My attention returned to the present moment, standing in the hallway of the Computer History Museum. I noticed Paul Graham, the founder of Y Combinator, walking in my direction. He looked down towards the ground as he approached me, shielding his eyes with his hands. "I can't even look at you," he said. "You're too much. Tone it down." He walked away, shaking his head in what appeared to be mild disgust.
I thought I'd done a good job with my pitch. There were sixty-four companies in my YC batch, and over two hundred founders — including a grand total of seven women. That's not to say that Y Combinator is sexist. Men certainly apply at far higher rates than women. But I knew I was operating in a man's world, where the rules and best-practices were constructed by men. That's just how the game worked. My batchmates were men. The speakers at our weekly YC dinners were men (because very few founders of the disruptive billion-dollar companies are women). The hundreds of investors at demo day were basically all men, too.
Having been to an all-girls school, I'd witnessed first-hand the fucked-up ways that girls were socialized. As a boarder, I wasn't allowed to leave the school grounds by myself until I was seventeen years old. Even on a clear, sunny Saturday afternoon, I couldn't sign myself out and walk ten minutes down the road to the local shops, just in case I got raped or something. If I wanted to go somewhere, I had to convince other girls to come with me. We'd agree on a familiar, consensus location (the list of places we were allowed to visit could be counted on one hand). When one girl wanted to go home, we all had to go home.
Meanwhile, my brothers were given a wide berth to do whatever they wanted at their all-boys boarding school. From the age of thirteen, they could sign themselves out and go on local solo adventures. They were also given far more freedom to wander into places that remained forbidden to me as a girl: the city, anywhere across the harbor bridge. I had to navigate the world in a group, constantly compromising to keep everyone else happy instead of doing things my way; doing what I wanted to do; going where I wanted to go. Meanwhile, the boys could explore the world like lone, independent wolves — holding contrarian views about what they wanted to explore and not giving a shit about whether anyone else thought it was a good idea.
When I pointed out this injustice to my mother, she said, "The school is responsible if anything goes wrong, so of course they have strict rules." What I heard was, "We trust the boys to take initiative and figure things out on their own. But girls? We don't trust them. They're delicate little roses that should stick to the safe areas pre-vetted by society." And then we wonder why the tech industry — an industry that rewards contrarian visionaries who don't adhere to the status quo — is dominated by men.
Having witnessed this kind of unfair playing field as a teen, I had an inkling of what I was getting into when presenting to a room full of male investors who had spent their whole lives subconsciously absorbing the same shitty programming that I had. I was quite used to assumptions being made about me based on how I dressed — as if men believed that femininity was negatively correlated with intelligence. I wanted to believe that the startup industry was a meritocracy, but I couldn't. To effectively navigate any system, you need to be aware of the system's bias and create a plan to get around it. If you don't do that, the bias will be used against you. You'll be ignored — not because you don't have anything interesting to say, but because men assume that you don't have anything interesting to say. Bias is just a Bayesian process at play, and therefore it's just math. Math can be frustrating, but it isn't personal.
Which is how I ended up on stage, delivering a very playful, cheeky, high-energy pitch for 99dresses. As one of the last pitches of the day, I knew everyone would be tired and bored. All the other pitches followed the same generic formula — problem, solution, an impressive growth graph. It was a very rational, dry, masculine way of presenting information, in my opinion.
My pitch was a bit different. It told a story. I was loud and passionate and excited, making big gestures that took up space. I'd tried this kind of fluid storytelling before and found that people engaged with the information on a much more emotional level than if I were to just pitch them using rational facts. My story's punchline was, "I had created crack for women" — a cheeky, irreverent way of planting an idea in a male investor's mind: 'Ah, she's built something addictive for females. Females spend lots of money. I'll go talk to her.' That's all my pitch was supposed to do — get investors to talk to me. My two teammates were walking around the event in t-shirts with 'Crack for Women' printed on the back — a tagline that successfully piqued the curiosity and broke the ice with many investors. In the end, I was just having a bit of fun. I was just being my most vibrant, playful, feminine self. As Charles Bukowski once said — "To do a dull thing with style — now that's what I call art!"
But there I was, watching Paul walk away from me, shielding his eyes and shaking his head — as if my loud, playful feminine self was just 'too much' for him to handle. I was an impressionable twenty-year-old girl watching a man I looked up to cover his eyes in visible discomfort instead of looking at me. If I hadn't received so much positive feedback from my YC batchmates ("Holy Shit! I wish I could pitch like you!"; "Crack for women. Best. Pitch. Ever!") then I might have muted and morphed my presentation last-minute to fit in, just like I was trained to do as a young girl. Paul isn't a bad person by any stretch of the imagination, and I was grateful for the guidance and opportunities he had given me through Y Combinator. However, I don't think he realized how much the world already tells women to tone themselves down and hide their femininity if they want to be taken seriously — as if femininity is somehow synonymous with 'stupid' or 'weak' or 'vulnerable' or 'can't get the job done' or 'not the change-making leader.' I don't want to assume Paul's intention, but from my vantage point, it was just another reminder that I was expected to mute myself and uncomfortably contort my personality to fit the shape of a system designed for and adjudicated by men.
The next day, I put on my lipstick, zipped up my dress, stepped into my high heels, stood up on stage, and said exactly what I wanted to say, exactly how I wanted to say it. Instead of toning it down, I turned it up even more. My plan worked better than expected. 'Crack for Women' helped me secure some great investors who liked me for me. They stood behind me, even as the ship eventually sunk ("You did great! Can't wait to see your next one," they said as their money went up in flames).
A year later, when I was back in Sydney, a teenage girl told me she'd seen a recording of my YC pitch. "I just remember looking at the screen and thinking — 'I want to be like her,'" she said. In that moment, I was glad I'd done things my way — if not for me, then for every other female looking at me, wondering if they also had permission to break out of their societal cages and be their most authentic self. By shining my light, I'd helped another young woman shine hers.
