Sophia Amoruso Is Ready To Retire the ‘Girlboss’ for Good (2024)

Sophia Amoruso was up onstage fiddling with her blouse, trying to remember why she’d agreed to do this event in the first place. It was the opening night of a two-day summit hosted by the tech outlet The Information, where top women in technology, media, and finance had gathered at a luxury Napa Valley resort last October. The “highly impactful gathering” for “elite and deeply engaged” women promised attendees “actionable tactics,” and Amoruso was there to cap off the evening.

Inspiration is the currency of the conference industry, and Amoruso, with her rags-to-riches story and her cool-but-relatable aesthetic, for a long time incited it without trying. She was the millennial patron saint for unconventional ambition, first as founder and CEO of the onetime mega fashion brand Nasty Gal, and then with her blockbuster business book #Girlboss, which told the story of how she got there. But it had been a while.

Amoruso was low energy. She’d had a long day of travel, and had been up early for a call with one of her founders—her job these days is as the head of an early-stage venture capital fund. She had also, to be perfectly honest, grown a bit allergic to this kind of forced empowerment. She was feeling a bit…sardonic. “I don’t use the word. I don’t really identify with it,” she said flatly when moderator Jessica Lessin, the CEO and founder of The Information, asked her how she views “girlboss,” a term she popularized when her book came out almost 10 years ago. The word had been formally added to the Merriam-Webster dictionary just a few months prior.

“I mean, we’ve seen a bloodbath,” she said later when asked for her opinion on how women founders have been treated in the press. Okay, but what about the future of women-led companies? Would she continue to invest in them, now that she was an investor herself? Amoruso looked a bit annoyed. “I want to invest in the best people,” she said. “If someone has great experience, has a great idea, if their company has great traction and they’re set up to win—that’s more interesting to me than, like, fulfilling some girlboss quota.”

“Was that bad?” Amoruso whispered to me when she returned to her seat. It may not have been the most motivating end to the night, but at least it was honest. And not sandpapered, saccharine honest, with mantras of “women supporting women” and platitudes about “the journey.” It was actually honest. And whether you once loved what she stood for or hated it or simply hated what the girlboss had come to represent, the half a million people who’d bought her book know that Amoruso has always prided herself in cutting through the bullsh*t. And, anyway, what did she care? She’d prefer never to utter the word girlboss again.

There was a time—before Nasty Gal was sued by a former employee (the lawsuit settled), before her fashion empire went bankrupt, before some people lumped her in with a cohort of women who’d become akin to corporate Karens—when Amoruso was paid thousands of dollars to do these kinds of talks. She was the “Cinderella of tech,” as the New York Times put it—a community college dropout who’d once worked as a stripper and built one of the fastest-growing retailers in the country, and who happened to be hot and stylish and charmingly self- deprecating, making fart jokes in professional settings and posting about taking Prozac on her Instagram account. She was a self-made multimillionaire who was at one time projected to be richer than Beyoncé—and who thought, “Well, if this doesn’t work out, at least I can laugh about it when I’m old,” Amoruso tells me now.

These days, she is running a VC firm called Trust Fund, which is a joke in name only; she never had one. She wasn’t being paid to speak at the summit—which, to be clear, she wasn’t complaining about—but it was kind of funny, since not compensating women to speak at a women’s conference is exactly the kind of thing she would have once been criticized for even suggesting. But it was good visibility for her new business, just over a year old, and she’d come with 300 “Trust Fund” bucket hats for the conference gift bags.

Amoruso chatted politely with a couple of fans after she stepped off the stage, then grabbed a drink and headed to her room to call her boyfriend. She had planned to stay. But the next morning, instead of joining the “crystal vibes meditation” or waiting to see Katy Perry speak about her shoe and aperitif brands, she put on a black sweatsuit and packed herself into another Uber. She had work to do, and it didn’t involve “al fresco networking”—at least not anymore.

In the TV version of Amoruso’s life, of which there was one on Netflix called, yes, Girlboss, you could see how this scene would play out: a flashback to 10 years ago—a younger Amoruso, in her Pulp Fiction black bob, sprinting toward a valuation in the hundreds of millions; appearing on magazine covers and on red carpets—the reluctant leader of a pseudo-feminist movement. Then cut to the present: the now blonde Amoruso, who spends more time in rooms full of men these days, quietly ducking out of the fancy lady conference, left wondering if she’ll ever be able to outrun the word she defined but that came to define her—and a generation of women entrepreneurs.

