On Startups and Gender

Andrew Murray Dunn
11 min readJul 29, 2019

2021 note: a lot has changed in my life and analysis since writing this three years ago. I intend on writing an updated piece in the coming year. Please do not freeze me in time!

The Bird of Humanity (Source: Baha’i Teachings)

How adopting ethical and inclusive business practices helped me understand, explore and embrace my gender identity.

Note: I drafted this in the fall of 2018, but did not feel comfortable sharing it publicly at the time. It is time now. Though many thoughts have changed in the last year, I have chosen to preserve what was drafted, and plan on expanding more in future writing (get excited for “On Queer Relationships with Money and Business”). All thoughts expressed here are my own experience and interpretation.

This piece is dedicated to my grandmother Rose.

In the last couple of years I have noticed an explosion in dialogue on the “masculine” and “feminine.” Ancient ideas of yin and yang, shakti and shiva energy are surfacing as mindfulness and plant medicine sweep across the globe, alongside increasing transgender visibility, #MeToo and other women’s empowerment movements. These trends are collectively raising awareness of the imbalances between the masculine and feminine on a civilizational scale.

I want to share a surprising and unique journey that has unfolded for me during this time, inviting me to explore the concept of gender through personal and professional lenses. I feel proud and nervous to share my experience and what I’ve learned in the process of connecting with a more true expression of myself.

How toxic startup culture forced me to question the status quo

I was assigned male at birth and raised male in the United States. I tried to live up society’s expectations of masculinity by doing the stereotypical machco [bro] things. There was an ambient discomfort to it all that I couldn’t name, as swimming in the hypnosis of patriarchy means segregated awareness, so the options on the menu are limited and stories of others’ experiences sparse. There was no LGBTQ+ visibility where I grew up.

The first few years of my career were then spent working for a number of venture capital-backed startups, i.e. businesses designed to maximize return on investment as fast and large as possible. Gradually, the ambient discomfort grew into pain, as some of these experiences reflected the widely-reported Silicon Valley cocktail of ego, fear, greed and discrimination. I increasingly found myself in spaces where I didn’t feel safe or seen, and noticed all the ways in which others faced more acutely oppressive experiences.

I couldn’t articulate each misgiving at the time, but after continuously experiencing what I’d later understand to be a product of toxic masculinity in the workforce, I vowed that if I were to ever start my own business, I would do things differently. I would explore how to allow for more inclusion, emotional intelligence, transparency, balance. General respect for each other’s humanity. These were intuitions based on my wanting to simply feel better as a worker, as a human being, and feeling like the wellbeing of the broader community truly matters.

Discovering new stories and allies

When I found myself in a position of leadership with Siempo, I started to make good on my vows, keeping my ear to the ground for progressive ideas to work with. I quickly came upon some life-changing maps.

First, I stumbled upon Zebras Unite and their articulation of the difference between a “unicorn” company (i.e. fast growing startup valued at more than $1B USD) and a “zebra” company. With fully female leadership, Zebras Unite was outspoken about how feminine qualities have been subordinate to male qualities in our dominant business mythology and desperately needed (in startup culture especially, which is emerging as one of our most influential institutions) to create a more beautiful and just world for all.

Source: Zebras Unite

It had never occurred to me that the male-dominated business world rewards more of the attributes concerned with the masculine energy, such as achieving and optimizing, brute force and domination. Nobody taught us that in business school.

Naturally, I then learned about feminist business school called Sister, and was struck by visuals of what our economy might look like that if it were more balanced and didn’t predominantly value masculine traits. The Feminine Economy proposes a new set of values and a redistribution of power based on feminine principles:

Source: Sister.is
Source: Sister.is

“Yes!!” Screamed my body when I saw this. All those vibrant and nourishing things I’ve started to love and value more. This feels right. That’s the world I want to live in. More of that please.

It’s not that all of The Masculine Economy qualities are BAD. It’s that when we don’t value the skills and gifts of half of our species, we get the world we live in now. A key difference is many of these masculine-associated qualities are concerned with “doing”, while those of the feminine are related to being, allowing, opening, receiving. We need both! We need a balance.

While these visual are somewhat biased and there are certainly pitfalls to gendering business practices, these pointers provided validation for my natural inclinations to be collaborative, intuitive, generous, high integrity, balanced. I started to tell people that our approach to business was “more feminine” and that this was one of our strengths.

