Inside the Rise of Emily Weiss's Glossier

"She was enthralled by the idea of being this tech founder-style entrepreneur, where the narrative in the media is not about their personal life, but their genius," said author Marisa Meltzer.

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There was always something about Emily Weiss.

She’s the kind of “It” girl who seemed to have both taste and pure drive flowing through her veins, and thus the unusual ability to envision something and then manifest it. As its founder and CEO, she grew Glossier to a $1.8 billion valuation at its peak, before leaving during the height of consumer disgust with “girlbosses.” Her life and leadership are at the heart of the fast-paced new book Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss’s Glossier, by journalist Marisa Meltzer.

Weiss started working in legacy fashion magazines in 2007 as an intern at Teen Vogue, which led to an appearance on MTV’s The Hills. Meltzer writes that Weiss could have gone on to become a reality star like Whitney Port, who later starred in The City. But Weiss had bigger ambitions — she dreamed of becoming an editor-in-chief. “I looked at someone like Anna Wintour and that was incredibly inspiring to me,” she said.

She grew up in Wilton, Connecticut, a town that Meltzer writes is one of the state’s wealthiest, but “whose money is less showy than the rambling homes of nearby New Canaan or the grandeur of Greenwich.” From a young age, Weiss was two things: entrepreneurial and stylish. As a kid, Weiss bred guppies and tried to sell them to a pet store. In high school, Meltzer writes that while other kids were wearing mall brands like J. Crew, “Weiss had a barrel-shaped Louis Vuitton Papillon handbag and wore pointy-toed shoes, all of which were very sophisticated and fashion-forward for the suburbs.” She has long been so capable and put-together, the way so many successful magazine editors are, that she made people feel inferior through her mere presence.

In 2010, Weiss founded the beauty website Into the Gloss, which took off thanks to its signature feature “Top Shelf,” in which fashion-world personalities opened up their bathroom cabinets for Weiss. Weiss realized that the best way to grow her business was not by doing more media, but by starting a product line. Glossier launched in 2014, and captured the zeitgeist in a way no other beauty brand did at the time (millennial pink, RIP).

The line took off pretty quickly under Weiss, who is undoubtedly smart and hardworking, but who also benefitted from a gush of media attention. While she courted press — I remember her pitching me a story about her as a business leader when I was last a magazine editor — she was also sphinx-like. Meltzer writes in the book:

Lancôme spent $5,000 to be [Into the Gloss’s] first advertiser. “This was more money than I’d ever had in my life, and more money than I ever had in my bank account,” Weiss said. That sounds unlikely for someone who routinely wore Gucci and Chloé, but she seems invested in her origin story

Weiss stepped down from her position as CEO of Glossier in May of 2022, at which point the company was faltering and a fascination with the end of the so-called “girlboss” archetype was peaking. (She was replaced by Kyle Leahy, who worked at Nike, Cole Haan, and American Express before joining Glossier in 2021.) I talked to Meltzer about Weiss, Glossier’s rise, and where the company stands today.

You describe Emily Weiss as reticent in your interviews. Why do you think she was so wary?

She really wants control over her narrative. Also, it was a weird time in everyone's life, and particularly in hers and her company’s. There was the pandemic, store closures, a racial reckoning, and layoffs and furloughs.

She was also really enthralled by the idea of being this tech founder-style entrepreneur, where the narrative in the media is not about their personal life but their genius. But I think that with a lot of those male founders, people are extremely interested in their personal lives.

The story I wanted to tell was very nuanced and fair, and that included criticism in a time when criticism is probably valued at an all-time low; culturally, it's considered mean.

I fully agree that the media ecosystem, including social media, is not particularly receptive to nuanced portrayals of women in positions of power and cultural influence.

Absolutely not. The Devil Wears Prada is a novel or at least a roman à clef, but [audiences] want that or they want Bad Blood or they want something so completely celebratory.

How did Weiss use Into the Gloss as a springboard for Glossier?

Into The Gloss had had a very small staff and made money from advertising. She wanted $1 million to start Glossier. She did the rounds talking to [venture capitalists]. I've heard from a lot of other female founders where you're talking to these rooms full of men, most of whom I imagine are white and cis and probably straight. And they're saying things like, “Let me take this moisturizer to my admin” or “to my wife.” And I just think of her bringing in these lab samples that she worked really hard on — it's just so demeaning. She found a champion in Kristen Green, who had funded direct-to-consumer brands like Warby Parker.

Marisa Meltzer

Raising money is not easy and it doesn’t sound like it was for her either.

What she originally presented to [Green] was a real work in progress. It was kind of like, “Well, I kind of want to do maybe an app, but I also want to sell products.” Over the course of several conversations, they landed on, “Let's start with product.”

Even though Emily was well-connected in the New York fashion scene and the media world, and that got her into some rooms, like when Karlie Kloss introduced her to her then-boyfriend, now-husband Josh Kushner, they still didn't invest right away. It requires so much time to pitch yourself and kiss babies and go to every meeting and then hope that even if they say no, that they'll say yes later on.

Glossier ultimately raised more than $266 million over six rounds.

Her having this [mentality], “I don't want to be written about” or “I don't want to say anything about myself” – it's like, none of this was by accident. Every step of Glossier was a choice. You didn't fall into this, you got the money, you got even more money. You took the company to a $1.8 billion valuation. That's a story. And this is someone's first business and almost her first real job. She’s a hustler.

What made Glossier so influential and successful?

