Whipsmart Ventures
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Lylan Masterman

Co-founder & Managing Partner

Lylan Masterman

Engineer-Turned-VC with a Deep VC Network

From building products to backing the founders who build them.

I am an operator turned investor, which is rarer in New York than in San Francisco. I spent fifteen years building technology before I ever wrote a check.

Background

I was part of the Microsoft team that shipped the first version of Visual Studio .NET, C# .NET, and the .NET platform, and I spent five formative years at Atlas, the software division of aQuantive, which Microsoft acquired for $6.3 billion.

In 2014 I took the risk of joining a then-unknown firm, White Star Capital, as one of its original six members. I helped build it into a global venture platform and became a General Partner of its $180M Fund II, where I held five board seats.

I am a first-generation high school and college graduate and a native French speaker, raised in Cornwall, Ontario, with a B.Math from Waterloo and an MBA from Kellogg. I back founders because I know what it takes to build the thing, not just to fund it.

I take a certain joy in being doubted. In 1997 I made my first online purchase, a pizza from a local shop paid for by credit card, and I told everyone that ordering online was the future. In 2016 I published a prediction that large language models would take off, while building some of the earliest chatbots. Now, in 2026, I believe we have finally reached the inflection point I had been waiting for: the marriage of software and hardware is the defining thesis in technology, and it is why I am investing in SpaceTech and DeepTech.

Get to know Lylan beyond the investor

Backgammon

An avid player of one of the world’s oldest games.

Fantasy football

Plays with the dedication of a general manager.

First-generation graduate

A first-generation high school and college graduate.

23andMe

23andMe changed my life in ways I never expected, and I love hearing other people’s stories.

The first movie I ever saw in a theater, or in my case at the drive-in, was Star Wars: Return of the Jedi. It turned me into the geeky kid coding on a Commodore, and ever since, I’ve known my career would end up in the software that powers space and robotics.