Be Bossy: Sophia Amoruso Has Advice for Millennials and a Bone to Pick With Sheryl Sandberg

Sophia Amoruso, photographed by Peter Hapak.
Sophia Amoruso, photographed by Peter Hapak. Photo: Peter Hapak

Nasty Gal’s office in downtown Los Angeles is a cool girl’s fantasy of corporate life. There are potted fiddle figs, Rihanna on the sound system, rainbow sprinkles in the communal fridge. There is a yoga room. There are printouts of Lil’ Kim and Shelley Duvall taped to the walls. There are dogs, but only cute dogs of cuddling dimensions: “We’re a dog-friendly workplace, but the dog has to be under 25 pounds,” says Nasty Gal’s 30-year-old founder and CEO, Sophia Amoruso. “That’s an official rule.”

Amoruso is pacing the headquarters of her seven-year-old company with YSL pumps on her feet and a toy poodle named Donna Summer under one arm. Wherever Amoruso roams, there are women: women with lilac hair and slouchy blazers, women in booty shorts, women juggling Starbucks cups and greeting each other with girlfriendly hugs. One hallway is lined with recent magazine clippings of Amoruso from the pages of Fast Company and Entrepreneur, which makes her feel funny, but she has no choice about the clippings: Her mom gets them framed and mails them over, then bills the company for her services. More than three-quarters of Nasty Gal’s 300 employees—a number that does not include Amoruso’s mother, who clips on a freelance basis—are women.

Those employees are still getting used to the capacious new office, finished just six months ago. The space is also an upgrade for Amoruso, whose online fashion retail business got its start in a rented pool house in 2006. Seven years later, Nasty Gal had picked up $49 million in funding from Index Ventures, a firm known for its e-commerce track record, and now the company is doing upwards of $100 million in annual sales and selling to customers in 150 countries. Within a year, it plans to open its first brick-and-mortar store in Los Angeles and expand from clothing and shoes into home goods. And in early May, Amoruso herself began infiltrating bookshelves with #GIRLBOSS, a hybrid business bible and memoir. The hashtag is part of the title. It was Amoruso’s idea.

Given this especially steep incline, perhaps it’s not surprising that on a breezy Los Angeles day a few weeks before her book’s release, Amoruso isn’t even sure how to sign it. If someone asks her to inscribe a copy, for instance, is she supposed to write a nice message or just her name? Is there a specific page she’s supposed to sign? Amoruso ponders these unknowns in her office with a pen in hand and Donna Summer on her left knee. After a moment of thought, she comes up with a template:

Hey [NAME], thanks for being a #GIRLBOSS
♥ Sophia

She pauses, reads it, adds an exclamation mark. Done.

Like most books by CEOs, #GIRLBOSS is a marketing tool—an effort to broadcast the author’s brand more widely—but it is also a passion project. When someone tweeted a complaint about the book’s title, suggesting that grown women shouldn’t be calling themselves girls, Amoruso responded immediately: “How’s #BROADBOSS? or would you prefer #MATRONBOSS?”

“I mean, come on,” she says later in her unruffled tone. “I don’t like when an old man says, [creepy voice] ‘Let’s invite the girls to dinner,’ but I think it’s okay to call girls girls.” Pause. “And I think it’s okay to call girls bossy.”

The little Sheryl Sandberg jab is one that Amoruso might be better off stifling; on the other hand, it’s a canny fight to pick (Sandberg’s book, Lean In, has sold more than 1.7 million copies). In March, when Sandberg launched her new “Ban Bossy” campaign, complete with punchy slogan and precision-engineered rollout, the message was tepidly received. It felt dictatorial (the idea of banning words) and unsophisticated (the idea that banning words is useful), and it was missing the sheen of inclusiveness that gave “Lean In” its appeal. Whatever you think of Sandberg’s corporate feminism, the misstep scooped out a wide-open spot for someone different to come along—someone without a billion dollars, a bulletproof résumé, a perfect husband, and a roster of friends in high places. The cover of Lean In shows Sandberg relaxed and radiant in a white sweater, chin resting on palm. #GIRLBOSS has Amoruso in a tight black dress and spiky necklace, fists balled against her hips. One of her eyebrows is arched, villainess style. She looks like a person with intimidating sexual preferences.

