The Mythology of Individual Self Achievement, Girl Bosses, and The Hero Founder

I began reading the book Equal Under the Sky: Georgia O’Keefe and Twentieth-Century Feminism by Linda M. Grasso in Chicago, after seeing an exhibit of O’Keefe’s New York work. I picked up the book because I was curious about how True Feminist Icon Georgie O’Keefe was rumored to not be a feminist at all, instead crafting her history in the style of American Hero, Rugged Individualist Edition.

Grasso analyzes O’Keefe’s relationship to the feminist movement and emphasizes that O’Keefe benefitted from her class status and the feminist movement both in her ability to receive an arts education and from the movement promoting her work. But, Grasso notes, O’Keefe rejected connection to feminist movements and created a mythology for herself as gender transcendent. “O’Keefe strips her artist origin story of Feminist history in order to mythologize individual self achievement,” Grasso says. Popular narratives of O’Keefe’s success present a testament of her exceptionalism and a story of American individualism. O’Keefe is not just an American painter, but the pursuer of the most elusive and exclusive freedoms - freedom from gender constraints and class expectations. 

It’s important here to note Grasso’s language - “O’Keefe strips her artist origin story” - because fundamentally, this is where the mythology originates. Only through careful curation of our origin stories can we create the façade of our own success story, unencumbered by  support and contributions from  anyone around us. Our culture has reinforced self-reliance as the most desirable quality, and the only story worth hearing.

The bootstrap narrative slithers its way into almost every “great” American story - art, it seems, is no exception.

The pride in telling your story as coming from nothing and pulling yourself up by your own bootstraps - a physically impossible thing to do - is as American as it gets. The Puritans, the Manifest Destiny-ers, the Cowboys, the Robber Barons - they all echo the ideal of a success  driven through personal achievement, rugged individualism, and self-reliance above all.  These stories reject any narrative of collective success; the story of the American Hero mostly defines other people as either barriers to overcome (emotionally, physically, or financially) or saboteurs.

We founded oVertone in the early days of the “Girlboss” movement. “Girlboss,” coined by Nasty Gal founder Sophia Amoroso, and further explored by Sheryl Sandberg and her contemporaries, outlined a particular view using business to attain empowerment. It relied on both entrenched and new narratives about what women will do “naturally” (nurture) and how they should use that “natural” ability in business. Amanda Mull, in her Atlantic article The Girlboss has Left the Building, summarized it succinctly. “[The] pursuit of power could be rebranded as a righteous quest for equality, and the success of female executives and entrepreneurs would lift up the women below them.” 

Throughout the 2010s, all female founders were lumped in the Girlboss movement, willingly or unwillingly.  Girlboss invited a more collective-driven version of success, one that could change the story of the ruggedly individualistic genius single founder. Not only could women excel in men’s spaces, but we could excel more, with an added dimension of helping others along the way. Even the economic data supports the Girlboss thesis - women owned businesses typically waste less money, put more back into their local economies, and have a statistically significantly increased likelihood of running profitably and efficiently, improving outcomes for potential investors. (Cnote, McKinsey, Forbes) 

But the Girlboss  position is based on the idea that gender is the ONLY reason that one might be excluded from parts of society, as opposed to intersectional schools of thought that recognize that it’s one of many factors. We - the Girlbosses -  believed if we could just force our way through, then we could both receive all the earned rewards of the role that are typically given to male counterparts, plus the power to permanently change the systems that had held us back. 

Traditional barriers to business ownership were dissolving with the advent of the internet, ability to work from home (yes, even in 2014), and quickly developing ecommerce and social platforms. Direct to consumer businesses were flourishing, and it was more straightforward and cheaper than ever for people with ideas to pursue their ventures and find their customers. Even recession culture played into Girlboss - side hustle was built so solidly into the millennial psyche that many of us had been pursuing small businesses already. With all of this colliding, it was easy to believe that the playing field had been leveled enough for us to be considered on our skills alone.

Girlboss pushed us to assume that meritocracy could exist in our culture, especially if we gained enough power to enforce it.

Over the course of oVertone’s existence, I found myself embracing, but then struggling with the title of Girlboss. At first, I liked being called Girlboss (or Lady Boss) - it was informal, tongue in cheek. It was a movement I both aligned with and wanted to be a part of. We could treat our and our communities' needs as equally important - no more convincing a middle aged man that period panties really are critical, or HR really should reflect the needs of a team, not just insurance against lawsuits. We could build a company and a future that we wanted to be a part of, as opposed to one that demanded we fit an uncomfortable mold. This is the entrepreneurial appel du vide - the incessant intrusive thought - that pushes us to jump. Things can be different, and I can make it that way.

