Failure

With Girlboss, Sophia Amoruso Is Using Past Failures to Fuel Her Latest Success

And she's launching a brand new social network to help other women thrive.
With Girlboss, Sophia Amoruso Is Using Past Failures to Fuel Her Latest Success
Image credit: Emily Shur
Magazine Contributor
15+ min read

This story appears in the October 2018 issue of Entrepreneur. Subscribe »

During the spring of 2017, the world was getting nasty toward Nasty Gal’s Sophia Amoruso. It wasn’t a treatment she was used to. Until then, she’d been an entrepreneurial darling: the It-girl founder of a booming clothing retailer, frequent subject of magazine covers (including Entrepreneur’s: January 2013), regular headliner of conferences and author of a best-selling memoir. And then, on April 21, the TV version of Sophia streamed out to 130 million Netflix members. It was a comedy called Girlboss, based on her book -- a loose retelling of Amoruso’s life (“real loose,” the opening credits stress), in which a Dumpster-diving college dropout launches her fashion empire from an eBay store at only 22.

Related: How to Make a Career Comeback

The series, frankly, wasn’t very good. But that wasn’t the problem. The problem was that, simultaneously, in a rather spectacular back-assward feat of timing, the real Sophia, 33, was out of work, having sold the company she was celebrated for after it filed for bankruptcy amid a pile-on of troubles. The crisscross of Sophia narratives was catnip to critics, who suggested Amoruso was a narcissist and wrote headlines like “Girlboss is a feminist fraud.”

As if that weren’t enough, on top of the dueling Sophias was a third reality: Amoruso had already launched a whole new company she was beyond excited about, for better or worse, called Girlboss. It was, she says of the misaligned stars, a total “mind fuck.” It was also an entrepreneur’s nightmare: a seemingly inescapable failure.

But almost nothing is inescapable.


This is how Girlboss -- not the book, not the TV series, but the company, the thing that now defines Amoruso’s days -- officially began: In the spring of 2016, Amoruso asked to meet with Ali Wyatt. At the time, Amoruso was still riding high at Nasty Gal, which had 300 employees and a net annual revenue of $85 million; Forbes was about to estimate her personal net worth at $280 million. Her book had spent 18 weeks on The New York Times best-seller list, and Netflix had recently announced the show based on the memoir, with Charlize Theron as executive producer and Kay Cannon, creator of Pitch Perfect, as writer. Amoruso was showing up everywhere in a swirl of descriptives, like edgy, ambitious, cool, hashtaggy, bangs and swagger. And Wyatt, a consultant who’d held top positions at Refinery 29 and Goop, braced herself for the meeting. “I expected someone who would brag and peacock,” says Wyatt. But to Wyatt’s surprise, when the two sat down to talk at La Pecora Bianca in New York City, Amoruso opened up her journal and started taking notes. “She was incredibly disarming in how honest she was, so self-­deprecating,” says Wyatt. “And she wanted to learn.”

Amoruso asked to meet because she had an idea burning a hole in her side-hustle pocket. Through the book and her Girlboss Radio podcast, she’d collected legions of young female followers, literally, in the palm of her hand; she just had to look at her phone to see what they wanted. She could feel the opportunity. But for what? She’d toyed with the idea of a “Sophia show” before realizing she was more of an enterprise girl. That day, she and Wyatt batted around the pros and cons of taking a Girlboss concept to a big media company versus flying solo. After excited goodbyes, Amoruso pretty much went off the map.

Back at the Nasty Gal offices, troubles were coming to a head -- sales slumps, layoffs, lawsuits from employees charging pregnancy discrimination. Staffers vented in Glassdoor reviews. (“It was fucking brutal,” Amoruso says, “having to stand in front of a team you know has written things like that.”) The Chapter 11 papers were filed the day after Trump was elected. To top everything off, Amoruso’s marriage fell apart. “In a six-month period, I was on the cover of Forbes, my husband of less than a year left me and my company went bankrupt. Very publicly,” she says. “It was kind of incredible.” It’s not like she hadn’t seen it coming. “You don’t go bankrupt overnight,” says Amoruso, who has always been open about her failures, but with the kind of consideration that comes from knowing your personal story is your brand. When the collapse came, she gave herself space to call “every clairvoyant and psychologist and basically anyone Goop recommended.” And she realized something: When the dominoes started falling, she had very few resources. “At that time, there weren’t any young female entrepreneurs, or very few, who had experienced the level of crisis or anything like I had,” she says. “It was a very lonely place to be.”

