Most entrepreneurs don’t start with a string of high-powered connections and money to burn. At least, the ones in the most inspiring business stories don’t begin that way.
Those entrepreneurs begin with the germ of an idea, a hobby that becomes side hustle, or a series of odd jobs that somehow coalesce into a company. They add a little snap to what they’re doing. A little sizzle to their efforts. Then after about ten years of incremental additions to their seedling idea, they get a break-though. And all of a sudden, everyone’s buzzing about their “overnight success.”
Sophia Amoruso, the entrepreneurial former CEO of Nasty Gal & founder of GIRLBOSS, knows all about starting small and growing into greatness. Or as she puts it, “Each time you show up to work and work hard and do your best at everything you can do, you’re planting seeds for a life that you can only hope will grow beyond your wildest dreams.”
A Childhood Struggle with Mental Illness
Sophia Amoruso was born on April 20, 1984 to middle-class parents in San Diego, CA. Her family attended the Greek Orthodox church, and both her parents worked traditional jobs to support themselves and their daughters. In Sophia’s teens, her mother Dena Kouremetis emerged as an advice columnist who specialized in raising successful, confident daughters. But as a child, Sophia was anything but confident.
“I wasn’t a particularly happy kid,” she later told a reporter. “Mostly, I was impatient and had a bad attitude toward authority.” For a while, doctors thought Sophia had Tourette’s Syndrome, but they later determined she was living with Attention Deficit Hyperactive Disorder (ADHD) and depression. These challenges didn’t inhibit Sophia’s innovative spirit, however. And she opened a lemonade stand at age 9, read books about startups as a teenager, and had worked 10 different jobs by the time she was 22, including stints at Subway, a dry cleaner, and a mobile plant shop.
Dumpster Diving & Dropping Out of Community College
After her parents’ divorce and bankruptcy, Sophia left home at age 17 and headed for Portland, Oregon. She first gave community college a spin but decided it wasn’t for her. After dropping out, she lived with a step-aunt in the area and tried to make a living as — ironically — an anti-capitalist crusader. With a boyfriend who lived in a treehouse and a personal penchant for shoplifting and dumpster diving, Sophia didn’t look like the sort of person whose classmates would name her “Most Likely to Get Listed in Forbes as a Top Self-made Millionaire.” Yet, that’s what happened.
Sophia got started down the road to wealth when she picked up a book called Starting an eBay Business for Dummies. “I didn’t have any great aspirations,” she later said. “I just wanted to make a living doing something I thought was fun.”
Launching Out on eBay
Still holding down her day job as a security guard at San Francisco’s Academy of Art University,Sophia opened an eBay shop she could work in her spare time. She named her online store Nasty Gal Vintage after the 1975 album of that name by singer Betty Davis. “I loved how she had reclaimed the word ‘nasty’ as something empowering,” Sophia said.
Nasty Gal Vintage sold vintage clothing and other used items. In fact, the first piece of merchandise Sophia sold was one she’d stolen. After a while, however, she didn’t have time to steal anymore. Sophia was going at her new business with gusto, styling, photographing, and shipping the products by herself using tips she’d learned in a photography class. With just 55 words to describe her products and space for only a few photos, Sophia became a master of description and imagery.
She also developed an eye for product selection. Once, she bought two Chanel jackets at a yard sale for $8 each and sold them on eBay as a pair for $3,000. Sophia became so successful that in 2008, she left eBay to start selling exclusively on her own website.
“A Cinderella of Tech”
Once on its own, Nasty Gal grew at an astonishing rate. Sophia’s skill with brand and product marketing and her sophistication with social media drew a massive following of young women who snapped up products as soon as Sophia put them up. Her first day on her own site, Sophia sold out her entire inventory. Things ramped up from there. In 2008, Nasty Gal was pulling in $223,000 in revenues. Three years later, the company was raking in $23 million. The New York Times dubbed Sophia “a Cinderella of tech.” INC named her to its top 30 under 30 list.
All the money and all the accolades weren’t enough to keep Sophia on top, however. She lacked the necessary management skills to run a company that was growing as fast as Nasty Gal. Large layoffs made team members skittish. Four employees said they’d been fired for getting pregnant. Lawsuits soon followed. Other employees told the media that Nasty Gal was a toxic work environment.
Things soured in the C-suite. By the end of 2015, Sophia had resigned as CEO but kept a senior executive post. The next year, the day after Donald Trump was elected president, Nasty Gal entered chapter 11 bankruptcy proceedings. Sophia exited the company completely. Her Cinderella story seemed to be playing itself out in reverse, and Sophia was going from rags to riches to bankruptcy at an alarming rate. She wasn’t done yet, however.
In the midst of all the financial brouhaha going on at Nasty Gal, Sophia published her autobiography entitled #GIRLBOSS. The book spent a phenomenal 18 weeks on the New York Times’ bestseller list. Sophia was wined, dined, and idolized by the entrepreneurial set. She took the stage to tell the Nasty Gal story at the biggest conferences, and she toured Australia to talk about entrepreneurship and her philosophy of life. She launched a podcast, a website, and a conference.
