Campside Media. From Sony Music Entertainment and Campside Media, this is Infamous. I'm Natalie Rubamed. So this week, we're talking about a pet obsession of mine, The Girl Boss. You know who I mean. The cohort of 2010's businesses like Glossier, Nasty Gal, and The Wing, that were run by this very specific set of of highly marketable young women. So where did The Girl Boss come from? Is she a second-wave feminist nightmare dressed like a daydream? And what led to her downfall? Joining me today to talk about all this and more is Marissa Meltzer, the author of Glossy, the inside story of Glossier, who has written extensively about Girlbosses. How did you get started writing about Glossier's founder, Emily Weiss, and the term Girlboss more broadly?

I had followed Glossier since the Into the Gloss days, which was the beauty blog that it was initially based on. And I had watched The Hills whenever it had come out. And Emily Weis had this cameo on the hills, I think over two or three episodes. They were extremely memorable. She was this hyper capable Teen Vogue intern. Hey, you're Lauren, right? Hi, I'm Emily. Nice to meet you. Nice to meet you. We do it at the Florista Eleven and pick out the flowers. We have some things being delivered for the table settings to Kevin Haley's house at 3:00. I have 18 credits on two days, and then I work two days at Teen Vogue and one day at Chanel. It was like the devil wears Prada, and she was both the devil, Anna Wintour character and Anne Hathaway in the movie, hapless assistant character at the same time, which in some ways is very what the girl boss is. They Okay. But anyway, I was fascinated by her, and I had profiled her once for Wired magazine, and then had done a really long profile for Vanity Fair. So, Girlboss was always something that I knew I wanted to cover.

It was just so emblematic of that time, this weird Frankenstein's monster of corporate feminism, community, outreach, money, all of these things that we're seeing jammed together and sewn up.

Totally. I mean, I was going to ask you, in your idea of it, what is a girl boss?

I think probably the most important thing about girl boss is that, with the exception of Sofia Amoroso, who wrote a memoir come business book called #girlboss, it was one of those words like hipster that no one really wanted to claim for themselves. I'm not sure there were that many people who were proudly being like, I'm a girl boss. And yet people were happy to label other people a girl boss. So a girl boss was you are a business person and you're also an unapologetically female. Often the businesses were catering to women or femme things. But mostly it was about the presentation, which they were these young, beautiful, socially really connected entrepreneurs, mostly in postal, LA, New York, maybe San Francisco. It was Hello Kitty version of business, where it was like... I love that. In some ways, or Barbie or something like that, which now we've really reckoned with and have this new appreciation for. But in some ways, the girl boss was really important because business fame is such a thing. And so little of that leaves a place for women. And even then, it's like a Sheryl Sandberg, like women in a male-dominated industry.

And instead, in the your kindest notion, a Girl Boss, was this way to talk about women, proudly making things for other women. I remember from growing up, doing some home tour, but you're a business leader, and was the way the magazine was going to cover you. Or like, seven days of my outfits in Lucky magazine, and that's how you got covered as a businesswoman, which are all valid and probably more pleasurable in some ways than reading a profile of someone. It's demeaning. It's demeaning. I mean, maybe not so much in the context of those women's magazines, but it was a way for them to be taken seriously. But I think it's doing a lot of heavy lifting. A lot of lifting.

So what's interesting to me is during the early 2010s, I was working at Forbes, actually, covering startups and then moved to the wealth team, covering billionaires and figuring out that network. Yeah, you were in it.

I was deep in Girlboss Central.

But I do remember this specific period where there was such hope around startups. And I mean, it's funny now, we can't not look back at it and see great skepticism over tech. But at the time, there was a lot of hope and a lot of money being poured into these companies. And there was this feeling that there was a startup boom happening. There was this gold rush in Silicon Valley, right? But there was also deep-seated, and still is, sexism in business and in startup culture. And then you already mentioned Sheryl Sandberg. She wrote that 2013 book, Lean In. And I really see the girl boss snowballing from there, emerging perhaps as a reaction to women not getting funding and wanting to be a part of this startup boom.