She needed to change that -- for herself and for all the women coming up. Girlboss, she now saw, would be the answer. Amoruso’s vision centered around building a strong community of entrepreneurial young women -- actually, they would build it -- to help each other through hard times and level up together. The brand would include digital content, live rallies and a social network the likes of which had yet to be seen. And she would approach it differently: Instead of following her nose, as she did at Nasty Gal (she was, like the character in the show, a punk college dropout without a drop of office experience), she would lead with intention. “I know it’s cliché,” she says, “but vulnerability and making mistakes is at the core of learning. I wanted to build Girlboss with everything I did wrong or didn’t know better to do.”

She got herself up and running, and fast. The Netflix show was coming; she’d seen the early cuts and loved it. At this point, Amoruso, who had an executive producer title but says she mostly weighed in on the clothes, saw the whole thing as a giant opportunity to get the name of her new venture out into the world. Quickly, she prepared the Girlboss site. She wanted to launch it with a big rally -- something full of empowering female speakers and hundreds of attendees. When she first reached out to women she’d interviewed on her podcast to see if they’d participate, she wondered, Oh my God; am I damaged goods? Is this even -- ? But overwhelmingly, they said yes, and on their own dime. One of them, Jane Buckingham, founder of marketing firm Trendera, remembers being a little dubious. “I’m like, Wow, really? These 20-somethings are going to pay money to come on a Saturday, their day off?

Amoruso called in Wyatt, who later came aboard as president and CRO. Then Amoruso used her own savings to pull it all together. On March 4, 2017, it happened: Five hundred women showed up at the Hudson Loft in Los Angeles for a day of wisdom, swag and connection. “I know that’s what these young women want,” says Buckingham, an expert on millennials and now informal adviser to Girlboss, “but then you see it. They’re there. They’re all networking. They’re all approaching me, they’re all approaching each other. They’re sucking out every element.”

For Amoruso, the exhilaration of launching Girlboss just four months after filing bankruptcy for Nasty Gal was only matched by how badly Netflix backfired. “I’ve gotten a lot of press,” she says. “But there’s nothing that compares to what comes with a television series like this. It’s unimaginable, the amount of eyeballs, the criticism.” Trying to build a meaningful company to help young women succeed, while being questioned as a feminist and businesswoman over the company she’d moved past? It was, she says, like entrepreneurial whiplash. “There were times I thought I would never bounce back.”

Related: 15 Celebrities Who Got Fired and Made a Comeback

But she reminded herself of the advice she gives to others facing adversity: You wouldn’t be here if you hadn’t taken a risk, and that’s what you do if you’re an entrepreneur. She began imagining the scene in Indiana Jones and the Last Crusade where Harrison Ford stands on the ledge of a chasm that separates him from the Holy Grail and, after a long moment, takes a step out into thin air on the sheer faith a bridge will appear underfoot. Still today, a year-plus later, she thinks about this regularly. In some sense, Amoruso is still on the ledge herself, one foot extended over the abyss. “It’s a very high bar that I have to reach to even start a company called Girlboss, especially with what the past few years of my career have been,” she says. “It’s masochistic to expose myself again. It’s terrifying.”

Image Credit: Emily Shur

Drive down Sunset Boulevard in Los Angeles’s ever gentrifying Silver Lake and you might miss the small cinema-style marquee: this sign is a lot of pressure. girlboss.com. The low-slung building that serves as Girlboss headquarters sits on the corner of Lucille Street (note the girl name) and, like much of the neighborhood, is muraled. “When we moved in, we demanded it be repainted because the guy whose mural it was had been accused of rape,” says Amoruso. (The artist was never prosecuted.) Now it’s a colorful abstract called Rare Bird.

On a recent Monday morning at the weekly staff meeting, everyone is gathered in the kitchen, taking turns sharing their latest Girlboss moment, with account manager Lindsey O’Hara in the middle of hers: a full-body reenactment of a cooking class she took at Benihana, which at one point involved turning an onion and a zucchini into a train. “You have to turn the lights on and off and go, ‘Choo-choo,’” O’Hara says. Her colleagues are in hysterics.

After Amoruso finally catches her breath, she says: “I don’t know how I can follow that up.”

If you took Nasty Gal and turned it upside down, you’d be here. At her former company, Amoruso was often not in sight, either out promoting the brand -- “I drank the fucking fanfare” -- or hiding in her office. But at Girlboss, she’s deliberately one of the crowd, often wearing a mechanic’s jumpsuit and a fisherman’s cap and planted at a table crowded with five others, including the team’s lone dude (which is not for long, she promises). For emphasis, she’s made every employee -- 22 so far -- a co-founder, a policy she plans to continue as the company grows. “In a way, it’s a really small thing,” says Neha Gandhi, editor in chief and COO (and co-founder). “But it’s also really powerful. I think it reinforces that everyone here is responsible for the outcome of the business.” 

