Choices We Made: Magazine Makeup Artist or Cosmetics CEO? (with Bobbi Brown)

Bobbi Brown, Founder of Jones Road Beauty, joins Sam fresh off the plane from Paris to discuss her new book, Still Bobbi, and to explore her career trajectory from behind-the-scenes makeup artist to two-time cosmetic company CEO. Bobbi talks about how some of her most important choices were choosing men—both her husband, who she knew within weeks was “the one” and Leonard Lauder, who she decided to sell her eponymous makeup brand to when it wasn’t even for sale. They talk about the importance of knowing who you are and when to stop trying out other personas, why at their age it’s necessary to prioritize being able to lift your own suitcase, and the common sense of “no-makeup makeup.” Bobbi tells Sam she is a life-long “non-agonizer” and how her big regret in life not getting a photo with Tammy Faye Baker when she had the chance, and how in her 60s she’s become an accidental Tik Tok influencer. Keep up with Samantha Bee @realsambee on Instagram and X. And stay up to date with us @LemonadaMedia on X, Facebook, and Instagram. For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

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Choices We Made: Magazine Makeup Artist or Cosmetics CEO? (with Bobbi Brown) is an episode from Full Release with Samantha Bee by Lemonada Media.

This episode is 47:20 long.

This episode was published on Dec 25, 2025.

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