Courtesy of Nasty Gal Photo: courtesy of Nasty Gal

If Amoruso is hoping to capture some of Sandberg’s book-buying demographic, she’s also warning them to adjust their expectations. When Sandberg published Lean In, most readers already knew the marquee items on her CV: Harvard, Google, Facebook. Amoruso is both lesser known and less accredited, and she twists both liabilities into advantages. #GIRLBOSS begins with her own résumé: an informal diagnosis of Tourette’s syndrome as a child, a formal diagnosis of ADD as a teenager, a high-school dropout, a shoplifter, and now a CEO. It’s a gleeful fuck-you to the notion that life is a series of crescendoing achievements. And while Amoruso has a much tinier platform than Sandberg, is much less prolific on the conference circuit, and has not received praise from Oprah or Chelsea Clinton, her publishing debut does have one big selling point: #GIRLBOSS is a surprisingly good book.

The Nasty Gal mythology begins, maybe appropriately, in the pubic zone. In 2005, Amoruso was working at a shoe store in San Francisco, helping wealthy ladies into Prada pumps for $12 an hour. Her career was in a gray area: After a couple years of hitchhiking, she’d been caught stealing a George Foreman grill from a big-box store, which felt so comprehensively lame that it embarrassed Amoruso away from crime entirely. The shoe-store job that followed was lame in its own way, and a shabby attitude got Amoruso fired right as a hernia was developing in her groin. With no health insurance, she tried to make a joke of the hernia, shaving off all of her pubic hair except for a tuft covering the bulge. It eventually grew large enough to become visible through pants.

For insurance, Amoruso found a desk job and spent a few months browsing MySpace behind a computer. Friend requests from eBay sellers kept popping up in her in-box. Their stores were bare-bones: photos of thrifted clothes, measurements, a few lines of description. For a stylish introvert with no career path, selling clothes seemed like an amusing way to make money. Amoruso got the hernia fixed, quit her day job, and bought a copy of Starting an eBay Business for Dummies.

Most of her future competitors had eBay shops with woo-woo bohemian names, so Amoruso went the opposite direction, selecting the title of a 1975 Betty Davis song with aggressively horny lyrics. The next step was inventory. It turned out that a history of recreational thrifting was not adequate preparation for the world of professional scavenging, which had its own black-market economy with codes and power brokers. The scarcity of good vintage made sellers protective of their sources, and nobody was eager to tell a newcomer where they’d scored their best stuff. “You have to establish relationships,” Amoruso says. “One person leads you to another person, if that person is willing to talk. It’s like the drug trade.”

The main sources were rag houses— warehouses of Salvation Army rejects waiting to be sold in bales to Africa or picked through by vintage sellers. It was a needle-in-the-haystack situation, with every tissue-thin Rolling Stones shirt buried under a thousand preshrunk Ozzfest tees. (Memories of Ozzfest mountains still make Amoruso shudder.) To locate value in so much junk, a buyer had to develop a pin-sharp sense of what eBay ­users were willing to pay a premium for. Amoruso discovered that it was possible to predict trends by tracking the rise of popular search terms—batwing, lamé, and lumberjack were big in 2007; studded and architectural and origami in 2008. She noticed that rag houses had regional peculiarities, which allowed her to optimize her buying trips: California houses specialized in lightweight hippie dresses and tooled leather bags, while East Coast plants ran heavy on fur, sequins, and formalwear. Even with diligence, there were dead ends. A proprietor might promise acres of vintage treasure only for Amoruso to drive ten hours and discover a depressing pile of last year’s Forever 21 dresses. A significant portion of each day was spent among bad smells.

Courtesy of Nasty Gal Photo: courtesy of Nasty Gal

The fun part came later, when it was time to package the goods. Thanks to its constraints, eBay provided an accidental master class in the art of visual merchandising. At the time, sellers had 55 characters and an 80-by-80-pixel image to grab a browser’s attention. Amoruso figured out that clicks were more likely when her pictures featured items on a human model, not slumped across a duvet or mannequin. It further helped if the item’s silhouette—baby-doll, bodycon, trapeze—was clearly visible in the thumbnail image. She recruited models off MySpace, paid them in hamburgers, and analyzed their conversion rates to see which ones were most effective. “If I saw a sequined Golden Girls tracksuit on the floor of a warehouse, I’d take the jacket and sell it,” she says. “Anyone could have sold it for $9.99. But to put it on the right girl, with the right hair and the right attitude, showing people how they could wear it—that was everything.”

On a Friday the 13th in 2008, she launched an independent site for Nasty Gal. Around the same time, eBay had suspended her account for promoting the future URL on its site. Amoruso was annoyed, but not terribly: She sold out of everything the day her new business launched. When Kelly Ripa’s stylist called to see if she had a particular vintage jacket in a size extra small, Amoruso had to say no. (Duh, it was vintage.) But she began to think about selling new clothes.