This time around, Amoruso has taken great care to ensure that she has the right team, requiring every hire to complete a project with a tight deadline and then present it. She has also surrounded herself with ready mentors like Beth Comstock, former vice chair of General Electric, whose new book, Imagine It Forward, is all about what it takes to be a changemaker. “Reaching out and asking for help is a really good sign of a leader,” says Comstock, who now, like Buckingham, is an informal adviser. She says she’s impressed by Amoruso’s commitment to her audience, as well as her resilience: “Nasty Gal was tough.” 

At the Monday-morning meeting, everyone quickly popcorns their goals for the week. Several on the team are working on the site, which is updated daily with pieces about subjects like working life, mental health and identity. Wyatt, who videoconferences in from New York, is nailing down logistics for this fall’s rally -- their fourth -- for which they’re expecting to sell 1,000 tickets. A staffer is booking talent for Girlboss Radio, which has grown to 700,000 downloads a month across its four shows. (One of the hosts, Jen Gotch, founder of the colorful gift and accessory brand Ban.do: “When Sophia asked me if I’d do a podcast on mental health, I said, ‘Oh, no. Definitely not.’” She laughs, standing head-to-toe in gumball orange. “And here we are.”)  

But the team’s big focus this week is on launching a test model for the social media platform, Girlboss Collective, their most ambitious product yet. Using what they’ve learned from a closed Facebook group of 5,000 members over the past year, the platform allows each user to create a work profile with as much personality as she wants. (Men can join but have to behave.) “We’re Instagram over here and LinkedIn over there, and that’s just not how life works now,” says Amoruso, who likes to describe the Collective as both in one: “a place where a woman can show not just what she does but who she is.” The pièce de résistance is the conversational feed that resembles Reddit or Quora -- long threads for members to connect, asking each other questions, getting advice, commiserating and supporting.

Related: How 10 Billionaires Faced Failure (Infographic)

At one point, when the team seemed to hit a wall with the prototype, Amoruso called in a friend from her new mentor gang, Payal Kadakia, who founded ClassPass, the fitness service that gives access to a variety of classes. Happy to come by, Kadakia sat with the team and told them how she’d put out two total duds before finally hitting on a winner. By then she’d had so many fails, she hadn’t even bothered to develop the back-end technology for booking the classes -- she and her team had to make the first 20,000 reservations manually before they were up to speed. She emphasized that no one gets a product right on the first try, and urged the Collective team to “just put it out there” and then tweak, much to the relief of everyone.


Going out to investors was tough at first. The Netflix fallout was still fresh, and Amoruso felt slightly radioactive. “In some of the early interviews, it was like, ‘In case you’ve googled me, these things did happen, these things were blown out of proportion and this is not what we’re doing now.’” But she soon stopped mentioning it. “When we met,” says Alexis Ohanian, cofounder of Reddit, who’s now general partner at a firm called Initialized Capital, “it was clear that Sophia has learned hard lessons and become a much better founder as a result.”

Initialized Capital would go on to lead her latest fund-raise of $3.5 million, bringing her total raised to $6.6 million. That’s a tenth of the funding she got for Nasty Gal, but Amoruso prefers it that way. She wants Girlboss to grow on its own steam. She’s always lived for the scent of pixie dust, that magic something that drives revenue. And so far the company has paced beyond expectations; it’s on track to triple revenue from the first year. In July, it passed its 2018 revenue target.

The smallest chunk of income comes from banner advertising on the site -- in this market, a wise move. The company also makes money from its events, where tickets go for $275 to $700, as well as podcast sponsorships, and it’ll soon start selling subscriptions for membership to Girlboss Collective. (Some access will be free.) Eventually, it also plans to add paid-for job postings and video tutorials. But today, its main revenue comes from creative brand partnerships, which average in the six figures, according to Amoruso -- a strategy she first got excited about when Prudential approached her in 2016 to promote its 4.01K race at the Rose Bowl. She was still at Nasty Gal then and worked with Prudential to create customized podcasts about saving for retirement. With Girlboss, she could get much more creative. 

For a new venture like Girlboss, says Laura Beaudin, a partner in Bain & Company’s San Francisco office, attracting brands “is a big opportunity that the current digital platforms haven’t really been able to unlock.” She points to a shift in the ROI-obsessed digital advertising market toward cultivating more authentic, lifetime connections with customers that might include, for example, making an indelible impression at a Girlboss rally.

