Harley Finkelstein and David Segal are back with Season 3 of Big Shot! Today, we chat with beauty industry icon Bobbi Brown. Known for her work as a makeup artist, Bobbi’s expertise has been showcased on the covers of leading magazines, including Cosmopolitan, Allure, Mademoiselle, and Teen. She’s the author of nine beauty books, with five achieving bestseller status.

In 1991, Bobbi founded Bobbi Brown Cosmetics, which Estée Lauder acquired for $74.5 million four years later. Bobbi had a 25-year non-compete with Estée Lauder, and as soon as that expired, she launched her latest company, a clean beauty brand called Jones Road.

In our conversation, we discuss the following: 

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In This Episode We Cover: 

(04:28) How Bobbi got started by cold-calling models and agencies 

(10:30) How Bobbi learned entrepreneurship skills at Emerson 

(12:52) Bobbi’s first lipstick and the beginnings of her makeup empire

(17:39) The Bergdorf Goodman deal that almost fell apart

(21:30) A chance encounter in an elevator that led Bobbi to her second chemist

(22:10) Meeting Jeff Zucker’s grandmother and landing a regular spot on The Today Show

(26:15) Trailblazing the natural makeup movement 

(34:10) Bobbi’s meeting with Leonard Lauder of Estée Lauder

(35:59) How Bobbi was able to prioritize her kids 

(39:20) The sale to Estée Lauder 

(42:54) How Bobbi celebrated and shared her wealth with her family 

(43:45) The first freestanding store, and how Leonard Lauder supported Bobbi

(47:00) The decline of Bobbi’s relationship with Estée Lauder that led to her leaving 

(51:30) The Just Bobbi curated collection at Lord and Taylor 

(53:30) How Bobbi moved on from the drama at Estée Lauder 

(1:00:01) Launching Jones Road

(1:08:55) Miracle Balm’s instant popularity

(1:10:20) Bobbi’s response to a TikTok influencer trashing her foundation 

(1:13:43) Bobbi’s thoughts on selling her new company 

(1:14:45) Bobbi’s partnership with her son, Cody

(1:17:03) New learnings at Jones Road

(1:18:28) Bobbi’s thoughts on chutzpah

(1:19:25) Bobbi’s perspective on health and longevity

(1:20:36) What being Jewish means to Bobbi 

(1:23:15) The secret to Bobbi’s successful marriage and partnership

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Where to find Bobbi Brown:

X: https://x.com/justbobbibrown

Instagram: https://www.instagram.com/justbobbidotcom

Facebook: https://www.facebook.com/JustBobbiDotCom

TikTok: https://www.tiktok.com/@justbobbibrown

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David Segal: ⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠

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