Faceplanting, Feedback, and Finding Aligned Success with Sophia Amoruso - Jenna Kutcher

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Faceplanting, Feedback, and Finding Aligned Success with Sophia Amoruso

Jenna Kutcher 

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Sophia Amoruso started her business on eBay and it turned into the massive fashion name of NastyGal. Her story transitioned from a 22-year old millionaire to a very public journey through incredible business challenges… And that was just the beginning of the wild journey of business and life this GirlBoss has continued to ride, straight into the fine-tuned version of success she’s creating for herself and others today.

I’m so thrilled for an opportunity to have a candid conversation with Sophia about business highs and lows, of creating a company that aligns with what you actually want, and taking everything she’s learned — from public success to missteps — and turning it into valuable teachings for others. 

Where It All Started

Sophia Amoruso has been an entrepreneur for quite some time, and it all started with flipping vintage items on eBay. “It sounds like small beans, and it was,” she explained. “But it became a very big company called NastyGal.”

Sophia bootstrapped that company to $28 million with no debt and no investors. Then, she reached a point where bringing on investors was the next step. “That changed things pretty significantly,” she shared. The company grew to over $100 million in revenue. The company experienced many ups and downs through the 10 years Sophia was part of it. “Not a great exit,” Sophia said simply. 

From there, she wrote a book called #Girlboss that went on to become a New York Times bestseller. It started a conversation about women becoming entrepreneurs and their own bosses. Sophia explained, “That became even louder than NastyGal in a lot of ways. I was really ready to serve that community.”

She sold the Girlboss company just before COVID hit the United States and had planned to stay on for quite some time, but with the primary business being in events, they had to scale down, “To the point of me not being needed there.”

That brings us to this moment. Now, Sophia has moved on to teach entrepreneurs through her course Business Class. “It’s really fun sharing all of the stuff I’ve learned instead of just learning the hard way,” Sophia shared.

Starting Over

“I have the distinct privilege of not starting from zero,” Sophia began. 

With every new phase of entrepreneurship, Sophia reinvented herself, but in each new endeavor she was equipped with the experiences, knowledge, and skills that she acquired from her previous business ventures. “But people don’t see moving on from a business as a positive thing,” she explained. 

There’s a struggle when your audience only wants to see one version of who you are and the brand they know you for, even when you don’t want to be that brand anymore. Sophia’s advice for anyone in a similar situation of transition, “treat it as an experiment.”

“I feel very strongly that if people are thinking about starting a business, they should,” Sophia continued, “We’ve seen that our employers and our jobs aren’t as secure as we thought they were. Nothing is as secure as we think it is, and nothing is permanent.”

Are you waiting to be pushed into starting that business or pursuing your dream? Sophia says, “Push yourself off the ledge.”

Failing with an Audience

“I had been this poster child of entrepreneurship and so celebrated,” Sophia explained. When NastyGal filed for Chapter 11 bankruptcy, the noise around her was loud. Headlines were brutal, the press was sensational, and they even made her the example of an entire generation. 

“I’m not alone in faceplanting, and I thought I was,” Sophia explained. Sophia watched her peers succeed in the midst of NastyGal’s downfall, but now with perspective, she sees that her public failure, “paved the way for others to fail, too.”

And then came the Netflix series and her story was broadcast into 150 million homes. “It became a haze of identity crisis,” she explained. 

“I’ve had to weed through a lot of feedback, a lot of unfounded and out of left field speculation,” Sophia explained, but instead of shutting it out completely, she used it as a tool to look inward and ask hard questions of herself and the choices she made in business. 

What is Success Now?

“There was a time when success was all the things I was experiencing,” Sophia explained. From the magazine covers to the speaking engagements, the celebrity customers and celebrated moments in her career, so much of her entrepreneurial journey in her 20s was fun. She told me, “I bought into it.”

But there was also a bit of herself that felt lost in that. As she stepped away from that first business, Sophia realized that the person she was before it all was still in there. Sophia realized that she didn’t want to be out late, she didn’t want to be flying around the world speaking at conferences. She finally got to a place where she felt comfortable saying no.

Sophia also learned that her vision of success could be fulfilled in ways that didn’t involve the things that didn’t align with who she was. Enter, online education and her course called Business Class. It runs for 10 weeks and she’s extremely invested in her students for those 10 weeks, but it doesn’t require a huge team or the same work over and over again, she doesn’t have to do it live, and the lifestyle choice is just more fitting to her version of success.

About Business Class

Sophia is combining all of her experience in entrepreneurship and teaching it in a fun aviation-themed course called Business Class. 

The course covers defending your strengths, having clarity about your idea, should you be an LLC or corporation, what is intellectual property, what’s a design mark, managing finances and marketing… All covered in a 10 week program.

“It’s a comprehensive course — everything for someone who has an idea and wants to start a business, they can really get there with it,” Shopia shared.

More from Sophia Amoruso

Follow along and learn from Sophia on Instagram and with her course Business Class.


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