Trans Hacking Startup Land

Battling gender bias through performance and deception

“Oh I’m trans.” There’s that moment when you’re chatting and the words sink in, the sudden lull in conversation, the blink between confusion and comprehension, when they realize that the person they perceive to be a woman was assigned male at birth. How people react, says a lot.

Early-stage fundraising is 20% fact and 80% spectacle, a magic show performed to convince, seduce, entice to follow a game changing vision and world changing riches. As someone who is non-binary and transgender, I learnt to dress and act neutrally, to sustain the magic circle of enchantment. I bound my budding breasts and wore baggy black clothing in sweltering summer heat, fabric layers as hot and oppressive as the identity performed. This magic circle was sustained, but narrowly. Always on the horizon edge, was the potential of a breakdown.

It’s an additional weight, being a founder. The founding team is a crucial component in the startup narrative, which must be represented in heroic, epic and relatable terms. “I can be tricked by anyone who looks like Mark Zuckerberg,” said Y Combinator founder Paul Graham in an interview by NYT, and that’s the crux of the problem. Appearances matter, and it’s hard to fundraise or get any sort of exposure while trying to change your name, gender and pronouns. Before I was visibly trans, I had connections with people in one gender, one name that was different than my current one. When I met them in person, the charming startup narrative disintegrated.

It’s easier to pitch, to tell a story and present your product with one clear personal identity. My nebulous genderfluid and non-binary trans identity was difficult for people to understand, much less empathize and relate with. Besides, how else can you tell a 30 sec elevator pitch? The entire format, the magic show, is based on distilled soundbites made simple with helpful stereotypes. The hardest part was the transition period, the (git)merging of identities conflicting online and in person into a single, easily swallowable story. Still, there’s an awkward air when friends and acquaintances from separate life-spheres collide into a combustion of pregnant pauses, long silences and no eye contact.

Even though investors and other connections were more receptive now, there was still the problem of appearances, and being relatable. It was a structural problem, where the top tier investors tended to invest in those like them, and as such, this homogeneity restricted the flow of capital to a larger, more diverse community of entrepreneurs. After all, there’s only so many people who can look like you, talk like you, go to the same school and work in the same few companies that “everyone” goes to. As you move down the capital stream to smaller funds, you can see more diverse funding sources open up.

My co-founder and I did our best to find like-minded individuals, angels or venture funds.

After I moved away from being gender ambiguous, I unbound myself and started presenting as a queer woman. I reached out to many LGBTQ* startup allegiances for help with fundraising. That was where I met more hostility than ever before.

Every community has an extremist cell. Unfortunately for lesbians, whom I identify with, one loud vocal minority known as Trans Exclusive Radical Feminists (TERFs) overwhelm the 99.8% that are amazing people.

Ideologically, TERFs believe in the classic gender binary, female and male. They don’t accept transgender or any non-binary gender identity. They are particularly hostile towards transgender women for what they believe is appropriation and exaggeration of the feminine. They’ve fought hard to re-define femininity away from this stereotype and see trans women as reinforcing it.

To some degree it’s understandable, since newly self-realized trans women tend to go towards an extreme form of femininity to “pass” as women. This performance of hyperfemininity can be read wrongly especially in a delicate situation. At the same time, trans women need to adopt feminine signifiers to blend in and lead a normal life, else they risk being questioned, harassed, threatened in their daily lives. Trans women tend to be disproportionately targeted by hate groups, and they would feel despair and terrified if they can’t “pass” in general society.

There’s so much micro-aggression against being trans that it’s hard to recall specifics. One incident sticks to my mind, and that was my first lesbian tech meetup. I remember how excited I was, discovering meetups dedicated to lesbians and queer people, whom I identified with, their front page proclaiming how this was a new type of tech meetup, one that was open and embracing diversity, a safe space and alternative way to the typical Silicon Valley “bro-sphere”.

The evening started great. I met other startup founders, and exchanged stories with them. It felt good to be able to express myself, and talk about the startup and product without worrying. One investor seemed especially interested. She was connected to a large funding network, she said, one of the LGBTQ* friendly ones.

The questions started simple. Who we were, what was our space, what was our product and how it fit the market. I was prepared for those. Then it started getting personal, more strange. You’ve accomplished a lot, she said, how did you do all that as a woman? She scanned my clothing, from boots to shorts to tunic t-shirt and stopped at my breasts. I wanted to cross my arms, or put on a jacket. I wanted to hide. I told her some of issues I had at different workplaces, but didn’t mention the trans part. I didn’t think it was important.

I guess she did think it was important. I guess I should’ve mentioned it sooner. I guess she was shocked, or angry. I guess she felt cheated, that I had “fooled” her. I wouldn’t know, because she never connected back to me. Nothing. 5 emails, 3 Linkedin connect requests, 2 tweets, 2 Angelist requests and 1 warm introduction from another angel group later, still nothing. Just absolute silence.

Such silence, while hurtful, wouldn’t matter as much if it didn’t affect a large number of entrepreneurs. TERFs partially control many LGBTQ* startup funding groups, such as the investor I met at the lesbian and queer tech meetup. When I met them or some cases video-chat across the country with them, they read me as cis-lesbian. However, when the conversation continued or due diligence started and we went into our personal backgrounds, they’ll inevitably discover the trans part. Instantly, the conversation stops. No more meetings. No more emails. I’ve gone through this process before, but never so abruptly and unprofessionally from anyone else. Even the most tech bro-iest of bros, and that’s saying a lot!

We like to believe that one kind of openness begets another, and that one call for diversity, creates more willingness to explore new possibilities with different types of entrepreneurship. Unfortunately, this isn’t the case. Top tier funds are now more exclusive than ever, since there are now other dedicated funds for diversity. The logic goes: if someone else is being diverse, then I don’t need to be. I can stay in my own enclave. It’s now someone else’s responsibility. And this echo chamber effect downstreams, where each community becomes less risk-opportunistic, less open and less willing to engage with anyone who doesn’t fit their narrow definition. The echo chamber of Silicon Valley has expanded into an echo labyrinth.

I don’t know if there’s a solution to this, or if human behavior can ever be truly ‘disrupted’. All I can do is keep pushing forward, keep improving our product, keep pitching and smiling and hope that one day, we can make the future we dream of, magically, beautifully, openly, real.