It’s strange to have created something that is entirely out of your control. Maybe even stranger when that thing has now come to mean the exact opposite of the message you set out to deliver. Amoruso, 39, wavers between feeling proud, feeling jaded, and wanting to cast off her association with it entirely. “I made this thing, and it took on a life of its own,” she says as we drive toward the Oakland airport. “It’s not that I’m embarrassed by it, but I don’t want to be defined by it.” Later, she texts me in all caps, “I DO NOT SPEAK ON BEHALF OF THE GIRLBOSS.”

So, what was a girlboss? Before it was an insult, or shorthand for a certain kind of craven millennial careerist, it was a book, one with Amoruso on the cover in blunt-cut bangs. The title was tongue in cheek: It came from the 1972 movie Girl Boss Guerilla, part of an obscure genre of Japanese films called “pinky violence,” which mixed action and erotica, and featured a series of characters known as “delinquent girls,” which Amoruso thought described her arc well. In the book, she defined it simply: A girlboss was someone “in charge of her own life,” who “gets what she wants because she works for it.” She also wrote, “Sometimes you break the rules, sometimes you follow them, but always on your own terms.”

There are plenty of books full of such maxims, but Amoruso had actually walked the walk. She grew up in Northern California, an introverted kid who listened to Bad Religion, was a regular at the Bay Area Anarchist Bookfair, and wanted to be a photographer. Her parents divorced when she was a teenager, and when I asked her what they had hoped she’d be when she grew up, she says, “I think just not sad.” She hitchhiked up and down the West Coast in her late teens, and lived briefly in Olympia, a dreary town south of Seattle where Kathleen Hanna cofounded Bikini Kill and famously scrawled the words “Smells Like Teen Spirit” on Kurt Cobain’s bedroom wall. There, she shoplifted books from the local Barnes & Noble—they had a no-chase policy, she explains—and resold them on Amazon, her first foray into “business.” “Ten cents less than all the other resellers, rent paid overnight,” she says.

As the story goes, she set up an eBay shop selling vintage clothes out of her boyfriend’s apartment in San Francisco in 2006, after reading a book called Starting an eBay Business for Dummies. She named it Nasty Gal, after the album by the funk singer Betty Davis—the underappreciated ex-wife of Miles Davis—and it soon grew so popular she reluctantly moved to the suburbs for more space, where she worked and lived in a pool house, cooking on a hot plate and washing dishes in the bathroom sink. By mid-2013, when she was just 29, she had grown Nasty Gal into a full-fledged business, one with a 50,000-square-foot headquarters in Los Angeles and a projected annual revenue of $100 million—hustle culture, personified. When her lawyer, whom she’d hired to help her sign a home renovation contract, suggested she write a book, “I was like, Sure, why not?”

#Girlboss was as much Amoruso’s story as it was advice for young women, written for those “more prone to be voted ‘Most Unique’ than ‘Most Likely to Succeed,’” as the New York Times review of the book put it. It wasn’t for everyone, but the writing was lively, and the girlboss made for an effective narrative device: “As a #Girlboss, you take control and accept responsibility,” Amoruso told her readers, anointing them part of the tribe. “You’re going to take over the world, and change it in the process.”

The book might have sold on its own. But it helped that it came out a year after Sheryl Sandberg’s business manifesto, Lean In, and just as the criticism of that book reached a fever pitch. If one of the critiques of Lean In was that it taught women to rise in the corporate ranks by playing by men’s rules, then #Girlboss was the antidote—the scrappy misfit younger sister who would forge her own path. The book spent 18 weeks on the New York Times Best Sellers list and became, depending on whom you asked, a movement (though Amoruso finds the suggestion that she was trying to organize anyone “creepy”), a marketing coup, or everything that was wrong with a kind of feminism that called women “girls” and made capitalism the goal.

