Nasty Gal just went bankrupt. What are the lessons for nasty gals (and guys)?

I never would have done it had I known it was going to become this big. ~ ex-CEO of Nasty Gal (and now ex-Chair), Sophia Amoruso

As Nasty Gal prepares for bankruptcy (last week was a bad week for nasty women) it's worth reflecting on how an anarchist dumpster diver with shoplifting tendencies landed on Forbes' list of richest self-made women and #1 on Business Insider's list of the Sexiest CEOs Alive (LinkedIn's Jeff Weiner also made the list). And how she pushed it all aside.

A story this epic must be instructive.

Nasty Gal began in 2006 with eBay auctions of vintage clothing. The name Nasty Gal comes from a Betty Davis album. Not Bettie Davis with the Bettie Davis eyes. Betty Davis the 1970's funk rebel briefly married to Miles Davis, a woman too raw for the mainstream who wrote this lyrical memento for Jimi Hendrix.

I used to beat him with a turquoise chain ~ Betty Davis from He Was a Big Freak

Now that's nasty.

Nasty Lesson #1:You can have a hero but don't forget their story. As Marshall Goldsmith recommends in a heroic LinkedIn post, you should choose a hero to model your life after, but the nasty lesson from Sophia Amoruso is that you should make sure you understand the implications of their story.

Betty Davis is Amoruso's hero because she's a badass who wrote all her own music and lyrics and produced all her own songs. Sophie Amoruso started Nasty Gal because she too is a badass who wanted to do something creative in the rebellious spirit of Betty Davis, and she wanted go it alone.

Let's take a five minute break for a Betty Davis Nasty Gal primer.

Sophia Amoruso is a tireless scavenger who waited in line at 6:00 a.m. for estate-sale doors to open so that she could be first to run to the closet in search of a disco gown, mod minidress or Golden Girls tracksuit. She sifted through every rack at the thrift store in search of buried Chanel jackets to buy for $8 and auction online for $1,500. She didn't know what gross margin was, but right from the start Sophia Amoruso knew she was onto something.

Soon she outgrew eBay and launched a website, but it grew so fast that she could no longer satisfy demand for vintage so Amoruso added small designers then as demand grew even more, designed and manufactured her own Nasty Gal brand. Today there are two Nasty Gal retail stores in Los Angeles and Santa Monica. Amoruso called them #brickandmurder.

Nasty Lesson #2: Growth doesn't necessarily equal business success. A few months ago Nasty Gal was ranked the #1 internet retailer with a 92.4% five-year compound annual growth rate. Today it's bankrupt. In our obsession with growth it's too often forgotten that revenue and profitability sometimes clash. Nasty Gal sacrificed profitability on the runway of continued growth.

Sophia Amoruso built her company debt free with the mantra "sell things for more than you pay for them and save more than you spend." She had to save because she couldn't get credit. Once Amoruso had achieved some material success she paid for a Porsche in cash because the dealer wouldn't give her financing. It must pain her to know that her company has racked up hundreds of thousands of dollars in unpaid bills.

Amoruso is an expert at using social media to generate free marketing, yet as it grew Nasty Gal invested heavily in paid online advertising to keep the growth engine running. Then there was the litigation, the most corrosive of expenses. Its mistreatment of pregnant employees generated lawsuits and nasty press. Nasty Gal was born out of scavenging but when it started scavenging designs from Chanel, Givenchy and jewelry designer Pamela Love, it came at a tall litigious price. The company even lifted from Hell's Angels. That's nasty.

Nasty Lesson #3: Growth doesn't necessarily equal personal success. Amoruso went from solo founder in search of the perfect thumbnail silhouette to display its vintage wares to reluctant CEO in search of venture capital. Becoming CEO took her further and further away from the creative work that drew her to the fashion business in the first place.

As if to underscore her ambivalent relationship to her Nasty Gal creation, Amoruso's 2014 memoir #GIRLBOSS is more Get Out than Lean In.

As the CEO role evolved I lost the ability to feel the results of my own work. ~ Sophia Amoruso, #GIRLBOSS

In January of 2015, after knowing for years that she didn't want to be CEO, Amoruso finally got out. Sheree Waterson, the former Chief Product Officer at Lululemon became CEO of Nasty Gal and Amoruso moved to the executive chair position.

Nasty Lesson #4: Dreaming big doesn't come with autocorrect, but you can course correct your dreams. By the time Nasty Gal filed for Chapter 11 bankruptcy protection last week, Sophia Amoruso had moved on. Fittingly she was far away in Sydney Australia at a Business Chicks event (is the word women out of fashion?) when the news broke and although she shed tears, there must have been a few tears of relief. Surely she saw it coming. Old Navy hit $1 billion in sales in four years, but there could never be an Old Nasty Navy Gal. Nasty doesn't scale.

And so Sophia Amoruso went from rags to $280 million in riches, to fashioning a life of her own creation. She has a new book out called Nasty Galaxy "a lushly illustrated embodiment of the collective spirit of the Nasty Gal brand, Sophia’s own personal brand" the podcast Girlboss Radio and a Netflix Girl Boss comedy series with executive producer Charlize Theron that will debut next year. She may not be worth $280 million anymore but Sophia Amoruso has returned to the place where she started, doing it for herself. Which brings us to our final nasty lesson.

Nasty Lesson #5 is for all the nasty women who have felt the sting of defeat.

About the Author: She wishes she got more sh*t done.