When Nasty Gal Fell, Sophia Amoruso Set About the Business of Being the Boss

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“I’m so excited! How many times do you think we’re going to say that today?” a woman in a pink blazer asks her friend, who has pink hair. The two are waiting for a freight elevator in downtown LA’s Hudson Loft building, which arrives with an interior painted hot pink and glowing neon. At the top, doors open to a cotton candy-colored vista and a roar of voices and music.

That morning, 500 women, some of whom had traveled from as far away as London and Australia, had made their way to an Instagrammable oasis of mod-shaped couches and banana leaf plants spray-painted pink for Sophia Amoruso’s Girlboss Rally, an event that promised the opportunity to “meet and network with other talented, like-minded women while developing tips and tricks from some of the best minds of our time.” Networking never sleeps, so at 8:20 a.m., women were exchanging Instagram handles over alkaline water, trading websites while in line for kale Sweetgreen salads, and primping for profile pictures in the Bumble photo booth.

“What’s Girlboss?” Sophia asked after she made her way, to much applause, to the main stage in a black jumpsuit with a plunging décolleté and pink headset. “I’m going to start by telling you what it’s not. It’s not a book, although I did write a book called Girlboss. It’s not a new Netflix series, although there’s a really funny show coming out on Netflix in April called Girlboss. Girlboss is a feeling, a philosophy. It’s a way for women to reframe success for ourselves, on our own terms, for the first time in history.”

Reframing success is ripe for Amoruso, who in November left online retailer Nasty Gal, which she built from scratch to the tune of $300 million in revenue in 2015 and garnered her a personal net worth of $280 million. Her departure coincided with the company filing for Chapter 11 bankruptcy, the culmination of now well-known turmoil. Just four days before the rally, Nasty Gal's assets were acquired by the UK retailer Boohoo.com for $20 million.

On social media, Amoruso remained candid about the company’s final months of turbulence as well as her own, the biggest headline of which was the dissolution of her marriage. That Saturday morning, however, the mood felt more like a welcome home party, with speakers extolling the virtues of failing upwards and celebrating the palpable energy that stemmed from hundreds of women in one room. The day kicked off with a keynote speech from Gabrielle Bernstein, the number one New York Times bestselling author of The Universe Has Your Back, whose sermon segued into a daylong itinerary of impressive and proven leaders and entrepreneurs that included Moj Mahdara, Alyssa Mastromonaco, Emily Weiss, Lilly Singh, Whitney Cummings, and Sallie Krawcheck, who held forth in spaces called the “Ballerroom,” the “Dream Den,” and “Hustle Hall.” The day’s penultimate session saw a conversation and group selfie with Kevin Systrom, CEO and founder of Instagram.

“I’m here because I want to learn and find support. Everyone here is a hustler,” explained a 26-year-old named Gol Ara, an Iranian-born college student from Virginia who was so inspired by Amoruso’s first book that she rendered her in a mural. Like #Girlboss, the book, Girlboss, the event aimed high and hinged on catchy aphorisms, many of which were writ large on the walls (“Be Unafraid,” “Own Your Life”). If those were approachably ambiguous, the advice dispensed throughout the day was pragmatic: how to raise money, manage people, build a media channel. Burnout, meditation, self-care, and side hustles were common denominators, as were answers that began: “There’s actually a chapter in my book that talks about this.” (These were available for purchase in the Squarespace-sponsored gift shop.)

It was an overwhelmingly friendly group of strangers. In one exposed moment, a woman asked Sarah Robb O’Hagan, CEO of Flywheel Sports and formerly of Nike and Equinox, for advice on how to broach an uncomfortable topic with her husband. His job was far less lucrative than her business, she explained, and she needed him to quit and care for their kids full-time.“Where I come from, most women stay at home.”

This was when the Girlboss Rally’s meaning really started to crystallize — that when you peel back the neon lights, the irreverent one-liners, the provocative pantsuits, and the elaborate branding around Amoruso, what has resonated with women is the unapologetic vulnerability, the potential in the unorthodox, and the entrepreneurial spirit that’s less rooted in the tactical than it is in generally motivating, no matter your geography or enterprise. What may have been borne of the brazen fashion and unfiltered moxie in Nasty Gal has been channeled into something easily adaptable for women of all career paths, not to mention sartorial leanings. (For a brand that cut its teeth on latex crop tops and spiked platforms, the Girlboss Facebook page had members overwhelmingly in favor of wearing Banana Republic and Ann Taylor Loft to work.)

“Fashion was never intentional,” explains Amoruso a few days after the event. “I love fashion, I love getting dressed. But I did 10 years of physical inventory and I’m taking a break. And honestly, the purpose of Girlboss feels like something I’m ready for in this chapter of my life, which is hard when you’re selling clothes, at the end of the day. I struggled with that at different points in Nasty Gal’s trajectory.”

Part of the appeal of the Girlboss message — redefine success on your own terms, be the boss of your life — is that it is overarching enough to accommodate nearly any profession. Back at the elevator, where a woman in a pink pantsuit was posing, album cover-style, next to a spray-painted tree, I met three IT consultants from a predominantly male office. They were bright, charismatic, assertive, and frustrated by the ways in which they were second-guessed and overlooked by their coworkers.

