Why Female Entrepreneurs Welcome The End Of The Girlboss Era—Once And For All

Published 1 year ago
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The resignation of Glossier CEO Emily Weiss inspired another wave of obituaries for young, female founders. Nevertheless, they persist—and refuse to be put on glass pedestals again.

In October 2021, Rent the Runway cofounder Jennifer Hyman took her 12-year-old subscription fashion company public at a $1.7 billion valuation, valuing her 5.1% stake at nearly $49 million. The 41-year-old CEO was one of only about 25 American women in history to go public with a company she had founded. But Rent the Runway’s IPO was even more unusual for not only having a female founder but also a female CFO and a female COO.

Hyman celebrated the moment on a flowery Nasdaq podium surrounded by the key women on her team, her two daughters and a shower of pink confetti. But for all the femininity on stage, there is one word that Hyman would not use to mark the moment: “Girlboss.”


Making History and Bank: In October 2021, Rent the Runway became the first company to go public with a female CEO, COO and CFO—at a $1.7 billion valuation.RENT THE RUNWAY

“We’ve created a false narrative because we looked at two or three examples of women who were building businesses who happen to have a high social media following, and we call it a Girlboss Era,” Hyman says. “The Girlboss Era has never existed.”

Except it did.

The now dreaded hashtag dates to 2014, when then-30-year-old Sophia Amoruso, founder of the retail brand Nasty Gal, published a memoir called #Girlboss. In eight years, Amoruso had grown Nasty Gal from an eBay startup into a business with $40 million in funding, customers in 60 countries and a brick-and-mortar store on Melrose Avenue in Los Angeles. The book spent 18 weeks on the New York Times bestseller list and propelled Amoruso to launch Girlboss Radio, a podcast featuring interviews with other female founders.


Leaning Out: After eight years of running the beauty brand she founded, Emily Weiss stepped down as CEO of Glossier in May amid turmoil.JOEL BARHAMAND

The Girlboss phenomenon is on Hyman’s mind because in late May, 37-year-old Glossier founder Emily Weiss announced that she was stepping down as CEO from the company she launched in 2014 and, after a maternity leave, becoming executive chairman. Weiss’ beauty business was growing into a $1.8 billion makeup juggernaut at the same time “Girlboss” was expanding in the public discourse.

It was around this same period that J.Crew included Ty Haney’s two-year-old athleisure company, Outdoor Voices, in a ‘brands we love’ feature. Haney opened OV’s first brick-and-mortar store in Austin in the fall of 2015. The then-27-year-old Haney would go on to raise more than $60 million for Outdoor Voices from investors including General Catalyst, GV, and former J.Crew CEO Mickey Drexler.


Since Sophia Amoruso published her memoir, #Girlboss, in 2014, videos with that hashtag have been viewed more than 6 billion times on TikTok with an additional 26 million posts on Instagram. #Girlboss has also been used more than 4.5 million times on Twitter during the past 8 years, with about half of that coming in 2021—just as some of the more prominent female founders were being canceled.

That same year, two former Warby Parker prodigies, Steph Korey and Jen Rubio, founded Away, the smart-luggage company that eventually landed Korey on the cover of Forbes in November 2018 with a $1.4 billion valuation by 2019. And a year after Away was born, Audrey Gelman launched The Wing, a female-only coworking space that offered an A-List roster of speakers (including Christiane Amanpour and Hillary Clinton) for Wing members to enjoy after business hours. Ambitious women paid up to $2,700 a year for access to the Wing, and the buzzy brand hit a $400 million valuation before the pandemic took hold in 2020.


With such meteoric success stories, each of these women was soon hailed as a “Girlboss”—which often came with the benefits of being young, attractive and white. And when their high-flying brands fell back to earth over the next few years, the schadenfreude was relentless. A Netflix show called #GIRLBOSS was not enough to buoy Amoruso’s Nasty Gal brand; in 2016, the company filed for Chapter 11 bankruptcy, and was purchased the next year by The Boohoo Group for $20 million, a fraction of its peak valuation of $86 million in 2014, according to PitchBook.

