In 2014, an ecommerce entrepreneur named Sophia Amoruso published #Girlboss, a mixture of memoir and career advice for women. While judging a book by its cover is frowned upon, the #Girlboss dust jacket—Millennial pink, aggressively hashtagged, its subject front and center with a little black dress and a triumphant smirk—reveals the whole plot. It’s about a woman who gets rich by selling a fast-fashion vision of what a woman on her way to getting rich should be like. It was a bestseller.
By 2017, Amoruso had expanded her #Girlboss universe to include a digital media company of the same name. “Girlboss is a feeling, a philosophy,” she said at its launch party. Like Sheryl Sandberg’s “Lean In,” the slogan yoked careerism to feminism. Never mind that Amoruso’s business ventures weren’t wildly successful. (Her online store Nasty Gal filed for bankruptcy in 2016.) While she struggled in the retail world, Amoruso found longer-lasting success publicizing this new archetype. Her potent personal branding? That was scalable. The Girlboss was everywhere in the 2010s. She was hawking luggage (Stephanie Korey, founder of Away) or makeup (Emily Weiss, founder of Glossier) or workout gear (Tyler Haney, founder of Outdoor Voices). She was almost always white, thin, and charming. She was always Instagrammable. She understood what the modern woman wanted, and how to sell it to her. She would break the glass ceiling, and the shards would fly into the eyes of her haters.
If anyone was most likely to out-girlboss them all, it was Audrey Gelman, a gamine public relations whiz who’d already reached a certain tier of New York–centric fame for her friendship with Lena Dunham. In 2016, she founded The Wing, a meticulously chic women’s social club with devoted members and carefully cultivated celebrity endorsements. (Representative Alexandria Ocasio-Cortez’s praise was splashed on its website; fellow niche celebrities like Tavi Gevinson and Hari Nef were members.) Perhaps more than any other woman in the startup world, Gelman excelled at commodifying feminism as a lifestyle. She expertly sold the idea that joining an upscale coworking community was a progressive, empowering political choice. Media coverage of The Wing was largely positive and frequently glowing, and Gelman hustled to win over her detractors.
For several years, it worked beautifully. The 2016 election imbued Gelman’s fledgling company with resistance-tinted patina. “The Wing was conceived amid great expectations for the Hillary Clinton presidency, but it was her defeat that sharpened the company’s sense of mission,” cultural critic and reporter Amanda Hess wrote in a New York Times Magazine story from earlier this year. What had originally been pitched as a resting place for ladies on the go became recast as membership-as-direct-action. “Gelman began to speak about a Wing membership as analogous to political agitation,” Hess continued. The Wing raised over $100 million in funding. It expanded from its original Flatiron location to a handful of equally lavish spots in Manhattan and Brooklyn, then nationally and internationally, opening spaces from Los Angeles to Paris, taking its bougie womb aesthetic global. Gelman was the first visibly pregnant CEO to appear on the cover of a business magazine. Girlboss 2.0 had arrived.
Leigh Stein, a writer who herself cofounded an online community and event series for women during the 2010s, has written a delightfully tart literary satire of the Girlboss with her new book, Self Care. The novel, out this week, arrives at an opportune moment, as the world Stein skewers is going through the same kind of upheaval she creates within her fictional universe, so much so that some of the passages appear nearly clairvoyant.