Kaitlyn Henry is a Vice President at OpenView Partners, where she focuses on infrastructure, security, developer tools, and data at the Series A and B stages. She also leads OpenView’s diversity, equity, and inclusion initiatives. She brings a history of partnering with technical teams and founders to the role, most recently as a senior financial analyst on Amazon’s machine learning team, and before that as the founding operations leader at an AgTech startup in Central California.
EVCA: How do you stay connected with and cultivate relationships with co-investors over time?
Kaitlyn: Focus on the relationships that allow you to be your most authentic self. I definitely go out of my way to meet new people on a regular basis, but I cut bait after the first meeting if we don’t naturally hit it off. This job can take a lot of energy, and your time is too valuable to spend it with people where you have to put on a front (no matter how good the deal flow might be). If the relationship feels easy, the more likely it is you’ll strengthen and maintain it over time. Hopefully the end result is a small, close set of peers that you genuinely enjoy spending time with and who can help you navigate the ups and downs of this job.
EVCA: What's your favorite thing about working in venture capital and why? How about your least favorite thing and why?
Kaitlyn: The best part is the ability to be constantly learning. There’s not many other jobs where you get to let your curiosity lead the way as much as venture. I’ve really been trying to lean into that lately, and use my natural sense of curiosity to be proactive rather than reactive in how I find great investment opportunities.
My least favorite part is how gatekept venture has been historically, and how that’s contributed to a pretty homogenous investor base. There are folks working on really great DEI initiatives at their firms or across the venture community, but broadly speaking I still don’t think these efforts are prioritized as much as they should be. Seeing the world in a unique way and diversity of thought in a partnership is a real defensible competitive advantage. I hope more and more firms start to see that, and lean into DEI initiatives accordingly.
Kai Cash is an Analyst at Primary Venture Partners and is a native of The Bronx. Kai focuses on investing in enterprise technology across all industries. Most recently, he was a Financial Rotational Program Analyst at Microsoft, where he aided in maintaining financial models related to Microsoft’s carbon tax revenues, carbon offset portfolio, and venture capital arm (M12). As a lover of Latin dancing, Kai spends his free time learning every form of Latino and Afro-Latino dance, from Colombian and Cuban Salsa to Angolan Kizomba.
EVCA: How do you stay connected with and cultivate relationships with co-investors over time?
Kai: I focus on having real conversations that extend beyond venture and creating spaces for shared vulnerability. I’ve found that relationships exist in conversation, and that the quality of conversation defines our relationships. I aim to build trust, understanding, and relatedness first. These are the conversations where people share the seemingly insignificant things like taste in music, favorite food, how many siblings we have, that time we got lost at an amusement park, or just how we are feeling with current events.
It’s this space that you enter into together where everything feels possible. Once possibility is in the air, there is room to talk about actions and collaborations.
It’s much easier to have these conversations while bowling, walking in a park, playing pickup soccer or basketball, or while listening to music. I find that most people want to connect again when it feels right if you feel right after a good conversation.
Tactically, I use an app called UpHabit which is a personal CRM, and it resurfaces contacts and relationships over time that I want to continue to invest in. I also think it's really important to be connected with underrepresented investors and so I’ve been consolidating a list to collaborate with.
EVCA: What's your favorite thing about working in venture capital and why? How about your least favorite thing and why?
Kai: For as long as I can remember, my singular obsession in life has been to realize a future where everyone and everything has an opportunity to contribute. I often think about what the world would look like if everyone got to ask their stupid questions, how different products and services would be with equity, inclusion, and reciprocity baked into the foundation of them. Working in venture capital is the closest thing that I have felt to making that a reality. I get to be educated by brilliant people every single day on how to make the world a better place.
My least favorite thing would be the flip side of that, which is watching as many brilliant people never get the chance to build. It’s an irrational thing to start a company, and the fact that there are large populations of people getting denied the opportunity to live their dreams and capitalize their business, based on nothing other than poor circumstances, is disheartening.
Further, on my own day to day I find it hard to shift from a mindset of finding reasons to say yes to a mindset of finding reasons to say no. My whole life has been about creating something out of nothing for myself and for my family, so when I see someone who is almost there and just can’t tell the story of their business well enough, I want to help them get across the line as much as I can. It doesn’t always work out that way though.
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