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an hon­est con­ver­sa­tion with an en­tre­pre­neur who built – and lost – it all, and is on a mis­sion to re­frame suc­cess

An “an­ar­chist mis­fit” and “un­likely busi­ness­woman” is how en­ter­tain­ment direc­tory IMDb de­scribes the main char­ac­ter of Girl­boss – the new Net­flix com­edy se­ries that’s based on the life of Sophia Amoruso. And, it’s a pretty ac­cu­rate de­scrip­tion of this fash­ion en­tre­pre­neur.

An angst-rid­den, dump­ster-div­ing teen who, at the age of 22, started an eBay store in 2006 sell­ing ‘preloved’ items (the first thing she ever sold on eBay was a shoplifted book), Sophia had never planned to go into e-com­merce. Yet, she has man­aged to cram a life­time’s worth of suc­cess (and challenges) into the past decade. That small eBay bou­tique turned into a boot­strapped e-tail fash­ion em­pire, Nasty Gal, and trans­formed the for­mer op-shop­per into a self-made mil­lion­aire – and su­per­star author.

She con­nected with cus­tomers over MyS­pace, scouted young mod­els on­line and paid them with burg­ers. Her book, #Girl­boss, be­came a New York Times sen­sa­tion – and a so­cial move­ment. Part mem­oir and part call to ac­tion, it doc­u­mented her rise to the C suite with un­flinch­ing ad­vice for fe­male lead­ers (one chap­ter is called ‘Money looks bet­ter in the bank than on your feet’).

In 2012 Nasty Gal leased a 45,000 square me­tre dis­tri­bu­tion cen­tre and re­ceived US$40 mil­lion in in­vest­ment fund­ing. Three years later, Nasty Gal re­port­edly sur­passed US$300 mil­lion in rev­enue, tripling sales in three years. It topped the list of 500 top e-com­merce per­form­ers, beat­ing Ap­ple and Ama­zon with a 92.4 per cent five-year com­pound an­nual growth rate.

But in 2016, the same year Sophia’s mar­riage ended, Nasty Gal filed for bank­ruptcy. Rev­enue had been sharply drop­ping and Sophia, who had a 55 per cent stake in the com­pany and stepped down from CEO to ex­ec­u­tive chair in 2015, de­scribed the de­ci­sion as the most re­spon­si­ble op­tion to pre­vent clo­sure. In Fe­bru­ary 2017, af­ter years of lay­offs and law­suits, the brand’s in­tel­lec­tual prop­erty was ac­quired by the UK fash­ion web­site Boohoo for just US$20 mil­lion. That same month, Sophia re­ceived a no­ti­fi­ca­tion that she had been re­moved as an ad­min from the Face­book page of the com­pany she had built with her bare hands. Nasty Gal con­tin­ues to op­er­ate, but with­out Sophia’s in­volve­ment.

The rise and fall – and rise again – is all part of this en­tre­pre­neur’s jour­ney and cultish like­abil­ity. A few months af­ter the bank­ruptcy an­nounce­ment, more than 500 women in Los An­ge­les came to­gether for the Girl­boss Rally, a day of talks and ac­ti­va­tions to in­spire women to rise up and re­de­fine suc­cess for them­selves.

Far more than just a snappy book ti­tle, Girl­boss Me­dia is now a me­dia com­pany that en­ables women to con­nect across so­cial, dig­i­tal and ex­pe­ri­en­tial plat­forms to share knowl­edge about their ca­reers, fi­nance, re­la­tion­ships and busi­nesses, and em­power each other. To date, the #Girl­boss Foun­da­tion has awarded more than US$120,000 in fi­nan­cial grants to women in the worlds of de­sign, fash­ion, mu­sic and the arts to help fund their pas­sion projects.

The fem­mepreneur, who over­shares, swears, and isn’t afraid to be flawe­some, has filled a gap, not only in what she does but how she does it. She’s a role model for lead­ers who don’t wear a power suit, play golf or con­form.

As Girl­boss launches on Net­flix to loosely retell her Nasty Gal jour­ney, Sophia the busi­ness­woman is re­defin­ing suc­cess in an era where ca­reer paths are rarely lin­ear.

She re­cently sat down with Lisa Mes­sen­ger to dis­cuss it all.

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