The Unstoppable Sophia Amoruso

Entering the corridor of 523 W 6th street is a trip. The Beaux-arts style PacMutual building just west of Pershing Square in Downtown LA feels unmistakably adult. Scrolling through the directory, the words Nasty Gal stick out among the dentists’ offices, law practices, and white-collar firms.

I arrived at the lavish headquarters early to get my bearings. Sophia Amoruso was early too, walking in with her chief of staff and an arsenal of beverages. She showed up in character: a long, villainess black dress and stilettos; unlike the picture on the cover of her New York Times Best Selling book #GIRLBOSS, her black hair was long and trademark bangs grown out. Her makeup-free skin was pore-less. We walked through the notorious 50,000 square foot open-plan workspace lined with intimidatingly trendy women (80% of Nasty’s Gals employees are female) and settled in to her corner office.

Everyone from Forbes to Vogue has profiled the brand’s narrative. Even the most casual observer of pop culture is probably acquainted with Nasty Gal’s story: hip online retailer helmed by entrepreneurial anti-hero, Sophia Amoruso—the unexpected businesswoman who forged her way into the industry thanks to a keen eye, street smarts, and considerable moxie. The ultimate millennial rags-to-riches story.

Shoplifting, hitchhiking, eBaying, MySpacing her way to owning and running a multi-faceted company worth over 100 million dollars before its first round of investment (from Index Ventures, a firm whose notable portfolio also includes Dropbox, Etsy, and Asos), Amoruso succeeded with next to no marketing other than consistent, astute social media content. She’s been branded as the anti-Lean In—the “bad girl” of female empowerment. This moniker is accurate if taken as a verb instead of a noun, as an approach rather than a character.

It can feel strange to talk with someone whom you’ve been following for years. Like a lot of girls, I was “friends” with Sophia on MySpace in 2006. I often used her vintage eBay shop as a mood board, well before I knew what those were. Virtually every cool girl I know has either shopped at Nasty Gal or applied for a job there. Last year, I read #GIRLBOSS and the op-eds written about it. Later, I read about the layoffs and the controversy. I even creepily looked up her birth chart (she’s an Aries/Taurus cusp, otherwise known as “The Cusp of Power”). Sophia knew nothing about me. I worried this familiarity chasm would create an awkward, one-sided conversation. It didn’t.

We chat a little about the Downtown neighborhood, her recently wrapped #GIRLBOSS book tour, and her impending trip to St. Barths. “I’ve gotten more selfish as I’ve gotten older. It was probably at least five years before I took a vacation after I started the company.” We talk about what it’s like becoming a public figure, and how it feels to suddenly have a platform, and consequently an audience that craves a neatly packaged message.

“I mean, I believe in ‘leaning in’—it was a term I had heard before the book came out,” she says. “I don’t have a philosophy per se, so I don’t know if that means that woman can have everything. You know, like, whatever works for you. Some people have husbands who would probably be a great stay-at-home dad—I probably do, but I’m not gonna tell anyone to go for that. It’s too much responsibility and dogma to give people a formula for shit.”

Aside from crafting a digestible ethos, being a celebrity invites a more logistical set of challenges. “I’m still getting comfortable in front of the camera,” she says. “None of this stuff is natural, but it’s in my best interest to be good at it. Public speaking is probably the hardest thing. That’s something I’d like to be really good at cause it seems lame to be doing Q+A’s all the time.”

Back in March, Amoruso sheared at least some responsibilities from her plate, appointing former Lululemon chief product officer Sheree Waterson to run the business side of Nasty Gal, a decision that was a long time in the making; Sheree worked as chief of product for Nasty Gal for a year before the transition. “There wasn’t a catalyst, it was something that I wanted to do for a long time. It was like, as Sheree’s ready, I’m gonna do this.”

Amoruso often speaks to the value of playing to your skillset. But if I had to name her superpower, it would be seeing around corners. For a candid and intuitive person, Sophia is surprisingly deliberate and self-aware. “I’m not good at repeating myself and I’m not good at giving praise. I’m someone who just started a business by myself. No one gave me praise. I was my own critic and I was my own cheerleader so [leadership] is something that I’m still learning. I think that’s affected our culture, and I think people need encouragement. I’m just really impatient. I like to be doing things rather than feeding the things that are being done, or keeping the wheels on the bus.”

A lot has happened since #GIRLBOSS was published in spring of 2014. Sophia turned 30. She became a full-blown public figure. She went from CEO to creative chairman. She married her long-time love, musician Joel Jarek DeGraff. Nasty Gal suffered significant turnover, public restructuring, and consequential bad press. The pixie-faced rebel The New York Times dubbed “The Cinderella of Tech” in 2013 became human in 2015.

As you might imagine, Amoruso is still moving, still in the kitchen. The #GIRLBOSS brand is quickly becoming a multi-platform movement with a recently launched podcast, the #GIRLBOSS Foundation, and an impending second book.

“I do think that #GIRLBOSS can be a hub of inspiration for girls,” she says. “#GIRLBOSS is a brand. There’s a book and a podcast and we can have all these amazing events. There’s so much more to do to engage this community and build the foundation and just have fun with it. All these things need to connect, and I’m figuring out how that’s gonna work.”

As we wrap up, I ask her what it all feels like now—after the rise, the money, the press—how it feels to succeed when you’ve spent a lifetime self-identifying as an underdog.

Leaning back in her chair, Sophia takes a sip of her smoothie (one of 4 beverages in front of her), “I still feel like an underdog,” she says. “It’s definitely strange to meet people on the book tour and have them say, ‘You’re my idol.’ The book says not to do that! But I did put myself on the cover of the book standing in a power pose. It’s a weird sense of responsibility, but it’s something that I really cherish. I just want to pass on the underdog story/feeling. The knowledge just from experience—that there’s hope for you even if you don’t fit in. I feel like everyone relates to that on different levels and hopefully my story makes it possible for other people to admit that.”

If Sophia Amoruso were Cinderella in her twenties, she’s Iron Man in her thirties.

Photographer: Emman Montalvan

Assistant: Stephen Paul Stocker

Stylist: Ashley Roberts

Hair: Ryan Richman @ Starworks Artists

Makeup: Rosie Johnston @ The GRID Agency