40 Years of Business Advice in 60 Minutes (Makeup Artist Bobbi Brown)

Makeup artist, mogul, author, hotelier—Bobbi Brown has built more than one empire (and reinvented herself along the way).

In this episode of The Burnouts, Bobbi sits down with Phoebe Gates and Sophia Kianni to talk about what it really takes to build an iconic brand, sell it for millions, and then start all over again. From mixing her first lipstick with a chemist and cold-calling agencies out of the Yellow Pages, to selling Bobbi Brown Cosmetics to Estée Lauder and later launching Jones Road Beauty, Bobbi shares the unfiltered version of how she built—and rebuilt—her career on her own terms.

She opens up about confidence, burnout, and building businesses with her husband and family. Plus: the 25-year non-compete that changed everything, why “retirement” is not in her vocabulary, how she clapped back at viral TikTok criticism (and won), and the simple beauty rules she swears by for every generation.

Also: how she accidentally went from makeup artist to hotel owner, why she still cold-DMs influencers, and her #1 piece of advice for young women chasing their dream career.

🔍 CHAPTERS

00:00 – Starting Bobbi Brown Cosmetics
06:30 – Reinventing beauty around natural looks
09:20 – Vogue covers, Naomi Campbell, and early breaks
12:00 – Building a billion-dollar brand with Estée Lauder
20:00 – Family, partnership, and working with her husband
27:20 – Selling for $74M and the 25-year non-compete
30:00 – Going viral with Jones Road Beauty on TikTok
34:30 – Personal brand, social media, and DMs that changed everything
40:00 – Jones Road’s growth and what’s next
46:00 – Advice for entrepreneurs (luck vs. hard work)
51:00 – Hiring, culture, and leading a scrappy team
57:00 – Self-care, health, and why she’ll never retire

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Subscribe to The Burnouts for exclusive conversations with today’s top founders and culture-shaping entrepreneurs. Hosted by former Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, this isn’t just another founder podcast—it’s untold conversations and the unfiltered reality of what it takes to build your dream career in your 20s. Guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more visionaries defining the brands—and blueprints—of our time. Whether you’re dreaming big or building now, these are the conversations that will show you how it’s done (and what no one else tells you).

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