Title:GTA Alumni Spotlight: Catherine Henry Diffley (C’11)

Meet Catherine Henry Diffley (C’11), Director of Platform at AlleyCorp!

AlleyCorp is a New York-based venture capital firm that incubates and invests in companies across consumer and enterprise tech, healthcare, and other industries. Catherine oversees how AlleyCorp shows up across the tech ecosystem and strengthens the firm’s relationships with founders throughout their portfolio.

What influenced your career path in the tech industry?

I had an unconventional path into tech. After an incredible experience with Georgetown’s art history department, I began my career in the art world at Gagosian Gallery. A few years later, I joined a growing art/tech startup called Artsy, which is a global marketplace for buying and selling art. I spent five years there during a period of rapid growth, from about 40 employees to about 200 employees. I fell in love with the momentum of the tech industry –– the focus on constant iteration and change was a stark contrast to working within the traditional systems of the art world.

At Artsy, I became fascinated by how startups are built. That curiosity led me to join the founding teams at two startups: Resident, in hospitality, and Parlor, another in art/tech. Building from the ground up and fundraising from VCs gave me firsthand exposure to early-stage investing, and ultimately brought me into venture capital.

What does the day-to-day look like in your current role?

Being the Director of Platform at a VC means that no two days are alike. You might be planning an industry conference, developing a strategy to reach a specific founder niche, supporting investment partners with thought leadership, or working directly with portfolio companies to connect them to resources as they grow. 

These days, I’m laser-focused on launching an exciting project: a new building in the Nolita neighborhood of NYC that will serve as both AlleyCorp’s new HQ and a central hub for the broader tech and VC community in New York. It will house other VC firms, multiple event spaces for industry events, a new restaurant concept, and a bakery. An unexpected bonus of launching this real estate and hospitality project is the chance to tap into my art knowledge again as I help lead some really exciting contemporary art acquisitions for these spaces.

What do you wish more people knew about the tech industry?

I wish more people knew that tech is an amazing place to land if you consider yourself a creative, or even an artist. People are often surprised that I moved from the art world into venture capital. I see a throughline very clearly, because working with entrepreneurs is so much like working with artists: like artists, the best founders are visionary, creative, obsessive, and idiosyncratic. The cliché is true: early-stage investing is much more about ideas, people, and opportunities than it is about spreadsheets.

I’ve found that getting to spend your days learning about cool new ideas is more creatively energizing than many of the jobs you can find working at big art galleries or fashion magazines. Taking the leap on a startup, whether as a founder or early employee, is of course a deeply creative endeavor as well.

Creatives I meet are often intimidated about moving into tech or finance, but I firmly believe that a unique way of seeing the world, as creatives and artists often have, is tremendously valuable in this industry.

What is your favorite app or website, and why?

My favorite apps extend our online world into the offline world. One that’s evolved as a powerful community builder recently is Substack –– it’s become one of my most-used apps, and the way I use it has changed.

I spend a lot of time reading various newsletters, and a few writers have started building real communities within their newsletter niches –– inviting readers to participate in discussions and meet up IRL. I recently attended a really fun book club organized by a writer that I follow, and it was full of interesting people that I wouldn’t have otherwise met. I even ended up contributing a guest post that resulted from a discussion in the newsletter’s group chat.

What aspects of your time at Georgetown inspired your career journey into tech?

My time at Georgetown was all about falling in love with art –– even though I originally planned to study Government. The art history department at Georgetown is small but exceptional. I was fortunate to study with wonderfully inspiring professors who were also established curators, like Professor Elizabeth Prelinger. Access to all the major museums in DC meant that I rarely had to write a paper about an artist or artwork that I couldn’t go see.

At Georgetown, I figured out that I wanted to spend my life working with creative people. I would have been surprised if you told me then that this would eventually mean working with tech entrepreneurs.

What is one quick piece of advice you would give to a Georgetown student that is interested in tech?

Become a power user of at least one or two AI tools. Right now, even industry veterans can’t really predict where AI is going, and learning how to use the tools yourself is a free and easy way to gain an edge. If you are looking to join a startup, you should be prepared to talk about how AI tools will improve efficiency and reduce cost. If you are looking on the investment side, you should have a perspective on how early-stage companies should be using these tools and where we are on consumer adoption. The best way to do that is to know how to use the tools yourself.

And more broadly: try out every possible seat in the ecosystem. Get operating experience at a startup (this will help you no matter what you do in tech), explore the investor’s vantage point at a VC internship, experiment with both big and little tech. Firsthand experience is the best way to figure out what role within the ecosystem resonates with you and where you can add the most value –– it might end up being different than you think.

For more GTA Alumni Spotlights, click here.