And it proved to be. Discernment over what kind of money we accept has preserved alignment with our values. Taking time to disconnect and be around nature has allowed creativity to flow into the product. Prioritizing diversity on our cap table has introduced different ways of knowing into our organization. Showing up in this way has attracted world class talent that has a higher bar for integrity.

Ultimately, expressing this pride was an important bridge for identifying with traits and communities that I had previously felt disconnected from. And this provided a critical foundation for when things started getting personal.

Gender 101

Before jumping into the personal, let’s visit some 101. Please meet The Gender Unicorn, here to illustrate the spectrum of human gender and sexuality (Skip ahead to the next section if you know this already. If not, it’s okay — I didn’t really understand it until this year, and I forgive myself for not knowing).

Source: Trans Student Educational Resources

Gender Identity: One’s internal sense of being male, female, neither of these, both, or another gender(s).

Gender Expression/Presentation: The physical manifestation of one’s gender identity through clothing, hairstyle, voice, body shape, etc.

Sex Assigned at Birth: The assignment and classification of people as male, female, intersex, or another sex based on a combination of anatomy, hormones, chromosomes.

Sexually Attracted To: Sexual Orientation.

Romantically/Emotionally Attracted To: Romantic/emotional orientation.

Today, a newborn’s sex assignment at birth largely assumes a fixed equation of the other aspects of gender and sexuality, along a strict binary. You’re either one or the other: male or female; straight or gay. However, there’s a growing awareness of the infinite possibilities on the spectrum between these binaries, and that it’s fluid, i.e. it can change over time.

Looking inward

As a result of the professional journey described above, I opened up to a synchronistic series of events, that helped me sense some personal growth edges with regards to my relationship with femininity. I’m still in awe of how dozens of seemingly random threads transpired (a blog post or conversation here, a meditation or inquiry there) to create the headspace to just feel comfortable sitting with the questions:

Where am I on those gender spectrums? How do I really, really feel inside? Who do I want to be? What is my truth?

I had started exploring sexuality a few years earlier, but in a secretive and shameful way, as I found it to be fluid (which was confusing) and require lots of healing around the ways in which I had been socialized. Not once though had I questioned my gender identity.

Until I actually befriended some wonderful people who identified as transgender, genderfluid, gender nonbinary or nonconforming. Hearing real stories and seeing unique expressions of gender shattered misconceptions and revealed the potential for so much beauty and joy in breaking out of modern society’s narrow narratives. It doesn’t hurt to be living in Oakland in 2018 😂

I realized all the ways in which I had suppressed feminine qualities in me and actively avoided feminine expressions out of fear of humiliation. So I asked:

What if I stepped into these expressions? What can I learn? What are the gifts? How could I be more thoughtful about this process, be a better ally to the LGBTQ+ community, educate myself and share wisdom outwards?

I’m very much still feeling into this gender exploration, and I’m happy to report that it has been magical :) The sense of freedom and spaciousness to just be me. Feeling accepted and celebrated by friends and strangers. I believe I am a better friend, teammate, partner, stranger for taking the time to intellectually, somatically and spiritually understand a little more of what it’s like to identify and express oneself as a different gender. I feel more connected to my body than ever. It’s scary and wonderful. Coming full circle, I believe it is a powerful strength to be in touch with both masculine and feminine energies, especially as a steward of a tech product that users are trusting as their experience of the mobile internet.

My experience so far has been less gender dysphoria (distress a person experiences as a result of the sex and gender they were assigned at birth) and more gender euphoria (feeling great about living as your desired gender). The idea of being trapped in the wrong body had never crossed my mind. Rather, in doing some of these scary things (e.g. experimenting with clothing, mannerisms, pronouns) brought me a newfound sense of joy and connection with another side of me that had long been internalized.

It’s incredible how a relationship with a business–or anything for that matter–can act as a powerful mirror to help you understand yourself and practice showing up in a different way.

I must credit my relationship with Backstage Capital as an important puzzle piece here. Arlan Hamilton (one of my company’s investors) exclusively supports founders who identify as a woman, person of color, or LGBTQ+. One of our original co-founders fit this criteria, but I did not. Well, I identified as queer for my sexual orientation, but not publicly, frankly because of fear. Naturally, the universe presented me with the opportunity to come out and connect with the LGBTQ+ community, in a way that felt safe and inclusive. I’m forever grateful for this association. Isn’t it amazing how much of an impact a bold individual or brand can have beyond the thing they are focused on measuring?

