In 2014, Emily Weiss—then known for being the “superintern” who upstaged star Lauren Conrad for knowing the word “chinoiserie” on MTV’s The Hills and popularizing the “shelfie” through her blog Into the Gloss—introduced her beauty brand Glossier.
Its millennial-pink aesthetic, DTC strategy, and no-makeup makeup products with cheeky names like Balm Dotcom and Boy Brow became a phenomenon, disrupting the beauty category and making Weiss a defining face of the girlboss era.
A new exposé out today, Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss’s Glossier, by author and business journalist Marisa Meltzer, traces the brand’s journey from Weiss’s teenage years to Glossier’s eventual unicorn status through last year’s announcement that Weiss would step down from the CEO role, examining how Weiss’s unwavering ambition drove the brand’s successes and missteps.
We spoke to Meltzer, who conducted in-depth interviews with Weiss, new CEO Kyle Leahy, and many Glossier employees and investors for the book, about how Weiss became the “last girlboss standing” and digging into the truth behind Glossier’s storytelling.
Marisa Meltzer, Simon and Schuster
Dew diligence: Weiss wasn’t afraid to ask for a favor, even a bold one, Meltzer wrote. She turned a babysitting job into a Ralph Lauren internship (“[It] can’t hurt to ask,” Weiss told Meltzer) and was known to cold-email or cold-call beauty execs and magazine editors. Yet, Meltzer writes Weiss often demonstrates a tendency of “undermining herself,” wanting “the world to think she lucked out,” part of her tendency for “self-mythmaking.”
This self-mythmaking was popular among fashion and beauty leaders from Coco Chanel to Ralph Lauren, as well as in industries that are “less aesthetically coded,” Meltzer noted to Retail Brew, pointing to Elon Musk and Steve Jobs.
“Emily Weiss was kind of borrowing from both,” Meltzer told us. “She was borrowing from both in her leadership aspirations, too. She wanted that mythic, powerful business of the tech founder, like philosopher-king types, but then I think she also wanted that kind of meticulously executed aesthetic vision of some of these fashion and lifestyle legends.”
It girl: Alongside Nasty Gal founder Sophia Amuroso (who coined the term) and founders like Thinx’s Miki Agrawal, Weiss was a prominent face in the era of the “girlboss”—a term that’s now become “an insult,” Meltzer writes. As many of these founders faced controversies, Weiss became the “last girlboss standing,” partially because of her “guardedness.”
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That wasn’t necessarily a bad thing: Meltzer told us that when reporting on Weiss for a Vanity Fair profile in 2019 on a busy day at the Glossier store in New York City’s Lafayette Street, few customers recognized Weiss. She and Meltzer both considered this as a good thing, she said, indicating that the brand could stand on its own, its success not tied to her notoriety.
A business leader embracing a label like “girlboss”—even if it makes them cringe or they don’t necessarily identify with it—can “help people understand your brand or make your brand or you more famous,” Meltzer told us. But on the flip side, “when you are put on a pedestal or made exemplary or a public figure, it can bring a certain unwanted attention where people can’t wait to bring you down.”
Pink slip: After years of expansion, Glossier hit a “crisis point” as its valuation dipped in 2021, and Meltzer wrote that “it seems undeniable that Weiss’s leadership had inhibited Glossier’s success and growth.” Meltzer told us this realization “was gradual,” a culmination of many missteps outlined in the book, like the creation of less-than-inclusive product shade ranges, insistence on being known as a tech company with secretive development of an app that never came to be, and accounts of toxic culture at its retail showrooms.
Getting answers about Glossier’s journey, particularly about Leahy taking over the CEO from Weiss last year, wasn’t straightforward. Leahy and Weiss met on Zoom in April 2021, late at night when Weiss was on vacation in Hawaii. Leahy claimed the meeting wasn’t about a specific role at the time, but it was “kind of organic from there.” But Meltzer told us she pushed back on that, and Leahy admitted succession was “part of the master plan” from when they first spoke, Meltzer wrote.
“So much of Glossier is about storytelling, and that’s why they’re a great brand, but that also is part of why they can be a little bit cloaked in mystery or good at giving a convenient version of what might be a very complex and probably sad story,” Meltzer said. “Or at least, if not sad, then deeply rooted in the reality of why it’s hard to grow and run a company.”