Yeah, I think you're right. And that's a real issue, right? The disparity of how women are funded and what women are funded. That's real and important. But the way that Girlboss was marketed and sold to us and who was covered in those articles was far from the actual issue at hand.

You wrote this great story for Vanity Fair, Where Have All the girl bosses gone? And you talk about that where you're like, oh, who gets to be considered a girl boss? And a lot of women entrepreneurs don't get to be girl bosses if they're not very online and marketable and good at branding themselves in that way.

Yeah. And one reason why I wanted to do the book was reading a Forbes list of self-made richest women. Actually, so many of them were rich from beauty industries. But also, if you look at the other half of those women, they're people you've never heard of because they own some B2B company or trade publication, or they're some car dealership magnate or something like that. And so I remember this CEO of a large company was telling me she had been in tech, she had had some B2B company. I can't even tell you what it was because it wasn't sexy. And she had sold it for a decent amount of money and had gone on to become CEO of larger and larger companies. And she was like, Why was I never a girl boss? But she was living in the South. She was a woman of color. She was working on STEMI projects. She also didn't have a publicist. I don't think that she really wanted to be a girl boss, but that, I remember, moment really made me understand that it was this real product of marketing.

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Back to the Forbes self-made woman list. I worked on that inaugural list of America's Richest Self-Made Women back in 2015. And if I remember correctly, this is obviously my perspective, but there was a sense that, damn, a lot of the people who get put on the cover of Forbes all look the And it was an eternal struggle to get somebody who was not an older white man in his 50s, 60s, standing with their arms crossed in a gray suit with a blue shirt on the cover of Forbes. And it was a self-fulfilling prophecy, right? Where women didn't have these high networths in order to be on these lists. So then these lists would be incredibly male dominated. And then a lot of times when women were on the list, it was like, oh, they inherited this from their husband, X, Y, or Z.

And they're all like Walmart heiresses or whatever. In and out heiresses. Exactly. Love the woman. Just to name some of my top heiresses.

Look, I'm sure at one point I ran a slideshow of America's top heiresses. But yeah, I think that part of the genesis of that list was like, hey, how can we capitalize on this renewed or new interest in female entrepreneurs and also put a dollar amount on it, which is Forbes' whole thing. We did a big spread with all these women together. I think it was a group group of 10 women. And Sofia Amorosa was one of the women who was on that. And then we ran several covers, and she was on one of the covers. And I looked at her Twitter recently, and in her Twitter bio, it says, Returned the dress I wore on the cover of Forbes. And I just love that because it's- Are we supposed to think that she's thrifty? I just love it because that encapsulates her relatable thing and also how our ideas towards girl bosses and maybe the benefits of capitalism have changed. But What did you make of Sofia Amruso, who arguably coined the term or just at least popularized it?

I always found her the least compelling to me because the business of Nasty Gal didn't seem particularly interesting to me. It began, I believe, as a vintage selling business on eBay, and then basically turned into a Forever 21 meets reformation, whatever else.

A lot of blazers.

Yeah. Sexy blazers. Nasty gal. There's a certain woman, pop cultural figure who's like, I'm different because I tell it like it is, and I swear. And she took that.

That is a great summary of her.

I haven't read the book, which is actually, now that I'm thinking about it, probably a failure on my part. But I remember a good friend of mine had read it, and she was backhandedly praising it because she was like, It's pretty cool that she just spends a lot of time talking about how rich she is now. I walked in and I bought a Porsche.

Which makes the returning the dress that she wore on the cover of Forbes even funnier.

Yeah. So I was very interested in Emily Weiss. I was fascinated by The Wing, which was Audrey Gelman's women's co- Working/Communityenter. I had once met one of the founders of Reformation and found her terrifying but fascinating. Miki Agerwal of Things. I was fascinated by period underwear But so I participated, I guess, to a certain extent in some of this economy, both in terms of my attention and my memory.

You pretty much just named them, but these are the this 2010's cohort of Girlbosses, if you will. It's like, Audrey Gelman of the Wing, like Jenn Rubio of A Way, Mickey Agerwell of Thanks, Emily Weiss of Glossier. Do you see any through line between all of those?

