When she was 5 years old, Sophia Amoruso picked up a red string and ran outside with it flying behind her. She told the rest of the neighborhood kids it was a kite.
“Soon everyone had red strings and we all ran together, our kites high in the sky,” she writes in her debut book, #GIRLBOSS, a half-memoir, half-instructional guide released earlier this year for prospective entrepreneurs. As Amoruso explains in the book, that kind of magical thinking has been with her all her life and has propelled her forward. She now commands Nasty Gal, an e-commerce fashion retail destination with a nine-digit valuation and more than 350 employees in a sizable downtown Los Angeles office.
She’s graced rising-stars lists like Fortune’s 40 Under 40 and Inc.’s 30 under 30, but it wasn’t mere magic that took Amoruso from the playground to the boardroom. After a few detours—what she calls her lost years (spent hitchhiking, Dumpster-diving, working odd jobs and even shoplifting at times)—Amoruso finally opened an eBay shop in 2006. Calling her auction platform Nasty Gal Vintage, she sold vintage pieces discovered at thrift stores and slowly grew an empire on trial and error, with her own self-confidence (not to mention blood, sweat and tears) making up for a lack of outside assistance.
SUCCESS wanted to know the details of how Amoruso grew from a solopreneur into a #GIRLBOSS.
Q: In your book, you tell the red-string story to outline the importance of confidence. How do you think self-belief translates into achievement?
A: I like to say that where I hesitate, I fail. I snowboard a little bit, and it’s like this: You’re flying down a mountain and you’re like, Oh my God, am I going to fall? Every single time I think I could totally fall and knock my teeth out. And when I think like that, I will fall. You lose your confidence.
It’s not about going out in the world and being like, I’m the best thing ever. But I never doubt myself because that’s not a great way to be either. Just say to yourself, I can do this. When you believe in yourself, other people believe in you, too. When you believe in yourself, you do your best. It’s when I think I’ll fail that I do.
Q: A lot of people find ways to make the best of setbacks, though, including yourself. What’s your take on dealing with failure?
A: Success and failure sound like such ultimate things. But they’re not. There are small successes and there are small failures, but ultimately no one is actually a success or a failure. We are all in some amount of motion between those two things. Failure is failure only if you don’t learn from it. But if you try something and don’t get the results you expected, then you try something else. That is not failure. I think that’s success. The real failures are the people who try something, blow it and just give up.
Out of the first stuff I put on eBay, a few things sold, but not everything. If I had decided that nobody liked me and it was just too hard, if I had given up at any point along the way, I wouldn’t be where I am today. But I was like, OK, what sold? Great. What are other people selling? Cool. I’m going to find things like that. I improved every day, and, of course, certain things still failed—certain things still fail.
All you can do is learn and tweak and learn and tweak.
Q: One of the things you mention learning in the book is how to look at things really critically. For any product or idea to make the cut, you first insult it. How does that strategy work?
A: I think it’s easy to like things and get carried away with them. Christina, my buying director and first employee, and I insult a new product as much as possible. Does that look like a hospital gown? Are those stripes too Charlie Brown? And if it still holds up, we buy it. It’s kind of a tough-love strategy, but I think when you realize something is good after having rejected it, you like it for the right reasons.
I’m not saying walk around and reject everything and everyone. That won’t work. But a certain amount of scrutiny will help you navigate the world. This “rejection strategy” is ultimately not taking everything at face value, but asking, “What is that, actually?” and “How do I feel about this?” before diving headfirst into anything.
Q: As you tweaked your strategies, you stumbled upon some other important lessons, including the importance of social media. How did you use it to grow?
A: Social media is responsible for Nasty Gal’s success. At the start, I didn’t have a marketing budget, and had I not figured out how to talk to my customers for free, to find new ones, to evangelize the brand and allow them to evangelize the brand via social media, there’s no way we would exist today. It’s massive what social media can do.
Having an online business is freeing in so many ways. The Internet is a place where anyone can be an entrepreneur. If you do a good job and create compelling content, whether that content is your product or something you’re writing on a blog, people will notice. Just give people a reason to talk, and they will.
Q: The heart of the Nasty Gal brand is you and your philosophies. How did you infuse the brand with your spirit?
A: The spirit of Nasty Gal is one of irreverence and confidence and making stuff happen for yourself. It’s about getting dressed for your life and not being a wallflower. And I think that’s just a great approach to have in life.
Our business philosophy is about personal accountability and teamwork. It’s about being open, learning from each other and asking obvious questions—it’s OK not to know. It’s about making friends and reaching out to people across the organization whether or not you usually work with them. And it’s about having fun and not taking ourselves too seriously. That’s something we’ve always been pretty good at. We’re not wacky for the sake of being wacky, and we’re all pretty much down to business at the end of the day. But it’s OK to be weird.
Q: As the company grows, how do you keep that culture?
A: Here’s an example: I just personally handed out a copy of #GIRLBOSS to every person who works in the office, and I signed it and drew a mustache on my face on the cover. I have an important job to do, but I still try to be accessible and approachable.
As for our workplace environment, I think the trend in open offices is really awesome. People aren’t stuffed in cubicles or in closed offices, except for a few of us. We have a lot of autonomous work areas, such as conference tables out in the open and sofas where people can take their laptops, hang out, work together and have conversations. It’s a casual atmosphere—and people actually want to be at the office.
Q: What other aspects of your personality have created opportunities for Nasty Gal—and yourself—to grow?
A: What creates opportunities is trying new things and not being afraid of taking smart risks. What closes doors is, obviously, not doing that, and not learning from everything that you do. I believe in having dreams and getting up and trying again when things don’t work out.
But sometimes things just aren’t meant to be. Being okay with changing direction when something really isn’t working, I think, is important. I had a dream. I first wanted to be a photographer, and had I been so adamant about that being my sole future, I would never have found myself selling on eBay or realizing that vintage clothing was a path to something a lot bigger, which it was.
Jessica Krampe is the digital managing editor for SUCCESS.com. A graduate of the Missouri School of Journalism, Jessica has worked for news, entertainment, business and lifestyle publications. Outside of the daily grind, she enjoys happy hours, live music and traveling.