Sophia Amoruso is the Founder of Nasty Gal and Trust Fund, an early stage venture capital firm.

We talk through her journey of starting Nasty Gal as an Ebay store in 2006 to sell vintage clothing, bootstrapping it to $28 million in revenue, raising $50 million, scaling it to $120 million and a massive team, turning down a $400 million acquisition offer, and ultimately declaring bankruptcy.

She takes us inside what it was like to fail so publicly, what she’d do differently next time around, lessons from building the brand, and why she started her VC firm Trust Fund to back the next generation of founders building consequential companies.

Thank you to Numeral, Flex, Amplitude, and Merge for supporting this episode

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Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz

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Timestamps:

(0:59) Selling vintage on Ebay while working at an art school

(04:31) Lessons in marketing and perceived value

(12:38) Knowing when to make your first hire

(18:31) Borrowing from others to build a unique brand

(25:17) Growing to $120m revenue in seven years

(27:24) Sharing the pitch deck that raised $50m

(30:17) Mistakes scaling to 100’s of employees too fast

(34:48) Downsides of raising at too high of a valuation

(39:56) Why being a CEO is fun

(42:57) Declaring bankruptcy

(50:38) How it feels to fail publicly

(54:41) Writing a book, Netflix series, starting the Girlboss movement

(59:13) How to start a new brand in 2026

(1:05:34) Starting Trust Fund to invest and help founders

(1:13:45) Raising $5m from a poker game

(1:18:47) Sophia asks for Turner’s LP pitch

(1:26:53) Traits of the best founders

Trust Fund: https://www.trustfund.vc/

Pitch Trust Fund: https://www.trustfund.vc/pitches

Nasty Gal: https://www.nastygal.com/

Follow Sophia

Instagram: https://www.instagram.com/sophiaamoruso

Twitter: https://x.com/sophiaamoruso

LinkedIn: https://www.linkedin.com/in/sophiaamoruso

Website: https://www.sophiaamoruso.com/

Follow Turner

Twitter: https://twitter.com/TurnerNovak

LinkedIn: https://www.linkedin.com/in/turnernovak

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Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders

The Peel with Turner Novak

Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders