The Rise, Fall, and Remaking of the #GirlBoss

Glossier, Emily Weiss, and how we talk about business leaders

I could introduce this interview asking you to remember the first time you saw an ad for Glossier: the stark, minimalist aesthetic; the models with slicked-back hair wearing makeup that made them look like they weren’t wearing makeup, the frankly confusing website with just a handful of products. I guess I just wrote a version of that intro, but I also want to start write one that simply says: even if you’ve never heard of Glossier, you probably do have a memory of some beauty product, and what that beauty product seemed to promise.

This is true for all genders, for all locations, for all ages: you didn’t have to use it or even covet it to understand what sort of person, what sort of life, was associated with that product. Glossier is simply the most recent, most visible, and most successful version of that. That’s part of why it matters. But it also matters because the story of its ascension is also a story of how we talk about women in leadership positions, and what sort of women those leadership positions are open to in the first place. And journalist Marisa Meltzer tells that story with incredible verve and nuance.

Glossy is a non-fiction book, but you’ll devour it like a thriller. It’s not quite Bad Blood levels of intrigue, but it’s juicy and twisty and smart — which I think you’ll also see on Marisa’s answers to my questions about her reporting below.

You can buy Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss's Glossier here, and find more from Marisa Meltzer here.

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Let’s start with some context. On the first page of the book, you write that “Glossier is not just a beauty brand but the millennial and Gen Z brand.” Some of us reading this know exactly what that means (and have been precisely targeted by Glossier’s advertising) and some of us, not so much. What does it mean to be a millennial/Gen Z brand — and a beauty brand in particular? 

Glossier was inspired by things like streetwear more than they were by competing beauty companies. So for example, beauty companies–large ones like the kinds that we would buy from a drugstore or a department store like a Lancôme or L'Oréal–would be taking inspiration from runways and whatever Hollywood star or supermodel they had on contract as their face. And it would be like: these are the colors this season, these are the products. 

And when Glossier launched in 2014, they only had four products and I honestly didn't really understand it at first. It felt a little bit random to me. This was a balm, a rosewater spray, a kind of makeup hybrid product and a moisturizer. And it wasn't even enough to do a full before bed routine and there was no color cosmetics. And I was like, where are the 12 shades of lipstick?

But really what they were inspired by something more like Supreme, the streetwear brand, where they were giving consumers a few, very cool products and you're going to be super excited dying to know what we give you next, and you're not going to know when that's going to happen. And so Glossier created this kind of frenzy around the brand and its products from the start. 

And I would say one of the great successes of the brand is that it's not so much that who is the Gen Z version of Glossier? Glossier is the Gen Z version of Glossier. They do very well on TikTok and it speaks to a younger generation as well. There's something very magical that they tapped into with these easy products that are priced a little bit between drugstore and department store. So it feels a little bit aspirational. I always think of it as when you're done using proactiv for acne, you go to Glossier until you're ready to spend maybe a lot of money on some serious, I don't know, vitamin C serums or something for wrinkles or dark spots or whatever you start worrying about towards your mid thirties and beyond.

Glossier’s founder Emily Weiss in 2016 (via Getty)

I am so fascinated by Emily Weiss — as are so many others, as evidenced by the hunger for this book. I’m particularly interested in her cultivation of quasi-privacy (modeled after male CEOs) and, well, her willingness to sit for interviews for this book. If you had to explain Weiss to someone in a few sentences, how would you do it?

What makes her so interesting? (I’m particularly interested in this demand for women in publishing and fashion to somehow make their lives “consumable” for others, and how she has both exploited and resisted that) 

She is a cipher. I guess that's one sentence. She's someone that is so charismatic and at the same time so unreadable. I have been in the room with a lot of famous people for my job writing celebrity profiles, and it's a little bit like being with Gwyneth Paltrow where when she focuses all of her attention on you, and it's just the two of you in a space, it's hypnotic. It's like, I want you to be my friend and also my cult leader, and I'll do anything. It's like you sort of forget who you are a little bit. 

Emily Weiss is tall and thin and beautiful. She was a teenage model. And for someone like me who grew up fat and awkward and made fun of a lot and was kind of like a brainy nerd, having someone like that give you attention– as embarrassing as it is to say–is a little bit like having the most popular girl in school who's also pretty and smart, give you attention and be nice to you and it's very flattering. And then you realize it's because she wants something from you. Because as a journalist, I have something that she needs, which is to give her good PR and to spread the word of her own kind of leadership and Glossier. So it's transactional. I won't lie, it brings up a lot of adolescent weirdness. 