“It’s reminding everyone that there is a style of being a boss. And no matter how hard you work, you’re still a girl—you’re a girl in a man’s world.”–Kristen Syrett, Rutgers professor

At Outdoor Voices, Haney found her leadership capabilities under fire in early 2020, with colleagues whispering to reporters that she was “spoiled and mercurial.” By March of that year, Haney was pushed out of the company she founded. During the same period, Korey and Gelman also found their leadership styles pilloried in the media and by the peak of the pandemic in 2020, both women had resigned as CEO of their respective companies.

By the time Weiss stepped down as Glossier’s CEO in May, obituaries for the Girlboss Era had been written for at least two years. Yet the resignation of Weiss, who had been the face of one of the trendiest millennial companies, provided new fodder for commentary and conclusions about what it means when a female founder moves away from the brand she built. But working female entrepreneurs say these post-mortems are both sexist and unfair to the women who are still running disruptive, high-growth businesses.


“When a female founder steps down, it’s a headline like The Death of the Girlboss,” says Laura Behrens Wu, who was featured on the 2017 Forbes 30 Under 30 for founding logistics outfit Shippo. “When a guy does it? There’s no real headline because it happens so frequently that it’s no big deal.” Wu points to 41-year old Flexport founder and CEO Ryan Peterson, who announced plans to resign from his CEO seat soon after Weiss stepped down. But the news about Peterson didn’t launch 1000 thinkpieces about the future of male CEOs, Wu notes, whereas a deposed Girlboss “becomes an extrapolation about the entirety of female founders.”

While the Girlboss concept began under a guise of empowerment, it has ultimately been damaging, a Scarlet G, for female entrepreneurs. The condescending moniker diminished female founders seeking investors, who judged them not on the quality of their companies but by their gender.

“The heyday of female founders or Girlbosses has actually made the situation more difficult because it clouds the reality that it’s as difficult as ever to raise money as a woman.”– Jennifer Hyman, Rent the Runway CEO and Cofounder

“As soon as you modify something like ‘boss’—and you don’t have ‘Boyboss’ or ‘Maleboss’—it really does make it incredibly salient that we are still, as women, fighting against [an image] that was not shaped by us,” says Kristen Syrett, a professor of linguistics at Rutgers University. “It’s reminding everyone that there is a style of being a boss; that there’s being a boss and then there’s the girl boss. And no matter how hard you work, you’re still a girl—you’re a girl in a man’s world.”


In early June, no less an expert than Sophia Amoruso implored her Twitter followers: “please stop using girlboss thanks.”

Amoruso might be ready to move on, but Rent the Runway’s Jen Hyman and the other founders interviewed by Forbes are left grappling with the wreckage of the GirlBoss Era.

“Sometimes, the positivity that the media has had about the heyday of female founders or Girlbosses has actually made the situation more difficult,” Hyman says, “because it clouds the reality that it’s as difficult as ever to raise money as a woman.”

Lilla Cosgrove is living that reality. In 2017, she cofounded the orthodontic aligner company Candid and set out to become the Warby Parker of braces. Since then, Cosgrove has raised over $150 million. Like many CEOs over the past two years, she’s had to pivot her company, in this case from a direct-to-consumer brand to a business-to-business model selling retainers straight to dentists. “It’s hard being a human in the world right now with everything going on socially and economically, let alone being a founder,” the 31-year-old Cosgrove told Forbes, shortly before the Supreme Court ruled on Roe v. Wade. “And then being a female founder on top of that? Access to capital and support still feels harder than it should be.”


Indeed, only 2% of all venture capital goes to female founders, and just 0.2% of all venture funding goes to female founders of color, a rate that has barely budged in the four years since #MeToo and #TimesUp transformed the national dialog.

recent study published in the Organization Science journal showed that, among some 2,100 startups, the female-founded companies that received money from female investors in early funding rounds were less likely to receive funding in subsequent rounds. The researchers’ conclusion was that their early-stage capital was a token gesture based on shared gender, not a strategic investment in a promising idea.

