How Sophia Amoruso Turned a Side Hustle Into a $350M Brand (Nasty Gal)

Sophia Amoruso built a $350M fashion empire from her bedroom—and lost it all before rebuilding her life from the ground up. In this episode of The Burnouts, the original “Girlboss” and founder of Nasty Gal joins Phoebe Gates and Sophia Kianni for her most unfiltered conversation yet. From selling thrifted clothes on eBay to becoming a CEO on magazine covers, Sophia reveals how she built a cult brand that defined a generation—and what really happened when everything came crashing down. She opens up about walking away from a company she founded, navigating bankruptcy, and learning to lead with empathy instead of ego. Sophia also shares the untold lessons behind Girlboss, why she believes failure is her greatest teacher, and how she’s redefining success through her new venture fund, Trust Fund. Whether you’re building your first business, chasing creative independence, or trying to rebuild after a setback, this conversation is a raw, honest masterclass in resilience, reinvention, and freedom. Chapters 00:00 – From eBay seller to $100M brand 05:00 – Building Nasty Gal and first hires 10:00 – Leaving eBay and going solo 13:00 – Going viral before social media 18:00 – Raising venture capital too soon 24:00 – The downfall and lessons learned 30:00 – How Girlboss was born 35:00 – Starting over with Trust Fund 40:00 – Life in London & redefining success 46:00 – The truth about ambition and burnout 🔗 FOLLOW US Phoebe Gates Sophia Kianni Sophia Amoruso 🔥 FOLLOW THE BURNOUTS Instagram TikTok Linkedin 📲 Support What We’re Building Phoebe and Sophia aren’t just your hosts—they’re the founders of Phia , a fashion-tech app that helps shoppers find the best prices across retail and resale. Try it out and join the movement. About The Burnouts The Burnouts brings you raw, unfiltered conversations with today’s most iconic founders, creators, and entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond headlines to share the real stories, lessons, and mindset shifts that define your 20s. Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and Tommy Hilfiger. 🛎️ Subscribe for more unfiltered stories on success, failure, and everything in between. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.