Nasty Gal CEO Sophia Amoruso: 'Wisdom is Earned Through Experience, Particularly Mistakes.'

The fashion-retail founder explains why entrepreneurs shouldn't be afraid to veer off of the prescribed track, why it is okay for them to make mistakes and how founders should strive to be like Indiana Jones.

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By Nina Zipkin

Sophia Amoruso has never been one to do things by the book. Nasty Gal, her online fashion company started its life in 2006 as Nasty Gal Vintage, a one-woman eBay operation selling unique vintage clothes she found through Goodwill, the Salvation Army and her dumpster-diving expeditions. At the time, California native Amoruso was 22 years old, with a history of shoplifting and a series of odd jobs under her belt.

Fast forward eight years and nearly $50 million raised later, Amoruso, who never attended business school, oversees a fiercely daring fashion empire. It was most recently reported that Nasty Gal brought in $100 million in revenue a year. Amoruso recently wrote a book called #GIRLBOSS, in which she shares hard-won experience and advice with her "bad-ass" fans and future CEOs.

We caught up with her to talk about trial and error, the importance of following your gut instinct and creating a culture that works for you.

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Q: Knowing what you know now, what would you have done differently when you were first starting up?
Quite honestly, I would never want to know what I do now when I started. Who knows if that would have gotten me to where I am today? If I had known how hard it was to build a company the size of Nasty Gal, I would never have set out to do what I did. Had I started with an end goal in mind, I would never have accomplished what I did.

I often say my naiveté early on in my career worked in my favor. For example, I didn't pick investors based on their portfolios. I picked them based on my gut, their passion and understanding for my vision for my business.

I'm still learning every day. Interview me five years from now, and I'll tell you about my triumphs and the mistakes I'm making right now.

Q: How do you think young entrepreneurs might benefit from this insight?
My book #GIRLBOSS is about trusting your instincts, being comfortable taking risks and sometimes blowing it and knowing that falling on your face is the only way that you can pick up and move in a different direction. It's about turning your failures into lessons, trying new things -- and if they don't work, not doing them again. Sometimes in the world, there's such pressure to follow a certain path that we forget the importance of learning as we go.

I think many people go to business school and learn ways to play it safe, ensuring that they avoid some of the pain that entrepreneurs endure while taking less calculated risks.

Related: The First Step to a Great Personal Brand? A Distinct Look.

Q: Besides inventing a time machine, how might they realize this wisdom sooner?
Just do it. Stop and listen, then keep moving. Evolve. Don't be too attached to the result. Sometimes you end up with something even better than you set out to accomplish. The best wisdom is earned through experience, particularly mistakes.

One of my favorite quotes is from George Bernard Shaw, "Life isn't about finding yourself. Life is about creating yourself." I think we as a culture spend too much time looking at role models or other fascinating lives instead of spending time creating our own. And that's probably the best lesson to learn from my story.

Q: What are you glad you didn't know then that you know now?
I'm glad I didn't know how successful Nasty Gal would become. If I had known that, I don't think I would have been as spontaneous, creative and unconventional with my choices. I'd have been terrified.

Q: Best advice for aspiring entrepreneurs?
I think there is a lot of practical advice in #GIRLBOSS about how to be financially aware, how not to get too deep into debt at an early age and how to save 10 percent of everything that you earn, even though it seems like a very boring thing to do. And to not act like you've arrived when you're only just getting the invitation.

As I say in my book, great entrepreneurs are like Indiana Jones. They take leaps before seeing the bridge, because they know that if they don't, someone else will get that Holy Grail. That Holy Grail is yours for the taking.

-This interview was edited for clarity and brevity.

Related: 7 Ways Fashion Startups Can Become the Next 'Rent the Runway'

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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