What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next?

In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition, and finding meaning beyond business.

Timestamps:

00:00 Intro

01:56 Family background and kids

03:47 Childhood struggles and early mindset shift

06:32 Discovering Wayne Dyer and self-growth

09:00 Letting go of law school plans

09:46 Intuition and coping mechanisms

13:25 Selling fax machines and rethinking her path

14:17 The idea for Spanx is born

18:40 Building Spanx and landing Neiman Marcus

22:37 Growing Spanx without advertising

25:30 Selling Spanx and facing an identity shift

31:51 Midlife change and grief

34:44 Creating Sneaks brand

43:54 Psychology behind the second venture

47:32 Perimenopause, health issues, and PMDD

50:19 Modern Elder Academy experience

53:37 Focusing on presence and meaning

55:42 Introverts, extroverts, and integration

58:17 Feminine energy as a superpower

59:42 Wisdom bumpersticker

1:02:26 Chip’s final thoughts

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