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Nasty Gal CEO Sophia Amoruso shines a light on failure and financial health

Sophia Amoruso Shoppers Drug Mart Business Girlboss
Photo: George Pimentel

In our Masterclass series, Sophia Amoruso shares five lessons for future entrepreneurs.

Written by Christina Gonzales

Sophia Amoruso floats through a packed room in an ethereal blue dress, chatting with media who have come to see her just-launched Shoppers Drug Mart’s Be Bold with Beauty campaign. The Girlboss founder and former CEO of Nasty Gal, a cheeky fast fashion e-tailer for women, is somewhat of a superstar amongst driven trend-conscious millennials. She’s of the same cohort as Emily Weiss (Glossier), Chiara Ferragni (The Blonde Salad), and Erin Kleinberg and Stacie Brockman (founders of the Coveteur). All of them are young, female powerhouses, now in their 30s who young women grew up following on social media as they grew their respective empires.

Amoruso is different than the rest, though: most recognize her from her very public resignation as the CEO of Nasty Gal, which filed for bankruptcy in 2017.

Before the crash, Amoruso did a lot of things to inspire budding entrepreneurs around the world, because she embodied the idyllic entrepreneurial journey. Young and passionate about fashion, she sold vintage clothing on eBay, eventually creating a multi-million dollar business from nothing. Then came the hallmark pillars that often litter any rags-to-riches stories of success. She wrote a book (Girlboss), spoke in front of hundreds of women at conferences across the globe about how they too could kill it in their respective careers, and co-produced a Netflix series based on her life. And right at her peak she flunked–and she flunked hard.

In front of the prying eyes of aspiring women across the world, Amoruso’s Nasty Gal went bankrupt, her marriage fell apart, and her Netflix series was cancelled. Talk about a buzz kill.

Under the rubble, Amoruso knew there had to be a way out. Her book, Girlboss, had become a brand and entity of its own; one she could leverage and build. Fraught with the story of defeat, a very public breakdown, and immense shaming as tales of what happened inside the offices of Nasty Gal came to light, Amoruso used Girlboss as a foundation to rebuild after the storm. The company, through its platform of community and content, proposes to show female go-getters the how-tos of everything from debt management to making a career change in your 30s.

In the middle of her phoenix moment, Amoruso shares her insight on how to start over, why being a CEO can be isolating, and financial due diligence.

There is no shame in failure

According to Statista, there was a ratio of 60 percent male entrepreneurs to 40 percent female entrepreneurs in the United States in 2016. Because there are less female entrepreneurs, when one succeeds it’s a big win, but when one fails, “it attracts more attention because there’s few of us,” Amoruso says. Yet, in fact, some of the world’s most notable entrepreneurs like Steve Jobs, Walt Disney, and Steven Spielberg have had their own share of failures. “[Failure is] part of life and everybody experiences it, but not on a public stage. I’m glad I have. I can handle failure: [my experience has] paved the way for other women to have similar experiences and not feel so alone. Some lessons we have to learn more than once before they really stick; we don’t necessarily make every mistake just once.”

Make your next big business move by using your resources

Be creative and use the resources you have at your disposal. “There’s always a resource that you can take and alchemize into your next move,” Amoruso says. “It’s challenging, but no one is going to start over for you. No one is going to make those steps for you. No mentor is going to drop out of the sky and tell you exactly what you need to do. You just have to keep going and take risks. [My resource] was Girlboss. It’s been four years since I wrote the book, and a community built around it. The book had a life of its own. The hashtag has been used almost 12 million times on Instagram. It was a partially built business, and I had a whole MBA in entrepreneurship over the course of the 10 years that I was at Nasty Gal. I thought, ‘I can’t not pursue this,’ and it couldn’t be a better time. It couldn’t be more important.”

Hold your team accountable

As a lead, it’s vital that you hold every individual on your team accountable, regardless of the experience that they have. Never make assumptions based on someone’s professional pedigree. After all, their shortcomings will ultimately be a reflection of your ability to lead. “[At Nasty Gal,] I hired C-level executives and said, ‘You’ve been in your career longer than I’ve been alive. Write your job description and tell me what the company needs.’ I didn’t know how to organize myself around the larger strategy, set goals, and hold people accountable.”

Being a CEO means being ready to make hard decisions.

It can be isolating to be a CEO; everything that happens within the company is reflected on you. Be ready to make decisions that are unpopular. “Sometimes these decisions affect individuals in ways that are unfortunate, but they’re decisions that are best for the company as a whole. Even if you do your very best, things will still happen that are out of your control. To me, it’s terrifying to wake up every day and do this again but it’s also something I’ve been through, so it’s less scary. I know there will be road bumps and I know I’ll get flack but it will probably be easier than last time.”

Monitor the financial health of your business

While it should go without saying, keeping a close watch on your company’s fiscal health can be more difficult than it seems. If this isn’t your strong suit, hire someone dedicated to the task as early as possible. Schedule regular updates with this person and learn as much as you can. As an entrepreneur, the finances are your responsibility. “I think Nasty Gal would have had a very different trajectory had I not raised venture capital. I bootstrapped the company to 30 million dollars from a few hundred bucks. If I had kept it profitable, we would have a lot more choices in the end.”