Sophia Amoruso attends Girlboss Rally NYC 2018 at Knockdown Center on November 17, 2018 in Maspeth, New York.
Cindy Ord—Getty Images for Girlboss Rally

As CEO of Nasty Gal, Sophia Amoruso Failed Spectacularly. Now She's Turning Failure Into A Movement

January 30, 2019

In an old warehouse on the edge of Queens, N.Y., a thousand-some #Girlbosses have assembled.

They sit on folding chairs, filling a cavernous space that once belonged to a door factory, but now looks more like a Suze Orman fever dream. Neon lights twist toward a massive stage; a banner the size of a billboard screams, “PAY ME PAY ME PAY ME” in selfie-perfect block lettering.

Every #Girlboss is wearing something Meant to Be Seen. A fuchsia pantsuit, a faux fur statement coat, hair the color of a radioactive lime. Her nails are bright and fresh, her eyeliner is winged. And her attention is rapt.

Onstage, Sophia Amoruso—the #Girlboss-in-Chief—is flicking through a slideshow of the defining moments in her career: ambivalent college student, part-time eBay seller, Forbes magazine cover star.

They’ve heard this story before. Most of the audience has read, and reread, Amoruso’s 2014 memoir, #Girlboss, which detailed her rise from California crust punk to e-commerce superstar. They dog-eared pages and underlined quotes. Some made the book a permanent nightstand fixture; others still keep it in their purses for quick inspiration.

They know what comes next too. How, a few months after that Forbes cover, Nasty Gal, the clothing brand that shot Amoruso into the public eye, filed for bankruptcy. How her company imploded the same year she published her second book, Nasty Galaxy, and Netflix announced it was adapting a TV series based on her first.

“I’d gotten everything I’d ever dreamed of, but I was the loneliest I’ve ever been,” she tells the audience. “And I’m the Girlboss.

At 34, Amoruso is rebranding failure.

Krista Schlueter—The New York Times/Redux

She’s still the #Girlboss, a hashtag-able superhero, of sorts. But here at the “Girlboss Rally,” the fourth of its kind in less than two years, she has a new stump speech. A testament to tenacity, and failing in the right way.

She’s a #Girlboss with a war story.

“Very few women have blown it on the scale that I’ve blown it,” she’ll tell me from a greenroom later on.

When Amoruso steps offstage, the crowd thins.

Those who stick around are treated to a “movement break” from an enthusiastic Nike trainer, who leads them through a series of stretches “designed to help harness our power.” Others mingle on mustard-color couches or trickle into breakout session rooms. They’re guided by a floor plan printed on their welcome packets (“Balleroom,” “Hustle Hall”), coupled with their horoscopes (“The potential for you to grow and shine is powerful this month, Leo.”)

Near the entrance, a maze of merchandise tables buzzes with activity. Vendors sell rose-colored crystals and neon nail polish. You can get a #Girlboss lighter for four bucks and a #Girlboss hoodie for $65. If you’re looking for a more permanent way to tell the world you’re living your #bestlife, there’s a tattoo artist in the corner inking quickie designs (among them: an Old English version of “PAY ME”).

The vibe of the crowd is fittingly defiant. Billed as a “Noah’s Ark of ambitious women,” the Girlboss Rally is a weekend-long affair for mostly young, mostly up-and-coming entrepreneurs. They came to hear Amoruso and her contemporaries—women like Arianna Huffington and actress-turned-entrepreneur Brooklyn Decker—talk about how to exist outside the boundaries of a “normal” job. To get their professional head shots taken and their tarot cards read. They came from all over—40 states and 31 countries, according to a Girl-boss spokesperson. And they paid good money to be here: around $500 to $800 for two-day admission.

Many of the #Girlbosses have their own war stories to tell. These are resourceful, tenacious women who have broken from corporate America, or are planning to. They’re small-business owners and freelancers. Or they have desk jobs, and work on a side hustle on weekends.

