Cheddar Awards: Sophia Amoruso Is 2018's Best Comeback

December 12, 2018

By Carlo Versano

As Cheddar reflects on 2018, we are profiling the most innovative, flamboyant, and often-controversial entrepreneurs and corporate leaders who delivered the year's most memorable moments in business. Of the CEO Class of 2018, who was crowned Prom King? Biggest Flirt? Check Cheddar.com for all the Cheddar Awards and more year-end coverage.

Sophia Amoruso owned it.

Speaking to Cheddar at the Women on the Move conference in September, she admitted that she “blew it with Nasty Gal,” the trendy clothing line she founded in 2006 that became one of the fastest growing retailers in the country before it crashed into the ground.

Amoruso was also victim to some epically bad timing.

Just as the company she built was unraveling, Netflix ($NFLX) premiered a series based on her “#Girlboss” autobiography. Soon after, Nasty Gal filed for bankruptcy and was sold for parts, and the Netflix show was cancelled after a season. She went from it-girl entrepreneur and millennial whisperer to cautionary tale of the perils of the start-up universe, almost overnight.

For a lot of founders, that would have been the end. But Amoruso already knew what her next chapter would be. She just had to convince Wall Street and Silicon Valley that she wasn’t yesterday’s news.

So that’s exactly what she did. Amoruso spent the bulk of 2018 giving interviews and attending or speaking at conferences ー telling anyone who would listen about the work she is doing to transform the Girlboss brand into a multi-faceted media and social platform with a laser focus on women and their careers. In many ways, the network already existed ー in group chats, Facebook ($FB) groups, and elsewhere on the web. Amoruso said she’s just creating the conduit for it to flourish.

Amoruso would have been forgiven for choosing a new name for her fledgling company. But as she explained to Cheddar earlier this year, the Girlboss brand felt more relevant than ever, post #MeToo and #TimesUp ー especially for the audience of ambitious millennial women that Amoruso herself had cultivated.

The company says its mission is to “redefine success for millennial women by providing the tools and connections they need to own their futures.”

"A 'girlboss' is someone who doesn't take no for an answer," she told us. "It's a philosophy."

To that end, she wanted the new company to reflect that philosophy and the values she held as a founder. So every new Girlboss employee is also named a "co-founder" and given equity, Amoruso explained.

Now she is coming off her fourth Girlboss Rally in two years, a community building event held in New York that this year grew to over 1,000 women from 30 countries.

In an interview last month during the rally, Amoruso credited the bankruptcy of Nasty Gal ー which was filed on Election Day 2016 ー with getting her to a “pretty powerful” place.

Next year, Girlboss’ new “community” platform will come out of stealth, acting as a sort-of private LinkedIn for professional women to negotiate raises, ask for career advice, and socialize.

At TechCrunch Disrupt this year, Amoruso said she’s all in on this next iteration of the Girlboss brand: “I have a chip on my shoulder. I really want to get it right this time.”

Cheddar salutes Amoruso for owning her failure and using it to build something new.

Read all the 2018 Cheddar Awards here.