“I just kind of do things my way,” says makeup guru, Bobbi Brown, whose appearance on today’s show proves that we are all the masters of our own destiny. Real Founder Stories often start with a simple move: say what you want out loud, then ask for it. That’s exactly how this conversation happened. Lindsay mentioned Bobbi Brown as a bucket-list guest on Instagram, and Bobbi replied, “DM me.” A reminder for female founders and women in business that sometimes promoting your business is less about a perfect plan and more about being brave enough to put the ask into the world.

In this episode of Dear FoundHer, Lindsay sits down with Bobbi Brown to unpack the Real Founder Stories behind two iconic brands: Bobbi Brown Cosmetics and Jones Road Beauty. Bobbi shares how she built her career by doing makeup “her way,” why resourcefulness is basically the job description, and what it really felt like to leave the company that carried her name. She also talks about company messaging and women in business, including how teaching and expertise build trust, brand awareness, and long-term loyalty without constant hard selling.

You’ll also hear the behind-the-scenes truth of starting over. Bobbi describes the emotional whiplash of becoming an employee after selling her company, the moment she realized it was time to walk away, and how she launched Jones Road the day her non-compete ended. These Real Founder Stories are honest about imposter syndrome, control, leadership, and the “human scaffolding” that makes growth possible.

In this conversation, you’ll learn:

• Why entrepreneurship is often “making it up” while staying clear on what makes sense
• How Bobbi used teaching to build authority, strengthen brand awareness, and support promoting your business in a way that feels natural
• What it’s like to separate your identity from your brand, and why that shift matters for women founders
• How Bobbi runs Jones Road differently, with simpler decision-making and sharper company messaging and women in business lessons
• Practical “life systems” that help you stay steady while building, leading, and growing

Real Founder Stories don’t just highlight wins. They show the tradeoffs, the pivots, the doubts, and the decisions that actually build lasting brands. If you’re growing something of your own, this episode will leave you with a clearer mindset, better language for your company messaging and women in business approach, and a few tactics you can use right away to increase brand awareness while promoting your business with confidence.

Connect with Bobbi Brown:

Instagram | http://www.instagram.com/justbobbidotcom

Website | http://www.jonesroadbeauty.com

Connect with Lindsay:

Instagram | http://www.instagram.com/dearfoundher

Get on the Marketing Made Simple Waitlist: https://lindsaypinchuk.myflodesk.com/waitlist

Dear FoundHer Forum: https://www.dearfoundher.com/dear-foundher-forum

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Hosted on Acast. See acast.com/privacy for more information.