Like Amoruso, they share a discontent with the nine-to-five grind, and the chutzpah it takes to forge a career outside it.

“We’re all like-minded women aspiring to do something with our lives,” says Holland Colvin, a 25-year-old graphic designer who traveled to the Girlboss Rally from Bloomington, Ind.

Working toward someone else’s bottom line can be stifling, especially if you’re in a creative field. If you happen to have two X chromosomes, that sacrifice comes with a 20% pay disparity compared to the dude sitting next to you (and that’s if you’re white—the average black woman earns 38% less than the average white man). So most of the #Girlbosses have rerouted their careers to favor their own goals—not some corporation’s. They work hard, after all. And they expect to #getpaid for it.

“They’re all curious, and smart,” Amoruso tells me backstage. “This isn’t a group for dummies. They’ve had a few jobs or just started their own businesses. And at the end of the day, they’re in transition.”

Amoruso’s own second act is still unfurling. That’s part of her appeal.

A self-professed introvert, she’s the first to admit she’s no Tony Robbins (“I’m an okay public speaker,” she says). But for Amoruso’s followers, seeing her act like a regular person, with regular insecurities, only adds to her charm. She’s open about going to therapy and says the word “f–k” a lot. And when she talks about her failures, she doesn’t sugarcoat the details. Amoruso knows she f–ked up.

In her late twenties, she was the CEO of Nasty Gal, one of the hottest clothing brands around—an online treasure trove of noticeable but wearable clothes (think fuchsia pantsuits, faux fur coats). From 2010 to 2015, the company grew from $10 million to $300 million in revenue, according to reports. In 2016, Forbes named Amoruso one of America’s “richest self-made women,” estimating her net worth at $280 million.

“She’s richer than Beyoncé,” the piece read. “And at 32, she’s just getting started.”

After all that hype, Amoruso’s downfall played out like a Greek tragedy. Rumors that Nasty Gal was run more like a popularity contest than a global business were fanned by damning employee reviews and a lawsuit claiming the company discriminated against pregnant employees. In 2015, Amoruso ceded her CEO role, acknowledging that Nasty Gal needed a more experienced leader at its helm. Plagued by flatlining sales, the company filed for Chapter 11 bankruptcy protection the following year.

At this point, Netflix was already mid-production on a streaming series based on Amoruso’s “rags-to-riches story.”

When it aired in 2017, the response was overwhelmingly sour. The Guardian called the show “a tone-deaf rallying cry to millennial narcissists.” Vanity Fair proclaimed: “It’s not a good time to be a Nasty Gal—or at least, to be Nasty Gal founder Sophia Amoruso.” Netflix canceled the series after just one season.

All told, this was a wildly embarrassing experience for Amoruso. She knew she’d gotten in over her head—Amoruso doesn’t come from a business background and was still learning how to scale, invest, and do all the other things the head of a company valued at nearly a quarter-billion dollars should probably have a firm grasp of.

But under intense public scrutiny, fueled by Netflix’s version of her life, she started to question everything else too.

“I put myself on the cover of a book called #Girlboss, and with that comes some kind of accountability,” she says. “But reading every awful comment you could ever read, written by people who know so little about you, is a really challenging thing. And there’s a Stockholm syndrome that can happen. If everyone is telling you that you’re blonde when you’re actually a brunette, then you’re like, ‘Okay, maybe I’m color-blind.’ ”

Krista Schlueter—The New York Times/Redux

Rallying cry: Women flew from 31 different countries to attend the Girlboss Rally in New York in November 2018.

As everything crumbled around her, one constant remained. Women were still buying Amoruso’s then-three-year-old book and were still passing their crumpled, annotated copies through their inner circles. They were still launching side hustles and leaving their desk jobs to start their own businesses. And they were still reaching out to Amoruso—their imperfect heroine—to tell her how #Girlboss had inspired them.

