Suggestions
Lylan Masterman
Venture Capital Tech Investor | Board Member | Product & Engineering Lead | Scaled to $6.3B Exit to Microsoft
Lylan Masterman is a venture capital investor and former head of product and engineering with a career spanning over 15 years in operational roles and six years in venture capital.2 He is currently associated with White Star Capital, where he focuses on late Seed and Series A investments.13 Masterman is a Kauffman Fellow and has been involved in various startups, contributing to their success through his roles as a board member or observer.2
Before his venture capital career, Masterman worked at Microsoft and aQuantive, where he played a significant role in the development of Visual Studio .NET and other products.12 He transitioned into venture capital after completing his MBA at Kellogg School of Management and initially joined Sierra Ventures as an intern.3 Masterman is recognized for his contributions to the New York City tech scene and has published insights on venture capital and diversity in technology companies.2
Highlights
I think the startup world has become a little too obsessed with speed.
Launch in a weekend, ship 10 features a week, build an MVP in three hours, and apparently you’re the next unicorn.
It’s impressive how quickly people can build software now, but nobody seems to talk about how quickly they’re building things nobody asked for.
AI has made writing code dramatically cheaper, but it hasn’t made understanding customers any easier.
You can build 20 products this month and still have absolutely no idea what people need.
The bottleneck in startups isn’t writing code anymore. It’s figuring out what’s actually worth building.
Shipping faster doesn’t help much when you’re going in the wrong direction.
I think one of the most overrated things in startup fundraising is the “strategic investor.”
A big corporation wants to invest $2M in your seed round.
Amazing. They have thousands of customers, a massive sales team, and relationships you could never build yourself.
Except six months later, you’ve had 14 meetings, met 23 people, and generated exactly zero revenue.
Your champion got promoted. The partnership team got reorganized. Legal is still reviewing the agreement.
And everyone keeps telling you how excited they are.
Corporate investors can be incredibly valuable. Some genuinely open doors and accelerate growth.
But founders need to ask one simple question before taking their money:
What are you actually going to do for us that you wouldn’t do if you weren’t an investor?
If the answer is vague, congratulations.
You didn’t get a strategic investor.
You got a very large company on your cap table.
