Intro

This chapter explores how branding shapes personal identity, using the journey of Nasty Gal as a focal point. It also discusses the transition to Trust Fund and the humorous branding strategy behind it.

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Episode notes

Sophia Amoruso is more than a founder, she’s a cultural icon. 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 and 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, and Eight Sleep, and 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), and yes, even Jason Calacanis.

Sophia opens up about:

• How to build a $100M+ cult brand.

• Building Nasty Gal & GirlBoss from scratch into cultural movements

• The brutal reality of inflated VC valuations, fundraising, & collapse

• Why consumer businesses face unique challenges with venture capital

• Building Trust Fund with Marc Andreessen, Paris Hilton, & more

This is a conversation about ambition, failure, resilience, and the power of branding, told by one of the most iconic entrepreneurs of her generation.

Connect with us:

1. Sophia Amoruso: https://x.com/sophiaamoruso

2. Molly O’Shea: ⁠https://x.com/MollySOShea⁠

3. Sourcery: ⁠https://x.com/sourceryvc⁠

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Chapters:

(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 That Matter

(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 & Right Eyeballs