Whatever it was, it catapulted the idea—and its author—into the zeitgeist at a time when prominent women founders were few and far between. Amoruso appeared on the covers of Forbes, Money, Entrepreneur, and Inc., and spun the book into a podcast, a foundation, and the Netflix series. The word, meanwhile, took on a life of its own—plastered on Etsy mugs, T-shirts, and baby onesies (“Future Girlboss”) too numerous to count, and at one point prompting a trademark-related cease and desist from Hugo Boss. “I remember interviewing her at an event at the Apple Store in Soho,” says Audrey Gelman, the cofounder and former CEO of women’s coworking space The Wing. “It felt like any minute the women in the audience might start throwing their bras onstage.”

The book inspired women—it really did. There were multiple copies lying around the offices in the early days of Bumble, the dating app Whitney Wolfe Herd took public in 2021, making her the youngest self-made female billionaire in history. Amoruso still gets messages daily from women who tell her she inspired them to start companies, quit jobs, leave abusive relationships, tattoo “Girlboss” on their forearms. “Sophia just blazed out of nowhere, with like zero pedigree, no degree, smoking cigarettes,” says Moj Mahdara, the former CEO of Beautycon, who has known Amoruso for close to a decade. “I think for me, as a queer nonbinary person, watching that was like, ‘Hey, maybe I can have a shot at this, too.’”

Whether #Girlboss capitalized on a moment or contributed to one already brewing is hard to say; probably a bit of both. But from 2014 to 2019, businesses headed by women grew by an estimated 21 percent, according to one report. And when it came to venture-backed companies, by 2016, a slew of women founders were running companies that would become household names.

This, of course, was back when it seemed likely Hillary Clinton would be president; when “The future is female” wasn’t just a political slogan but a way of life, and millennial pink the shade of our collective rose-colored glasses. So it made sense that the women running these companies—who, like Amoruso, tended to be young, telegenic, and white—made feminism, or at least womanhood, part of their platforms. The slogans alone seemed to complement the moment. Girlboss: “For ambitious women with big dreams.” The Wing: “Girls doing whatever the f*ck they want.”

But the phenomenon was short-lived. By the time the pandemic hit, and then racial justice protests erupted over the killing of George Floyd, the vibe had shifted. In the face of so much death and inequality, the girlboss started to look more like your average boyboss: She benefited from the system more than she’d done anything to overturn it. And so began the Girlboss Reckoning, in which many of the same founders who’d been eagerly hailed as the future of entrepreneurship—plastered on the covers of countless magazines, “like pinups,” as one founder put it—were toppled in quick succession.

Over a period of about nine months, amid complaints of “toxic” workplaces, poor leadership, or, in some cases, allegations of racial insensitivity at their companies, at least eight prominent women founders resigned, one after the next, each with their own version of an accompanying “takedown story” in the press, as Amoruso says. As Alex Abad-Santos of Vox wrote at the time: “The girlboss is one of the cruelest tricks capitalism ever perpetrated.”

To look back on it now, there’s no doubt there was a gendered undercurrent to it all. “Obviously, women are capable of the same heinous atrocities and labor oversights as men,” says Samhita Mukhopadhyay, the former executive editor of Teen Vogue and the author of a forthcoming book about workplace feminism, The Myth of Making It. “But, like, why is Elon Musk not canceled?”

But it was more insidious than that, too: In the breathless coverage of the women’s rise, owing in part to the pressure on business outlets to diversify their pages. In the assignment of the “girlboss” label, like a glossy little pick-me-up, at a time when “‘perimenopausal-boss’ would have been more apt,” says Yael Aflalo, the founder and former CEO of Reformation, who is in her forties. And, too, in just how gleefully their downfalls were embraced—“with popcorn,” as another founder put it—by throngs of people following along on social media from home. Was the backlash fueled by a sense of abandonment? Anger at their hypocrisy? Or schadenfreude, simply feeling good to watch a wunderkind fail? “It was almost soap-opera-ish,” says Laura Huang, a professor at Northeastern University, who teaches a course called The Social Psychology of Entrepreneurship. “There’s something about falling from that pedestal, when it happens to women, that we just can’t get enough of.”

