Sophia Amoruso’s Newest Venture Is About to Take Flight

Welcome to Second Life, a podcast spotlighting successful women who've made major career changes—and fearlessly mastered the pivot. Hosted by Hillary Kerr, co-founder and chief content officer at Who What Wear, each episode will give you a direct line to women who are game changers in their fields. Subscribe to Second Life on Apple Podcasts, Spotify, or anywhere else you listen to stay tuned.

Sophia Amoruso’s entrepreneurial career has been in the spotlight since her 2006 eBay store took off and became the pioneering online retailer, and phenomenon, Nasty Gal. The brand expanded beyond its initial collection of vintage to include curated designer pieces, as well as its own in-house label, and by 2015, Nasty Gal had grown to over $100 million in revenue. Amoruso was on the cover of Forbes and on Fast Company’s Most Creative People in Business list and was touted as the rags-to-riches, million-dollar millennial #Girlboss—all by the time she was 32. But behind the scenes, Nasty Gal’s rocket-ship growth and $350 million valuation had put immense pressure on the business. "Having a valuation that high that early on was really the first nail in the coffin for us,” Amoruso tells Kerr in the latest episode of Second Life. 

In 2015, Amoruso stepped away from her role as CEO, and the following year, the brand filed for bankruptcy. During that time, however, Amoruso had written the first of her three books, the New York Times best seller #Girlboss, which she turned into her second business a few short months later. Girlboss became a digital community for ambitious women, held highly attended events—Girlboss Rallies—and produced the hit podcast, Girlboss Radio, which garnered over 20 million downloads. "Getting up again, it was so scary, but it was also really therapeutic because I worked through a lot of the things that I know I did wrong at Nasty Gal. And I got a lot of them right at Girlboss,” she says.

After a successful three years scaling the business and an acquisition intended to spur further growth, the 2020 pandemic hit the business especially hard and handed Amoruso, like many CEOs, a set of challenges she never could have prepared for. Revenue came to a screeching halt, including a $10 million deal that was all but a few signatures away from closing. "It just vanished overnight,” says Amoruso. In June, she announced on Instagram that she’d be moving on from Girlboss as the brand downsized and restructured.

Now, just three months later, Amoruso is using her hard-earned experience as a founder, CEO, and serial brand builder to inform a new project, Business Class. The in-depth online entrepreneurship course is providing the next generation of founders with the tools they need to build and scale businesses positioned for long-term success. The material is dense, but captivating her audience has always been a strength for Amoruso. Plus, it's flight themed. "I'm 36 years old, I've been building businesses for 15 years, I've extracted a lot, and all I want to do is give back,” says Amoruso. "I've stepped in a lot of the land mines. I know how to step over them now.”

Tune in to this week’s Second Life to hear the stories behind the building of each one of Amoruso’s iconic brands and what it's like to be on the precipice of a third major career pivot. And don't forget to subscribe on Apple Podcasts, Spotify, or anywhere else you listen so you don't miss an episode.

Next up, Hear How Renee Dua, MD, Is Creating a New Healthcare Model