The public undoing of Nasty Gal didn’t make these women change their minds—it galvanized them. And as Amoruso rebuilt her life post–Nasty Gal, a new community took shape.

In 2017, she launched Girlboss Media, a digital company that now has a podcast network with six different shows; an online, career-centered women’s magazine; and a biweekly newsletter.

Later this year, she’ll unveil a paid social networking site for female entrepreneurs. It’ll look a bit like LinkedIn—with a fresh, millennial-pink sheen—plus Q&A threads and videos from past Girlboss Rallies. The site will target young, bootstrapping women working outside the confines of a desk job, Amoruso says. Women on their own imperfect career path.

“I don’t want to be the poster child for failure, but a lot of people want to know how I got back up,” she says. “Because regardless of the scale of what you’re doing or how public you are, you need to know that it’s an incredibly normal thing. It doesn’t mean that you need to go hide; it means that you learn and do better.”

* * *

Valerie Lollett, a 37-year-old who traveled to the Girlboss Rally from Miami, has weathered plenty of her own storms.

Born in Venezuela, Lollett moved to the U.S. four years ago amid an economic crisis that continues to rattle the country today. She’s run her own creative agency since 2011 and was able to relocate her business successfully—in 2018, she sold a female-focused cannabis brand to a big international holding company. As Lollett carves out a life for herself 1,600 miles from her home country, there’s little certainty about what will happen next. But she says Amoruso’s own storied, uncertain career path is helping her tackle those unknowns.

“Sophia is pushing one of the most positive and productive movements of today,” Lollett says. “She’s showing us how to get up and be better each time you fall. I think the Girlboss Rally is the most amazing thing in the world right now.”

A quick word on that hashtag. As of this writing, #Girlboss has been used 14 million times on Instagram alone. It is ubiquitous. Every wannabe Instagram model proclaims she’s a #Girlboss. So do “influencers,” that catchall term for people who get paid to hawk products on their social media accounts. Ditto every woman who sells LuLaRoe or Rodan + Fields or any of the other “multilevel marketing” companies that persuade people to sell things like leggings and essential oils through their social networks.

For Amoruso’s followers, being a #Girlboss goes beyond knowing how to use an Instagram story. These are women who own their own companies and whose livelihoods are steeped in risk. “Failure” isn’t something they talk about in inspirational quotes—it’s a reality they have to expertly navigate, over and over, in order to pay their bills.

So at the Girlboss Rally, in between a schedule packed with workshops (“7 Steps to the Perfect Pitch”; “Swimming in a Sea of Tech Bros”), guided meditation, and rice-bowl lunches, there’s a battle cry they keep coming back to.

To sum it up: S–t happens, so learn to use it to your advantage.

Invision/AP/Shutterstock

Amoruso attends the premiere of the Netflix series Girlboss.

On day one, Amoruso hosts a “fireside chat” with Arianna Huffington, who speaks about her departure from the Huffington Post and how she parlayed a spell of exhaustion into a new career as a sleep advocate and founder of Thrive Global, a wellness startup.

The next day, Bozoma Saint John, CMO at talent agency Endeavor (and former chief brand officer at Uber), tackles the same subject. “I fail constantly. I really do,” she tells Amoruso. “There’s no success without failure. I go looking for it.”

Saint John, like most of Amoruso’s speakers, exudes authenticity—a certain “I’m going to level with you” ethos that intoxicates audiences.

That’s Amoruso’s thing too. She knows she had the passion, creativity, and drive to launch a global brand, but lacked the requisite managerial experience. When presented with criticism, she retreated, sequestering herself in a corner office.

Today, she’s embracing these mistakes; they’re part of her origin story now. In a banner era for corporate mistrust, and a growing skepticism of notoriously private executives like Facebook’s Mark Zuckerberg and Amazon’s Jeff Bezos, it’s no wonder her approach is sucking people in.

