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Entrepreneurship as a Trans Man

May 16, 2024

Entrepreneurship as a Trans Man

Finnegan Shepard Founder of Both&

There’s a way in which being trans is perfect training for being an entrepreneur. For me, transitioning was an act of simultaneously holding extreme conviction and a wide range of fears, doubts, and insecurities. It was knowing and not knowing and not knowing what I didn't know. And perhaps most bluntly, it was creation: it was putting bits and pieces together such that a new identity, a new form, appeared. All of this is extremely similar to the process of entrepreneurship. It requires, on the surface, contradictory things–as is commonly stated, being an entrepreneur requires you to be both “resilient” and “flexible.” You have to hold to your vision, to persevere, to keep pushing, but you also need to be able to contort, to accept that things are maybe entirely different than you thought they were, and to pivot.

This essay is not prescriptive, it is not a ‘how to’, and it is not a universal account. Instead, it explores my personal experience as a trans entrepreneur and the ways in which being trans has both presented additional hurdles and also been a kind of superpower. I’ll start on the shakier ground, with the ways in which the challenges are parallel, then move into the empowering parts.


What is so scary about transitioning and entrepreneurship?

Everyone’s journey with gender and with entrepreneurship is different, and I’m not going to pretend to make universal statements about it, but it’s safe to say that the beginning of both journeys tend to be characterized by a leap from the known into the unknown, and this leap is usually precipitated by a dissatisfaction with the current state of affairs. We are tired of having a boss, or of work feeling banal and draining, or that it doesn’t have enough meaning or impact on the world. We have an idea, something we think could be really great and that people would love and that does not yet exist on the market–but, the idea of risking it all is terrifying. We don’t know if the idea will actually work. We don’t know how to make it happen, and we DO know how to continue on in the life we already live. It’s secure. It’s predictable. It may suck in some ways, but at least we know exactly what those ways are.

Transitioning is a completely different beast, but there are elements that are similar. Most trans folks feel some level of discomfort in their bodies/identities/perceived gender. There is a dissonance between who they know themselves to be and how the world reads them. They have a strong sense of what is right, what walking through the world in a more accurate way would feel and look like, but the process of getting there is intimidating/terrifying/paralyzing. And of course, while on the one hand we as trans folks tend to have extremely profound conviction, we are also human, and naturally have our fears and doubts. (An unfortunate by product of how the medical and legal world has been set up to ‘allow’ or not allow trans folks to transition means that there is no room to express these very natural doubts).

To borrow from the modality of literature, both are hero journeys. We set out into the unknown, aware that what will be required of us will radically alter who we currently are.


Is the start up world transphobic?

Like most things in life, yes and no. (Both and). I’ll start with the positive. It has been my experience that the start up world (and business world more broadly) is actually a really great space to be ‘dealing’ with trans issues, because there is a certain objectivity to business that ultimately comes down to the same universal numbers and metrics. Is there a market? How big is that market? How quickly is it growing? What is the cost to produce the garments, what is the cost to acquire a customer? I have had more than a few experiences interacting with the kinds of people I would not assume are particularly educated about trans issues, in which using Both& as a kind of trojan horse to smuggle in a conversation in a form that is familiar to them has led to an extremely positive outcome. As an example, I once had a conversation with a finance bro at crossfit who at the end of the conversation was saying, “I am so happy I came to class today, I learned so much. This is such an amazing idea.” Twenty minutes earlier, this person had been asking, “what is transmasc?” and “Wait, but you’re a man.”

When I’m talking about the business of Both&, I am both talking about transness and not talking about transness. Transness is the content, but the form is recognizable to folks who haven’t otherwise thought through or confronted these issues, and that makes the process seemingly a lot more open and tolerant and curiosity/self-interest based, rather than threatened by something they don’t understand. So, perhaps the most surprising and wonderful thing I’ve experienced about transness in the start up world is that it’s an area where you can touch on many minds that were likely not transphobic before, but maybe hadn’t had the opportunity to really think through their stance or feelings and steer them towards a much more aligned outlook.

Now entering into the more challenging territory: if folks are open minded to hear about the idea and understand what a good business proposition it is, there is still all of the mountains of unexamined bias floating beneath the surface that makes access to capital more challenging. This is a phenomenon not limited to trans founders–96% of venture capital goes to white cis men. For all of us underrepresented founders (and the research backs up that we are quite literally better business bets, as we bring higher returns on investment), we tend to drown in an ocean of goodwill and no action–everyone and their mother wants to be our advisor or mentor or cheerleader, and very few actually take out their checkbooks and write a check.

While the reason for them not writing the check is never listed as such (it takes all the usually forms–we need to see more traction, we aren’t sure the market is big enough, we are raising a fund ourselves but come back to us next year) and it is impossible to delineate partial truth from complete fabrication, it is safe to say that bias is a part of that calculus, whether they are aware of it or not. I have only experienced one explicitly transphobic investor in my experience pitching, but that experience was a bit of a slap in the face, a wake up call that of course the fact that I am trans (and further, designing for a trans community) impacts the internal calculus. I am confident from my interactions that it is rarely malicious, but more a hard-to-quantify calculus of the unknown. They don’t empathize with the trans experience. They don’t really know what it means to be a trans consumer. So much of investing is art rather than science, is a gut feeling. If the gut is even just a little bit uncomfortable, that can have an outsized impact on the likelihood that your business will receive funding.

Finnegan Shepard, trans man and founder of Both& Apparel


Do you get put in the position of a ‘token’ representative?

The short answer is yes. We unfortunately live at a time where there are not enough trans entrepreneurs, and so my positionality can put me as a kind of token representative. I don’t ethically think the right thing to do is to shy away from the conversation, but nor do I want to speak on the behalf of an incredibly diverse group of people. My experience is my own, I am confident aspects of my experience will resonate with other folks in the community, and aspects won’t.


What’s great about being an entrepreneur?

For me, entrepreneurship is all about dynamism. I am somehow who has never been good at routine. Every time my life threatens to fall into a rhythm, I upend it. There are ways in which I think this is a bad thing and ways in which I love what it has created for me, but one thing I know for certain is that it has made me very well suited for entrepreneurship. When you are creating something out of nothing, there is literally everything to do. Every challenge it’s possible to have will come along. Infinite opportunities, infinite obstacles, infinite puzzles. You will end up in places entirely different from where you predicted going. You will have amazing days and days when you feel like you are “eating glass and staring into the void.” You will meet extraordinary people along the way, people who want to help, people who want to join, people who you think will change everything, people who will let you down. You will become more resilient then you knew you were capable of becoming. You will want to quit. You will have days when you are winning and you will think you are invincible. You will build teams that feel like family, have to let folks go. You will have to deal with the seething beast that is the internet. You will meet people whose lives have been changed by what you created. Every day will be different.

To me, it is that raw horsepower, the energy to continue pushing, even when the way feels impossible, that is the elixir or entrepreneurship. It always sounds romantic on the outside, but from the inside it requires an insane amount of grit and a willingness to roll up your sleeves and do the things, every day, that no one else wants to do. And along the way, you will witness yourself in a constant state of transformation. This ties back to the connection between being trans and being an entrepreneur: it is committing to a process, one that is radically empowering, disorienting, scary, and ultimately rewarding, all at once.