“I feel a very strong ethical and philosophical obligation to be a part of the dialogue about transness today.”

My favourite food is: Artichokes My favourite car: I had a 1978 classic Subaru. I loved him deeply, but he's living a better life now

Finnegan Shepard

Creating a space where trans people feel normalized and celebrated.

RECOGNISING YOUR OWN POTENTIAL TO MAKE AN IMPACT. If nothing else, Finnegan Shepard wants to leave a legacy of multiplicity. “But not the millennial-hustle-burnout kind. I just want to live a life that's really enriched from a lot of different angles, I also think it's wonderful to make a mark by just leading a very holistically well-rounded life.”

It’s this non-linear approach to life that caused Finnegan to break out of the obvious career path laid out for him in favour of the unknown. After studying literary fiction and ancient philosophy, he assumed a career in academia was his only option. But as someone whose interests and skills range from etymology to canoeing and ceramics, it’s hardly surprising he faced challenges with the structure and limits of academic life.

“When I got into the startup world, it felt like this whole new vista of a space where my skills, temperament and personality could be used in a way that felt higher impact.”

Finnegan’s startup journey has deeply personal roots, tackling a problem that seemingly nobody had yet fixed. In summer 2020, after deciding to leave his first co-venture, a philosophy platform, he found himself back at his parents’ home. He’d left academia and had begun medically transitioning. “My whole life was very unmoored. One day, two months into healing from top surgery, and looking for a light at the end of the tunnel, I thought about swimming in the public pool. It was something I hadn't done in many, many years. I knew that swim trunks were never a good fit on me, so I Googled ‘trans swimwear’.”

The results yielded very little, bar one big discovery: that gender in fashion was dealt with almost exclusively at a branding or marketing level. Rather than a wholesale t-shirt embellished with the trans flag, he was looking for high quality clothing that actually fit the proportions of his body. “Suddenly, I found myself asking, can we create our own fit and sizing system? Can we produce clothing that creates the silhouettes for this demographic that they actually want?”

It led Finnegan to launch Both&, a transmasculine and non-binary fashion brand with inclusive design. Immediately, and perhaps surprisingly, the most requested item was in fact t-shirts. “I think people thought, if I could just have a t-shirt that actually fits me, that could make me feel euphoria year-round. So that's where we started.” With limited knowledge of the clothing industry, Finnegan set out to develop early prototypes and test them on the community. “Along the way, we met Amiram Assouline, a veteran designer and creative director in NYC who fell in love with the project and decided to come on board.”

LEAVING A LEGACY. At a time when trans rights are under what feels like a relentless attack, Finnegan’s hope for Both& is to create a space where trans people are normalised and celebrated. “I feel a very strong ethical and philosophical obligation to be a part of the dialogue about transness today. What I see is a real calcification on both the left and the right, and not a lot of space for nuance or dialogue.”

As Both& continues to evolve and develop its offering, Finnegan now feels comfortable with his unlikely entrepreneur status. “It really is the community's reaction that has got me going. The more I engage with the startup world, the more I realize that what it desperately needs are creative, rigorous, dynamic thinkers who are good at communicating and good at thinking through the problem from 360 degrees. For me, it aligns with how I want to spend my days and feel challenged. It’s daunting how much work there is to be done, but I also love that.”

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Presented with Pride Here is the first collection of one hundred incredible and inspiring LGBTQIA+ venture-backed entrepreneurs featured in this year's Gaingels 100.