“She’s so open to talking about those aspects of her life,” says Christine Medina, a 27-year-old who lives in Staten Island, N.Y. “That’s why I look up to her.”

Medina is a jill-of-all-trades in the brand marketing space—she does a little consulting, a little design, a little content creation. (One side of her business card simply reads, “LET’S MAKE MONEY.”)

She sits next to Jennifer Lyn, a 27-year-old accountant from Queens.

Last year, Lyn started a podcast, The Weekly Hustle, inspired by Amoruso’s #Girlboss radio show. Instead of interviewing mega-famous guests like designer Rebecca Minkoff and television host Maria Menounos, though, Lyn talks to people “in the midst of figuring it out.” Like a digital marketing consultant she went on a Bumble date with. Or a friend who moonlights as a burlesque dancer. Or her own mom, who moved to the U.S. from the Philippines at 24 and took as many housekeeping jobs as she could find.

“Success looks different for everyone,” Lyn says. “That’s something Sophia constantly reiterates.”

Shortly after launching the podcast, Medina—a friend of a friend Lyn had never met before—reached out to her on Instagram. They quickly became close friends, calling each other up for advice on professional dilemmas and brainstorming ideas for creative projects. And when Lyn heard about the Girlboss Rally on Amoruso’s podcast, they decided to go together.

The truth is, being a #Girlboss isn’t easy. The entrepreneurial grind can be long and lonely. Dealing with rejection, and uncertainty surrounding projects and payments, takes thick skin. Friends and family don’t often “get it.”

At the rally, Lyn and Medina mingle with kindred spirits—staying until it’s dark outside and they each have a pile of business cards in their tote bags.

“When you work on your own, it’s hard not to feel alone,” Medina says. “Being in a setting where it’s all women with the same mindset as you, and the same struggles, there’s something powerful about that.”

JP Yim—Getty Images for Girlboss Rally NYC 2018

Endeavor CMO Bozoma Saint John and Amoruso in conversation at the Knockdown Center in Queens, N.Y. “I fail constantly,” Saint John said.

* * *

These days, Amoruso likes to tell people she’s “90% healed.”

She’s got some residual wounds, and they reopen a little every time she talks about Nasty Gal onstage. Or when a reporter comes calling.

But overall, she’s in a much better place than she was a few years ago. And as the CEO of a media company that’s, per its own tagline, “redefining success for women in progress,” she knows being candid about her past is what got her here.

“I feel like yesterday’s iPhone, because there are so many amazing entrepreneurs who are telling stories of the kind of growth that we had,” she says. “But I’ve never been dependent on what’s to come. I have to keep hustling and not retire on whatever could have happened on Nasty Gal, and that feels really good.”

“I know that sounds like spin, but it’s not,” she adds. “I’m happy.”

At Girlboss Media, Amoruso says she’s more willing to pass the baton to people with experience in the areas she’s lacking. She works in an open office with everybody else now—no more corner office.

Her evolution underscores the simple idea guiding #Girlboss 2.0. This is a community content with being a work in progress—and scraping by together. If Amoruso can come out on top, everybody else’s failures, and potential failures, don’t seem so harrowing.

This summer, Amoruso will host the fifth Girlboss Rally, in Los Angeles. If everything goes to plan, her new social media network will launch around the same time. The company is exploring different tiered pricing, but expects entry-level membership to cost less than $20 per month.

There are still kinks to work out. And there’s no telling whether this, or any of Amoruso’s post–Nasty Gal endeavors, is built to last. But having an audience of enterprising, self-sufficient fans certainly works in her favor.

Nasty Gal’s early years were a knockout success because she tapped into something already happening—fashionable twentysomethings buying cute clothes online—and made it a little easier. As a career guru, Amoruso has more experience, resources, and woman power than she ever did as an e-commerce wunderkind.

“I like to think this is my second brand, but the first I created on purpose,” she says. “I have a chip on my shoulder to get it right.”