#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

UPDATED: September 12, 2016
PUBLISHED: September 12, 2016

Sophia Amoruso has had a lot of jobs.

She starred in commercials as a child model, performed sandwich art at Subway, helmed the information desk at a Borders bookstore, sold orthopedic shoes at an outlet mall, scrubbed men’s dress shirts at a dry cleaner’s, balanced the pH levels of water at a hydroponic plant store, maneuvered a wheelbarrow as a landscaper and checked student IDs at a college. The route had a lot of twists and turns, but ultimately proved to be a circle. Amoruso was going nowhere fast.

Then she founded Nasty Gal, a vintage-inspired, ineffably hip, too-cool-for-school fashion brand. The online retailer now rakes in around $300 million each year and is set to celebrate its 10th anniversary. Amoruso never made more than $25,000 a year before she founded her company, initially as a vintage eBay shop. Now she’s worth $280 million and was featured on this year’s Forbes list of the richest self-made women. She’s the second-youngest on the list behind Taylor Swift.

Related: 15 Traits of Unabashedly Successful Women

Before Amoruso, 32, founded Nasty Gal, she struggled to make ends meet living a “free,” anti-capitalist lifestyle that included dumpster diving at a donut shop, dating a man who lived in a treehouse, hitchhiking, not shaving her legs, eating magic mushrooms and otherwise living as a scofflaw. After a shoplifting attempt went awry, Amoruso had a moment of clarity: She deserved something better than her dead-end, barely-scraping-by life. She realized she had it in her to create something great.

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know


Amoruso never quite fit in growing up. She went through myriad fashion phases (including—but not limited to—grunge, skater girl, crust punk, goth and preppy) and says, “No matter where I went, I was an outsider.” She hated capitalism because, in her eyes, it was the source of all greed and inequality in the world. She couldn’t fathom working the 9-to-5 life—she wanted a life of spontaneity and freedom.

As Nasty Gal skyrocketed to success, people came to appreciate her quirks. “I just feel more accepted, and that’s a great thing,” she says. “I don’t want to take that for granted, because I struggled. Everyone struggles with feeling accepted and feeling weird or like we don’t belong. Somehow I made a career out of being a misfit, and thank God I did, because I don’t know what I’d be doing now.”

A low point during her time as a freegan (an anti-capitalist who dumpster dives for unopened food) changed the trajectory of her life forever. While living in Portland, Oregon, as a misguided 20-year-old, she was caught trying to steal a George Foreman grill and shower curtain rings, among other items. The store did not call the police, but the encounter still put her life into perspective. In her first book, 2014’s #GIRLBOSS—part millennial-woman manifesto, part memoir, and what some have dubbed an edgier version of Sheryl Sandberg’s Lean In—Amoruso says she had hit rock bottom.

With a silver-studded, black-leather moto jacket draped across her shoulders, she contemplates this moment from her downtown Los Angeles office. It’s a workspace most young women would die for: a winding terra-cotta leather couch dominates the room, which features exposed brick walls, a bookcase filled with colorful coffee-table books and retro albums, and a white shag rug. The bulletin board behind her desk has several pieces of white computer paper tacked on, one of which reads, “Deftly—Deftly.” A mosaic coffee table adorned with a tall gray crystal and the mockup of her new book, Nasty Galaxy, rounds out the room.

“Being caught shoplifting was one of those moments where I was like, What am I doing to myself? This is totally my fault. Why did I think I could get away with this? This is no way to live. I’ve got to figure it out. I was being creative with how I made a life for myself, but it wasn’t as a productive member of society.”


“It’s good to feel out of your league. You should try to spend most of your time feeling out of your league, Because then you’ll grow into it and find another league.”


She calls this a pivotal time in her life, when she realized her lifestyle would no longer cut it. She was capable of something better. “I think it just really drove home that there are no shortcuts. It’s only because I learned it early on that I have the drive and maybe the tenacity to realize the only way to manifest great things is by… ” she pauses to redirect her thoughts—something she does often. “The only way out is through. There really is no way out—it’s just through and through and through.”

She packed up her stuff in Portland and drove to San Francisco (she is originally from San Diego) with the intention to do “something legitimate and something brilliant.” Meanwhile she took a job at an art school checking student IDs so she could obtain health insurance for a hernia surgery. While working as a pseudo security guard at the art school, she spent ample time on MySpace, where she would receive friend requests from eBay sellers with vintage clothing for sale. She wore almost entirely vintage clothing at the time and thought to herself, Hell, I can do that, too.

