There’s a schadenfreude that accompanies the news that a beloved female founder was actually a hard-charging tyrant from a privileged background with unrealistic expectations. Hardly any founder has been more publicly scrutinized than Sophia Amoruso, an entrepreneur who bootstrapped her first business to $100 million in just a few years and then went on to build two more successful operations. 

To be sure, some of the allegations against these women were serious—but there’s a funhouse mirror effect to much of the coverage, where the substantive criticism blurs with thinly veiled misogyny. Once open season began on the girlbosses for their legitimately harmful missteps, the mediagenic female founder became a meme. To be worthy of power, we seemed to collectively decide, a woman must be perfect. 

It didn’t come into focus for me until I read Meltzer’s book, Glossy, which told the story of “ambition, beauty, and the inside story of [another prominent female founder] Emily Weiss’s Glossier.” There was something that didn’t quite sit right with me—it was framed like a tell-all, but didn’t seem to reveal much in the way of genuinely problematic behavior from Weiss. 

Ashley Mayer, former head of communications at Glossier, wrote a reaction piece that went viral after Glossy dropped. “While [the book] isn’t another female founder ‘takedown,’ it also isn’t a book that would be written about a male CEO. The dominant critiques of Emily focus on her privilege and ambition, two traits I can’t imagine being used to undermine the successes of her male peers.”

Of course, exploitation, harassment, and discrimination should be rooted out regardless of the perpetrator—the criticism is not, “Well, women should be allowed to treat people like shit, too.” But as Mayer wrote, “When even the most successful women leaders are picked apart, there’s a widespread silencing effect.”

Some suggest this is a good thing. Elizabeth Segran, witnessing the pile-ons the first generation of girlbosses suffered, advised us in Fast Company to keep going, but just do it…more quietly. As in, Be a little more ladylike about it. 

But in a world where only 10% of Fortune 500 CEOs are women (despite making up 47% of the workforce) and only 2% of venture capital funding goes to female founders, our ambitions will only be as strong as the interconnected support system we can build around them. 

We need to be careful about deducing that the solution is to fly under the radar. Doing so keeps us isolated; separated.

Instead, we must loudly, proudly, and publicly align ourselves with one another. For all their internet philosophizing, I think that’s the most important lesson we can learn from the thinkbois.


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