After years of looking fruitlessly—and furiously—at the unsmashed glass ceiling, women in business decided to paint it pink instead. Suddenly, the start-up world was female-led, female-friendly and female-focused.

The Wing opened its first all-female co-working-space club in Manhattan in 2016 and soon grew to 11 locations serving 10,000 members in the U.S. and the U.K. If you’d visited the Wing around that time, you might have worn your dress from Reformation and sung sweetly about its ethical manufacturing practices. That dress might first have been spotted on one of the many female-focused websites—Refinery29 and ManRepeller among them—that blend fashion with feminism and mental-health advice. And you could have used an Away suitcase, which debuted in 2016, to pack it up in.

Each of those companies had a charismatic female founder, and suddenly these women were everywhere—styled and smiling and telling their success stories. The naysayers mostly focused on price: The online publications were free to read, but everything else required a significant disposable income. Were they really inclusive? But these comments were eclipsed by the overall rosy glow. Here was the representation we’d all been clamouring for.

It was the “golden age for women in power,” Wing founder Audrey Gelman told The Washington Post of the moment the company launched its first space, when it still looked like Hillary Clinton would be the 45th U.S. president. Clinton wasn’t the only woman forced to concede a powerful position. In one week in June 2020, as the Black Lives Matter movement gathered strength, Gelman stepped down from her role, publicly apologizing for “leadership mistakes,” as did Refinery29’s Christene Barberich, who wrote on Instagram: “I’ve read and taken in the raw and personal accounts of Black women and women of colour regarding their experiences inside our company. What’s clear […] is that R29 has to change.” Yael Aflalo of Reformation and Jen Gotch of clothing company resigned around the same time for similar reasons. In the same month, Leandra Medine Cohen moved away from ManRepeller, issuing an Instagram mea culpa for “failing to deliver” on her mission. In June 2019, Shannon Spanhake left Cleo, a company designed to help working parents, when it was revealed that she had fabricated her professional background, taken six years off her age and created a toxic work environment. And in December 2019, Away’s Steph Korey resigned as CEO after a report by The Verge exposed, again, a “toxic workplace” and “a culture of intimidation and constant surveillance.” (She later returned as co-CEO before announcing in July 2020 that she was stepping down again.)

Men in senior positions also stepped down in 2020. Reddit’s Alexis Ohanian—often seen cheering as his wife, Serena Williams, wins tennis games—left his company’s board so he could be replaced by a non-white board member. CrossFit’s Greg Glassman resigned after saying that he wouldn’t mourn George Floyd. Adam Rapoport, editor-in-chief of Bon Appétit, stepped down after staff spoke out about discrimination and a picture of Rapoport and his girlfriend, both white, dressed as stereotypical Puerto Ricans for a costume party circulated.

But, Rapoport aside, male resignations attracted much less attention.

Meanwhile, the death of the girl boss was analyzed in countless articles. Sometimes the focus was collective; sometimes it was on individual companies. Screenshots of Korey’s demands on staff circulated on Twitter. Gelman issued an apology on Instagram. The general tone of the cultural response was one of shocked glee, as if each founder were Regina George and the buses just kept on coming.

It’s also worth noting the wild disproportion behind these numbers: There are far fewer women in senior positions. In the U.S., only 14 percent of start-ups have a female CEO. A study published in the Journal of Management showed that female CEOs are far more likely to be fired than their male counterparts, even if the company is performing well.

Should 2020’s fallen women have stayed in their roles? Probably not. Did they deserve to pick up a disproportionate amount of attention for their failures? That’s where it gets complicated. The women in question are alleged to have behaved badly or, at the very least, thoughtlessly. There is a real need to address inequality and damaging work cultures. But the invisible hand of sexism was also present, as were the usual questions about money: who has it and who doesn’t and what that means.

It was as if each founder were Regina George and the buses just kept on coming.

So, how does this break down? First, there was betrayal. All those brands that had a female CEO step down had traded on their ethics, either explicitly, like the Wing, or implicitly, as Away did. They were supposedly feminist companies run by supposedly feminist women, and, between them, they promised everything from ethical supply chains to mental-health support.

“There’s a metaphor used in marketing called ‘brand-as-person,’” says Cleopatra Veloutsou, professor of brand management at the Adam Smith Business School at the University of Glasgow. “We give brands a character the same way we do with humans, ascribing a social class, values and so on. There’s also recent research showing that when firms are based on one entrepreneur, the company will take on their personality—they will make decisions as though they are the brand, so the brand then becomes consistent with the characteristics that that person has. As consumers, we look for brands that share our values. They form part of our emotional life.” So when brands fail to live up to the ethical standards that first made them appealing, we feel betrayed in the same way we would if a friend were to lie to us.

“There’s a very real emotional disappointment when we feel that we’ve been sold a line,” says Catherine Connors, a California-based serial entrepreneur and CEO of the League of Badass Women. “I may be overstating it, but part of the reason this [feminist] marketing works is that we really want to hear it—to hear that we can do it, can chase our dreams—because we haven’t been hearing it for very long.”

This, says Connors, leads to elevated expectations of women. But, she continues, women are also “expected, for the most part, to use a feminist lens or a female-empowerment angle because a business opportunity is recognized. Look at Away. It’s a suitcase brand, but nothing about suitcases screams feminist. And no one cares if [a male] CEO is rude to his employees.”

