Essential Thinking with Michael Dempsey

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Essential Thinking is a series that captures the thoughts, routines and attire of unique New Yorkers.


Essential Thinking | Mike Dempsey | Tech Investor | West Village

Tell us about yourself, Michael.

I’m a Partner at Compound, an early-stage venture capital fund. I mostly focus on investing in “frontier technology” areas, so categories that will shape our future in a big way but aren’t quite developed yet like VR/AR, driverless cars, robotics, drones, synthetic biology, and more. I spent a lot of time looking at venture capital as an industry and realized that few people were investing in deep technological problems or contrarian/early areas. I love this focus because if only one of the categories actually come to fruition, it will have a large impact. I also like that these areas scare a lot of other investors away.

When I’m not investing I write a fair amount, run on the westside highway, and play basketball.

I’m also a big cocktail nerd and kind of a foodie so I like to try out new places as often as possible. I once built an SMS (text) service so that friends/friends of friends could text a number and get food/drink recommendations throughout NYC from me. It was really fun while it lasted but was a bit too much to manage independently.

I’ve lived in the West Village for almost 8 years now, and wouldn’t live anywhere else. Some of my favorite places for a drink are Little Branch, BoBo, Death & Company, Amor y Amargo, Dram, Donna, Maison Premiere, and Dead Rabbit. I’m also increasingly on the hunt for the best breakfast sandwich in NYC. Right now, that’s White Gold, but open to suggestions.

What are the first apps you look at / listen to / read / rely on when you wake up? Has that changed over the last few years?

In the morning it’s a combination of twitter, email (via Spark mail), Tumblr, and Snapchat. I’m pretty intense about reading my RSS feed so I try not to do that on my phone until I get situated for work. Then I use Feedly.

There’s a quote somewhere on the internet that I’ll paraphrase but it goes something along the lines of “Twitter is where you go to find information, Tumblr is where you go for inspiration.” I think that’s true and that’s why I always go to Tumblr in the morning. It balances me out along with Snapchat (I haven’t gotten to the point where I follow celebrities and such, so it really is just a feed of my friends doing random things).

In terms of behavioral change, I used to be a lot less tied to email but then you grow up and email and your calendar become a larger part of your life than you had ever anticipated.

I also used to be even more intense about reading and seeing everything (aka Feedly/Twitter). It partially had to do with work and being exposed to the stock market at my first job, but also just the naive thought that exposure to everything meant knowledge. I now prefer to go deeper on subjects and so I removed a lot of the standard publications from my RSS feed.

If you're not in the office, what are your favorite places to be productive? Do you have certain favorite spots in the city?

As insane and privileged as it sounds, I’m really not a fan of being in an office. Because of this, a large portion of my work is done at home in my apartment. I have a desk in my room, but I mostly just sit at my dining room table and have come to really love it. When I’m not working from home my favorite spots are Toby’s Estate on 7th ave and Merriweather on Hudson St for laptop work, and the west side highway if I’m going to read something for awhile.

If I happen to be in Brooklyn, Devocion in Williamsburg is 100% the go-to spot. It’s massive and bright and beautiful, and the coffee is great.

When do you feel most comfortable wearing undershirts?

I usually wear undershirts when I’m dressing up and wearing white shirt with a suit (this happens maybe 1x/year) and then casually just lounging around. If we’re getting super detailed, occasionally I’ll wear one underneath an open button down or a sweater. They are one of those essential pieces that I never think about but can wear whenever.

How does your profession dictate what you wear, and how does that differ when you have an in-person meeting with an Entrepreneur versus another Investor?

Luckily, working in tech I can wear (almost) whatever I want. Generally some combination of t-shirt/button down, jeans/chinos, and sneakers. I’m not too worried about dressing up most of the time, so my clothing pretty much stays the same no matter who I’m meeting with/what I’m doing.

I think there’s a bit of a cultural divide in VCs that dress up vs. the rest of the tech industry. It gives off a weird buttoned-up, conservative vibe that feels super un-relatable. In reality, we’re all in the trenches, and we’re playing just a slightly different game than startups that we invest in. But maybe I’m super jaded about that stuff so who knows?

What is your idea of a successful morning?

Mornings are increasingly about starting the day off the right way vs. just getting going/to a meeting. What I mean by that is -- I try to wake up and spend time making coffee and reading something non-clickbaity/mainstream tech-y. I think about how I can be more methodical about doing things that put me in a good headspace for the day. That can manifest itself in a morning where I can get some sort of physical activity in, where I learn something new, or just have a good conversation.