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. Creators of their own worlds. 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 some controversy over the treatment of workers. Elon Musk went from a proudly neurodivergent wunderkind into a political bad-boy billionaire on the loose. Martha Stewart began as a type A entrepreneur moving at the speed of the Energizer Bunny, 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 posting thirst-trap photos of herself that people take seriously.
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.” Those are worthy things to care about, but a bit cliché, as if interests in nurturing longevity and gurus come standard when you become a tech queenpin.
It was a cultivated image, a measured and crafted persona fashioned after the Silicon Valley tech model of the founder philosopher. Much posturing is accepted as standard practice for a rising star company and its founder. The way Weiss spoke about Glossier – literally the language she used – 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. “I’ve spent my life relying on light bulb moments and just jumping in full force,” she told the Business of Fashion. “That’s fine when you’re making something on your own, but not fine when you’re thirty-plus people and there are a ton of stakeholders, as well as knock-on effects of pretty much every initiative we take on.” 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,” and that it fundamentally made beauty products that were essential for everyone. 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.
“Wow, I wish I could have that every day,” she said in a humbled and impressed tone that sounded mostly genuine, referring to the crowd cheering at one live interview for the podcast How I Built This. The audience of fans literally chanted “Glos-see-yay” as she entered. In that roughly hourlong interview, she mentioned Duckworth’s book Grit at least three times. “People often ask me what amount of your success is attributed to luck? Um, I really believe in kind of grit, and I mean I didn’t make that up, that’s Angela Duckworth’s and her book Grit, a very good book.” A few minutes later, she said, “Back to that power of grit…I think my personal superpower, if there’s one thing that I think I’m really good at, I’m super curious.” And again: “When I hear the word ‘grit,’ that’s what it says to me is there’s a resiliency to just, to just brush, shake it off, right? And, and keep going.” She ended by answering a question about good advice by invoking a business book. “The Phil Knight quote from Nike of, like, ‘Just do it.’ I mean, it’s as cheesy as it sounds,” she said. “Be courageous. Be curious and be courageous because the worst – it’s like my friend says about dates, it’s either a good date or a good story. I think that’s really good advice. Try things, it’s going to help you grow and learn, you know, learn something, learn something about yourself.”
Weiss hosted fireside chats at the Glossier headquarters, where she interviewed people such as Deepak Chopra, Disney CEO Bob Iger, Reddit cofounder Alexis Ohanian, Warby Parker cofounder Neil Blumenthal, Chobani founder Hamdi Ulukaya, president of Planned Parenthood Cecile Richards, Shake Shack’s then CFO Tara Comonte, Spanx inventor Sara Blakely. Weiss would pull from her own contacts to see who she could get. Meant for education and enrichment, such sessions are par for the course at plenty of tech companies and start-ups. It was an impressive list of people, but some employees found them to be an elaborate vanity project, less for their own enrichment and more for Weiss to cement her founder status. 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 was good at making people feel special, listened to, showing that she was present. She lived to hear from someone who was an expert on something she didn’t know about. “Emily would always do this thing where, depending on which leaders she talked to, she would soak up whatever they said. After the Warby Parker talk, she went on a big kick where she would just quote him a lot, which was kind of funny because it wasn’t always hyper-relevant to what we were doing,” said a creative employee who attended many of the chats. Weiss would compare Glossier to Amazon for how people stole their packages from customers’ doors and Shake Shack for their dedication to pleasing customers. “After talking to the Disney guy, she was comparing the showrooms to Disney World, in the idea of really exciting experiences in a couple select locations. And then the showroom employees were characters like Mickey Mouse, and meeting them is so cool and nice and awesome you might want to take pictures with them.”
She was buying her own good press. Weiss often talked of revolutionizing beauty and seemed to relish any opportunity to compare herself to a legacy American brand or use the “Glossier is your friend” metaphor. 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.” To both journalists and employees, she also compared the potential of Glossier’s trajectory to those companies. Once, in a meeting with Nike to potentially partner with them on a product, Weiss advised that what Nike was missing in its stores was curation, that customers shouldn’t walk into a pop-up and see fifteen shoes. “Pick one that’s the shoe you’re going out with,” she said. Glossier wasn’t going to offer five types of something, and that was why people trusted them: they had a perspective. 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 was happy to hear that people were stealing Glossier packages off people’s front steps. She compared the pink bubble-wrap pouches to the visibility of Apple’s AirPods. She referenced Apple when talking about concepts for retail stores. “I think a lot about the Apple Store,” she said.
“About creating hubs where you can touch and experience a product, yes, but you can also connect with like-minded people.” To the New York Times in 2015, she said, “What is the Steve Jobs quote – ‘Stay hungry, stay foolish’? . . . I think I’m probably pretty foolish.” 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. “Yeah, it’s a club that everyone can be a part of. And there hasn’t been a beauty brand like that in a while. And one that takes its customers’ involvement – that really relies on its customers’ involvement. It’s our lifeblood.”
Any CEO of a company is busy, but Weiss spread herself thin. Her Google calendar, where her assistant kept her schedule, was a block of text: interviews, creative meetings, product development. She was traveling a great deal, once a month at a minimum, for fundraising or a speaking engagement or going to a new city or country that Glossier was looking to expand into. She liked to be involved in every detail of the company, from larger questions about fundraising to decisions as small as what color the font should be on a new product package. A bit of an echo of Anna Wintour’s notorious “AWOK” sign-off that Vogue employees needed to get on virtually every aspect of their professional lives. Morgan Von Steen would try to schedule time for Weiss to have a break, like a quiet solo lunch or meditation, but she would invariably end up deleting it as the tide of the day went on. She made herself too available, answering texts early in the day and late at night and encouraging employees to reach out no matter what. She missed taking photos of people for Into the Gloss, less because she didn’t trust anyone else to do it and more because she found it all so exciting. She had a hard time letting go of anything.
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. Weiss, for her part, said that the ultimate lesson was that no book can tell you how to be a CEO. And being a young, female CEO came with a lot of challenges that older men weren’t exposed to.
Excerpted with permission from Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss’s Glossier, Marisa Meltzer, Simon and Schuster.
