Boston-Bound: Leaving USV and Next Steps
I’m leaving NYC for Beantown.
My fiancée Lisa and I just found out last week that she matched into an excellent residency program in Boston, so in June we’re going to pack up a UHaul, barrel along I-95, likely pass a monument or two along the way, and park it in Boston.
I write this post with bittersweet enthusiasm for the future. On the one hand, Lisa and I are excited to start our lives together in Boston. On the other hand, leaving Union Square Ventures is a difficult decision. Back in 2006 Fred and Brad took a chance on me: a young guy with no finance experience and not much direction. I was two weeks away from enrollment in a MS in CS at Columbia, thinking I should try to become a developer, when I tumbled over backwards onto my job at USV, through a blog post. I owe Fred, Brad, and Albert a lot for the confidence they had in me and the support they have given me as I have matured as an investment team member.
I have some great memories from USV, and it’s hard to walk away from working with people whom I feel share my values in both investing and, more importantly, how to live and prioritize life.
Professionally, working with USV’s portfolio companies and meeting amazing NY tech entrepreneurs has been an invaluable experience. When Charlie left USV four years ago, he described his experience as a MBA 2.0, which feels right in retrospect. With gratitude to USV for giving me access to their network and an education in VC, I look forward to continuing to foster the relationships I’ve made with the entire tech startup community from a new perspective in Boston.
From a practical perspective, I will continue to work with USV over the next few months (timeline is still in the works) in order to ensure a smooth transition for everyone involved.
So, what’s next?
I have not figured that out yet. One thing I’ve learned about venture capital over the past four years is that it fits the way my mind works very well. Mark Suster describes well the pros (and very few cons) of VC and investing in early stage startups. I agree with all his points, so I won’t rehash them, but I will elaborate on one. In VC you have the opportunity to see a variety of businesses from the 20,000 ft level, which is great for gaining general perspective. Then you get the chance to dive down to the 20 ft level with a given company or market sector for a week, and then come back up for air and start again in a different company/sector. In short, seeing many different businesses from multiple angles is perpetually intellectually stimulating, so my goal right now is to continue working in early-stage investing.
However, I’ve received good advice from a number of sources that I should make sure to take this opportunity to really evaluate and self-reflect on what’s going to make me happy and what kind of person I want to be. Therefore I am approaching this transition with a very open mind, and look forward to having conversations with as many smart people as possible in order to answer these higher-order questions.
What do I have to offer?
Behind my desk, I’ve seen roughly 70 equity transactions across a portfolio of roughly 30 companies in a wide variety of markets. I have met with many talented entrepreneurs and signed-up for countless web services in order to source new opportunities. I saw the VC fundraising process first hand when USV raised their second fund in 2008. I understand how to contribute to an investment team and work cooperatively within a venture partnership.
Additionally, I make it a priority to get out from behind my desk and meet both interesting entrepreneurs and startup communities frequently. My experience in New York will prove useful, particularly as more Boston-based firms stretch their roots southward in order to better access the New York market.
All my finance experience is self-taught on the job (with great coaching from Fred); my academic and professional background prior to USV is in product design and product management. As you can tell from prior posts on this blog, I always view a new market or news event through the lens of my experience in interaction design, and it has been relevant to me in the process of evaluating early-stage startup opportunities.
In closing I want to thank Albert, Brad, Dorsey, Eric, and Fred (alphabetically, because they’re all very important to me!) for the time and interest they have invested in me over the past four years here at USV. I look forward to my continued relationship with them in the future. I want to thank Lisa, who is always incredibly supportive of me - I can’t wait to spend the rest of our lives together. Finally, I’m excited to discover what Boston has to offer me and what I have to offer Boston.
If you’re interested in chatting or have some advice for me: ping me or comment below.
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