The Washington PostDemocracy Dies in Darkness

From anti-capitalist to CEO: How Nasty Gal’s Sophia Amoruso made it big

(Sophia Amoruso | Photo by Autum de Wilde)

Typical business books are definitely not written by a former dumpster-diving shoplifter. Then again Sophia Amoruso, the CEO of online fashion site Nasty Gal and author of the new book #GIRLBOSS, is not your typical CEO.

The 30-year-old founder of the online fashion phenom started the site in 2006 as an eBay project, selling vintage clothing while she worked as a security guard checking IDs at an art school. She had no college degree, no experience in business, and writes that as a teenager and in her early twenties, "I thought that I would never embrace capitalism." Yet without taking out a dime in loans, she started a business that has led her to be called one of the most creative people in business and the "Cinderella of tech." Eight years later, the site is an online mecca for stylish young women, with more than $100 million in revenues.

Her book, released last week, is part memoir, part management guide and part girl-power manifesto. A sort of a Lean In for misfits, it offers young women a candid guide to starting a business and going after what they want. We spoke with Amoruso about what she's learned, what she reads and what advice she has for people just starting their careers. The discussion below has been edited for space and clarity.

Q. Why did you decide to write the book?

A. I’ve learned a lot from reading business books along the way. My first business book, I guess, was technically Starting an eBay Store for Dummies, and  from there they've gotten slightly more sophisticated. My favorite magazine is the Harvard Business Review. If someone sat across from me in a restaurant and didn't know me, that might surprise them. There’s so much to learn in business that I think anyone — even if you don't own your own business — can learn a lot about how to navigate the world and the workplace, and being a manager and being managed.

There's also no one really speaking to the audience that I'm trying to reach. Every woman who has a business book has a platform. For the most part they're either a television personality or someone who had the perfect pedigree and worked their way up the career ladder. If you look at my Instagram, girls are just beating down my door for tips or a job or mentorship. I can’t hire every single one of them. My story is one thing that gives them hope. It's an unconventional story with anecdotes, commonsense advice and a big dose of permission to figure things out for yourself.

Q. What have been some of your favorite or most influential business books?

A. Well it's not really a business book, but The Richest Man in Babylon is a must-read that’s more about managing your own personal finances. I also read No Man's Land, which is about that middle stage where you're too small to be big and too big to be small and you're hiring middle and senior managers. That was good.

Q. What’s the story behind the title #GIRLBOSS? Why did you choose to focus on women, and not just any up-and-coming entrepreneurs who never thought they’d end up business?

A. Well I’m a girl. I’m a boss. I think it would be boring to call the book "Boss," but it’s not just for girls. There are a lot of parents who've come to me and said about their daughters, "Oh my god, she’s 21, she’s totally flailing. Your story gives me hope." I put my mom through that. She’s totally earned what she’s experiencing today.

As for the hashtag, part of my story is about using social media as free marketing. By putting the hash tag in front of the title, you kind of have to use it. It's built in. The title is also a riff on this '70s Japanese movie called "Girl Boss Guerilla," which is like a female revenge movie. It's pretty campy — very campy — something like the style of film Quentin Tarantino stole from. That's initially part of where the title came from.

Q. The company has grown immensely since you started it. How has your job as a leader changed over time? 

A. As the company grows, you have to move from a team of generalists to a team of specialists. I was the ultimate generalist. I hired the first employee, another generalist. And in a certain way even today I still preach that there’s no such thing as "that's not my job." Everyone needs to do what they need to do to get the job done.

But my job also went from whatever it takes to get job done to leading people, hiring people directly under me, and creating strategy and holding the company accountable to it. I'm making long-term goals, which I never had in the beginning, and am trying to create meaning and have conversations about it, so that everybody can take that and do a better job. It's a completely different team I’m managing today compared to the team I was managing six years ago.

Q. One of the challenges of being a young CEO is how to deal with having senior executives on your team who are older than you. The book recounts meetings where people incorrectly addressed them as the decision makers. What do you do when that happens? 

A. That rarely happens, and those are the people I usually don’t have a meeting with more than once. It’s generally pretty clear — and with this book it’s even more clear — that I’m the one running the business. I’m the one calling the shots. I own the majority of the business. I control the board.

There's mostly upside [to having older executives on the team]. Not only do the people who need mentorship have amazing, experienced managers; but, for the most part, I get to manage people who need to be managed very little. It's a different kind of relationship when you manage people who have the level of my experience that my direct team does.

Q. What was the hardest thing you had to learn as a new leader?

Q. There’s a lot of talk about the macho culture in the tech world. As an e-commerce site run by a woman, how much have you faced that?

A. It may be for some, but for me that hasn't been the fact. I waited to talk to [venture capitalists] until I didn’t need anything from them. I think as a person and especially as a woman, putting yourself in a position where you've already done something — where you've already proven something, where don’t need anything — is key. I’d proven that I could responsibly run a profitable business that was growing very quickly before I talked to them, so the macho piece didn’t really come into play.

I also don’t really leave room for it. If I was working my way may through Silicon Valley, what I've achieved might have been more of a victory for me as a woman, specifically. But I don’t celebrate my success because I’m a woman. I’ve endured a lot of hardship, and I've put myself in a lot of stupid places, and I've done that to myself.

Q. What about when women haven't yet proven themselves? What would your advice be to them?

A. You don’t have to be a dude at the table. If you think they’re going to treat you differently as a woman, they're going to treat you differently. What you expect will happen, if that's what you think about it.

I just personally never want to be in a position where I owe anyone anything unless I’m 100 percent sure I can keep my promise. That's how I work. I know that's not the case for everyone and some businesses are more capital intensive. But I would never have an idea on a piece of paper and ask someone to give me money. I just wouldn't do it. I have a pretty healthy sense of entitlement, but only in places where I feel like I can bring something to the table. As much as you can, be a peer in any relationship. It's much healthier than being indebted to anyone.

Q. You’re 30 years old. It’s graduation season. Much advice for recent grads comes from people who haven't been there in a long time. What advice do you have for someone just starting out on their career?

A. If you haven't had an [expletive] job, go out and get one. If you have, then you'll figure it out.

Read also:

An animated leadership talk with Pixar's president

The consigliere of Silicon Valley

Like On Leadership? Follow us on Facebook and Twitter.