Lylan Masterman
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Lylan Masterman

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Venture Capitalist | Board Member | Technologist

Lylan Masterman – Fundraising and Trusted Relationships

“You regret the failure, but you know that you can take another swing at that.”

ABOUT

Lylan is an experienced operator, investor, and board member. As an investor over the last six years, Lylan has been a Principal, General Partner, and Venture Partner at White Star Capital and an Executive in Residence at Breakaway Growth. He has served as board member, observer, and advisor at several startups — Drop Loyalty, Unacast, mnubo, Salesfloor, Immunio, Digg — as well Raines International, a 50 year old executive search firm. Lylan previously led Product and Engineering organizations in his 15-year operating career, and most notably worked 4.5 years at aQuantive, acquired by Microsoft for $6.3 billion. Lylan is a Kauffman Fellow, an educational, networking, and leadership development program for venture capitalists.

He is a first-generation high school & college graduate and holds a degree in Computer Science from the University of Waterloo and an MBA from Kellogg School of Management. Lylan has lived in Canada, and the east and west coasts of the US and has called New York home since 2011. Lylan has appeared on live TV on Cheddar and TDAmeritrade Network, has been interviewed in Inside The Mind of a New York VC, his writing has been featured in Business Insider, VentureBeat, Entrepreneur, and Thrive Global, and he has been interviewed in the podcasts Something Ventured, Venture Studio, and The Successful Pitch. In 2019, Lylan was selected as one of New York City’s Top 50 NYC Movers & Shakers in technology and in 2020, Lylan was invited to the Quebec Government in New York’s 80 for 80.

REQUEST INTRODUCTION Arrow

THE FULL INTERVIEW

Lylan Masterman

The full #OPNAskAnAngel talk

Jeffery:
Okay. Perfect. Well, as we always do, we like to start right away by just having casual conversation. Make it nice and simple, clean and easy. So, Lylan, I’d like to, uh sorry…

Lylan:
Lylan.

Jeffery:
Lylan and I was going through. I’m like, which is the best way I want to make sure I won’t screw it up.

Lylan:
It’s on my Linkedin, actually, how to pronounce it. It’s on my LinkedIn. It shows how to pronounce it.

Jeffery:
I went on there, actually went on there to see if I could listen to the audio recording, and it didn’t show.

Lylan:
So my LinkedIn actually, my bio has a little blurb about how to pronounce my name.

Jeffery:
I went in because you can do the same thing now in Linkedin where you can see that you can press

Lylan:
Oh, you can record..?

Jeffery:
your button. Yeah, and you don’t have it, so it doesn’t say that. So I’m looking at it right now. And that’s why I was, um, here. I’ll show you

Lylan:
view profile.

Jeffery:
I went there specifically just to make sure you can look on my screen. You can see

Lylan:
Yeah. Yeah.

Jeffery:
It’s right beside your name that it shows it. It did not like, damn it. So I was already gone through all your videos, and I thought, maybe it’ll show there.

Lylan:
I wonder. I don’t know where to upload that feature. Where to upload the voice. The recording.

Jeffery:
That’s okay.

Lylan:
I’ll figure it out. Yep. I’ll fix that.

Jeffery:
Done. Well, either way, I didn’t want to butcher your name, So

Lylan:
yeah, the two tricks that I get my friends, if they’re into Disney characters, I’m the Lion King. Or if people are into alcoholic drinks, long island iced tea

Jeffery:
Island iced tea.

Lylan:
Yeah.

Jeffery:
All right, Well, welcome. Thank you. Uh, our podcast today. Ask an angel. Very exciting to have you today, um, for many reasons, but I’m going to start with the more prominent one is that you’re a Canadian living in New York so that’s pretty cool. And that always starts off a great conversation because we look for Canadians globally, and when we find them, they always seem to be, uh, the fun people that we get to have really good conversations with. But outside of that, um, there’s lots of other things I want to dig into, but maybe we start off by if you could give us a little bit of a background in yourself a little bit about where you kind of come from. And then where you’re kind of currently at now and then one thing about you that nobody would know.

Lylan:
Yeah. So I was born and raised in a city of 45,000 people called Cornwall, Ontario. Uh, at the time, when I was growing up, the big two employers in Cornwall, Ontario, were Domtar, which is a pulp and paper mill in CL Paint Factory. So it was really a factory town, and it’s bordering between Quebec and Ontario. So very much of a bilingual city. I was one of the few kids in class with an English name. Come time to go to undergrad. As most of my friends went to the local French speaking schools, University of Ottawa or Lavel etcetera. I decided to break away and go to the University of Waterloo, where I could study with a bachelor mathematics, major in computer science, minor and combinatorics and optimization. And really, the two key things that drew me to Waterloo were the strength of the academic program in the global ranking of the school, as well as a fantastic co op system where we do six co ops or by US terms internships. And my last two were in California at Cypress Semiconductors and then Microsoft Web TV. And then I continued to work for Microsoft first for Microsoft Research. Then I moved to Redmond, Washington, to be part of the team that built the first ever version of dot Net and visual studio dot net Microsoft.

Jeffery:
You’re the guy we need to go after about that dot net stuff. (inaudible)

Lylan:
You know, it was one of the most academically gifted teams I’ve ever been part of. Um, still, I was there 18 or 19 years ago, so the technology has evolved since then. Um, you know, one of the reasons that Microsoft suggested the dot net team for me was because one of my prior co ops was at IBM on the product that is now called Eclipse. It used to be called visual age for Java and visual age for small talk. And so and that was before IBM released Eclipse to the open source community. So yeah, Seattle was great. Was at Microsoft. And then I really had the itch to go to a start up. And so I went to a company called Ask Me. Ask Me product was similar to yammer, which was similar to what slack eventually became, and the difference. The key difference being that we did not know about the Freemium business model in 2003. The idea of giving your software for free to the enterprise with the understanding that at some point you’ll charge the enterprise that really didn’t exist much. And so at Asked Me, We’re trying to sell our product at a high cost per head. Um, and most of the enterprises really loved what we were building but could not justify the spend to sign on the dotted line with us. From there I stayed another Seattle based company called a EQuantive and specifically the Atlas Division of a EQuantive, and I had five of the best years of my care