Bio — Lylan Masterman

Lylan Masterman is a venture capital investor, Kauffman Fellow (Class 19), and former technology executive based in New York City. He is currently building Whipsmart Ventures, a fund making Series A and larger seed investments in SpaceTech and DeepTech startups.

Masterman was raised in Cornwall, Ontario — in the 1980s, one of the most polluted cities in Canada, with an economy based on pulp & paper (Domtar), paint (CIL), and textiles (Courtaulds). His father worked cattle farms, mine shafts, and city trucks: plowing snow in winter, laying asphalt in summer. His mother sold beauty products for Concept Now Cosmetics. A native French speaker and first-generation college graduate, Masterman earned a B.Math Honours from the University of Waterloo with a major in Computer Science and a minor in Combinatorics and Optimization, and holds an MBA from the Kellogg School of Management at Northwestern University.

Before venture capital, he spent 15 years as a technology leader. He was part of the team at Microsoft that built the first version of Visual Studio .NET, C# .NET, and the .NET platform. Five of his career-defining years were at Atlas, a division of aQuantive, acquired by Microsoft for $6.3 billion. He held operational leadership roles at four startups, including DoubleVerify (now a public company, NYSE: DV) and Figure Eight (acquired for $300M).

Masterman has been a venture capitalist since 2014, joining as one of the original six members of a then-unknown firm, White Star Capital (now over $1B AUM). He has led investments and served on the boards of eight companies.

His profile in the New York tech ecosystem grew through research, media, friendships, and recognition. He published a 47-page report on VC in NYC, authored The Entrepreneur Playbook for Sourcing a Lead Investor in NYC, appeared on Cheddar TV, and was named one of NYC's Top 50 Movers & Shakers. He is a vocal advocate for diversity in tech — his piece in Entrepreneur.com on bias against women became his most widely shared article.

Outside of work, Masterman is an avid player of one of the world's oldest games: backgammon. He plays fantasy football with the dedication of a general manager, and cheers for the Seahawks, Blue Jays, Habs, Raptors, and GSP.

He has lived in Cornwall, Waterloo, Toronto, San Francisco, Seattle, Chicago, and now calls New York City home.