According to Heidi Patel, a managing partner at Rethink Impact, the largest venture capital firm in the U.S. that invests exclusively in female leaders ($300 million under management), the term “Girlboss” is a byproduct of this environment. If investors wanted to feel confident writing a check to a female founder, funding someone with a high public profile was more of a vehicle aimed at raising personal brand awareness—and eventually capital. “It was something really unique to consumer businesses,” Patel says. “It was really a marketing angle and it’s an aspirational storyline, I think, that was created to appeal to young female consumers.”

Ty, Ty Again: Two years being ousted as CEO of Outdoor Voices, 33-year-old founder Ty Haney has a new web3 platform—Try Your Best.JAMEL TOPPIN FOR FORBES

Emphasis on young: As the name implies, Girlboss was aimed at Millennials and Gen Z. By contrast, the top five women on the 2022 Forbes Richest Self-Made Women list are worth more than $30 billion and each was born before 1948 (average age: 60)—and none would self-identify as a Girlboss.

Interestingly, Outdoor Voices founder Haney insists she’s never actually been called a “Girlboss” or used the word self-referentially. “I’ve never been or associated myself with the term Girlboss and it’s time journalists stop trying to get clicks off our stories and this theme,” Haney wrote on Instagram after Weiss announced her resignation. As Haney admitted to Forbes in a 2021 interview: “Being a female founder helped me. I was a darling in the press and that helped create a direct relationship with a budding community [of customers]. And from a fundraising perspective, it helped.”

The positive press that lifted Haney, and other female founders like her, also drew greater attention to her failings—creating a cycle that feeds the perception that “cancel culture” is eager to claim the next female leader who misspeaks or missteps.

It’s a vicious cycle many young, female founders CEOs are hoping to avoid. Eliza Becton, who was on the 2014 Forbes 30 Under 30 list after founding the smart water cooler company Bevi, has raised $95 million to bring internet-connected natural drink dispenser to 4,000 offices (and counting) in the United States. “I don’t like a lot of attention,” says the 38-year-old Becton. “I really enjoy what I do, and I like spending time with family, friends and customers,” says Becton, “But I prefer to be head down in the work and doing product development. It’s what makes me happy. I don’t love being public-facing, and frankly, I find it distracting.”

Alexa Hirschfeld is another entrepreneur who has seen these distractions and opted out. As the cofounder of digital stationery company Paperless Post, Hirschfeld oversees 100 employees and runs an entity that has attracted over 175 million users to its platform. Paperless Post is valued at a healthy $115 million, but like Becton, Hirschfeld isn’t looking to elevate her personal brand.

“I don’t wake up in the morning and say, ‘What am I going to do today as a woman in tech?’” she says. “I’m worrying about my product, the company, the job; I’m worrying about what everybody worries about who puts themself out there, and takes risks and has a lot of responsibilities.”

For Ashley Edwards, the founder of MindRight Health, the lessons of the Girlboss Era are painfully obvious, especially as a woman of color. The 31-year-old founder just closed a $1.8 million funding round from investors, including Melinda French Gates, to grow her mental health coaching platform for underserved teens. “I’m really proud of what I’ve accomplished as a woman and as a Black woman,” says Edwards. “Most of my time is just spent doing the work.”

Laura Behrens Wu, whose Shippo hit a $1 billion valuation this month, agrees and believes she’s avoided many of the Girlboss minefields because she’s rejected most media–including social media.

“It’s not been a priority,” she says. “I haven’t been able to tie it to some kind of business priority, or something that I really care about as a CEO.”

Which is exactly the advice many older executives have for women in the post-Girlboss Era. Anita Carmichael Roberts is a military veteran, the founding partner of Silicon Hills Capital, and a member of the Forbes 50 Over 50 list, has never been burdened with the Girlboss mantel because of her age and race. Indeed, many in the business world wouldn’t even assume that a 53-year-old Black woman could be in charge of millions of dollars and investment decisions. “People don’t see us as the boss, right?” Roberts says. “When I say I’m a boss, that means that I’m the baddest thing in the room—women or men.”

By Maggie McGrath, Forbes Staff and Alexandra Sternlicht, Forbes Staff