NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239

Sophia Amoruso traces her path from an unhappy San Diego/Sacramento childhood marked by parental conflict, ADHD, and depression to a rebellious, transient young adulthood of stripping, shoplifting, and odd jobs. She explains how reselling stolen and then vintage clothing on eBay grew into Nasty Gal, which scaled from $75K to a $28M profitable run rate before a $60M index Ventures raise at a $350M valuation overextended the company. The brand collapsed within roughly a year that also saw her divorce and the unflattering Netflix series 'Girlboss' premiere. She reflects on overvaluation, naivety versus convention, leadership mistakes, and self-doubt as a motivator. Now she deliberately keeps her ventures small, focusing on Business Class and early-stage investing.

• She turned down a $400 million offer to buy the company after her investor told her to ask for more.
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• The first thing she ever sold online was stolen merchandise she shoplifted from big-box retailers.
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• Nasty Gal went from doing $150,000 a year to $150,000 over a single lunch during its explosive growth.
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• Index Ventures invested $60 million at a $350 million valuation on a business with only a $28 million run rate.
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• Within about 12 months she hit the Forbes cover, her husband left, the company collapsed, and the Netflix show aired.
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• She names the $350 million valuation as the nail in the coffin because it forced impossible growth expectations.
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• She says her hardest day was when her husband of about a year left her after she'd made a huge personal commitment.
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• Both her parents worked entirely on commission, and generations of her family ran a motel rather than holding salaried jobs.
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• As a child she watched her parents cut up their credit cards and file for bankruptcy in a credit counselor's office.
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• She took the campus-safety host job at an art school only to get health insurance to fix a hernia she couldn't otherwise cover.
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• Nasty Gal is named after a Betty Davis album; Betty Davis was briefly married to Miles Davis and 'too wild for him.'
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• Nasty Gal's revenue trajectory ran $75K, then $250K, $1.1M, $6.5M, and $12M before venture capital arrived.
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• After her first raise she bought a $13,000 blue slide for the office before even buying desks.
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• She attended the Hoffman Process, a seven-day retreat with no phone, internet, books, or music.
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• Her Business Class entrepreneurship program runs with one employee, twice-yearly launches, and 8 hours of pre-recorded video.
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• She compares 'magical thinking' to Indiana Jones trusting an invisible bridge across a chasm.
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