The fact that they've all... People have tried to cancel all of them.

Well, that's a good one.

They're all charismatic. They're not awkward public speakers. They are mediogenic, too, in that way where they look cool in pictures and they're very good at selling their company, their self, their whole ethos, them and the brand are somewhat interchangeable. They're savvy, they're socially connected and conventionally attractive. There's nothing particularly brave beyond just the fact that women are so rarely on the cover of a magazine like Forbes or business things about covering one of those women. If you are going to do a Vogue profile of a business person, these would be compelling women to cover, but also not terribly controversial because they have, if not name recognition themselves, the brands certainly did.

Them and their brands are somewhat interchangeable. And that makes me think about how the last 10 years or so, we've all had to become a brand in a certain way. And each of us as individuals have had to become brands and also commodify our image. All of us need to be mediogenic.

Oh, I mean, I was watching TikTok two nights ago, and Kim Gordon, the musician, was on there. Yeah, was on there doing a what's in my bag? Looking like she was doing it by hostage, gunpoint.

She's so funny. Yeah, yeah, yeah. I guess something we haven't said yet, and maybe it's obvious, but all these women that we're talking about, they're out and proud female capitalists. In Sofia's book, she talks about just having money and owning that. That was something I saw while at Forbes, we would do these horribly gauche lists of how many millions of dollars celebrities were earning every year and who was the highest earning celebrity. And time and time again, we'd ask these high earning female pop stars, for example, to be on the cover. Almost always they would decline because even in the 2010s, it's seen as impolite for a woman to talk about money. And when you think about it, I guess it hasn't even been that long since women could have credit cards.

It really hasn't. It's only been 40 or 50 years.

I'm loathe to call them progress, but there is, of course, a way in which a certain swath of the population would see these girl bosses who are out and out capitalists as progress.

I think what you're saying is the core of why the girl boss is so compelling to talk about and think about, because there is something important about talking about money, wealth, power, and women, right? There's something in real old-school daughter of a second-way feminist in me that's like, representation is important. Never share your bank accounts if you get married. Never change your last name. I do think there is something really valuable and even radical in that to this day. But it's also And so the way that it was talked about is so cringeworthy. It doesn't even begin to describe it. It's cringeworthy. It's incredibly limited who they were talking about, the way they were talking about it was limited. People were looking at a relatively small group of people.

Yeah, absolutely. It's interesting to me thinking about this now and thinking about that specific time period. I can't help but think that it's also has to be tied into the rise of Hillary Clinton and leading towards her presidential run, where this was- Okay, I have so much to say about this. Okay, but this was the fulfillment of promise. This is the fulfillment to a certain extent of second-wave feminism, right? And all the issues that second-wave feminism has where it's not intersectional and it leaves out specific groups of women.

Well, here's where the wing and Andrew Gelman really become a story of that era. Andrew Gelman worked in politics.

She was a pressee for Clinton in 2008. Exactly.

So she had this bona fide, blue-chip, democratic political background in the press side. I was an return on Secretary Clinton's 2008 campaign. I think that if I had known them when I was 21, that a space like The Wing would have existed, that it would have played some part in its creation, and that she would be sitting here across from me today. I think I would have needed some smelling sauce. Meanwhile, her best friend from college was Lena Dunham, who was creating Girls at this time. You have this cocktail of a person, and I forget exactly when she decided to start developing the wing. Maybe it was 2013 or something. But I had heard rumblings of it from friends that she was starting this place inspired by her and many other women's experiences. Experiences of like, Oh, I need somewhere to get some work done, but also where I could take a shower between appointments and have a coffee and answer some emails and that thing. And by the time the wing opened, the branding was very commodified feminist.

I don't know if there actually was a pink neon sign saying Girlboss, but in my head there was that.

It definitely had custom wallpaper of iconic feminists or something. But yeah, so the wing, when it came out, was very pink. I believe they launched with a slumber party, giving these founding membership to a lot of notable people, including many journalists I know. I think I was both relieved and slightly offended that I was asked to be on it.

How dare they?

But also was like, I don't need to for feminism or friends or community.