The great promise of entrepreneurship is that you get to build your business in alignment with your values - how you think the world could or should run. Strong, accountable leaders build cultures and businesses that reflect their deepest thoughts about how things could or should be. But titling this experience Girlboss began to feel diminishing after a time - what started as empowering became a title used to other us and keep us apart. We were participating in the entrepreneurial eco system like all other founders, building our worlds. Why couldn’t I just be Boss? Founder? CEO? Why “Girl,” or “Lady?” Why was this the prioritized noun, and not the other part? Why did it have to be cute? Why shouldn’t it be?

I was dedicated to the actions of uplifting, training, and coaching women and other marginalized folks in my daily life as a part of my leadership at oVertone. At the same time, I found myself rejecting women-only environments because they felt isolationist, preferring to integrate into the male-dominated environments instead, forcing them to contend with “women’s issues.” The women-specific spaces felt isolating - they felt less like a place for women to pool their resources and work to dismantle the systems that held us back, but more like a container to protect our colleagues from having to think about us at all - like hiding a tampon in your hand as you walk to the bathroom so you don’t make anyone “uncomfortable.”

I can relate to O’Keefe when  she said, “…in speaking of me as a painter, you do not segregate me as a woman painter, because when that happens, there is generally an implication that one is not a serious worker.” (Grasso 121) It felt as though accepting womanhood as a part of my business identity, I would be consigned to the roles of not-a-male founder or not-a-male owned business, regardless of accomplishment. My experiences in entrepreneurial communities continued to confirm this; regardless of the company’s financial performance or other incredible accomplishments, I was hidden away on panels, sometimes in literal basements, dedicated to only speaking about women’s empowerment at work instead of work and business itself. Eventually, I stopped calling myself a Girlboss. Its power was taken from us and reformed into a marker of perceived fragility. It became a way to discredit us immediately. 

I soon only began to speak of my business in entrepreneurial circles in terms of revenue - the only metric by which I would be perceived as deserving of being in the “true business” environment. Instead, I could be revered as an American Exceptionalist, Hero Founder, Winner of Capitalism. I could embrace bootstraps. Girlboss, at the time, marked you as not a real capitalist - that your power would always be given away through the recognition and prioritization of everyone that got you there, instead of to yourself and the shareholders. Were you one of the real founders, even though you would never really be recognized as one, or were you a Girlboss - more loyal to your gender than the game? Could you be counted on to promote the shared story of rugged individualists making it happen by themselves for themselves, or would you fall into the unforgivable pit of collectivism, championing your employees and others who got you there? Why give credit to anyone else unless you absolutely have to? - You’ll kneecap your own success.

Ultimately, Girlboss fell hard into ridicule. Its many faces were revealed, and the women at the helm who were once considered axe-wielding glass breakers, eager to let us all in, turned out to still embrace and uphold the systems that were holding us back. They parroted the same American Hero talking points, were surprised by communal emphasis, and turned their axes on those trying to come up through the broken floor. Even if the central promise of entrepreneurship held, the central tenets of Girlboss did not. Mull articulated this with blistering acuity.  “Women are still people” she wrote, “which means we can respond in similar ways to the incentives and privileges of power that sometimes make male bosses tyrants or harassers or wealth-hoarders. Slotting mostly white women into the power structures usually occupied by men does not de facto change workplaces, let alone the world, for the better, if the structures themselves go untouched.” (Mull, The Girlboss has Left the Building)

Me, Girlbossing a little too close to the sun holding up our “Best Place to Work” Award with our CFO, VP of Marketing, and CTO

A critical component was lacking in the Girlbossification of the American story - in our eagerness to show our merit in a system we had never been let into, we failed to recognize that, “[Liberal feminism] is a political position that seeks women’s integration into existing structures rather than attempting to remake society in order to achieve a more equitable distribution of social, economic, and material resources.” (Grasso, 18) We thought that by inserting ourselves into the narrative we could be the difference we wanted to make. Those that got closest also were able to make forward strides - no effort to change things and show a different way should go unacknowledged - but the system at the head has no real reason to change, and every incentive to let us think we can try. 

Even now we’re still desperate for Girlboss to be real on some level - you have to look no further than Hailey Bieber’s success raising money for her brand Rhode. Headlines touted her as Hero Founder, seemingly ignoring the privileges that allowed her to succeed, instead lauding her incredible vision and ability to understand her consumer. The amounts of money thrown around were staggering; the multiples for her exit inflated. Comments sections were clogged with requests, demands, and prayers from other women founders that she would use even some of it to lift up others “like her.” The reality is that almost no one is like Hailey Bieber, and the system doesn’t reward her in any way for collectivist behavior.

oVertone’s core value of Intersectional Feminism - to which I largely attribute our success for multiple reasons -  was all but immediately abandoned post acquisition as a remnant of a bygone era.  oVertone may never have been started without my and my cofounder’s audacity and persistence, but it only flourished due to the community that grew around it and inside it and wanted to see its full potential realized. Instead of these truths, the bootstrapped success story is what remains - the hero founder(s) - still visible on the website.