In the same way that some people are born with extra-bendy thumbs, there are people who are born with the will to work. As Amoruso explains in #GIRLBOSS, one theme of her wobbly adolescence was an urgent desire to be an employee somewhere, working at something, for some amount of money. Topics like friends, boys, and family get a few sentences each in the book, while a string of menial adolescent jobs gets a whole chapter. That section, “Shitty Jobs Saved My Life,” is where Amoruso itemizes her industriousness: There were stints at a hydroponic-plant store, a dry cleaner, an orthopedic-shoe store, a restaurant, a Borders, a factory-outlet mall, a landscaping outfit, and, before that, babysitting gigs and a paper route. The high-school years, she writes, “were like speed dating, but for jobs.”

The rest of the book is about work, with the exception of an odd little sliver about magical thinking. (Eleven pages starting on page 119; skip it.) Amoruso has loads of advice about the workplace, all of it shrewd and unsweetened. Don’t ask for a promotion until you’ve held a job for a year; don’t mistake your boss for a friend; fight the natural human impulse to consider yourself an exception; and never have your phone visible during a job interview. Don’t compliment your interviewer’s outfit, because “making small talk about what someone is wearing is just another form of unsolicited feedback.” Spell-check your cover letters, for fuck’s sake. These rules may seem rudimentary to anyone born before 1982, but they’re aimed at millennial-specific bad manners. A #GIRLBOSS would never take a funeral selfie or wear pajamas on an airplane.

If there’s one generational habit that galls Amoruso more than informality, it’s entitlement. Even as a thief, she was diligent. “A lot of people in my generation don’t seem to get that you have to work your way up,” she writes. “I don’t care if filing invoices is beneath you. If you don’t do it, who do you think is going to? Your boss? Nope. That’s why she hired you.”

The obsession with hard work is the reason Amoruso gets away with publishing a memoir at age 30 in the first place, and it’s also what makes the book resonate. For a lot of young women, work is life’s central drama: a source of power and fulfillment and something worth worshipping precisely because of its increasing scarcity. Novels and blogs about the workplace proliferate; the best female characters on TV—Peggy Olson, Selina Meyer, Leslie Knope—are zealous achievement machines. Amoruso has intuited this hunger and answered it with a glittery snapshot—part candid, part art-directed—of the alpha career woman. (Lena Dunham, a fellow alpha, endorsed the book as “brain-inspiring” on Instagram.) It’s easy to get the sense, reading Lean In, that Sandberg is writing for women who’ve already made it. #GIRLBOSS is for those who haven’t, which means it is aimed at people who have nothing to lose, which makes it a much riskier and more enjoyable manifesto. “Don’t you dare alter your inner freak,” Amoruso tells readers.

The hope, of course, is that all these freaks become Nasty Gal customers, if not employees. (Amoruso’s Instagram account unofficially doubles as a jobs bulletin board.) It’s all bound up in a certain idea of what a young woman can be: stylish without being a fashion victim, ambitious without sacrificing attitude, and possessing an internet-inflected goofball sense of humor. Nasty Gal sells poly-blend halters that say WTF in huge letters and dresses printed with giant renditions of Pepe Le Pew. A subspecialty of the brand is the Tumblr-ready category of things-that-look-like-other-things: an iPhone case that looks like a slice of pizza, earrings that look like emojis, socks that look like cats. Skimpy numbers are styled with a jokey wink to offset the hubba-hubba factor, like a crop top printed with two flowers, one per boob. (“Two lovely blossoms for your two lovely blossoms.”) A pair of hot pants is patterned to resemble a watermelon: super-skimpy but super-wacky, which means they’re not super-slutty. #GIRLBOSS includes a list of interview no-no’s that will doom readers to a life of unemployment, and one of them is “Dressing like you’re headed to a nightclub instead of a job interview.” It doesn’t say anything about dressing like a watermelon.

Courtesy of Nasty Gal Photo: courtesy of Nasty Gal

So what kind of Girl Boss is Amoruso? Today she drives a white Porsche and shops for $2,000 Delfina Delettrez rings and works in a corner office with a couch that looks like a giant leather croissant. “It’s kind of the rap dream,” she says. By this she means her upward hustle, but also her right to luxuriate in it. To have a giant print of Donna Summer (dog, not human) installed at the house she’s remodeling in the hills. Or an assistant to arrange her takeout hamburger elegantly on a plate. Or the privilege of dialing J.Crew CEO Millard Drexler when she has a question about retail. Calling shots suits her. What’s the point of being a boss if you don’t act like one?

