From Girlboss to Trust Fund: Sophia Amoruso's Bold New Era (Ep 338)

What happens when you're on top of the world—and everything changes overnight? In this raw and unfiltered episode of the Why Not Now? podcast, Amy Jo Martin reunites with entrepreneur, author, and cultural force Sophia Amoruso. This is Sophia's second time on the show, nearly a decade after her first appearance. From founding Nasty Gal and Girlboss to navigating public scrutiny, financial highs and lows, and deeply personal transitions, Sophia opens up about what she's learned from building (and rebuilding) her life and career. You will get a rare behind-the-scenes look at the real woman behind the brand, including her thoughts on intentionality, burnout, reinventing your identity, and learning to say "Why Not Stop?" as much as "Why Not Now?" Sophia shares her approach to time, money, trust, and relationships - with a refreshingly honest take on startup culture, success, and failure. You'll also hear about her latest venture, Trust Fund; a disruptive early-stage investment fund, and her unexpected passion for poker, which she's parlayed into strategic business development. She also shares what she's learned about ambition, regret, and aging gracefully in the spotlight. Learn more about Sophia: Get Amy Jo's newsletter: amyjomartin.com/newsletter Watch Amy Jo's Speaking Reel: amyjomartin.com/speaking Learn more about Renegade: Learn more about the Renegade Accelerator: Follow Amy Jo… Instagram: X/Twitter: twitter.com/amyjomartin Facebook: YouTube: Why Not Now? Instagram: Buy Amy Jo's book: amyjomartin.com/book Follow Renegade Global:

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From Girlboss to Trust Fund: Sophia Amoruso's Bold New Era (Ep 338) is an episode from Why Not Now? with Amy Jo Martin by Amy Jo Martin.

This episode is 52:41 long.

This episode was published on Jul 3, 2025.

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