Inside the Mind of a New York VC

Earlier this summer, I sat down with Bart Clareman of AlleyWatch for a wide ranging interview. We talked about my accidental path to venture, the evolution of the tech ecosystem in NYC over the last decade, my human-centric approach to investing, how Primary provides a unique approach to supporting our founders and much more.

Below is the full transcript of the conversation. Enjoy!

Bart Clareman, AlleyWatch: Tell us about your journey into the venture business and how you came to be a partner at Primary Ventures?

Steve Schlafman, Primary Venture Partners: I would say that I didn’t really have the desire to become a venture capitalist, it all happened by accident. I was in the right place at the right time at a few points in my career. Luck and serendipity have definitely played a big part. I started my career at Microsoft, interning for six months on the Deal Governance team, which monitored all the strategic investments that Microsoft had made in the dotcom era. That was really my first exposure to the venture capital business.

After graduating from Northeastern University, I went back to Microsoft and spent four years working in Redmond [WA] and living in Seattle. The first two years was in a corporate finance-leadership rotation program where every six months I would rotate into a new area of finance. Then I spent two years effectively doing strategy and M&A for the Microsoft Business Division, which was responsible for Microsoft’s Business Applications such as Office and SharePoint.

After nearly five great years at Microsoft, I wanted to move closer to family and friends – I’m originally from Boston – and I wanted to get a taste of the startup life. That brought me to New York for a first tour of duty here in the city. I worked for a company called Massive, which was an advertising network for video games. It was the first ad platform for connected consoles and PC games. We worked with some of the largest publishers, including EA, Activision, and others, and served ads into games like Call of Duty and Madden. In this role, I was able to marry two of my passions: new media and video games.

I was about one year into my job at Massive, when an unexpected opportunity literally fell in my lap: I had a chance to move home to Boston to work for The Kraft Group. They own and operate the New England Patriots and a number of other businesses in sectors ranging from paper and packaging to real estate. My role at The Kraft Group was to support Mr. Kraft and his son Jonathan, who is the President & COO, on a variety of strategic projects that ranged from venture investments all the way through to digital media strategy to incubations to acquisitions and even random one-off projects. It was a perfect blend of investing, operating and strategy roles. I have to admit for a while it was my dream job. During this time, we made a number of direct investments into startups as well as some venture funds. This was my first real taste of the venture business. I owe a huge amount of gratitude to Mr. Kraft and Jonathan for giving me a shot. At the time, I didn’t really know what I was doing.

While I was at The Kraft Group, we made a number of investments and strategic partnerships with companies in the New York ecosystem. I saw first-hand the burgeoning community that was growing here and I wanted to be a part of it. It was impossible to ignore all of the startups and innovation that was happening here – around 2009 and 2010. As much as my wife and I loved being in Boston, we both knew New York was where we wanted to be long term. You could just feel the wave that was coming. Betaworks had just gotten formed, there were a handful of relatively new funds and some incredibly innovative companies were being started like FourSquare, Tumblr and Kickstarter to name a few.

I was recruited by Seth Goldstein and Billy Chasen to join an early startup as effectively the first business hire. It was called Stickybits, and it was backed by First Round Capital and Chris Sacca and a bunch of other well-known angels. I was effectively responsible for Business Development, Finance and other admin functions. I helped broker partnerships with Pepsi, Ben & Jerry’s, Unilever, Toyota and some other amazing brands. About nine months into my time at Stickybits, we pivoted into Turntable.fm, so I lived through that whole experience. It went viral, but I ultimately didn’t want to be in the music business for a whole bunch of reasons. I like to joke that all of our servers were named after dead music ventures, so that was kind of the writing on the wall.

At that point, I had the very good fortune of joining Lerer Hippeau as the first investing principal. At the time it was four partners and an admin, and they brought me in to help build out a lot of the infrastructure for managing the deal pipeline and the support platform. It was a wild time.

I was at Lerer for roughly 2.5 years. While I was on the team, we made about 100 investments, 40-50% of which were in New York, the other half were spread throughout the rest of the country. We invested across every sector imaginable, including e-commerce, software as a service, hardware, healthcare, media, marketplaces, and everything in between.

After an amazing run at Lerer, I was recruited to join RRE Ventures to focus not just on Seed but also Series A. I figured it was a great opportunity to see which stage of investing, Seed or Series A, was right for me in the long term. I knew I loved Seed investing from my time at Lerer – we were effectively making an investment per week, if you can believe it. At RRE it was a more traditional Series A fund, where we made two to three investments per partner per year and no more than ten per year for the entire fund. Essentially, I wanted to know whether Seed or Series A investing was more compelling to me if I was going to make a career in venture capital.

My four years at RRE were incredibly productive. During that time, I sourced more than twenty investments and was on the Board of a handful of those companies. I was fortunate to partner with a pretty eclectic group of founders and companies, including Boom Aerospace, Bowery FarmingHightower (which merged with VTS), Giphy, Brightwheel, Managed by Q (sold to WeWork), Breather, Groups, theSkimm, Care/of, Citizen – those are some that come to mind. While I was there, I also made a number of angel investments in companies like Zipline and Lola.

I left RRE roughly 2 years ago. I took a year off to find myself and figure out what I wanted to do with the rest of my life. I actually considered leaving venture altogether for a variety of reasons. About three months after I had left RRE, I went back to school to get trained and certified as an executive coach. I just love nothing more than helping founders and executives in transition bring their visions to life.

After months of reflection and soul searching, I decided to join Primary Venture Partners which is one of the top seed funds here in New York City. I initially joined as a Venture Partner which allowed me to focus on both investing and coaching. But after three months, Ben and Brad convinced me to come on board as the third partner. I’ve now been at Primary for about fifteen months

My mission and my life’s work is to marry venture capital with human capital. The venture capital comes from deploying capital into companies, and the human capital comes through the leadership coaching and really focusing on a human approach to not only picking companies but also partnering with founders to help them navigate the everyday challenges of company building.

You’ve been in New York City’s venture investing community for nearly 10 years. How has the ecosystem here changed in that time?

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Why I Invest

Last Friday night after a long week, I decided to go for a long run and listen to a Buddhist lecture on the true nature of existence and the self. About ten minutes into the run, I started to contemplate why I have chosen various paths in life such as becoming a venture investor. Since I have decided to make this my life’s work, I began to examine what really drove this long-term decision and whether I was being honest with myself. As soon as I returned home and showered, I opened up my computer and published the following tweet.

Ryan Hoover of Product Hunt was the first to reply and suggested that I expand on the tweet and provide commentary and context on each one. I hadn’t considered writing a post, but ultimately decided it would be enlightening and cathartic to dive into each reason and expose myself.

Below is an expanded view into all the reasons that I have chosen VC as a career. I’ve also tried to be honest about what drives me. While this list captures how I feel today, I’m sure it will evolve over time as I learn more about myself and my worldview changes.

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