America, and American capitalism, thrives on the story of the lone, rugged hero - the cowboy, the immigrant who arrived with nothing but $5 and a name, the myth of the persecuted pilgrim (none of which are instantly recognizable female, queer, or non-white legends). To be purely American, you go at it alone, telling a solo story of how you made it, and that you deserve all that you can grab on your way to the top. Grasso describes O’Keefe isolating herself in this way - making gender transcendent work, editing out the movements that elevated her and the men that supported her - a pure artist, alone. I find this story everywhere in entrepreneurship, the myth of meritocracy and the hero founder. The story exalts the ones with real vision, who change the world, and for whom all behaviors are excusable due to genius - and the ones that aren’t male get taken down for the same sins that men are elevated for: failed promises and debt. Elizabeth Holme’s Theranos offers a clear example - her sins were astounding, and yet not dramatically different from those of her male contemporaries. Who got punished, why, and how?

The American Hero and the American Dream are myths. No one can do it alone; no one does it alone. We live in a tangled mess of dependency; when it comes to our successes, we owe as much to our races, zip codes, and other circumstances of birth as we do our intelligence, luck and work ethic. O’Keefe was no exception (looking at you, Alfred Stieglitz), I was no exception certainly, and neither is any hero founder you can think of. None of them. Not even tech billionaires. 

I frequently say to my clients, “Remember where your money is made. It’s likely not you anymore. It’s the people that perform the work of making your vision reality, and those that interact and purchase it in all of its various forms.”

Talent, persistence, and charisma are still critical players that make a difference in whether businesses succeed or fail - and founders do play critical roles throughout the life of a company and their relationship to it. Leadership matters - it’s just that our ability to be exceptional is as reliant on those who support and surround us as it is on our unique talents. We cannot simply choose individual exceptionalism without dealing with some very confronting realities - that we are only as good as those we empower and bring up around us.

American entrepreneurial culture has hung its hat on a series of false promises and inaccuracies: that interdependence makes us a risky burden, that collaboration and diversity lead to ruin, not excellence, that sharing credit will rob us of what we are owed. As a society, we continue to build and center these concepts. The latest hyper-individualistic fad involves relying on AI tools (which are largely compilations of anonymized data stolen from underpaid workers) because we don’t have to give them credit. We don’t even have to pay AI a living wage, though that will change either through premium/enterprise solutions or your electricity bill. The closer a founder can get to a one-hero-show, the more profit they can justify keeping. They can remove anyone around them who might’ve earned a piece and save the equity for more important vultures.

If we ourselves can’t be the hero founder, we valorize those who are, because we believe if they can exist through sheer determination, then so might we. We are living in the toxic myth that founders, more than anyone, deserve inconceivable amounts of money - trillions - just for being founders. Meanwhile, the workers that produce the reality behind the founder may struggle without food, housing, medical care, or certainty of citizenship. The lived day to day reality of most will never match the promise laid out by capitalism. “The bigger the promise, the more intense the anger and sense of betrayal when that promise is frustrated” (Grasso) The belief in individual exceptionalism created this society; to believe otherwise would leave us entirely and totally betrayed by the invisible hand that created it all. We hang onto this belief and when it fails to materialize, we try to force it down each other’s throats (see: Male Loneliness Epidemic and Tradwifery). This is a frustrated betrayal unlike any other, and this is its fallout.

I think back to O’Keefe. She wanted to believe “there was no sex in art” (Grasso 104) which meant that a there must be a “universal standard based on gender transcendent criteria that was unrelated to an artist’s or critic’s gender” (Grasso 104) She also believed her gender gave her unique, feminine perspective: “A woman who has lived many things and who sees lines and colors as an expression of living - might say something that a man can’t” (Grasso 124). Her desire to be seen as an artist, and not a female artist, while also acknowledging how her gender identity informed her work is so similar to what Girlboss hoped to achieve. To leverage the moment when the playing field seemed level, share our unique perspectives, and be treated as equally deserving in non-separated spaces.

Behind both Girlboss and O’Keefe, and all their nuances, lies the work of people dedicated to our understanding and leveraging interdependence. There could be no environment that even appears to be leveling without those acknowledging how unbalanced it is and working to correct it. To be an artist, activist, or entrepreneur is to be driven to remake the world according to our vision, and be vulnerable enough to show people things as they could be. To be a good artist, activist, or entrepreneur is to understand success as the work of many who execute excellent vision and integrous leadership.