Inside the mind of a beauty industry rebel: Bobbi Brown

Bobbi Brown changed the face of beauty in the late 80s and 90s by pioneering the natural makeup look — a philosophy that would grow into a billion-dollar global brand, Bobbi Brown Cosmetics. After selling her namesake company to Estée Lauder, she spent more than two decades inside the corporate beauty world before being abruptly pushed out in 2016. Now in her 60s, Bobbi is proving it’s never too late to reinvent yourself. With her new brand Jones Road and her memoir “Still Bobbi: A Master Class in Resilience and Reinvention,” she’s sharing what it really takes to build — and rebuild — a business. In this conversation Bobbi opens up about: Building Bobbi Brown Cosmetics into a household name What really happened when she left Estée Lauder Launching Jones Road in the middle of the pandemic Competing in today’s beauty world dominated by influencers, celebrities, and AI Her lessons on confidence, resilience, and staying true to your vision This isn’t just a story about makeup — it’s about entrepreneurship, grit, and second acts. 00:00 Intro 00:42 Building Bobbi Brown Cosmetics & selling to Estée Lauder 03:06 Leaving Estée Lauder: struggles, emotions, and lessons learned 05:00 Early PR, Today Show breakthrough, and media strategy 07:12 Launching Jones Road during the pandemic 09:27 Life inside a corporate beauty giant and industry challenges 12:06 Fighting against contour culture & staying authentic 15:24 Losing control of her brand & rebuilding identity 18:25 Why Bobbi stayed at Estée Lauder for 22 years 22:11 Fear of failure and starting over with Jones Road 24:41 Naming Jones Road & the vision behind it 26:08 Targeting women over 50 and redefining beauty standards 29:04 Social media, TikTok, and going viral 31:04 Miracle Balm and the backlash 33:05 Competing with celebrity brands 35:06 Jones Road’s retail strategy and future plans 40:01 Bobbi on teen beauty standards and social media’s impact 42:11 Innovation and product pipeline 44:15 Advice for entrepreneurs: breathe, learn, and differentiate Subscribe: https://goo.gl/FRleYo Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/42ntT7X... FOLLOW US Instagram: https://www.instagram.com/onwithkaras... TikTok: https://www.tiktok.com/@onwithkaraswi... LinkedIn:   / kara-swisher-b7213   Threads: https://www.threads.com/@onwithkarasw... Bluesky: https://bsky.app/profile/onwithkarasw...