One partnership around a diversity panel “was an overwhelming success for T-Mobile,” says EVP of customer care Callie Field, who spoke at the most recent rally. “A woman even came up and pitched me an idea on the spot, which I was truly inspired by.” At another rally, Google, another of Girlboss’s sponsors, ran a Startup Studio, with 50 Chromebooks on which attendees learned to write business plans using Google Docs. Neither T-Mobile nor Google would confirm numbers, but Bumble reportedly paid in the low six figures to host a photo booth and a glam squad for attendees to create professional profiles on Bumble Bizz, the event’s official social media platform. “Bumble Bizz was brand-new,” says Alex Williamson, Bumble’s head of brand, so the partnership “was monumental for us.”

Girlboss is, of course, not the only working women’s empowerment brand generating buzz. Other young girlbosses are leading companies like Create & Cultivate, Levo, The Wing, even Bumble, with its new platform, to court millennial climbers who, in a pussy-hatted, #MeToo world, see great value in women’s networks that never have to whisper again. But is the space getting crowded? Or is it a passing cultural moment? Will women get tired of paying to connect and confab?

Beaudin doesn’t think so. As long as there are working women, they will find these communities extremely attractive, she says. Inevitably, there will be some consolidation, but a platform like Girlboss is in a strong position to branch out to new audiences if necessary, and to add value to the one it has. “If the content can keep up with the need, and there’s a way to curate the community so they become an integral part of it,” she says, “then it will be very sticky.”

Image Credit: Emily Shur

Monique Bryan has followed Girlboss from the beginning. A longtime fan of Amoruso’s hustle, she read the book and listens to the podcast. When she heard about the first rally, no way was she going to miss it. Nor did she care that Nasty Gal had filed for Chapter 11. “For her to be able to throw something like this in the face of all that? Like, she’s not crawling under a rock. It only made me more interested.” Bryan had just left her second startup and didn’t exactly have the money, but it was 10 degrees in Toronto, where she lives, and she’d always wanted to go to L.A., so she bought the ticket and booked her trip for about $1,100 in U.S. dollars.

Between then and the time of the actual event, a lot changed. She celebrated her 36th birthday, went to the doctor, and was diagnosed with breast cancer. She was told she needed to do chemo and radiation, and to freeze her eggs, and she needed to do it all right away. But she took the trip. On March 4 at 8:00 a.m., Bryan stood outside the Hudson Loft in line with the other 500 girlbosses who’d gathered from around the world.

Bryan remembers the excitement of going in and getting her iridescent name badge, the Girlboss D.J., the glam squad room, her clear knapsack swag bag. “Everything was branded so beautifully,” she says, “and I’m super critical.” She also remembers the variety of speakers, from comedian Whitney Cummings to Glossier founder Emily Weiss. But the one she’ll never forget was the one she heard completely by accident, when she ended up at a talk by Samantha Paige, an artist diagnosed with thyroid cancer at age 21, who’d bared her preventive double mastectomy in a striking Equinox campaign.

Bryan soaked up the talk and the Q&A afterward, until there was time for just one more question. “I was on the edge of my seat, third row, with my arm waving: Can’t I just ask?” she says. “I remember Sophia looking around and finally going, ‘OK…you.’ And all of a sudden I was like, Oh, shit; I’m going to start bawling my face off. ” Bryan found her voice in time to tell Paige about the cancer and to ask what she wished someone had told her when she was diagnosed. “Samantha has these piercing blue eyes -- they look into your soul when she’s talking to you,” says Bryan. “She was like: ‘Feel it all. Be angry. Be mad. Don’t take care of other people’s feelings.’ ” With that, the talk ended, and Bryan was mobbed with women hugging her. “It was really moving,” she says.

Related: 10 Blessings That Come Hidden in Rejection, Losing and Failure

Back home, going through treatment, she took Paige’s advice to heart. “I didn’t realize how important it would be to me,” says Bryan, who was declared cancer-free in August 2017, and launched her latest business, a company that coaches women entrepreneurs. Does she plan to attend the New York rally this fall? Yes. Would she join the Girlboss Collective? Hell, yes. “I’m her target customer,” she says of Amoruso. “We’re all just ready to absorb her books, social media, whatever she’s giving out.”

Stories like this, of course, are Girlboss gold. They’re also what Amoruso knew was at the other end of her own troubles. After all, she was hearing from this audience. And she knew what it felt like to be knocked down and get back up again. “People tell you what they want -- you just have to listen to build something they will love,” says Amoruso. “Girlboss isn’t about me. It’s about her.”  

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