The medicine you need is the medicine you have to offer

This year’s Burning Man was a big moment for me, where I held an intention to live into deeper expressions of gender, for days at a time instead of minutes or hours.

I became a walking gift on the playa. In the first 24 hours there were several instances of cisgender, heterosexual men approaching me with curiosity, and then gratitude for showing them an example of that which they had previously not felt comfortable thinking or talking about. People telling me how beautiful I am and thanking me endlessly for showing it. For creating the opportunity to learn about pronouns. My mere presence was healing. You can’t be what you can’t see.

While watching the sunrise on my second morning, I was overcome with a feeling that my Andrew Murray Dunn identity was undergoing a metamorphosis, allowing something new to be birthed. Who is that person? What do we call them? The name came almost immediately:

Ava Rose.

Ava derived from my Hebrew name: Avraham. + I’m a lover of our aviary friends, and a yellow canary happened to land right next to me in this moment.

Rose inspired by my grandmother, Rose.

Ava = chosen name, Rose = honoring female lineage, Dunn = honoring male lineage. Yes.

I enjoyed playing with the name for the week and beyond, and plan on continuing to try it on. I can’t emphasize enough just much freedom I feel in this genderfluid/genderexpansive/genderabundant/etc. exploration. Freedom in mind, freedom of expression. Surrender.

More of what’s been amazing:

The overwhelming majority of people in my life have been extremely supportive. I feel empowered to express and share. I feel more connected to people. I’m told I look happier, shinier, sparklier, sexier. I have come to appreciate fashion. I now dance. I sometimes even sing. I love who I see when I look at myself in the mirror. I get regular opportunities to educate people. I get regular opportunities to grow by doing something that scares me. I feel permission to discover new gifts. There’s a whole new world I get to explore, right here, if I’m open to it.

What hasn’t been so amazing:

The pronoun thing is confusing. The name thing is confusing. Some are triggered by “identity politics.” Sometimes I don’t feel strong enough to show this side of me, and then I feel shame around it. Coming out is a lifelong process, so first it was telling people that I was questioning and exploring, now it’s name and pronouns, maybe there will be more. It takes up a lot of mental bandwidth. Do I adjust my social media presence? What if I change my mind about things? I still have to do certain things in secret. I sometimes get stares and micro-aggressions on the street, or nervous before stepping into a Lyft/Uber. It’s tricky to discern what’s true for me vs perpetuating society’s ideas of masculinity and femininity.

That’s where I’m at now. Like many aspects of my life, I acknowledge I’m starting on third base, with the privilege of being able to explore gender and sexuality in a place like the Bay Area, in a time like 2018, in a community that is accepting and supportive. The conditioning and laws in most places still renders such explorations dangerous and out of reach. So I feel a strong sense of responsibility to commit to my exploration and use my voice and actions in service of the transgender rights movement, regardless of where my journey takes me.

The Bird of Humanity

I’d like to close with a Baha’i prophecy that reads:

In the 21st century, it will be the time when the bird of humanity realizes that it has been flying with one wing for millennia. This male wing has gotten incredibly muscular, almost violent, in order to keep the bird of humanity afloat, and as a result the bird has been flying in circles.

At last, when the other wing, the female wing, fully expresses itself, the male wing can relax and the bird of humanity can soar.

The collective consciousness has already begun to shift. This is one of the greatest invitations of The Great Turning. It starts within each of us and it will change everything. This is no time to be small.

Thank you for reading. I’d love to share more details of my journey upon request, and help guide in the right direction if you are interested in exploring. Safe space. I have hours more to share on this topic. Feel free to write me at andrewmurraydunn at gmail dot com.

[July 2019 Edits]

Since publication, my grandmother Rose has passed away. At her funeral I shared: “They say we are our ancestors wildest dreams. Thank you for the life you have given us, for being a role model and a springboard, allowing us to spiral up and be even more free.”

Today I use the names Andrew Dunn and Ava Rose interchangeably. Both feel great. All pronouns feel great too.

Andrew / Ava is co-founder and CEO at Oakland-based Siempo: creating technology that supports life.