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Sophia Amoruso

Sauce Boss Meets Girlboss



Our guest today is Sophia Amoruso, founder of the first internet native fashion brand, Nasty Gal. Since growing Nasty Gal to global prominence and then taking it through a sudden bankruptcy sale, she’s subsequently founded three other businesses including Trust Fund, her VC firm. Sophia coined the term #Girlboss, which is the name of her second business, a Netflix show based on her life, and the title of her memoir which spent 18 weeks on the New York Times bestseller list.

I admire Sophia for her courage and action in the face of fear. Fear of failure and fear of not looking good can be overwhelming to the point of paralysis (certainly I am governed by these fears) but today we'll get into how Sophia has achieved a buoyancy to rise above them.

Good brands transcend the reality of the businesses they represent, and in this show, she talks about what it's like for her personal brand to decouple from her lived experience - to the extent of taking a company through bankruptcy just as a Netflix series debuted about her company's success. Talk about cognitive dissonance.

Sophia and I talk about the scrutiny put on female leaders, her recent rumspringa, what she thinks is cool right now in fashion and music, and I ask her to roast my outfit.

Enjoy my conversation with Sophia Amoruso, a refreshingly real storyteller and entrepreneur who's dedicated to living on her own terms.

Listen : Spotify | Apple | YouTube


“I feel like once you’ve quote-unquote ‘failed’ as big as I did with my first business, everything else just feels like the afterlife.”




Show Index

    07:30 - Sophia’s Relationship with Fear
    13:52 - Big Idea Behind Nasty Gal
    20:12 - Sophia’s Daily Fuel While Building Nasty Gal
    26:20 - A Travellog of Sophia’s Ups and Downs (It’s “f*cked”)
    33:50 - Why Female Leaders Get Scrutinized More 
    40:35 - Sophia Goes On a Rumspringa!
    43:39 - Sophia’s VC Firm, Trust Fund
    45:19 - At Large & Off The Cuff


Show Notes




Ep. 23 — Sophia Amoruso

Sauce Boss Meets Girlboss


Ep. 22 — Daniel Goldhaber

Movies by Any Means Necessary


Ep. 21 — Dinara Kasko

Have Your Cake and Tweet It Too


Ep. 20 — Nicolas Jammet

Greens to Greatness


Ep. 19 — Thomas Kemeny

Writing Your Way Ahead


Ep. 18 — Clare Vivier

Liberté, Intégrité, Simplicité


Ep. 17 — Alex Bogusky

Peace, Love, and Advertising


Ep. 16 — Alexis Gay

The Unprofessional Professional


Ep. 15 — Seth Godin

Idea Virus Patient Zero


Ep. 14 — Nicholas Coleman

Chasing Liquid Gold


Ep. 13 — Gabe Whaley

Making MSCHF


Ep. 12 — Kareem Rahma

Internet Funnyman


Ep. 11 — Amanda Hesser

Building a Digital Hearth


Ep. 10 — Shane Heath

No Mud, No Lotus


Ep. 9 — Michael Dubin

You Can’t Just Switch It Off


Ep. 8 — Scott Norton

Purpose & Play


Ep. 7 — Chris Nee

Creative Courage and Talking Stuffed Animals


Ep. 6 — Fabien Riggall

Silencing the Discursive Mind


Ep. 5 — Danielle Baskin

Striking Internet Gold


Ep. 4 — Alexander Gilkes

Givers Are Getters


Ep. 3 — Susan MacTavish Best

Hosting a Rave for the Intellect


Ep. 2 — John Fiorentino

The Hunt for Big Ideas


Ep. 1 — Eric Ryan

Good Artists Copy, Great Artists Steal



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