Related: 5 Ways the Power of ‘I Can’ Changes You

She quit her job to pursue her eBay shop full time. She named her shop Nasty Gal after a 1975 album from iconic funk singer Betty Davis. She spent countless hours scouting local thrift stores for the perfect items to sell; finding tall, lithe models to don the items; and taking photographs that emphasized the clothing’s silhouettes so they would stand out among the thumbnail masses on eBay. The first item she sold online was stolen.

Determined and enterprising, she lingered at the stores before they opened so she could delve into the new arrivals before they hit the racks. Through her striking photography, she also developed a knack for making the vintage items she found highly desirable on eBay—bidding wars were a regular occurrence for Nasty Gal’s dedicated following. One of her biggest early wins came when she bought two Chanel jackets for $8 each and sold them for more than $1,500 each.

After a couple of years of hustling, demand for her items soared. As she started planning to break out on her own, she got kicked off eBay for sharing her future website URL with her customers. It was a blessing in disguise. She launched NastyGalVintage.com (NastyGal.com was then a registered adult website) on June 13, 2008. Everything sold out on the first day. The shop initially limited itself to vintage items, but those pieces sold so quickly she brought in current designers, too.

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

She continued pouring time and dollars into her business. In 2008 Nasty Gal did $223,000 in revenue. That soared to almost $23 million in 2011 and nearly $100 million in 2012.

Amoruso says she doesn’t regret the misguided years before she founded Nasty Gal. Family and friends might not have noticed or suspected it at the time, but Amoruso was always persistent and ambitious. “I never really thought about being successful in the conventional sense,” she says. “I wanted to be good at something.”

Although her parents, who divorced when she was a teenager, might not have always supported her financially, they did always support her emotionally, Amoruso says.


“I always wanted to be great at something and I found out I’m pretty great at a lot of things. I think that’s what it takes to be an entrepreneur. It’s hard if you’re only good at one thing or you’re not adaptable.”


“I think my parents did a good job of telling me I was going to do something great, but I really had no idea what it was,” she says, adding that the “dumb stuff” before Nasty Gal certainly wasn’t it. “I found out I’m pretty great at a lot of things. I think that’s what it takes to be an entrepreneur. It’s hard if you’re only good at one thing or you’re not adaptable.”

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

Related: ‘The Get-It-Together Guide for Figuring Out What to Do With Your Life’


The first thing I notice about Amoruso is her unexpectedly petite frame. The second is how strikingly beautiful she is. Third are her tattoos, in particular a fairly new one inked on her inner left forearm that reads: “Words tend to be inadequate.” It is a quote from artist Jenny Holzer. “People judge other people based on their actions,” Amoruso says. “I think words are important, but I think actions are what people remember us by.”

Lastly, I notice that despite being in the limelight often, she avoids large groups of people and does not seem to enjoy being the center of attention. I learn she’s not ashamed of her awkwardness. In #GIRLBOSS, she calls herself, “essentially a young, half-Greek Larry David in heels—incapable of hiding discomfort, dissatisfaction, or doubt.” Despite the plethora of jobs she held as a teenager and young adult, she never worked as a waitress because, as she says, she’s not a people person.

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

“I know I don’t want to be around crowds of people as much as I possibly can,” she says. “I used to feel really weird about that, like, What’s wrong with me? That’s just who I am.”

A self-proclaimed introvert, she is good one-on-one. She does not have a particularly bubbly disposition, but you can tell she is genuine, contemplative and thoughtful. She takes our conversation very seriously.

Those close to her admire Amoruso’s authenticity. “The first thing that struck me about Sophia is that she’s egoless, she’s easily approachable and she’s endlessly curious,” says Sheree Waterson, Nasty Gal’s CEO.

Over the years, Amoruso has developed tricks for making her personality work despite existing in a space primarily geared toward extroverts. She struggles with public speaking. It’s something she’s working on. For example, she will choose Q&As at conferences. “I still haven’t figured out how to get up and just like… talk: Hello. I’m here. Welcome. How are you guys feeling? It’s just really hard.”

Comedian and actress Liz Carey, Amoruso’s close friend and the occasional co-host of the #Girlboss Radio podcast, says Amoruso is too hard on herself. She recently moderated a Q&A with Amoruso and says, “I feel like you have to be able to disarm a room, and she’s really good at that—at making everybody feel equal and important for whatever reason you’re there.”