“Amoruso is making feminism cool again,” Business Insider claimed. It seemed true. After hearing Sophia, enchanted Millennials, mostly women, scooped up so many copies of #GIRLBOSS that Netflix took notice. The streaming media giant turned Sophia’s life story into a 13-episode TV drama called Girlboss that attracted a lot of criticism but only a few viewers especially since the shine was already fast fading from Amaruso’s life and enterprises.
Amidst the hoopla, many observers felt like Sophia was starting to lose her way. As head of the company she founded, Sophia had begun focusing too much on her own personal brand. “If she wasn’t out doing press or interviews, she would be locked in her office; there was no visibility or sense of presence,” a former employee alleged. “Especially when #GIRLBOSS came out and her ego exploded, she began acting like a celebrity not a CEO.”
It would prove to be a downfall she almost couldn’t come back from.
Sophia’s Thoughts on What Happened at Nasty Gal
What was it that brought down Nasty Gal? Was it Sophia’s head getting turned away from the company that needed her leadership and toward all the adulation of the press and her fans? Or did her successor, Sheree Waterson, simply not have the skills or vision to lead the company effectively? Or did the enterprise simply grow too big too fast to be sustainable? All those reasons may help explain what happened and why.
But Sophia herself offers a broader explanation. “We hired 100 people almost immediately and made a growth plan without having a lot of data to back it. Nasty Gal was still a very young business, so we hadn’t captured what we would’ve needed to architect that growth plan properly. So, I think that was kind of what set things into motion. Things became too complex too fast.”
Bouncing Back from Bankruptcy
When you’ve gone from dumpster diver to mega stardom as an entrepreneur, what do you do when things go south? According to Sophia, you don’t give up. “How do you start over?” she asked an audience at Cannes. “You just get up and keep getting up.” In fact, Sophia got the news about her company’s bankruptcy just before she was expected to step on stage and discuss her successful life at an event in Australia. What did she do? Took the stage and told the story.
Though she lost most of her $280 million fortune in the collapse of Nasty Gal, Sophia got on her feet again within five months. Perhaps most importantly, she didn’t let the criticisms of what happened at Nasty Gal stick to her.
“The company sold for $20 million in bankruptcy,” she later told reporters. “So, in the grand scheme of things that can happen in your early 30s, yeah I’m proud of it.” But reframing the narrative of her Nasty Gal experience wasn’t the only thing Sophia did to bounce back. She also got to work on a fresh idea — Girlboss Media. This new company would provide Sophia with a platform to speak to other women like herself who needed to bootstrap their way to the top. She was, she said, “exhilarated” about the concept.
Leading #Girlboss Media
In a way, starting a media company from the ashes of Nasty Girl was more an obvious next step than it was a courageous choice. Sophia was, after all, a bestselling author with a popular podcast, a penchant for media stardom, and a Netflix series based on her life. Girlboss was also a step from helping women feel confident in how they looked to helping them develop practical opportunities to advance in life and careers.
In December 2017, Sophia officially kicked off her new company, which offered her audience of female entrepreneurs a full range of editorial content, videos, and podcasts. The company also held Girlboss Rallies, popular, all-female weekends focused on inspiring and connecting bright, ambitious, and talented women. In 2018, the Girlboss Rally attracted women from 430 cities, 31 countries, and 40 states to the Knockdown Center in Queens, New York.
“Girlboss is all about listening and hearing what people’s motivations are,” Sophia said. “I think the best thing we can do is actually be less obvious as a facilitator and letting the community build itself, like a church.”
Dealing with Divorce
Sophia’s story serves as a reminder that entrepreneurs’ careers and personal lives are inextricably linked. While Sophia’s career at Nasty Gal was imploding, her personal life also launched into a tailspin. Just three months before Nasty Gal declared bankruptcy, Sophia stood before a family court judge who declared that her one-year marriage was just as dead as her company.
The enterprise had obviously been in trouble for months, but the divorce came as a total shock. The way Sophia tells it, her husband woke up one morning, decided he didn’t want to be married, and left her and their three poodles to sort things out in a Beverly Hills hotel. As she did with her company, Sophia wasted little time moving on, though. Today, she’s in a relationship that she says makes her very happy.
Sophia’s Advice to Female Entrepreneurs
What does an entrepreneur with a life as dramatic and varied as Sophia Amoruso’s have to say about entrepreneurship? Here’s what she told Forbes:
1. Have a plan. “You (will) find yourself in a place where your gut and wit and street smarts begin to fail.”
2. Hold people accountable. “Get organized, hold people to their goals and coach them, but protect the business when those goals aren’t met.”
3. Find support. “Having a lot of eyes on your business, having a network of others to share the highs and lows and the resources and the tools to get there is such an advantage, and so easy to do.”
Perhaps the most important lesson? See your successes for what they are. A community college dropout who builds a $300 million company by age 32 is a success even if that one company fumbles. Get up. Keep going.
Stephanie is the Marketing Director at Talkroute and has been featured in Forbes, Inc, and Entrepreneur as a leading authority on business and telecommunications.
Stephanie is also the chief editor and contributing author for the Talkroute blog helping more than 100k entrepreneurs to start, run, and grow their businesses.