When a 22-year-old Sophia Amoruso started selling vintage clothes on eBay, she never imagined it would turn into a multi-million-dollar company or that she would eventually tell her story in a bestselling memoir, "#GIRLBOSS," or that her life would be made into a scripted Netflix comedy series.
"I didn't anticipate my eBay store becoming my career. ... And then it kept growing, and my auctions became more and more and more in demand, and eventually my average order value was $150 on something I probably spent no more than $20 to acquire,” Amoruso, CEO and Founder of Girlboss, told ABC News’ Rebecca Jarvis for a special "No Limits with Rebecca Jarvis" podcast crossover episode with her own "Girlboss Radio."
It was 2006, and her eBay store was called Nasty Gal Vintage, named after an album by the funk singer Betty Davis. Amoruso would spend hours picking through thrift stores, negotiating prices, photographing, posting and shipping items to buyers. Amoruso recalled an early conquest: nabbing two vintage Chanel jackets for eight dollars apiece, from a Salvation Army, each of which she sold on eBay for more than $1,000.
"A woman from London and a woman from Australia and a woman from New York all duked it out over the course of 10 days for it, and eventually sold for over a thousand dollars," she said.
It wasn’t long before Amoruso outgrew eBay and decided to launch her own e-commerce site, Nasty Gal. She brought her customers with her, and the site became immensely successful.
"It just sold out right away. Whowhatwhere.com covered it, Daily Candy covered it and I didn't have a publicist -- these editors were just customers of mine, and, you know, it blew up from there," Amoruso told Jarvis.
In 2011, only three years into the launch of NastyGal.com, the company boasted an 11,200% growth rate with revenue of $24 million, according to Inc. Magazine, which named the company as a "Fastest Growing Retailer" in 2012. Up until this point, the company had no outside funding.
"I bootstrapped the business to almost $30 million in revenue before investors started showing up. So we were profitable," Amoruso said.
Based on the initial success, what would happen next was hard to believe.
"Venture capitalists came knocking when they somehow caught wind of this thing called Nasty Gal, and I didn't need them to invest," Amoruso told Jarvis. "We were fine, but they seemed, like, really smart people and I did a lot of research ... and it seemed like a good deal to sell a small percentage of the company for $40 million."
"I still owned most of the company, I controlled the board, the risk was pretty low. But what happened after that as a very kind of like fabled long story to to tell.”
With new funding, the company continued to grow initially, opening a distribution center in Kentucky and opening its first brick-and-mortar store in Los Angeles. But things started to go downhill when the company couldn't keep up with rapid expansion. Amoruso explained to Jarvis that in a year the company was trying to grow by $100 million in revenue and had hired 100 people, but it still lacked infrastructure.
"And then we weren't profitable once all of that had happened, and it just became this really challenging environment to navigate to continue funding the business," Amoruso added. "And I had this very complicated culture that I hadn't grown intentionally. I didn't know what culture was, I never worked in an office. ... I was very young, and I didn't really know how to hold the company accountable and a lot of things happened, most of which I'll probably never know."
By the beginning of 2015, Amoruso had stepped down as CEO but stayed on as executive chair. By 2016, the company filed for bankruptcy.
"There were times where I felt like a lamb led to slaughter -- like I can't escape this, I can't quit, I can't be fired, I’m being held accountable for things I don't understand, I didn't intend but now I'm being criticized," she said. "You know, it's like, what you do intentionally is as important as what happens unintentionally, and sometimes you don't really know what the effect of those things are going to be and you learn through experience."
The "fabled story" came to a close in February of 2017 when the British-owned BooHoo group announced it would be purchasing Nasty Gal, explaining in a press release "a core team of original employees will be based out of L.A., to ensure the DNA of the brand is retained."
"The last two, almost three, years of my career I felt completely trapped in and unable to make change, positive change within," Amoruso said. The company "had been through many a P.R. crisis, layoffs, reports of toxic culture, all the things that like I never could have anticipated. I was taking advice from H.R. experts and employment attorneys and all these people who said look this is what you should be doing. And, in retrospect, there is a lot of things that I wouldn't have done the same. But I was held accountable regardless. By the time we filed [for bankruptcy] I was ready to build Girlboss."
Amoruso coined the term "Girlboss" after publishing her 2014 bestselling memoir of the same name. Part memoir, part business book, it details her life from a Dumpster-diving teen who dropped out of school to becoming the founder and head of a $250 million business. It was an explosive success, spending 18 weeks on the New York Times bestseller list and selling more than 600,000 copies worldwide.
"'Girlboss' was called 'Lean In' for misfits," Amoruso said.
Shortly after the book was published, Amoruso launched The Girlboss Foundation, which awards grants to female entrepreneurs. And next she debuted her podcast, "Girlboss Radio", where she interviews "boundary-pushing women who've made their mark."
In 2016, Amoruso turned her focus to building out the Girlboss brand by raising $3.1 million. She says that the book started a conversation about female leadership that she needed to carry onward. The hashtag "girlboss" has been used over 10 million times and the company has recently started "The Girlboss Rally", which are conferences that bring together hundreds of female entrepreneurs and activists.
"The conversation has been growing," she said, "and it feels amazing to start over and not be burdened by the legacy of the decisions that I didn't even make."
"I don't really take breaks between things to lick my wounds ... you strike while the iron is hot."
Hear more of Sophia Amoruso on "No Limits With Rebecca Jarvis", available on Apple Podcasts, Stitcher, Google Play Music, Spotify, TuneIn and the ABC News app.