to your audience the way they speak to themselves in the self-talk language we all use. 
   

2. Confidence is Contagious - Believe in Yourself—and Your Customer

   Bobbi believed in the women she was creating it for. Her philosophy was bold and deeply personal: real beauty isn’t about perfection, it’s about confidence and authenticity. Instead of talking about transformation, she focused on enhancing what was already there. That confidence gave her customers permission to believe in themselves, too.

   
   Own your voice. Let your passion and conviction shine through your story. Make your audience feel not just that you believe in your product, but that you believe in them. 
   

3. Stand for Something Bigger - Create a Lifestyle, Not Just a Label

   Bobbi didn’t just sell lipstick—she sold a philosophy based on a gap in the market and filled it with a message: “You don’t have to conform to look beautiful.” Her brand was a rejection of impossible beauty standards and a celebration of individuality. It empowered women to embrace who they are—lines, bumps, quirks and all.

   
   Define the deeper why behind your brand. What movement, lifestyle, or philosophy do you stand for? Great storytelling goes beyond features and benefits. It taps into values. Make your audience feel like they are part of something meaningful and watch it turn into long-term brand love.

Fun Fact:

Bobbi Brown didn’t just sell lipstick—she sold confidence, authenticity, and connection. According to a Harvard Business Review study, customers who feel emotionally connected to a brand are 52% more valuable than those who are simply satisfied.

They buy more, buy more often, and recommend more. Bobbi’s success proves that when your story taps into what people feel—not just what they need—you don’t just earn a sale, you build lasting loyalty. Connection isn’t fluff. It’s ROI.

Video to Watch:

In this The BUILD Series “Bobbi Brown Chats About Her MasterClass On The Fundamentals Of Makeup” interview, beauty icon Bobbi Brown shares how she built a career by doing things differently, embracing natural beauty when the world leaned toward bold trends.

She discusses her lifelong role as a teacher, her belief that beauty starts from within, and how her lesson helps women of all ages enhance what makes them unique. A must-watch for founders looking to build a brand rooted in authenticity and purpose.

Storytelling for Entrepreneurs Issue #030 - The $75M Power Of Natural Beauty And Connection


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