Empowering the Freelance Economy

Freelancer to founder: how to get up after a nasty fall

Sophia Amoruso: Investor @TrustFundVC . Mentoring founders @ http://BusinessClass.co. NYT Bestselling Author, founded Nasty Gal. Photo Source: Twitter
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We share tips and experiences from resilient entrepreneur and investor Sophia Amoruso who founded and rose to rapid entrepreneurial fame with her fashion business Nasty Gal. Her business was eventually sold for a fraction of its former valuation when it went bankrupt. However, there were valuable lessons this side hustler to founder learned along the way and she shares them with refreshing honesty.

Within 6 months in 2016, Sophia Amoruso, the serial entrepreneur behind the much-adored fashion brand Nasty Gal, landed the cover of Forbes Magazine, got dumped by her husband of 8 months, and filed for bankruptcy on the day Trump was elected.

Her response to this period in her life? “Fuuuuck.”

But did that stop her from getting up from a “nasty “fall”? No.

Amoruso kept her faith in love and business. Between 2017 and 2019 she fell in love again and founded Girlboss, a community and media company dedicated to ambitious women. She wrote a best-selling book based on her experiences and named it #GIRLBOSS. She sold the business for a multi-million figure and on top of that Charlize Theron produced a NETFLIX series based on that book.

Nasty Gal’s story is a cautionary tale for fast-growing businesses. Amoruso’s book and personal story highlight the importance of sustainable growth, strong financial management, and staying true to your core identity.

The Freelance Informer came across an episode of the Erica Taught Me podcast, where Amoruso was interviewed. It is probably one of her most off-the-cuff and informative interviews (watch it below). She shares her entrepreneurial journey, including the rise and fall of Nasty Gal which eventually sold to Booho for £16 million. Nasty Gal was once valued at $350 million.

Here are some key points and tips from Sophia Amoruso’s entrepreneurial journey:

  • Embrace the hustle but not at the expense of your values: Sophia didn’t have a traditional career path. She started selling vintage clothing on eBay while working odd jobs. Her first big break came when she found a Chanel jacket for $8 in a thrift shop and sold it on eBay for over $1,000. When she started to bring in sales higher than any annual salary had brought her to date, she was motivated to pursue her passion for fashion full-time.
  • Focus on your customers: Nasty Gal’s success was built on understanding its target audience and providing them with what they wanted. Sophia started by selling vintage clothing that she loved, but she quickly learned to adapt to her customers’ preferences.
  • Don’t be afraid to fail: Nasty Gal eventually filed for bankruptcy in 2016. Sophia admits that she made mistakes, but she learned from them and moved on. She emphasises that failure is a normal part of the entrepreneurial journey and shouldn’t be seen as a setback.
  • Build a strong community: Sophia has always been passionate about connecting with other women and entrepreneurs. She founded Girlboss Media, which included a website, podcast, and conferences, to empower and inspire women to pursue their dreams. She sold that business to a holding company called Attention Capital. She also launched a venture fund called Trust Fund in early 2023.
  • Be yourself: Sophia is known for her authenticity and vulnerability. She shares her struggles and successes openly, which resonates with many people. She encourages others to be true to themselves and not try to fit into someone else’s mould.

Check out the podcast: Erika Taught Me

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