And in fact, while revising the book, one of my early readers and editor feedback was that I needed to tone down on, I think the word was making myself sound like “such a troll” in front of her. They were sort of like, it gets old and also you're diminishing yourself and your own career. But that is how I felt a lot of the time around her. 

I think that Emily Weiss is so interesting because she didn't always give people what they wanted. There are other founders in her cohort, the so-called girlbosses who were a little more open to maybe doing a home tour or some of the traditional ways that women in leadership get press to cover them. And Emily didn't want to say what was in her bag. She did not even let a New York Times reporter see the beauty products she had brought on a trip to Europe. 

Even though she was promoting Glossier, she wanted to be seen as the same way a man would. And to her, this was like a political stance, which I understood. But I also think that is a misreading of how men in leadership are covered. I mean, if you look at current examples like Elon Musk, Mark Zuckerberg, Jeff Bezos, even Donald Trump their personal lives are very much of interest to everyone and covered in a way that’s sort of female-coded, heavy on what they wear, how they act. For better or for worse, that has become something that crosses gender lines. I understand her reticence to be covered in women's media in a way that hasn’t changed since Diane Keaton in Baby Boom or something. But I also think that there's some maybe inherent internalized misogyny in not wanting to be seen that way, wanting to be seen as someone who's not like the other girls. I'm not like the other leaders, I'm different.

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Along those lines, do you think of the book as a biography of a woman told through the lens of a company’s rise to power….or the story of a very 2010s company told through the story of a woman? I’m guessing the answer is “both,” in which case: how did you balance those two narratives throughout the book?

You’re right, I do think of the book as a biography of a woman told through the lens of a company's right rise to power and also the story of a very 2010s company told through the story of a woman. I wanted there to be both narratives. 

Really what I wanted was for many different potential readers to have a way into the book. I wanted super fans of Glossier to be able to love the cover in all its pink glory. And to hear about the behind the scenes of how their favorite products were made, or even just things like company offsites and camps and sort of just stuff that was for the real heads. I wanted someone who was fascinated about the intersection of feminism and capitalism and the cultural moment of the girlboss to be able to read the book and consider that moment in time in a way that was thoughtful and nuanced and new.

But I also want — and continue to hope — that someone who would read about the founders of PayPal or WeWork would read this book, maybe an older or male reader.  There were questions brought up during meetings about the book over whether or not having a pink cover would just eliminate that male readership. But ultimately it is getting press from people who are interested in finance and business and tech. 

I wanted to have something in the canon of books about companies and books about leaders that was entirely its own, meaning that it was about a woman and a young woman, and it was about a woman who had started a company that whose products were meant for women, but at the same time that it wasn't kind of like a self-helpy book in the vein of Lean In or something that was authorized by her in the sort of vein of Walter Isaacson's books or that was self penned like Shoe Dog by Phil Knight.

This book wasn't wholly about villainizing someone or was just this kind of candy-colored hagiography about someone either, and that it could exist in its middle ground. And I think once I understood and accepted that this book was going to be entirely its own, I was able see it as being a lot of things at once. It could live on a lot of different sections of bookstores! But that said, the first week it came out, I got a text from a friend who was buying it at a large Portland bookstore and had to get it from the craft section, and I was not very happy about that placement. 

In terms of research and reporting, I tend to kind of leave no stone unturned or at least I try to/ even now I will get a DM from someone who was like, oh, I interned for Glossier, or I worked at a competitor. And even though I don't know them and the book is out, I will kick myself wishing that I had spoken to them. But I just tried to reach out to everyone that I could and I'll follow up.  I'll be persistent. But I am not here to force someone to participate in a book that they don't want to.

Which is part of why the relationship with Emily Weiss was so unique. because when the book started, it was a little more broadly about the beauty industry as a whole. And I thought I would follow different companies. And she, via her press team, immediately said yes to participating in the book. And I interviewed her a few times and I thought I was communicating that the book was really going to be about Glossier, and she did not feel that I had communicated that clearly enough and felt betrayed. And so there is an inherent tension in the book of ambivalence, maybe even resistance, to even being there talking to me.  

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One thing I appreciate about the book is our relative distance from the #girlboss phenomenon — we’re able to look back, position Glossier and Weiss within that discourse, and talk about how “girlbossism” embodied some of the worst components of white (capitalist) feminism….while also considering the pretty gross misogyny that undergirded a lot of the discourse from the time.

