Emily Weiss wasn’t known to have many close friends. “I spend all my time with basically five friends. We all met in Florence during study abroad,” she told me in 2019 when I was visiting her apartment. “Emily would love to host you at her apartment (this would be a first for a reporter) to . . . wait for it . . . make a frittata with her!” wrote her PR rep. “If you follow her on social you might have seen that this is a new hobby of hers. After reading the book The First Forty Days she’s been cooking and hand delivering homemade frittatas to her friends who are postpartum.” I found this whole endeavor contrived but also quite sweet of her.
“And I’m freezing my eggs,” Weiss told me with a little smirk. She was wearing slippers with a skirt and an oversize button-up shirt from the brand Toteme, and I remember how real she seemed, for a moment. When I asked why, she pointed out that her oven is also a microwave—“Isn’t that awesome?”—and started to heat onion and butter on medium heat. I felt lucky to be in her space and didn’t want to make her regret inviting me over for the interview, but I could also palpably feel her wanting to tell a story, and stopping herself from doing so.
Now that she was in full founder mode, she stopped going to most fashion events. She gave up on having hair that required touch-ups every four weeks. Gone were the skinny jeans and sneakers, and in their place were more powerfully adult designer clothes: Chanel sandals and Gucci sweaters and power suits when the occasion necessitated it.
Weiss had a sense of how people perceived her, and she knew she had to change how she presented herself to both her company and the world at large, as Glossier grew. In the early days she would change clothes in the office, furiously busy between meetings, not caring who saw her. But she had to pull back and put a wall up around herself. Which could be alienating for friends and employees and isolating for her.
Even though she posted as frequently as you would expect of a young CEO, she was a more muted presence on Instagram. One could learn very little about her private life, or even her opinions, from her vacation selfies and broad support of reproductive rights. She straddled a line between being approachable and aspirational, normal and extraordinary. “She presents this air of being a normal person; in reality, she’s not a normal person. She’s a very well-connected founder who is worth several million dollars. But she looks like a normal person,” said one observer. An employee swore she was unchanged: “She hasn’t bought a yacht or anything like that.” Weiss was not the first founder of a company to take an assertive role in trying to change the way the public perceived them. Founders like Weiss, or the ones she shaped herself after, are big talkers. Showboats. They say they’re changing the world, and they believe it, and they’ll say it to anyone. Jeff Bezos started out as a dork wunderkind who changed the business world and has now evolved into a source of controversy over the treatment of workers. Martha Stewart began as a type A entrepreneur, taking the lemons of homemaking and turning them into billion-dollar lemonade. Sure, she happened to go to prison along the way, but she managed to emerge seemingly more likable and with a little bit of street cred. In her eighties, she is known for having a friendship with Snoop Dog, a cannabis business, and a propensity for thirst-traps.
The most obvious evolution was in Weiss’s interests. She personally had invested in the Co–Star astrology app and, in 2020, joined the board of the sustainable footwear brand Allbirds. She had a gratitude journal she wrote in for five minutes each day. At one point around 2019, she cut the accounts she followed on Instagram down to a lean 555 but was fond of Blue Zones, an account of “longevity and happiness secrets from the most extraordinary populations on earth.”
It was a cultivated image, a measured and crafted persona fashioned after the Silicon Valley tech model of the founder- philosopher. The way Weiss spoke about Glossier began to morph. Even though she didn’t have a business degree, she was becoming fluent in the patois of start-ups and MBA grads. She used words and phrases like “assess” and “lightning speed” and “our focus is very much on the digital.” At Disrupt SF in 2018, she said Glossier was “a psychographic rather than a demographic.” When she spoke that way, Weiss came across as someone who wanted to appear like a leader more than act like the chief executive of the massive operation Glossier was growing to be.
Weiss hosted fireside chats at the Glossier headquarters, where she interviewed people such as Deepak Chopra, Disney CEO Bob Iger, Warby Parker cofounder Neil Blumenthal, and Spanx inventor Sara Blakely. Meant for education and enrichment, such sessions are par for the course at plenty of tech companies and start-ups, but some employees found them to be an elaborate vanity project. Said one, “Emily would have her hair and makeup done by product development and then take a selfie in the bathroom and walk the people through the office.”
Weiss often talked of revolutionizing beauty and seemed to relish any opportunity to compare herself to a legacy American brand. In a blog post on Into the Gloss marking Glossier’s second anniversary in October 2016, she wrote that she had to remind herself how young the company was “and to look at the time it’s taken iconic companies like Estée Lauder, Apple, and Nike to become what they are today.” Weiss told the author of a Harvard Business School case study: “Girls take pictures of themselves with the [outdoor] ads and tag us. Can you imagine that happening with, like, Ford Motors?”
She looked up to Ralph Lauren and also Airbnb. “They have a product which is like people’s homes, but really what they have is this incredible community who are sharing with one another, and it’s very sort of self-sustaining,” she told me. “And I think of Glossier like an ecosystem, like people come in and they rarely leave.” Like the song “Hotel California”? I asked, making a bad joke. She didn’t seem to acknowledge it.
It’s easy, perhaps too easy, to bury someone like Weiss in her own words. Was reading all those business books and constantly invoking them cliché? Absolutely. But I also think it was how she was processing her changing life. And instead of letting the press in on her own challenges, it was easier to talk more broadly about grit or lessons she had learned or to speak in analogies. “My head of comms will kill me because I’m going to say something really weird right now,” she told one reporter, opening her eyes wide and pulling a self-deprecating face. “But I think about it a little bit like, how are religions scaled?”
Copyright © 2023 by Marisa Meltzer. From GLOSSY: Ambition, Beauty, and the Inside Story of Emily Weiss’s Glossier by Marisa Meltzer. Reprinted by permission of One Signal Publishers, a Division of Simon & Schuster, Inc.