A Conversation with Finnegan Shepard on Transgender Awareness Week

November 17, 2021 8:13 am
Written by: StartOut

Our trans founders and entrepreneurs are the leaders of the StartOut community. Their personal and professional achievements continue to inspire us as we make historic moves towards creating the level-playing field that all LGBTQ+ entrepreneurs deserve. While the road hasn’t been an easy one to navigate, we know that with the trans community shining the light forward, we’ll get there.

Continuing with our spotlight of StartOut’s trans founders during Transgender Awareness Week, we meet Finnegan Shepard.

Finnegan “Finn” Shepard (he/him/his) is a trans writer, classicist, and entrepreneur with a third of a PhD in Philosophy from the University of Cambridge and 3/4s of an MFA in Fiction from the University of New Mexico. Finn is the CEO and founder of Both&, as well as the creator of Limns. He’s been published in the Berkeley Review and the Dublin Review just to name a few, and his passions for literature, writing, and entrepreneurship have deep roots.

We met with Finn to discuss his journey, both personally and professionally, and get his take on Transgender Awareness Week. Here’s what he had to say:  

Finn, we understand that you transitioned largely during the COVID-19 pandemic. What was that like?

I began taking testosterone in the fall of 2019. I was scheduled to get top surgery in March of 2020, but then due to COVID-19, the date was pushed back six times. Transitioning during COVID-19 was fascinating inasmuch as an experience that is normally created relationally, in public, was suddenly occurring in a private space. I bought into this illusion that I could be in a cocoon and emerge fully formed out the other side. Of course it didn’t quite work out like that. 

Talk to us about your entrepreneurial journey. How did Both& come to be?

During quarantine, I read Tim Ferriss’ infamous 4 hour Workweek. In his chapter “Income Autopilot I”, he encourages his readers to perform quick, cheap experiments that can lead to passive income. His examples include how-to-yoga DVDs and reselling French striped sailing shirts. I pulled out my phone to google “Trans swimwear.” After maybe ten minutes of scrolling, I called a friend who worked in fashion and said something along the lines of, “no one is designing good swimwear for trans men. How hard would it be to add a mesh pouch into a swimsuit so people could pack while swimming? I’m thinking of running a little test online to see whether anyone would buy it.”

Eighteen months later, I haven’t run that experiment, but I have built an entire brand, complete with a four person design team in NYC, a global photojournalism series, avid customers, a 30,000 person social media following, and skyrocketing sales. At first glance, I find the story of what sparked my initial inspiration for Both& to be amusing – how funny that I thought this could be a quick and dirty experiment a la Tim’s suggestion about income autopilot generators. But on second glance, I see an important lesson about the nature of entrepreneurship: everything important in life takes exactly the amount of time it takes. No more, no less.

How did you find out about StartOut and has that relationship changed your process?

I found StartOut online after researching different organizations who could support my startup. Since getting involved, I’ve benefited enormously from working with my mentor Adam Domain, and using office hours. There are so many aspects to entrepreneurship that could lead to hours and hours of Googling and panic, or could be resolved by one quick call with an expert. That’s been fantastic.

This week as you know, we’re celebrating Transgender Awareness Week. What are your thoughts about this moment to reflect?

I’ve led an incredibly privileged and lucky life in terms of being trans and so for me, I feel that it’s a time in which I would prefer to focus on and commemorate those who’ve had it much harder than I have. In terms of the world of business however, I think it’s a time to realize just how wild it is that entrepreneurship has been, and continues to be, so skewed against underrepresented communities. We need to get more capital and experience circulating within the community to help lift each other up. Advice is wonderful, but honestly what we often need is financial support, which many of us have built through family or friend networks. I think that having a month in which angels commit to hearing pitches specifically from trans founders would be amazing.

Connect with Finn on LinkedIn, and follow our blog on Medium for more founder stories like this!