I’m rooting for female founders’ comebacks. And for the end of branding women, from girlboss to tradwife and all the way down

My portfolio is full of girlbosses at risk of cancellation

There’s no such thing as a ‘boyboss’

Leslie Feinzaig is founder and general partner of the venture firm Graham & Walker, and founder of the Female Founders Alliance.

It’s hard to remember now, but there was a time when the term “girlboss” was aspirational. I was a rising young tech executive at the time, so inspired

In retrospect, the golden girlboss era peaked right around the time of Audrey Gelman’s 2019 cover

Within a year, Gelman, cofounder and CEO of the Wing, had been “canceled,” as were dozens of prominent female founders of the time.

With the notable and deserved exception of Elizabeth Holmes, the accusations against most “girlbosses” were some variation of harsh people management. Bad? Yes. But also, rampant at startups. When girlbosses enacted what today would be called “founder mode,” their behavior was deemed egregious, shocking, unforgivable, and borderline career-ending.

Girlbosses were expected to be not just smart, attractive, and savvy, but nurturing, soft-spoken, generally inscrutable, bastions of DEI, and generally all around perfect. Anything short of that was a step too far from the confines of the girlboss brand. The very label that enshrined their power limited their ability to charge hard, and make mistakes in the process. 

I wrote a piece in 2023 standing up for a female founder’s right to come back from her mistakes. This was a very unpopular opinion at the time. But

In that article, I specifically named Audrey Gelman and Ty Haney, founder of Outdoor Voices, as women I’d love to see raise capital for a new venture. So count me as part of the group that’s thrilled about their recent comebacks—in fact I hope to see many more. 

But even as I celebrate these women’s second chances, I’m wary about what’s next. Because girlbosses may be a thing of the past, but the compulsive archetyping of women is not. Nor is the inevitable backlash when any one of us fails to meet her ideal.

Think about how we’ve categorized ambitious women in my lifetime alone: the 1980s-1990s’ “new working woman,” as seen in the classics Baby Boom (my favorite childhood movie) and Working Girl; the 2000s’ mommy blogger; the 2010s’ girlboss; and the 2020s’ tradwife influencers. 

Incidentally, the “stay-at-home mom”, and even the “trophy wife”, are also one-dimensional archetypes. 

I bet you can

Branding classes of women in this way makes us appear one-dimensional, each one of us a representative for our entire category. Girlbosses were not just CEOs, they were symbols. And the moment they stepped outside their narrow confines, it became a scandal. 

I don’t think we do the same to men. There wasn’t a “boyboss” fad during the girlboss era. Every industry has its bros, jocks, and nerds, but I’d be hard-pressed to name a category of businessmen that speaks for an entire generation of leaders. Can you? Note also: A man can fail, pivot, humiliate and fire 900 employees in a single Zoom call, even get caught cheating on his wife with his CHRO at a Coldplay concert viewed around the world … all without being accused of betraying his entire category of manhood. 

Now that’s freedom.

Unfortunately, for women, branding matters. You might think of the girlboss and the tradwife and all the rest as media-driven labels, but in reality, they affect how the women in question are perceived, what people expect of them, and how everyone reacts when they fall short. They shape the questions we get asked, limit the problems we’re allowed to solve, and impact the value investors place on our ideas. Innovation suffers when women are forced to carry the weight of symbolism instead of the freedom to experiment. 

There are signs of change. The founders making comebacks clearly learned from their experience, keeping the focus on the business, choosing the type of capital and investors carefully, and retaining more control over their business and narrative. Notably, they seem to have their choice of capital, which suggests that investors recognize these founders’ prowess. This is all real progress. 

But the real test of their comebacks won’t be whether Gelman and Haney can rebuild their personal brands. It will be whether we can resist the urge to immediately slot them—and the next generation of female founders—into new, equally limiting archetypes. Because until we do, we’ll keep losing brilliant entrepreneurs to the impossible task of being perfect symbols instead of imperfect, adaptable leaders.

It’s not a test for them. It’s a test for us. I hope we pass with flying colors—millennial pink included. 

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