I mean, look, I also went to several wings, and they were very beautiful. I always was put off by the interweaving of overtly feminine with feminism. I don't need a place to blow dry my hair, right? And maybe that's just because I have short hair and I'm slightly more masculine leaning than a lot of women. But I was like, this is not for me. But if you guys love it, I love it for you.

Yeah. It got very Marie-Antoinette doing her twalet in their vanity rooms. That took up an inordinate amount of space. So they launched, I want to say, summer 2016. And their big New York Times style story was to have a reporter cover them on election day, 2016, with the assumption that many of us had that Hillary would win, and you'd have this perfect narrative of our first female President, this watch party at the wing, this vibrant new business and community. And of course, that didn't happen. Something that was supposed to be this inauguration and event ended up being this crush with reality, which I think colored everything else that happened in their relatively short lifespan.

Do you think the night that Hillary Clinton when the election was the night that the girl boss started to die?

Maybe, but that was also when the girl boss was at its peak. I think maybe on some level, we had to confront the fact that there could only be so many pink pantsuits and messages of community and empowerment. That only got us so far because clearly, we weren't seen the culture in the country and the political climate for what it really was. Hello, I'm Elizabeth Day, the creator and host of How to Fail. It's the podcast that celebrates the things in life that haven't gone right. And what, if anything, we've learned from those mistakes to help us succeed better. Each week, my guests share three failures, sparking intimate thoughts thought-provoking and funny conversations. You'll hear from a diverse range of voices sharing what they've learned through their failures. Join me Wednesdays for a new episode each week. This is an Elizabeth Day in Sony Music Entertainment original podcast. Listen now wherever you get your podcasts. In France, in the 13th century, a teenager ascends the throne. He seems calm, collected, and as it happens, drop dead gorgeous. But looks can be deceiving, and no one is ready for It's a death, destruction, and chaos that lie ahead.

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So when do you think we reached peak girl boss? And is there a moment or an event or an artifact that signals to you the hype of girl boss culture?

I do think that 2016 lead up to the election where Hillary was marketed as this champion of women figure that even younger women were supposed to really coin to. She did that weird cameo on Broad City. Thank you, Ywanda. Thank you for all of your help. You know of me? Well, you're wearing a name tag. Oh, genius. I val to tweet once a week, vote for Hillary?

Yes, yes, yes.

That would be great. We need to drum up some excitement for the campaign, do everything that we possibly can. And the wing opened and Glossier had launched and Boy Brow had come out and they had their first real blockbuster product with a 10,000-person waiting list. And that was the year when Wired called me and was like, What do you think of Glossier? And it's like, Oh, this magazine Wired that is considered more general or serious or male-coated is taking this company seriously enough to write a feature on them.

So when did the girl bosses start to fall?

I would say their downfalls were somewhere in between Me Too and the proposed George Floyd racial reckoning mixed with the pandemic. So somewhere in 2017 to mid-2020. And we had this moment in history where people were really taking public figures to task. And there was a little bit of a, let's burn the witches, scent of blood in the air, I think. Miki Agerwell from Things. She was accused of various inappropriate behaviors from coworkers. Glossier was met with the same thing where you had a group of employees who united under the banner, Out of the Gloss, talking about their experience and how different that was to the more upper class, mostly people that were working in the corporate level. I think the important thing other than this list is that there was a real range of accusations, some of it being things that were truly illegal, like firing someone or harassment or whatever. Some of it was just problems with work that no 32-year-old woman who is founding her own company can be expected to solve, or problems of capitalism, or problems of race, or whatever. I think what's sad about it is that it's all all conflated as if all the girl bosses were bad and they all needed to go down, and there was this thirst for blood.

The issues with the companies were really varied.

Yeah, I think that's a great point.

And the companies themselves were at a weak spot. And also the companies reacted in different ways. Some simply fired the founders and others, like Glacier started a incubator program for Black beauty entrepreneurs that they still are doing that seems like it's done a lot of good in the world, both in giving those people access to lawyers and people who can solve real problems. But I think that what was lost is that these were often problems of life in America or in the West in general.

I think that's a really good point. And I feel really complicated about all of this because obviously, men have behaved similarly forever. Without any consequences or without nowhere near as harsh the consequences. Yeah.

