How Seed Investing Prepared Me to Invest at Later Stages

Just over four months ago, I took on a new role investing in Series A and later companies after spending nearly three years investing in seed stage startups. While there have certainly been a number of differences to contend with while investing at these later stages, for a variety of reasons, I believe that seed investing was great prep for the investing I’m doing now. Here’s why: When I invested at the seed stage, I always had to be “on,” or at the very least, I had to be prepared to turn “on” at any moment. I always needed to be prepared to look for or respond to the latest startup given the sheer number of companies being started and the high velocity of deal flow. Consequently, I was meeting more founders and making more investments per year, which ultimately served as great preparation. There is no substitute for meeting Continue reading "How Seed Investing Prepared Me to Invest at Later Stages"

My VC Code 2.0

Nearly a year ago, I wrote my original VC Code post, in which I outlined how I approach my role as an investor. Given that I recently started a new role at a slightly later stage fund (Series A — C, primarily) and that I have another ~year of investing under my belt, I figured it was time for an update to my original post. What follows is a slightly amended version of my original piece that takes into account investing at a later stage and what I will do in this new role. Being a VC and getting to work with entrepreneurs on a daily basis is the ultimate privilege. So, the purpose of this piece is to 1) enable founders with whom I meet to know what to expect from me prior to meeting, thereby allowing them to ask more specific (e.g. helpful) questions when we chat and start Continue reading "My VC Code 2.0"

In 2016, Everyday Is Picture Day

Gen Z and younger Millennials have been referred to as digital natives who grew up in front of screens, and the implications of that have been discussed ad nauseam. However, and more interesting, in my opinion, is the fact that this population has grown up in front of (and behind) the camera. This generation is like a group of child stars, surrounded by paparazzi in the form of their parents and peers. This unusual comfort being on camera has informed which products and apps get traction and which features resonate with users. Moreover, I believe it’s important to consider the implications of an entire generation that has such ease in front of and behind cameras. For me, on the other hand, growing up in the ’90s and early ’00s, pictures were reserved almost exclusively for special occasions and distinct moments that were worthy of being captured. Quite simply, I could Continue reading "In 2016, Everyday Is Picture Day"

What I’m Interested In Right Now

Throughout my two-plus years in venture, one of the most common questions I’ve been asked (in some form or fashion) is, “what sectors / spaces / types of companies are you interested in right now?” And whenever I’ve been asked this question, I typically give a non-committal answer or mention how I think consumer internet continues to be an area that investors struggle to develop conviction at the pre-seed / seed stages, so I think there’s an arbitrage opportunity of sorts there (and I still think that). However, generally, I have found that it’s difficult to be too thesis- or thematically driven at the pre-seed to seed stage of investing. First, oftentimes, themes haven’t emerged yet, and, second, I believe this approach can lead to deductive investing. By that, I mean you meet with lots of companies in a space and settle on investing in the best option because Continue reading "What I’m Interested In Right Now"

Keyboards: A Key to Owning Mobile

Now that Google and to a lesser extent, Microsoft, have both released iOS keyboards within the last month, can we please begin to take these things seriously? Since the release of iOS 8 and Apple’s concession to allow 3rd party keyboards, they have consistently been the ugly duckling of the App Store.
Thanks to the emoji keyboard, a significant proportion of iOS users are familiar with the concept of an extra keyboard — it’s like the gateway drug to installing more. However, keyboards are still 2nd class citizens in the App Store for a number of reasons. Partly, it’s because they’re hard to install and manage. Nearly every 3rd party keyboard has a “how to install this thing” as part of its on-boarding flow. When it comes to this issue, it’s on Apple to make it less painless. iOS has improved a bit when it comes to switching between keyboards, but the Continue reading "Keyboards: A Key to Owning Mobile"

My VC Code

Over nearly two years in venture, I’ve had nearly a thousand first meetings or calls with entrepreneurs. In virtually every one, I share some background on Deep Fork, myself, and how I spend time with founders to help give them meaningful context for our conversation and potential relationship working together. Below, I outline my personal code / principles / standards that I comunicate in these conversations and strive to follow before and after an investment I source / lead for us, and how I do my best to achieve this task. Some may seem basic and table stakes, and to be frank, much of it is. But I’ve heard far too many stories about VCs not doing these little things for me to take them for granted. By publicly putting this on “paper,” I hope to accomplish a couple objectives: 1) enable founders with whom I meet to know what Continue reading "My VC Code"

The Art-Technology Paradox

As someone who grew up playing competitive tennis and now works in venture capital, I’ve become quite used to objective results: the ball is in or out; an investment was successful or it wasn’t. These are objective, binary outcomes. As someone who appreciates art, I’ve often grappled with trying to understand the subjectivity that comes with evaluating a piece and assessing the art market, in general. To sate this curiosity, I even took a class in business school entitled “Entrepreneurial Leadership in the Creative Industries” — essentially a course on entrepreneurs and creators that changed the worlds of music, fashion, food, film, and art. Throughout my time in venture, I’ve continued to be fascinated by these creative industries and their overlap with technology, whether it’s looking at new types of brands, analyzing the evolution of creative networks to social networks, or, in this case, thinking about how technology influences the creative process Continue reading "The Art-Technology Paradox"