Episode 254 Sophia Amoruso built Nasty Gal into a company valued at hundreds of millions of dollars and became one of America’s richest self-made women before reinventing herself as an investor, author, and entrepreneurIn this episode, I sit down with entrepreneur and bestselling author Sophia Amoruso to discuss how to rebuild, reinvent, and thrive after major setbacks. From building Nasty Gal into a $350 million fashion empire to navigating the challenges that followed, Sophia shares the hard-earned lessons that shaped her entrepreneurial journey. We dive into the realities of failure, the power of resilience, and why imposter syndrome can actually be a secret weapon for growth. Sophia also reveals the biggest challenges of running a fashion business, how to build a successful brand online, create products people actually want to buy, and launch a seven-figure business without becoming overwhelmed. Whether you’re an aspiring entrepreneur, growing a business, or recovering from a setback, this episode is packed with practical advice, mindset shifts, and inspiration to help you achieve your financial and business goals. Guest https://www.sophiaamoruso.com Sophia Amoruso If you’re just finding me for the first time today, let me briefly introduce myself: I'm a misfit community college dropout from Northern California. I started selling vintage clothing on eBay when I was 22, called it Nasty Gal, and eventually scaled the business to over $100 million in annual revenue. Then I wrote an 18-week New York Times Bestselling book about it called #GIRLBOSS that sold 500,000 copies, and was adapted into a Netflix series (weird!) produced by Charlize Theron (weirder!). In 2020, I launched a digital course and membership called Business Class, where I teach entrepreneurs how to build businesses. It’s a pretty massive program, with over 8 hours of lessons taught by yours truly, 100 hours of video trainings, and 300 pages of worksheets to work through. Over the course of my career, I rather accidentally became an angel investor, writing over $1m worth of checks into over 20 companies like 1stDibs, Liquid Death, Eight Sleep, Therabody, Ceremonia, and Kindbody. From this, I realized I had great access to deals and loved helping founders. So in 2022, I decided to raise a venture capital fund called Trust Fund. Since then, I’ve invested in 14 early-stage software companies (see the full portfolio here), and have found the support of legendary backers like Marc Andreessen, Jason Calacanis, David Sacks, Paris Hilton, Andrew Chen, Jeff Jordan, Jeremy Liew, Ev Williams, Anthony Noto, Sam Parr, Andrew Wilkinson, and Codie Sanchez, to name more than a few. Host Olyasha Novozhylova @notbasicblonde_ NotBasicBlonde Podcast @nbbpodcast