Well, with some key exceptions. Public speaking is a weak spot. In public interviews Amoruso’s speech is speckled with “likes” and “you knows,” and her posture—stock-still, generally aimed away from the audience—can mistranslate as recalcitrant. If she has been media trained, it hasn’t stuck. And despite her glamour, there’s still a Dennis the Menace quality about her. The teetering YSL pumps make her gait sound like that of an approaching ogre. At dinner, she delicately sips a Shirley Temple through a straw while holding a piece of fried fish in one hand, like a burrito. She scratches her ears and stuffs Donna beneath her trench coat when the dog starts yapping. She had a horrible time at TED this past year. “You’re in a room with a bazillion people, and I don’t learn from listening, anyway—I learn from doing things, grappling, asking questions. It was fucking bewildering.” She got bored at the conference, then mad at herself for being bored, then interested to find that the self-loathing did not alleviate the boredom, and then she left early.

“Sophia has a major amount of chutzpah” is how Drexler puts it, citing this as one reason he took Amoruso’s initial call. “She’s forthright, she says what she thinks, she argues,” he says. “Sometimes she doesn’t listen that well, but other times she listens very well. I like her brain and I like her follow-up and I like her vision.” They met when Amoruso chased him down at a conference and asked for his number. Drexler thought it might be fun to talk with her, so he did, and he was right. They kept talking.

Like Drexler, Amoruso cuts a benevolently intimidating figure around the office and has a hair-trigger bullshit sensor. A meeting with the company’s president and senior team starts late but snaps straight to action once she arrives. There’s no small talk, no how’s-your-day or have-you-had-lunch-yet. The purpose of the meeting is announced and a deck presented while Amoruso takes notes on a laptop. When she speaks, she speaks quietly—her voice tops out at 80 percent of the volume of her colleagues. The meeting is allotted 30 minutes and finishes six minutes early. “I don’t lead with an iron fist, I don’t yell at people,” Amoruso says. “I have a way of making my opinion clear.” Last year, she tweeted, “Agree with Mr. Mickey Drexler—if you work in my office and walk slower than me, there’s something wrong.”

Warmth takes more effort, because Amoruso loathes chitchat and schmoozing. It depletes her. Still, she knows that her position demands it. “All of these little actions add up to a kind of lore,” she says. Neglecting to say “Good morning” or “Good night” to someone at the office has social consequences. Sometimes she’ll introduce herself to a new employee only to find out the employee has been there six months. “I recoil when I put myself out there and I blow it,” she says. “It’s embarrassing.” The antidote, she writes in her book, is to brainwash yourself into believing that every interaction is a giant experiment with failure built in. “I’ve always been willing to throw myself at the wall and see if I stuck when it came to general life experiences.”

This occasionally manifests in behavior that might not be sustainable as Amoruso’s profile grows, like strolling into Topshop or Urban Outfitters, introducing herself to the retail staff, and asking if she can poke around as part of her competitive research for opening a Nasty Gal store. (Nobody’s ever said no, and more often than not, employees request Amoruso’s email address so they can interview for a job.) Not many CEOs would pull this move, and it’s possible that Amoruso will decide one day to step down from the role and appoint a more conventional candidate. “One of the best things about Sophia is that she actually continues to question, as the business grows, whether she is the right CEO,” says her investor Danny Rimer. (Adding that he very much approves of her running the company.)

Chatting in her office, Amoruso brings up the leadership question herself, citing a phone conversation with Drexler that took an existential turn. “There was a time when I was like, ‘Mickey, should I hire a CEO?’ ” she remembers. Drexler said no, don’t do that, you’re crazy, but Amoruso hasn’t permanently ruled out the idea. “That day may come,” she says, though she’s not hurrying to get there.

She may never have to. In another era, a CEO who conducted herself like Amoruso might have been assessed as peculiar or wayward or seditious. But start-ups nourish social deficiencies (“quirks” is the preferred term), and a person with good ideas can get away with murder as long as it doesn’t compromise her ability to work like an ox. Plus: There’s nothing more inspiring than a successful weirdo.

Top photograph by Peter Hapak.

*This article has been updated since its original publication. It appears in the June 2, 2014 issue of New York Magazine.

Nasty Gal’s Sophia Amoruso on Millennial Advice