Sophia Amoruso was born April 20, 1984, in San Diego, California. Her childhood was turbulent—her parents divorced, she struggled with ADHD and depression, and by her teens, she’d dropped out of high school. She bounced between odd jobs, shoplifted for thrills, and lived in her car at various points.
By age 22, Sophia was diagnosed with a hernia and needed surgery. With no insurance, she enrolled in community college just to get student health coverage for the operation. After surgery, she took a job checking student IDs at the entrance to the San Francisco Art Institute—a $13/hour gig that barely covered rent.
Sophia’s life was aimless. She had no career, no direction, no prospects. Most people would have accepted mediocrity. Sophia stumbled into entrepreneurship by accident.
She loved vintage fashion and would scour thrift stores, Salvation Army, and estate sales for unique pieces. She started buying vintage clothing, cleaning and styling it, then photographing and selling it on eBay under the username ‘Nasty Gal Vintage’ (a nod to the 1975 Betty Davis album ‘Nasty Gal’).
The early days were scrappy. Sophia shoplifted books from bookstores to learn photography and styling. She shot product photos herself using natural light and creative angles. She wrote quirky, honest product descriptions that felt like talking to a friend, not reading corporate copy. Her eBay store started attracting attention.
But eBay had limits—high fees, restrictive rules, algorithmic opacity. By 2008, Sophia’s eBay store was generating $1 million annually, but she felt constrained. She needed her own platform. The problem? She had no tech background, no business education, no funding, and no safety net. Most people would have stayed on eBay. Sophia decided to bet everything.
The Turning Point
In 2008, Sophia launched NastyGal.com—her own e-commerce site. She hired a developer on Craigslist to build the site and invested everything she’d made from eBay into inventory, branding, and marketing. The risk was enormous: if it failed, she’d lose everything.
But Sophia had something most fashion retailers didn’t: authenticity and a cult following. Her MySpace page (yes, MySpace) had become a destination where young women discovered her style, personality, and product drops. She transitioned her audience from MySpace to the new site seamlessly.
Nasty Gal’s brand wasn’t polished or corporate—it was rebellious, bold, and unapologetically feminine. Sophia curated vintage pieces and contemporary designs with an edge. The website featured lookbooks that felt like fashion editorials, not catalogs. Customers didn’t just buy clothes—they bought into a lifestyle.
Growth exploded. By 2011, Nasty Gal hit $28 million in revenue. By 2012, Inc. Magazine named it the fastest-growing retailer, with revenue reaching $100 million. Sophia, the high school dropout who’d been homeless, was now running a fashion empire.
In 2012, she moved Nasty Gal from Los Angeles to a 500,000-square-foot warehouse in downtown LA. The company had 350 employees. Sophia graced magazine covers and became a media sensation. In 2014, she published #GIRLBOSS—a memoir-slash-manifesto about building Nasty Gal. It became a New York Times bestseller and inspired millions of young women.
But success was fragile. Behind the glamorous exterior, Nasty Gal was struggling. Rapid expansion had created operational chaos. Inventory management was a disaster. Customer service couldn’t keep up. Company culture became toxic. In 2015, Sophia stepped down as CEO, handing control to a hired executive.
It didn’t help. On November 9, 2016, Nasty Gal filed for Chapter 11 bankruptcy. The company Sophia built from nothing, scaled to $100 million, and turned into a cultural phenomenon had collapsed. British fast-fashion retailer Boohoo acquired Nasty Gal’s intellectual property for $20 million—a fraction of its former valuation.
For most people, this would be the end. For Sophia, it was just another chapter.
The Comeback
After Nasty Gal’s bankruptcy, Sophia could have disappeared in shame. Instead, she doubled down on her personal brand. Netflix produced a TV series based on #GIRLBOSS (though it was canceled after one season). More importantly, Sophia launched Girlboss Media in 2017—a community and content platform for women entrepreneurs.
Girlboss Media hosted conferences (Girlboss Rally) attracting thousands of attendees and featured speakers like Gwyneth Paltrow and Sophia Bush. The brand evolved from Sophia’s story into a movement empowering women to take control of their careers and lives.
But Sophia’s biggest reinvention came in 2019 when she founded Trust Fund—a venture capital firm investing in female-founded consumer brands. The irony? The woman who’d filed for bankruptcy now had $280 million under management, investing in 45+ startups including Anine Bing, Ritual, and The Outset.
Sophia proved that failure isn’t final. Nasty Gal’s bankruptcy taught her lessons no MBA could: operational discipline, sustainable growth, and the importance of culture. She took those lessons and applied them to helping other founders avoid her mistakes.