“I read Sophia’s book and I made the girls I manage read it,” explained one, who had instigated the trip from out of state. “I think there’s a lack of female leadership, and you need that constant motivation. We’re in a professional environment where I feel like I have to follow this path, but at the same time, I’m loud, I have a personality, and that’s okay.” (The logo for the rally was an open mouth, shouting.) Were there fewer networking opportunities available to them in their city? “To be honest, the speakers here are very different than someone I’d ask for advice at home,” one said. “They’re telling you: Not everything is going to be linear. It makes me re-evaluate everything. Like, hey, maybe I can break the system, why do I have to wait this long?”

Panelists echoed this feeling and gave compelling and unglamorous portraits of their roads to entrepreneurship. Oddly, for a woman who created a guest list of highly impressive people, Amoruso occasionally seemed timid. Speaking infrequently, she mostly refrained from her own anecdotes of bossdom, chiming in more as a moderator or with a joke. While she alluded to mistakes and referred to her current career status as “in a complete knot,” she played the specifics close to the vest. If there were reflections she had about her tenure at Nasty Gal, they were not going to be shared here.

I was curious about how Amoruso, a self-professed introvert, planned to navigate a new role that seemed to lean heavily on public speaking. “That’s something I’m really working on,” she says. “The next chapter is going to require a lot of communication about what we’re doing. But I’ll use whatever power I have with my following to inject firepower into Girlboss and all the women who can benefit from it, more than it being about me.” Days after the event, she was thrilled by how positively it had gone and that the 50 speakers — most of them her friends — were willing to appear at a conference for an audience of women largely in the beginnings and middles of their careers.

An experienced LA founder who attended echoed that many women seemed to be embarking on entrepreneurship rather than several years into its trenches — a widening she saw ultimately as a good thing, because who doesn’t want to see more women professionally empowered? “I think it’s very smart to make it broad,” she noted. “I looked at it and was like, ‘Wow, she could take this out to every city in America.’”

“I also think there’s an impetus to launch the brand in conjunction with the show,” she added, “and that’s why it came up so quickly.” Another woman I spoke to who works regularly with entrepreneurs expressed that while the event was undeniably impressive, hosting it without addressing the managerial shortcomings of Nasty Gal felt incomplete and irresponsible.

How does Amoruso envision the next chapter? “Oh you mean Chapter 11?” she quips. “I have to be able to laugh at the last 10 years of my life, because I worked really hard.” She sees the future of Girlboss as a platform for events and digital content that helps women achieve their goals and openly discuss their pitfalls and peaks. Like her responsiveness when her eBay business grew, and then when her e-comm site flourished, she is seizing the opportunity she created and acting while it’s hot.

“Girlboss could very easily have been an extension of my personal brand, something I keep on the side and I license out the name here and there. But by the sheer nature of the book having been a bestseller and the term ‘Girlboss’ being used almost five million times on social media, the equity as a name and an opportunity for a brand just grew and grew, without me doing a whole lot to promote it; Nasty Gal was my focus until late last year.” (Some articles reported that employees saw the promotion of the book interfering with her attention to the company.) “This next chapter is about other women writing their own stories, becoming authors of their future, because I realized sharing my story made a lot of people feel more capable and less alone.” There are currently seven employees at Girlboss, the company, for which Amoruso is raising money. “I’m still learning about being a good boss,” she admits. “Yes, I’m the Girlboss, but that takes a long time to be good at, and it’s something I’m re-learning with this small team, and that feels really good.”

Over and over again, Amoruso’s acolytes who attended the rally cited her candor as what they appreciate most about her, and business failure only seems to add to that appeal. “I think she’s willing to share her perfections and imperfections,” notes Mahdara, who is also an investor in and advisor to Girlboss. “There are a lot of people out there who try to do what she does but are really not willing to go to the bone in terms of showing that rawness. And when you say you’re a female entrepreneur, you’re really setting yourself up for criticism. People are pretty vicious.”

No one I spoke to that Saturday seemed bothered that they were at an event for Girlbosses helmed by someone with an uneven track record of being the boss — not least the long list of founders that showed up for Amoruso, whose orbit offers a reach that’s undeniably helpful for anyone building something or trying to affect change. The day after the rally, Whitney Cummings, who appears to have a genuine friendship with Amoruso, announced on her Instagram StorY that she had garnered 11,000 new followers.

So what did attendees, who paid anywhere from $350 to $600, get from the rally? A lot of advice and access; “A kick in the ass,” as one from Chattanooga, Tennessee put it, to get serious about carving out a career on their own terms; a guarded leader from whom they continue to draw inspiration — who lost a business and created a conference for people who wanted to learn how to start a business. And they got a digital community that, judging from the groups, Google docs, and conversation threads emerging after the event, looks like a space for women bouncing ideas off of each other, asking for help, and cheering each other on — an end much larger than any single Girlboss in the mix.