And I always think of another thing that my mother used to joke about, which is the line between where a woman is considered acceptable and fat is 10 pounds at best. But for a man, it's 75 pounds. And I think it's true with behavior as well. Any tiny infraction. And again, I'm not making any apologies, nor are you, about these office environments or behavior. Yeah, of course. But when we look at the superstar male business leaders, their behavior is truly wild and atrocious.

Right. I mean, I think for me, the downfall of a girl boss, part of it I understand and part of it seems valid, where a shared identity as a woman doesn't save you just because someone's a female CEO doesn't make them a good person or even a good boss, right? But at the same I can't help but look at this in a wider cultural lens and a lens of history. And I just feel like there's a through line between the campus rape debate that was being had about consent in this very complicated conversation that started happening around consent to the girl boss, to Hillary Clinton, to #MeToo, where there's this real moment of some women having power, even the women's march, which we can obviously critique for not being intersectional and a million other things. But that That was a huge moment and a huge outborn and a huge sign of power to some extent from women. And then for it to just be so torn down and baby thrown out with the bathwater as you're describing is it's complicated, right? Because obviously I'm critical of Girl Buzes, and I think the whole title is silly.

But I also am so frustrated by it.

It's this slice of culture and time that encapsulates It's everything that was going on, fashion-wise, beauty-wise, politically, socially, esthetically. It's completely fascinating. And it was all so easy to roll your eyes and watch as these companies went out of business or people were forced to leave or they were canceled. There was a lot of Schauenfreud involved, especially if you had seen some of these women in their press coverage, bragging about their accomplishments. It was easy to delight a little bit in some of their failures. I really forced myself to think, what was the good part of the girl boss? Or why were we so excited by their downfall? And what does that say about my own ambition and resentment and relationship with feminism and capitalism and other women and my own feelings about my own beauty and presentation and class and style and all of that? Those are very real issues. And And I think you can really examine all of that through the lens of the Girl Boss.

You wrote that every age has its newest flavor of business celebrity. What is the next Girlboss?

I I thought for a while that it was like, Crypto Bros, but that already seems something of a different era, right? With Sam Beckman-Fried and everything. So is it going to be the TikTok Live live entrepreneur. That is the new '90s infomercial. I wonder if some people will become celebrities or true influencers in a way in which when I was in school, I could chant with my friends, stuff from those infomercials. Stop the madness. I'm very curious as to what we're going into with regards to a recession or the downturn, where the New York Times's prediction for food of the year was soup.

Everything is much more frugal. So part of me is like, will the next business celebrity be this incredibly thrifty, very, I returned the dress I wore on the cover of Forbes, a recession- A younger, recession, Warren Buffet, so to be practical, the idea of loud budgeting.

I could see a Gen Z celebrity rising of personal finance, like a Susie Orman, maybe with a touch of the wellness of Jay Shetty, this spirituality, but this budgeting, personal finance, also with an emphasis that the problem is the system and the problem is not you.

But that's not aspirational. That's the huge problem of all this.

I know, it's too practical. I know.

It's got to be aspirational. It has to be something out of reach.

That's why it's going to be someone selling chamoy pickles or whatever the thing is that people are ordering or something. Love it.

Thanks so much to Marisa Meltzer for talking to us. Her book, Glossy: Ambition, Beauty, and the Inside Story of Emily Weis' Glossier, is out now, and we highly recommend giving it a read. If you enjoyed this episode, don't forget to rate and review us on Apple Podcasts or wherever you're listening. And next week, we'll be discussing the big social media news of the year, maybe the decade. I'm talking about the US government forcing the sale of the world's most addictive app, TikTok. You might like it for Billie Eilish's videos or makeup tips, or even political news. But Congress decided this spring, the TikTok, which is owned by a foreign entity with ties to the Chinese Communist Party, is going to not have that owner anymore. There is going to be a sale of TikTok, and it may never exist again. So we'll be talking about all of that the week after, just so you know, we are going to be doing one of our long series about the momfluencer Ruby Franky. But stay tuned next week for TikTok.

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