My First Six Months as a VC: SF vs. NYC

I’m coming up on finishing my first six months as a VC, and I’ve been reflecting on a number of things during the last few weeks. So, rather than keeping them to myself and a few close confidantes, I figured I’d think out-loud and jot them down, so to speak, in order to welcome feedback / advice / questions / etc.

The first post below details my thoughts on my move back to NYC after a year in San Francisco. I’ll publish a second post tomorrow on some learnings / takeaways / themes / etc. among investments I’ve sourced for Deep Fork, thus far. And, on Friday, I’ll write about challenges I have faced and am facing as well as some things that have surprised me so far.

As I mentioned in the initial post about my current role, my time in San Francisco was an amazing learning experience, akin to startup grad school, but I was excited to return to NYC and anticipated immediately immersing myself in the city’s startup community and the city itself. However, being back here has exceeded my expectations. I’ve been able to reconnect with people in the tech community whom I met during my first stint in NYC and have met numerous others, as I’ve come back into the fold fairly easily, primarily due to the collegial, collaborative, and inclusive nature of the city’s startup ecosystem.

My year in SF was the best possible (and essential) startup education, but, to be quite frank, it often felt like I was on a permanent work trip. My biggest gripe with SF wasn’t about “work-life balance” (I expect to work a shit load and love my job and the hours could never be as bad as banking)—it was about “tech-life balance.” Worrying about who overhears your conversation at Sightglass, explaining the startup at which you work while at a party (“I’ve never heard of Wanelo…what is it?”), making sure someone doesn’t look at your laptop when you’re reviewing a company’s AngelList profile or deck becomes exhausting. You need to work extremely hard to find a non-tech outlet in SF, and, if I’m honest with myself, I didn’t work hard enough to find one consistently. However, in addition to being closer to my family and long-time friends, what I love about NYC is the fluidity of being able to move seamlessly among industries and backgrounds and enjoy a balance naturally. Ultimately, I have become an ardent believer that personal happiness begets professional happiness (and success)—professional prowess can’t be a panacea.

Additionally, I believe that being in such a diverse environment, in terms of industries (i.e. finance, tech, fashion, advertising, etc.), people’s cultures and background, even neighborhoods, helps to make me a more well-rounded investor. On a daily basis, I am exposed to a wider array of ideas and concepts, tech and otherwise, in NYC than if I were based in SF full-time. Moreover, with a partner and portfolio companies and potential investments in SF, I have been returning to the west coast every 4 weeks since moving back to NYC. This bicoastal-ness has allowed me to maintain SF relationships, source investments outside of NYC (about a third of what I’m looking at is in the Bay Area), and be flexible when evaluating opportunities. For example, I sourced and we have backed at least one company in SF that would have had a harder time raising in NYC because it was “too early.”

Lastly, heading back to SF once a month is valuable not only for the reasons above but also because it’s a welcome change of pace from NYC. It’s a chance to loosen up a little outside of the tightly wound spring that is New York City. And more importantly, it’s an opportunity to quickly immerse myself in tech’s Mecca. Returning to SF requires leveling up in a variety of ways — it serves as a measuring stick of sorts — and I always welcome it. See you next week, San Francisco…