Lylan Masterman

An Operator and Investor

A Venture Capital Investor for 6 years, a head of Product and Engineering (and other operational roles) for 15 years. Proud New Yorker. A media speaker and content author. Highly attentive to diversity. First-generation high school and college graduate.

Six years of VC investing in technology startups that aspire to scale, improve economics, and build lasting companies

The operator-turned-investor is less common in NYC than it is in SF. I made the transition in 2014, where I took the risk of joining a new then-unknown firm, where I was one of the original six members of the team. I’ve now served as board member or observer on six companies. As an investor, I derive the greatest joy when I have an impact on a company’s success.

I’m equally honored to have participated in the Kauffman Fellows program – I’m still a proud alumnus and I participate in their events as much as possible. 

I’ve raised capital from Limited Partners, from sourcing to closing. Fundraising is a critical part of being successful for most VC firms.

15 year career as a technology leader


Headed up multiple product lines (often simultaneously), user experience, and internationalization.


Startups where I had operational leadership roles

It’s by being in the weeds of working at a startup that some investors hone their sense of what makes a successful company.


Release of world-acclaimed product

I was part of the team at Microsoft that built the first ever version of Visual Studio .NET, C# .NET, and the .NET platform.

Impact in New York City Technology, Startups and Venture Capital

NYC Top 50 movers and shakers

I'm honored to have been selected to this list of NYC's top 50 NYC tech influencers.

State of Venture Capital in NYC and US East Coast

I led the publication of a 47-page report on the state of Venture Capital in NYC

Entrepreneur's Guide to Finding a Lead Investor in NYC

As a response to the most common challenge I heard by NYC's startup CEOs, I published this article to address their biggest need when fundraising: finding a lead investor.

Inside the Mind of a NYC VC

I shared insights into many facets of VC, including career progression, verticals of interest, fundraising from LPs, and more.

My approach is to have a candid, genuine, thoughtful demeanor. To speak on topics where I have helpful insights. And to try to express my thoughts in a way that is helpful to a wide range of audience. Ultimately, the goal is to continue building my firm’s brand through this exposure.

Innovation in batteries, mining, agriculture, construction/buildings, hydrogen, carbon, water, ESG, and other related areas will improve the world, or at least slow the pace of damage

I was raised in Cornwall Ontario, which was in my youth in the 1980s one of the most polluted cities of Canada. The economy was based on highly-polluting factories: pulp & paper (Domtar), paint (CIL), textiles (Courtaulds). The rate of hospitalization for asthma was double that of cities such as Hamilton, Sudbury and Windsor. I remember days that school was cancelled due to the polluted air and when we were told to not drink our tap water. 

My grandfather worked at Domtar. My mom worked at Courtaulds. Until his 30s, my father was a cattle farmer and then a miner in the mines of Sudbury. 

The world is changing. I am part of this transformation.

A postcard of my hometown, early 1980s

Attentive to the impact of diversity on technology companies, I have published my unique views on the topic in major media outlets For Women in Tech, Bias Runs Deeper Than Most Think

My most shared published content on social media. In this article, I took a strong position on one of the most rare forms of diversity: highly technical women by education who are founders of highly technical companies.

Thrive Global: Women In The Boardroom: We Know They Are Great CEOs, But They Are Great CTOs Too!

I approached my dear friend Jay Rosenzweig to co-write an article with me: he is a thought leader on female diversity, and I have a passion for seeing more diverse people in technology. We are proud of this content that focused on the most under-represented CxO level role for women.