Related: 6 Tips to Be a More Confident Speaker


The ethos of the Nasty Gal shop on Melrose Avenue in Los Angeles is exactly what I expect—slightly edgy, refined, a bit retro and just plain cool. The salesperson who helps me, Nika, is tall, exotically beautiful and clad in a skintight black dress. Her lips are adorned with dark mauve lipstick and she wears her jet-black hair in a topknot bun. Most other girls in the shop radiate coolness. All are showing skin, whether by a crop top, plunging neckline or high-slit skirt.

As you enter the store, there’s a copy of #GIRLBOSS placed directly in your line of sight. Every product and element of décor in the shop seems meticulously chosen, all the way down to the fitting-room doors, which are two-way mirrors—you can see everyone bustling around the shop as you try on clothes, but they can’t see you.

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

Every piece of clothing and pair of shoes feels like something a Nasty Gal would wear, from a gladiator-style, metal-mesh bra and floral, high-slit maxi dress to a pair of cutoff blue-jean shorts emblazoned with ironic, retro pins: an airplane that reads “high as hell”; Edward Scissorhands and a woman saying “Hold me” as he says, “I can’t”; and a teddy bear holding a heart that says “dat ass.”

I chuckle, recalling Amoruso’s funny, no-shame, rarely embarrassed attitude. During our interview, I find myself laughing out loud multiple times: when she told me her tattoo probably seemed emo, when she said part of the reason she stopped drinking alcohol was because her face would get chubby, when I apologized for yawning and she smiled and said, “I’m tired, too. I’m not one of those people who’s offended when you yawn. I’m yawning all of the time and I don’t look around and think, Who’s going to be offended if I yawn?

In the now-available Nasty Galaxy (a hybrid personal development guide, stylish scrapbook and rush of creative that is made for coffee tables), she writes, “I am willing to be the clown who eases everyone into feeling safe. But who am I kidding—I was born the clown.”

Carey says she and Amoruso recently went on a hike, which turned into an uproarious poodle photoshoot (Amoruso has three small poodles). “[Amoruso] sent me a text that said, ‘We have fun no matter what.’ I think that’s the part about Sophia nobody knows: what a goofball she is.”


In addition to having a refreshingly dry, sometimes juvenile sense of humor (in Nasty Galaxy there are tips for using the bathroom quietly and properly slurping oysters), Amoruso is creative, more inclined to design a new storefront than hold hourlong meetings. In January 2015, she announced in a video blog that she had decided to step down as CEO of Nasty Gal. She handed the reins to Waterson, the former executive vice president and chief product officer at high-end women’s active wear company lululemon athletica and the former president of Speedo. Amoruso initially hired Waterson as Nasty Gal’s president and chief product officer in 2014. Waterson says the brand appealed to her at the time because “it was a cult brand—in some ways, a best-kept secret, like the style authority.”

Amoruso says stepping down as CEO of her company was a move focused on playing to her strengths so Nasty Gal wouldn’t suffer from her steep learning curve. (She doesn’t have a college degree, let alone a management degree from Harvard University like Waterson.) Amoruso now serves as the executive chairman and is in charge of the creative and brand marketing teams. “Nasty Gal was born out of my desire to be creative, whether it’s writing copy or taking pictures or selecting a product,” she says. “At a certain point, we had hundreds of employees, a C-level and an SVP-level executive team reporting to me, and I was touching bases all day long. Everything was about deliverables and Are we on track?” She says she didn’t feel qualified to lead in that way. “I can throw up really great ideas, and I’ve realized there are people much more qualified to catch them and organize them into something sustainable.”

Related: 19 Quotes About Following Your Passion

As the company she ran grew exponentially, Amoruso began to dislike the mechanics of her day. “Yes, there’s a lot only I can bring to the table and that’s not going anywhere. But leading an executive team—is that something I wake up every day to do? I wish,” she says, laughing. “I’d rather be thinking about the customer’s experience and designing the retail store than thinking about how to flow inventory or whether our ERP [enterprise resource planning] implementation is on track. Oh my God,” she says with an exasperated eye roll.

Despite steadily increasing sales, a dedicated, cultlike customer base and the wild success of #GIRLBOSS (it spent 18 weeks on the New York Times best-seller list), Nasty Gal’s press hasn’t always been positive. The company came under fire last year—first for several rounds of layoffs, and then for discrimination lawsuits in which four former employees claimed they were laid off for pregnancy-related reasons.

Nasty Gal responded to the lawsuits with a public statement in June 2015: “The accusations made in the lawsuits are false, defamatory and taken completely out of context. The layoffs in question were part of a larger restructuring of departments we completed over nine months ago. The lawsuits are frivolous and without merit.”

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

When asked what she thought about Amoruso’s decision to step down as CEO, Waterson says, “I’d like to correct that statement. I don’t think Sophia actually stepped down—I think she stepped up. I think she stepped into her strengths: She is entrepreneurial and creative.”


