My Path into Venture Capital

And my future articles

I’m a Venture Capital investor at White Star Capital, which invests in Series A technology startups (and some Seed and some Series B) across both sides of the Atlantic.

I enjoy being one of a small number of NYC-based VCs with real tech chops, having been groomed by the rigour of the University of Waterloo’s Math and Computer Science program.

It’s as a University of Waterloo student in the 90’s where I started working for Microsoft, first as a co-op software engineer on WebTV in Mountain View California, then Microsoft Research where I did tech evangelism (Embedded PocketPC developer tools and C# Beta) and where I had a VC-ish role supporting the Waterloo entrepreneurs that I determined to have the most potential, then in Product in the first ever Microsoft .NET team. With a yearning to work in the early stage, I joined a startup that won a Corporate (ie: B2B before such a term was popular) Newcomer of the Year Award and that could have been a huge success if the freemium business model would have been better understood in 2003. I then had the operational experience of a lifetime in the Atlas division of aQuantive. In my close to 5 years at Atlas, we doubled (or more) the business every year. I learned how to scale a business. I wore more hats simultaneously than I thought was possible (Product for Rich Media, Product for Targeting, I18N, and UX). Then we were acquired for $6.3 billion by Microsoft. It was a great way to end such a fantastic time of personal and professional growth.

With Microsoft experience already under my belt, I decided to go to Kellogg for my MBA and began to focus on Venture Capital. Mark Fernandes and the amazing team at Sierra Ventures made an exception for me and took me in for the summer. Then, following the advice from some VC mentors, I went back to operating roles into Director and VP roles at three NYC startups, where I managed Product teams, UX, Technical Writing, and a large engineering team. It’s at these startups where I redeveloped my early stage chops, where some of the challenges include hiring great talent without a known brand, where boards and management teams need to be aligned, where together we define the company culture that can last a lifetime, and where building for the longterm while achieving short term goals necessary for raising the next round should be one-in-the-same, though it’s sometimes a challenge to balance both needs!

Then in early 2014 I was introduced to Eric Martineau-Fortin at White Star by a fellow NYC-based VC (who I very much want to co-invest with sometime soon!) Eric and I immediately recognized that while we have some similarities, our differences were the reasons that we had to work together. We normally look at companies from different lenses: he’s a former investment banker with a solid angel track record and natural edge on FinTech, and I’m a CompSci & Product geek with solid knowledge and expertise in IoT, data science, and scaling technology businesses. We bring different value-add to our portfolio companies. We’ve been influenced by the cultures of different cities — he in Montreal, Los Angeles, Paris, London, Stockholm and me in Waterloo, Toronto, Seattle, Chicago, San Francisco. This is the way our whole team at White Star works across three different countries: complementary skill sets, different lenses, different value-add for portfolio companies, different origins and backgrounds.

I love being a VC and I plan to continue being a VC into my 40’s (coming soon… gulp!), 50’s, and yes even 60’s and 70’s. Every day is different. The intellectual diversity is what I most enjoy about being a VC. And of course the passion of entrepreneurs, the challenge of being helpful to companies while not being on site day in and day out, and the opportunity to take diversified risks. Ultimately, as the Kauffman Fellows as well as my professors at Kellogg instilled in me, the human element is the most important aspect of Venture Capital and it’s the one I value most.

What I Will Write About

I’ve been using Twitter to share articles and thoughts, but now I want to have a longer form platform.

Over the course of my articles, I plan to write about many of the following areas that I am passionate about:

1. My atypical perspective as a tech-geek in NYC VC
2. Geo-specific analysis of entrepreneurship & VC: I will likely focus more on NYC & Toronto/Waterloo because I have amazing colleagues who cover Montreal, London, Paris, Stockholm, Berlin.
3. Internationalization, global expansion, strategic geographic growth
4. My alma maters: University of Waterloo, Kellogg School of Management, and my beloved Kauffman Fellows
5. Computer Science, highly technical startups, and startups where technology is an important competitive differentiator and barrier to entry
6. The growth of the Canadian startup ecosystem, given that I am a proud Canadian living in NYC who sees potential for outsized returns by being an international investor into Canadian companies
7. White Star investment areas: IoT & Algorithms, Disruptive Commerce, FinTech. How data and AI affect all 3 areas. Also, the disruption of large non-tech companies is an area that I will discuss.
8. Advice & best practices to entrepreneurs on fundraising, scaling a business, running effective board meetings. Also, some “open the kimono” thoughts on VC, on topics that have not already been discussed by the likes of Fred Wilson, Brad Feld and Mark Suster.
9. Self-improvement, self-reflection, introspection. Career-building in VC.
10. Perhaps even some personal stuff, including meditation, smoothies, improvisation, Montreal Canadiens, mixology, pointed-toe shoes, and my last year before turning 40.

In most posts I will end by asking something of readers at the end of the posts. This practice is one I learned to appreciate from the Kauffman Fellows.

My Ask

If you would like to partner to co-write an article, let’s work together! I am already working on some interesting collaborations, and would welcome the opportunity to add more value to the ecosystem by tag-teaming with many of you.

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Lylan Masterman is a Kauffman Fellow and a Venture Capital Investor at White Star Capital, an early-stage Venture Capital fund backing exceptional entrepreneurs with global ambitions. www.whitestarvc.com