How has your thinking on the “girl boss moment,” for lack of a better phrase, changed over the course of your time reporting on Weiss, from the Vanity Fair profile you wrote pegged to the billion dollar valuation to Weiss stepping down as CEO to now? And as you’ve done press for the book, how do you think others’ thinking has changed? 

The girlboss moment was a little bit of an eye roll to me. Oh, look at all of these socially connected, rich, beautiful women with their cool companies trying to sell me feminism. It was not something I was particularly a fan of or rooting for, even though I was very obsessed with Glossier. But as a whole, I thought the girlboss thing was an eye roll at best, really offensive at worst. I mean, there is no boyboss, right? I would hate if someone called me a girlboss in any context other than a complete joke between friends. 

My relationship with the term did change when I was writing the book because I thought a lot about how Emily didn't want to have her life covered the way a typical female executive might be covered, and that the girlboss moniker was a way for her and women like her to talk about their jobs, their companies to be seen as executives and professionals, even if it had to rely on this kind of diminutive of fake word trend piece that I don't think any of them really embraced with the exception of Sophia Amuroso, who wrote the book #Girlboss. 

I came around to think, wow girlboss actually benefited these women in a lot of ways. And also these were women who were getting funding for their companies and who were putting probably very expensive publicists on retainer in order to get the kinds of stories that I and many other journalists wrote about them. So they could be as resistant as they claim they were, but they were still kind of courting the press, and that was part of their strategy for getting the word out and maybe scaling their brands. Or every time someone with a brand wants a story about them, it's probably because they're trying to get more money out of it, whether it's more funding or new customers or whatever. It's, like I said earlier, the popular girl who shines her bright light on you still wants something from you, which is, I guess something that's important to remember in every respect. 

This book has probably helped,  I don't know if the right word is rehabilitate the image of the girlboss, but it has led people to think about it in a way that is a bit beyond the trend pieces. I want us to think about the negative space around these girlbosses that they were white and photogenic and socially connected, and mostly from New York and Los Angeles. And so who weren't we looking at? It was women who owned maybe a B2B company. Maybe it was someone who didn't fit or didn't care about designer clothes. Maybe it was someone who didn't hire a PR firm. Maybe it was someone who didn't live on the coast or want to play by those rules. And I think that that has sparked some really interesting conversations. 

I will say that a few of the original girl bosses like Ty Haney of Outdoor Voices and Sophia Amuroso have tagged me in angry Instagram posts. I'm pretty sure they didn't read the book because it was before it came out, but they were just angry about some of the press around it and the girlboss, and I really wanted them to tell them to read it because I actually think the book is pretty fair about the phenomenon and why those women chose to participate in a moment that was a little bit embarrassing or cringe-worthy.

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If Glossier is a peak 2010s company — and was forced to grapple with that 2010s-ness, much like millennials themselves, as it aged — what’s a 2020s company and leader? And how do you think we’ll look at back on it, and the conversations and hype and CEO celebrification, when we look back a decade from now?  

I think of this in a few ways. For the girl bosses, it was the 2010s version of business fame. You think of the corporate Raiders like Richard Gere’s character in Pretty Woman in the ‘80s. And then you had these tech wiz-kids in the nineties and you had Crypto Bros maybe right around now. And in the 2010s you had girl bosses. Is the 2020s Glossier, the Crypto Bros now? Is that already over? It's hard to know. I imagine the 2020s equivalent of Glossier would definitely be in another field. 

I predict Emily Weiss will go on to found another company. My guess would be in the parenting sphere. She's been posting a lot about being a relatively new mom and making breastmilk soap and gifting it to people, which is really a turn that I did not expect coming. And then there's Julie Schott’s company that makes patches for zits called Starface and has also gotten into smoking cessation products and emergency contraception. They are a Gen Z and beyond answer to Proctor and Gamble, with a very young and kind of edgy bent.

If there is a quintessentially 2020s company, I don't know if we have it yet, or maybe it's in such a nascent form that I don't know about. Maybe it's in something like AI that I know so little about and frankly fear. Someone asked me an interview how I was using AI, and I was like, maybe just when I'm interacting with an airline’s chatbot trying to reschedule a flight? I think Glossier is still the Glossier of the 2020s, at least for now. ●

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You can buy Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss's Glossier here, and find more from Marisa Meltzer here.