Q&A with tech ‘Cinderella’ Sophia Amoruso

The Washington Post

Sophia Amoruso, the CEO of online fashion site Nasty Gal and author of the new book GIRLBOSS (Portfolio Hardcover), is not your typical CEO.

The 30-year-old 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 20s, “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 the “Cinderella of tech.” Eight years later, the site is an online mecca for stylish women, with more than $100 million in revenue. Excerpts:

Q: Why did you decide to write the book?

A: There’s no one really speaking to the audience 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 an unconventional story with anecdotes, commonsense advice and a big dose of permission to figure things out for yourself.

Q: What are 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.

Q: What’s the story behind the title GIRLBOSS? Why did you choose to focus on women?

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. The title is also a riff on this ’70s Japanese movie called “Girl Boss Guerilla,” which is like a female revenge movie. It’s very campy — something like the style of film Quentin Tarantino stole from.

Q: The company has grown immensely. How has your job as a leader changed?

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 even today I 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 different team I’m managing today compared to six years ago.

Q: One challenge of being a young CEO is how to deal with having senior executives 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 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.

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

A: I think it was being loyal to the company as a whole rather than any individual person. That’s really, really hard because I care a lot about the people I work with. But ultimately I have to set the company up for success. There have been times when the company outgrew somebody. I’ve tried to rectify that as quickly as possible.

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 proven something, where you 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.

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 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. Be a peer in any relationship. It’s much healthier than being indebted to anyone.

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