From billion-dollar brand to blank slate: Bobbi Brown’s comeback

Masters of Scale

WaitWhat

Entrepreneurship, Business, Management, Reid Hoffman, Mindset, Diversity & Inclusion, Jeff Berman, Bob Safian, Startups

4.6 • 4.4K Ratings

🗓️ 6 November 2025

⏱️ 42 minutes

🔗️ Recording | iTunes | RSS

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Summary

She built her first company, Bobbi Brown Cosmetics, into a billion-dollar brand. But when things soured between her and her parent company, Estée Lauder, she had a choice: retire from the industry, or reinvent herself with a new brand. Brown joins host Jeff Berman to reveal the lessons she learned from scaling – and leaving – her first company. She’s leveraging those decades of insights now in her new venture: Jones Road Beauty.

Still Bobbi: https://www.simonandschuster.com/books/Still-Bobbi/Bobbi-Brown/9781668082171

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Transcript

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0:00.0	If you're a Y-combinator founder hitting Series A, you could be hearing one phrase that keeps stalling big enterprise deals.
0:07.6	We love your product, but we need to see your SOC2 report to make sure our customer data is protected.
0:13.7	Compliance becomes a bottleneck.
0:15.9	But there's a shortcut, AWS.
0:18.7	AWS already maintains SOC2 compliance across more than 100 services, from Cloud Trail to
0:24.8	Security Hub, meaning instead of building it from scratch, you can inherit it and focus on
0:29.8	scaling.
0:30.7	It's the same playbook startups like Supabase and Substack used to unlock enterprise customers
0:35.6	fast.
0:37.0	Turn compliance from a roadblock into a competitive
0:39.6	advantage. Get up to $100,000 in AWS credits and a free SOC2 consult at startups.AWS.
0:48.3	The business world moves fast, and you don't have time to wait for your AI to turn into ROI.
0:54.4	Because any business can use AI.
0:56.8	The real breakthrough is how you use it.
0:59.4	IBM helps you turn AI into more than potential.
1:02.3	It helps you turn it into smarter ways of working and ultimately scaling.
1:06.3	Let's create smarter business, IBM.
1:09.7	My husband, he came to me and he said, all right, we've agreed on everything except they would
1:16.4	like you to sign a 25-year non-compete.
1:19.9	I started counting on my fingers.
1:22.9	25.
1:23.6	I'm going to be in my 60s.
	...

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