Male leaders attract criticism too, of course, but rarely the same absolute censure that female CEOs get. WeWork attracted billions in investment and never made any money, and CEO Adam Neumann was forced to step down just before the company made 2,400 of its staff members redundant. But he still walked away with a payout of more than $2 billion. Peter Thiel, one of the founders of PayPal, has funded former president Trump and is open about his right-wing political views. While this puts him at odds with Silicon Valley’s largely liberal outlook, he still holds a lot of sway in the technology world. Facebook has been criticized for everything from dismissing employee concerns to killing the media and even destroying democracy, yet Mark Zuckerberg, who strongly contests any such claims, remains in place. There’s a freedom for men to fail that’s not extended to women.

“Women do trend more toward ethical and socially responsible businesses than their male counterparts,” says Tara Sabre Collier, who specializes in gender-led investing. There are many reasons for this; as Sabre Collier points out, it’s partly because women are more likely to experience inequality in the world and wish to change it. But selling feminism is also a way to attract investment. We know that consumers respond well to feminist marketing. So it’s a clever move, whether genuine or cynical, for a woman seeking venture-capital funding to stress her ethical credentials. But having principles baked into your business model means that the world expects more from you, and so it becomes much easier to fail.

“Venture-capital money can come with weird strings,” says Sarah Drinkwater, director of beneficial technology at philanthropic investment firm Omidyar Network. “Look at the Wing. It tried to be all things to all people. To some, it was a venture-backed start-up; to others, it was a social-justice organization. It was not clear about its mission. For many founders, there’s a core tension that’s hard to overcome.”

There’s a freedom for men to fail that’s not extended to women.

Several of the women interviewed for this piece said that since venture-capital companies consist mostly of white men, people who do not match the pattern find it difficult to convince funders that their ideas have merit. June Angelides has worked as a banker and an entrepreneur and is now an early-stage-tech investor. She says women are often not taken as seriously. “As a Black woman, I am conscious of the fact that products for the Afro-Caribbean society may not get as much investment. That’s a large market to miss out on. We need to invest in women because it’s the only way we will break this cycle of tech products that are by men, for men.”

When investors do meet with women, they are often the women who are most like them: white and already wealthy. These women then become poster girls for female success. “The reason these women are visible is that they’ve raised a certain amount of money,” says Drinkwater. They are also photogenic and often operate in retail and lifestyle spaces that consumers can relate to. They “became the very public faces of their companies,” Maria Aspan wrote in an article for Fortune. “In a way, that’s more common if you’re selling leggings than, say, cloud-based enterprise software.” This increased visibility means that the “female founder” stereotype gets compounded and the patterns repeat.

A high profile also means that when a female founder fails, she fails in public—it isn’t just the business community watching. Part of this is understandable: We feel it is right and fair for the “mean girl” to be taken down. We all become Janis Ian, not realizing that this delight in failure makes us mean too. “We have an immense appetite for watching women suffer,” says Drinkwater. “Look at our films, our music.”

“It has to do with the way we hold women accountable in public, capitalist, democratic spaces—in a way that we don’t with men,” says Connors. “For thousands of years, women have been confined to the private sphere. We have so much socially ingrained self-doubt about being in the public sphere, so we look at women who move into it with some degree of suspicion—even hostility.”

There’s also a disconnect between supposedly feminine traits—compassion, empathy, nurturance—and those that we traditionally associate with CEOs: drive, ruthlessness, a willingness to break rules. Cleo, the company that was run by Spanhake, has a website full of smiling parents and children that tells employers it will help them “take care of [their] modern workforce.” Contrast this with a slide Spanhake showed staff. Forbes reported that one of the bullet points told them to “expect to work 50 to 60 hours a week.”

“There’s a cult of the male founder, where we expect them to have this boyish Peter Pan quality,” says Connors. “They’re rebels, right? They defy the system—Han Solo, Tony Stark— refusing to be grown-ups and profiting from it. The problem is that that kind of entrepreneurial hero’s journey doesn’t apply to women. They’re expected to be Wendy, not Peter, making sure everything is maintained and managed behind the scenes. Look at Sheryl Sandberg compared to Mark Zuckerberg.”

Silicon Valley has become our dream factory, edging out its neighbour to the south, Hollywood. It shapes our thoughts, our desires, our politics. Even the language is mythic: Investors are “angels,” start-ups valued at $1 billion or more are “uni- corns” and rapid growth is termed “blitzscaling.” But are we expecting too much when we expect business leaders to be role models as well?

The girl boss was almost set up to fail, and we enjoyed watching her do so.

“We are looking for heroes in all the wrong places,” says Carl Rhodes, co-author of CEO Society: The Corporate Takeover of Everyday Life. “With neoliberalism in the 1980s and 1990s, business became a lot more prevalent. The idea that private enterprise would lead us to a brighter, shinier future was linked to the political agenda. Do we want to look for heroes in that realm of life or is there a broader sense of what we might look for socially, politically and personally?”

In 2017, the Me Too movement showed men that the old ways would no longer work. Last year, Black Lives Matter turned the same spotlight on white privilege. The demands of the COVID-19 crisis and the increasing pressures of climate change mean that caring is no longer just for activists. The girl boss was almost set up to fail, and we enjoyed watching her do so. But she shouldn’t be excused because the system around her was wrong. The female founders started marking out a path, a different way of doing things. That path shouldn’t be abandoned just because they failed. We need to expect more from women and men. We should learn from the girl boss, even as we bury her.

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