Stepping down as CEO has freed up time for Amoruso to focus more on her creative pursuits, which include two brick-and-mortar shops in the Los Angeles area, two books, the podcast, the #Girlboss Foundation (an organization that provides grants to creative women), and an upcoming Netflix show, #Girlboss, which comes out in 2017 and stars Britt Robertson as a character loosely based on Amoruso’s life before she founded Nasty Gal.

One might think she’s overwhelmed by all of these endeavors. And one would be right.


“When the world seems to like what you’re doing for the moment, you really want to take advantage of it and ride it out. I don’t take it for granted, and I don’t know how long it’s going to last.”


“I pile so much on myself it’s like being buried alive,” Amoruso says. She’s learned to focus more, but says it’s hard when, “you look around and see opportunity everywhere. When the world seems to like what you’re doing for the moment, you really want to take advantage of it and ride it out. I don’t take it for granted, and I don’t know how long it’s going to last.”

Although sometimes blinded by her desire to eat up every opportunity possible, she regularly reminds herself that: A) It’s good to relax on the weekends, and B) Having a routine “feels amazing.” She married in 2015 and says luckily her husband, musician Joel Jarek DeGraff, is “super-independent.” Amoruso rarely drags him to events and she goes to fewer and fewer work-related functions herself. Her decision to stop drinking recently came not because she had a problem, but because she realized the countless, surprising benefits that accompany sobriety. “I’m learning to be a lot more motivated by the long-term effect of what I do, which feels very grown up.”

Like most introverts, she also values the occasional, blissful moment of alone time.

#GIRLBOSS Sophia Amoruso Is the Most Successful Misfit You Know

“I’m more and more vigilant about my personal time and space,” she says. “If I get an extra two minutes to just be alone while someone else connects a phone call and waits for everyone else—and I know that sounds diva-y—but that two minutes is really meaningful to me.” She also tries not to work on weekends and spends as much time as possible with the important people and poodles in her life.

The company founder turned media maven says that if there’s one ongoing hurdle she faces, it’s making enough time for those on her Nasty Gal team. “I think the most challenging part is feeling an eternal debt of time with the people who work so hard,” she says.

Those close to her have taken notice. “She’s just one of those people who truly make you feel comfortable,” says Carey. “I would imagine from afar, most people wouldn’t get that image from her. In a city like Los Angeles, finding truly dependable people you can count on is a rarity.”

Related: 9 Traits of Trustworthy People


In addition to wild success for Nasty Gal (she strives for a presence in all major cities as well as the eventual introduction of cosmetics and handbags), Amoruso hopes that in 10 years she’ll be remembered for “being someone who made a lot of people feel like they can make things happen for themselves,” something she thinks she accomplished with #GIRLBOSS. “It’s a gift to give back by being honest and sharing your story. It makes other people feel less alone, more capable, and like their struggle isn’t just exclusive to them.”

Women often write in to Amoruso to share their “#GIRLBOSS moments,” instances of female empowerment and strength. One recent anecdote stuck with Amoruso. A young woman wrote:

“After learning that the dudes at my work (I am the only female) made more money than me doing the same job, I sat down my boss and had one of the most difficult conversations of my life and negotiated equal pay and promptly took myself out for a drink after.”

Amoruso says women such as this will attribute their empowerment to her book, but she thinks they had the strength all along. “It’s totally in them. Being confident and strong makes other people feel like they can be confident and strong. I think you can inspire and be the spark for anything, but none of us are really capable of doing anything for anybody else.”

Although Amoruso is gratified by her numerous accomplishments—building a successful company from scratch, empowering young women through her book, making outsiders and freaks feel like they fit in—she might not describe herself as a beacon of success.

“Did I ever think I would be this successful? No. But do I wake up and think I’m successful? I feel like I’m still earning so much of what has come already. I’ve been a very celebrated entrepreneur and there’s so much I’m still learning. I think that’s success—owning up to what you don’t know, but then also playing to your strengths. I don’t think success is a final destination.”

Related: How 5 Successful People Define Success


Photos by: Jeff Katz
This article originally appeared in the October 2016 issue of SUCCESS magazine.

Jamie Friedlander is a freelance writer based in Chicago and the former features editor of SUCCESS magazine. Her work has been published in The Cut, VICE, Inc., The Chicago Tribune and Business Insider, among other publications. When she's not writing, she can usually be found drinking matcha tea into excess, traveling somewhere new with her husband or surfing Etsy late into the night.