An Operator & Investor

Investor,
builder,
technologist.

Venture Capital Investor since 2014. Head of Product & Engineering for 15 years. Proud New Yorker. Kauffman Fellow. First-generation high school and college graduate.

Lylan Masterman — venture capital investor and technologist based in New York City
$6.3B
aQuantive acquisition by Microsoft
2014
Began VC investing in technology
4
Startups with operational leadership
15
Years as a technology leader

SpaceTech & DeepTech

Investing in the technologies reshaping space, robotics, energy, and defense

Media & Speaking

Cheddar TV, media appearances, and speaking on tech M&A, IPOs, and startups

NYC Impact

Top 50 tech influencer, VC report author, and media speaker in New York City

Diversity in Tech

Published perspectives on the impact of diversity in technology companies

From building software to backing the people who build it.

The operator-turned-investor is less common in NYC than it is in SF. I made the transition in 2014, taking the risk of joining a then-unknown firm as one of its original six team members. I've now served as board member or observer on eight companies.

As an investor, I derive the greatest satisfaction when I have a direct 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.

Before venture capital, I spent 15 years as a technology leader. I was part of the team at Microsoft that built the first ever version of Visual Studio .NET, C# .NET, and the .NET platform — tools that millions of developers use daily.

Five formative professional years were spent at Atlas (AtlasDMT), a division of aQuantive — a big data and analytics company focused on advertising technology, which was acquired by Microsoft for $6.3 billion. That experience shaped how I think about data, scale, and what makes technology companies endure.

Whipsmart Ventures logo

Building Whipsmart Ventures.

I'm currently building Whipsmart Ventures, a fund investing in startups in SpaceTech and DeepTech that will transform our world. We focus on Series A and larger seed investments in companies where technology risk is proven and commercial inflection is imminent.

The thesis is simple: deep technology sectors — Space, Robotics, Energy, and Defense — are undergoing a software transformation. The companies that win will be the ones that apply modern software practices to domains traditionally dominated by hardware and legacy systems.

Visit Whipsmart Ventures

Whipsmart invests in startups where software creates defensible advantages in industries with massive TAMs and long innovation cycles.

Space Robotics Energy Defense

Board member, advisor, and observer.

Companies where I've held a board role:

Drop Loyalty

Board

Unacast

Board

Mnubo

Board

Immunio

Board

Salesfloor

Board

Panoplai

Board

JunctionConnect

Board

Raines International

Board
Lylan Masterman — casual portrait

Let's Connect.

Whether you're a founder, fellow investor, or simply want to connect.

Founders

Building at the intersection of software and deep technology? Let's talk about what you're working on.

Investors

Fellow VCs, LPs, and allocators — always happy to connect and exchange perspectives on the market.

Media

Available for commentary on venture capital, technology M&A, and the NYC startup ecosystem.

Speaking

Available for keynotes and panels on venture capital, deep tech investing, the operator-to-investor path, and diversity in technology.