How do you build a $100M+ cult brand? Ask Sophia Amoruso. Branding icon. In this episode we go deep. Getting into how she built Nasty Gal from an eBay store into a $350M fashion powerhouse, bootstrapping to $28M in revenue, owning 80% at peak valuation (!!!), & crossing $100M in sales before VC funding led to bankruptcy. At the same time, she created GirlBoss—one of the first major movements for women in business & culture. It became a bestselling book, a Netflix series, & a global brand, cementing Sophia as a media & branding legend, with nearly 1M+ followers across platforms. But Sophia didn’t stop there. She started investing, getting into companies like Kindbody, Superhuman, Pipe, Liquid Death, Public. com, & Eight Sleep, & eventually launched her own VC firm, Trust Fund. Her backers include some of Silicon Valley’s most famous names: Marc Andreessen, Paris Hilton, Ev Williams (Twitter), Chris Dixon (a16z), Andrew Chen (a16z), Rob Hayes (First Round), Josh Elman (Greylock, Twitter, Facebook), Anthony Nodo (CEO of SoFi), & yes, even Jason Calacanis (@Jason).. Impressive. Highlights: (00:00) Branding Icon: Sophia Amoruso (02:30) The Art of Naming: From Nasty Gal to Trust Fund (07:13) Rethinking Venture Culture (10:28) Angel Investing Early & Building Relationships (13:20) Investing in Liquid Death, Superhuman, Kindbody (14:30) Why She Invests in Software & B2B Brands (18:48) What Anduril Gets Right About Branding (22:18) Raising Trust Fund: Marc Andreessen, Paris Hilton, Jason Calacanis (24:45) The Power of the Right Audience & Eyeballs (27:29) AI in E-Commerce & the Future of Consumer-Brand Engagement (32:04) Angel to VC (37:23) Fundraising Myths: Why Raising Money Isn’t “Winning” (42:17) Building Business Class: Her Own “Internal Podcast” for Founders (44:18) Girlboss: The Book, the Netflix Show & Becoming Part of the Zeitgeist (47:07) Lessons in Leadership, Scaling & Why She Prefers Early-Stage (50:00) Life Today & Living in London @sophiaamoruso | @trustfundvc