They sort of combined Clinique and Supreme. The Clinique side was that it was this easy, relatively affordable, but still aspirational beauty system that could feel like it was meant for a [younger] generation. The products were effective if not insanely innovative. And the packaging and aesthetics around it felt completely of-the-moment and cool.

Then like Supreme, they instituted a drop model rather than a full line of products of skin and color. I remember so well going to a meeting to see the launch of the products, and I thought, That's it? There was no cleanser, no sunscreen, no makeup. There was a spray, a balm, a hybrid skin tint and a moisturizer. And it came in a cute pink bubble-wrap pouch.

How did Weiss view Glossier? To the outside world, it looks just like a beauty brand – but you write that that’s not how she saw it.

She was very fond of saying, “People ask, is Glossier a tech company? Is it a beauty company? And I say, yes.” It was a little bit trendy, a little bit sexy to be a tech company in that age. And if you are a tech company, that justifies the amount of funding you're getting and can potentially raise your valuation.

Glossier reached a $1.8 billion valuation in 2021. But by 2022, venture capital firm Lone Pine, which led the series E round, was valuing it at 30 percent less than that. You write in the book, “Private funds are not necessarily sufficiently conservative with markdowns, so it is possible that Glossier’s valuation could be as low as 50 percent less” than $1.8 billion — in other words, no longer a unicorn (a company with a $1 billion valuation). What were some of the things that went wrong?

The app — I don't know how much was spent on developing it and hiring all of the executives and engineers, but I imagine a huge amount. Not a single person I spoke to could even tell me clearly what the app was going to do or what it was going to look like or what the name was. It was half-baked.

And then there was a makeup line called Play. Instead of just making that a collection of Glossier products, they decided to make it a sub-brand. That was a lot of money. The development was chaotic, too many cooks in the kitchen, people cycling in and out, Emily changing her mind a lot about product development.

In the early days when there were 5, 20, 40 employees, Emily could be extremely involved. But as the company grew to 200 or so, she still wanted that level of signing off on everything, which wasn't always the best use of her time or the best use of the talents of people that they had recruited. When you're hiring product developers who spent time at L'Oreal or people who had worked in supply chain at tech companies in the Bay Area, you kind of have to let them do what they're good at, especially because you're putting a lot of money and effort into getting them there. And Emily Weiss wasn't great at letting that happen.

And I'd say the biggest mistake was that she never had that maybe older, business-school person who could take a lot of stuff off her plate so that she could be more involved in things that she was more familiar with and a genius in, like products and marketing and community.

Glossier also got swept up in the racial reckoning of 2020, which dovetailed with the downfall of the “girlboss,” which is how Weiss had been characterized in the press.

Their attempted cancellation involved a group of former employees of retail stores calling themselves “Outta the Gloss.” They started this Instagram feed about their treatment and had come to the executives with their issues. Emily resisted sort of being canceled because the accusations weren’t about her specifically. It was more about, I think, [a lack] of good human resources, which I imagine is hard to establish in a rapidly growing company.

Then, they not only donated money, which plenty of companies did, but they started this incubator for Black-owned beauty businesses. And they've really committed to it.

Weiss stepping down was a peg for the New York Times story about how “the sunsetting of the girlboss is nearly complete,” for which they used her photo. The headline seemed oddly gleeful and a lot of readers found it sexist. What was your reaction to that story?

I think “girlboss” is one of those monikers, like hipster, that no one wants to claim for themselves. So I think anyone who is lumped into that generation of female founder has probably resented it. They never wanted to be called that, but it was also an easy way for them to get attention and press and all the things that they've benefited from. With that article, the most important thing to think about is not who was included and what happened to them, but who wasn't included. Tons of women in business aren't young or photogenic, don’t have publicists just for themselves, don’t go to fashion shows, don’t have consumer-facing companies, and don’t work even in industries that can easily be explained to people.

The girlboss was always a pretty flawed and lazy idea. I imagine all of those women were sort of relieved that the era was over, but many of them probably left the public eye not in the way they would want to. People were really out for blood. That’s not to say that the founders of, say, Reformation or The Wing didn't make some big mistakes, but what we want of women is so different than what we will accept of men.

How is Glossier doing today?

The short answer is they're a private company and they're not releasing any of their numbers, so we can't know for sure. This year has been kind of a reboot of the company. After a lot of resistance to having a retail partner, they went into Sephora, and that will introduce them to a huge population of people that never have seen or heard of Glossier. It is long overdue.

Their exit strategy, I imagine, is some kind of acquisition. I think it would be a good fit for an Estée Lauder kind of company. There's a lot of talk right now about Kering trying to ramp up beauty. Glossier has this kind of fashion element, so that could be potentially an interesting pairing. I would be more surprised if it was acquired by a company like a Proctor & Gamble.

Why did Emily step down? She left the CEO role in May of 2022.

She was basically forced out. I think it was a case of, you could either stay and have very little authority, and the board is going to really make a lot of decisions and get the company back on track. Or you can step down while you're pregnant — she was having her first child — and craft your own narrative about leaving. It wasn't much of a choice.

What got lost in a lot of media attention around Glossier is that founders don’t last! Mark Zuckerberg is the exception, not the rule.

It's somewhat rare for a company's founder to stay on as CEO so long as it grows. She probably could have sold it a few years earlier and maybe had a better exit strategy. This is probably not how she wanted things, but everyone has a boss, so even those VCs who are writing the checks have to justify why to the people who oversee their funds. And I imagine it's much easier to say, “We're asking for a transition,” than to just keep saying, “We’ve got to trust her.”

Get Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss's Glossier.