Whether you believed it was a necessary correction or an overcorrection, the downfall of the girlboss became a fascinating case study in a particular cultural moment. It offered insight into what employees expect from employers in a workforce that, as Smith College associate professor Loretta Ross puts it, had become browner, queerer, and more demanding; what we expect from women leaders, who tend to be held to higher standards of morality; and the pressure placed on women founders to do, and be, it all. “It’s like both driving the car and being the hood ornament,” says Christene Barberich, the cofounder and former global editor-in-chief of Refinery29, who stepped down during that period.

If girlboss had been shorthand for a confident, capable woman pursuing ambitions on her own terms, it had now, for many, become emblematic of a pejorative. A term for a certain kind of woman—one who clawed her way into leadership, then turned around and reinforced the same patriarchal systems she claimed to want to smash to bits. Particularly during the pandemic, girlboss became code for the kind of overwork we were now rejecting. (For what it’s worth, some of those former girlbosses who stepped down during that time told me they regretted doing so.) “It became a symbol for the way women of a certain generation felt they needed to approach their careers: not just by entering the workforce, but by dominating it,” Mukhopadhyay says. “And how did you dominate the workforce but by playing by men’s rules?”

Amoruso managed to avoid being a subject of those headlines, but only because she had already faced her own reckoning. Nasty Gal’s first round of layoffs came a few months before #Girlboss was published, and Amoruso stepped down as CEO in early 2015, amid declining revenue, but stayed on as executive chairwoman. Nasty Gal was subsequently sued in a lawsuit that accused the company of firing three pregnant employees because of their pregnancies while Amoruso was still CEO. A spokesperson for Nasty Gal at the time issued a statement calling the suit meritless, frivolous, and taken out of context, as the layoffs were part of a larger restructuring of departments. The suit ultimately settled with no admission of wrongdoing. After the lawsuit, there were more layoffs, and a Glassdoor profile that “looked like a police blotter,” Amoruso says.

But the worst came in late 2016, when Amoruso was in Australia, preparing to speak to an auditorium of a thousand women. The day before, in a call with her board, they had decided that the company would declare bankruptcy. The news was breaking as she walked onstage. “I just remember being onstage crying and saying, ‘I did my best,’” Amoruso says. Nasty Gal sold for a reported $20 million, a fraction of its former valuation, and Amoruso left with the furniture in her office and a net worth that had disappeared overnight. She had a house with a pool in the Hollywood Hills and a small mortgage, but this was not Beyoncé money—she needed to work. And so she did what any girlboss would: She plunged herself into the IP that remained. Her followers didn’t seem to care that the business on which she’d built her personal brand had just imploded.

The following year, riding on the wave of anger fueled by the election of Donald Trump, Amoruso hosted conferences at massive industrial loft spaces in downtown L.A. and New York that had been transformed into puss*hat-pink utopias. Typographic murals with slogans like “Be Your Own Idol” hung from the exposed brick walls. Girlboss was now an aspiring media brand that aimed to be “one part Vice, one part Oprah,” as the Wall Street Journal put it, and these were its inaugural rallies.

About 500 women paid to attend the event in L.A., with speakers like Bumble’s Wolfe Herd, Outdoor Voices’ Tyler Haney, Glossier’s Emily Weiss, and Instagram’s Kevin Systrom—as well as Amoruso herself. But even as the women she’d inspired appeared onstage with her—noting how she’d paved the way—she was reeling. “I couldn’t be happy for them,” she says. “It seemed like they were all doing it right. And I was still licking my wounds, thinking, ‘Why couldn’t I pull it off?’ I felt like I’d let down the generation I inspired.”

I first reached out to Amoruso during the pandemic, after noticing she had removed the word girlboss from her Twitter bio. She sold Girlboss in 2019, then stepped down the following year, along with most of her staff, citing the financial havoc wreaked by the pandemic. It had become a liability, it seemed, even just to mention the word.

At the time, she was preparing to launch yet another business—this one called Business Class, a series of entrepreneurship courses in the style of MasterClass, with her as the chief flight attendant and instructor. But as story after story of the embattled girlbosses broke, followed by weeks, then months, then literal years of analysis about the term, she was feeling a bit off-kilter. At first, it was almost validating to know she wasn’t “the only one” whose business had failed.

But as the stories kept coming, she began to feel uneasy. “At a certain point, I was like, Holy sh*t, is it possible that we’re all awful?” she says. “I just remember watching, as a bystander, kind of shocked. It was an onslaught. And the accusations were really serious.” She called up Mahdara, as well as other founders of color, and asked them, “What could I have done better?”

For a while, Amoruso thought she could stay quiet, not talk about it, spiritually cast girlboss off, and hunker down and focus on her new business. Maybe she would never again have to engage with the word. But it just kept recirculating—with seemingly endless new meanings and memes, the butt of every Gen Z joke. “She girlbossed a little too close to the sun” became a phrase to describe overconfident recklessness. “Girlboss energy” was shorthand for a too-ambitious Tracy Flick type. “Gatekeep, gaslight, girlboss”—TikTok’s way of eye-rolling a millennial corporate feminist, with a kind of sneering version of “Live, Laugh, Love.” Still today, it seems that almost every workplace or cultural trend involving women that is not deemed pure unbridled ambition—whether it’s “quiet quitting,” the supposed rise of stay-at-home girlfriends, or just lying in a pile of moss (“girlmossing”)—is framed as the counterpoint to “girlboss culture.” “Somebody asked me about ‘snail girls’ the other day,” Amoruso says. “I was like, what?” (Snail girls, according to one woman interviewed by Fortune, have ditched corporate jobs to “live like I’m retired.”)

It ended up being something admittedly silly that jolted her back into the public eye. In 2022, The Information—the same tech outlet that would invite her to speak in Napa Valley in 2023—published an article suggesting readers “dress up as your favorite disgraced girlboss” for Halloween, citing Amoruso and former Theranos fraudster Elizabeth Holmes, among others, as inspiration. Amoruso was enraged.

“Elizabeth Holmes???” she tells me now. “I raised a too-high valuation, didn’t know how to build a great culture, and didn’t live up to people’s f*cking expectations. And years later, that’s who I am? Elizabeth Holmes, who put dying people at risk and is in f*cking prison?” The outlet removed the article from the website, and Lessin apologized. Then she invited Amoruso to speak with her onstage. Now here Amoruso was, talking about the girlboss, again.

And look, she would rather talk about her investment strategy, or the companies she is working with, or how she’s “picking winners,” which is actually the name of her LLC. But since she was here, she’d just say it: Maybe the girlboss reckoning made space for “women who don’t look like me”—she hopes it did. But she also worries that it cast a permanent shadow, deterring the next generation from taking “big swings.” There is less venture capital going to female-founded companies now than there was when her book came out, according to a 2023 report by PitchBook. The bar is higher, not lower, to prove value to investors. And, she says, there’s a persistent fear among the women she speaks with: to not screw up, to not be too brusque, to anticipate criticism, to avoid press, to think through “every last permutation of critique that could come our way.”

But perhaps most tragic, at least to me, is the number of women, including her, who are now hesitant to start women-focused companies, because of the added scrutiny that comes along with it. “It extends to how we present ourselves and how we wear our hair and what we post on Instagram,” she says. “Like, good luck living up to that.”

Back onstage in Napa, with a couple hundred women looking on, Amoruso thought for a moment about what she really wanted to say. “I think the impact of all of this,” she said carefully—“this” being the downfall of the girlboss—“is that a lot of women aren’t going to put themselves out there because they don’t have permission to make mistakes.” Later, in private, she says a bit more. “If the precedent is that if you go for it, and maybe you’re a new leader, or you’re moving too fast, or you’re in over your head, or just like every other founder are unaware of what’s happening in every last rung of your company, and, God forbid, you screw up, then you’re going to end up literally wiped out and your company obliterated—like, why even try?”

But the thing is, she does still want them to try. She just doesn’t want to be the spokesmodel.

Lately, she’s been thinking about writing a new book—maybe about failure. She jokes that she could call it Girl Loss. But at the end of the day, she just wants women to take risks, fail, screw up, make mistakes, do stupid sh*t, and own up to it—and not have it define them forever. “A man’s successes and failures aren’t attributed to his gender. So why should ours be? Why can’t I just good old-fashioned blow it and move on?”

Styling by Kevin LeBlanc; hair by Clay Nielsen for Leonor Greyl; makeup by Jessica Ahn for Armani Beauty; photographed on location at Oceana Santa Monica.

This article appears in the March 2024 issue of ELLE.

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