TSP075 | Lylan Masterman – Transcription

TSP076 | Dan Weinfurter – Transcription
TSP074 | Laura Rittenhouse – Transcription

John Livesay:

Today’s guest on The Successful Pitch is Lylan Masterman, who is a VC at White Star Capital. He talks about the importance of branding yourself and branding your company that they have to be in line. He said, “What are you doing for your personal brand that can make you memorable?” Whether it’s something you wear or something you are known for. He said, “It’s not enough just to be nice, you have to be nice and helpful.” He said, “Everything going on talks about investors love to invest in people that have a passion for what they’re doing.” He says, “Tell me a story that gets me excited. It doesn’t have to be something that’s necessarily an exciting product, money is sexy just in itself.” So have your passion for what you’re doing. He’s personally in passionate about the internet of all things, and tells us some really fascinating things that are coming down the pike as it relates to that.

The interview begins in 45 seconds right after this information on how you can get funded fast.

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Hi and welcome to The Successful Pitch podcast. Today’s guest is Lylan Masterman, who is a venture capital investor at White Star Capital in New York. He has primarily focused on late seed and series A investments. He’s also a Kauffman Fellow, where he is doing academic research project on the internet of things. He previously worked as a software engineer in product management for 15 years, and he joined Atlas division of aQuantive in 2004 where he focused on big data. He helped lead the company’s Rich Media advertising technology platform. He’s also led Product organization for 4 early stage companies, and prior to joining that he worked at Microsoft and he’s also worked at Sierra Ventures which is a San Francisco based VC firm, so we’ll be sure to ask him the differences between San Francisco and New York as I’m sure there’s quite a few. Lylan welcome to the show.

Lylan:

Thank you John. It’s a pleasure.

John:

Before we get into all the wonderful things you’re doing at White Star Capital now, would you take us back to your days of being a software developer at IBM, and then being a program manager at Microsoft, did you have a vision that you were eventually going to get into VC? Or how did you go from that to where you are now?

Lylan:

Yeah, I was a computer science geek. I went to University of Waterloo which, for people who are not familiar with the school, it’s considered the MIT of Canada, or for the people in France is the polytechnic of Canada. From there, my last internship per qua in the ’90s was at Microsoft WebTV in California, and my manager at the time, we’d discussed career options and there’s some people down the hall who were product managers, or by Microsoft Power Lens program managers. We kind of agreed that that could be a really good path for me because I was getting frustrated spending hours on that, then trying to fix a bug in the code that was a missing semicolon. I like the interpersonal aspect while also leveraging my technology background. So I went to Microsoft full time in Redmond, that was some of the first team to launch a Visual Studio .NET. So the first ever .NET team in C-sharp and J-sharp.

Then I went to a company that I’d never heard of that time actually, in Seattle called Atlas, part of aQuantive, and we doubled and tripled the business year over year. It was just fantastic. I ended up having 4 jobs simultaneously. I was running the Rich Media and a product, that Behavioral Targeting Product, User Experience, and Internationalization all at the same time, because that’s what you do when a company is growing quickly.

Then in my last year there, Microsoft required us, for the $6 billion which at the time was larger than all of Microsoft’s other acquisitions combined.

John:

That’s quite an exit there.

Lylan:

Yeah. Skype’s subsequently surpassed us. What was interesting there is that Mike Galgon, was one of the co-founders of aQuantive, and at one point I approached Mike for a little bit of mentorship. I was considering to go to my MBA and I was already in my 30s, so it was now or never. So Mike was a great mentor for me, and in the discussions we talked about the history of aQuantive. The web was different back then, knowledge about Venture Capital is different back then, your show is not on back then.

John:

That’s true.

Lylan:

And Mike, he told me what the history of starting aQuantive, which was then called Avenue A, he told me about how he and his co-founders started but also how he raised money from venture capitalists. I didn’t even know what a venture capitalist was. But similar to how my manager at Microsoft in the ’90s, urged me think about product. Mike didn’t necessarily urged me to think about venture, quite the opposite, but he did awaken my interest into it even though he didn’t necessarily — I think, having this as your best choice of career. Because, you know, it’s a dark side and all.

When I started thinking more and more into it, and I thought, “I might just absolutely love this.” It was a perfect timing for my career because I was going already to business school, business school’s a great time to try something new, right? While at business school, I decided that I was going to try venture capital. I did not know that the economy was going to tank, and that I’d be looking for an internship in 2009. So what I did is I networked, and for me what that meant was, I looked up every single VC firm I was aware of or could learn about online, I read the bios of every partner in principle in the firm, and I would find the one person in the firm who I thought had the most similarities to me, or most affinity to me as some people put it, and I would email that person.

I’ll give you the clue. The colloquial version of the email, because the email’s very formal, but the colloquial version email basically said, “Hey, we have this in common. We both study mathematics, we’re both Canadian, we both work in online advertising, et cetera et cetera, and I think what you do for your career is interesting. Do you have 20 minutes? I’d like to pick your brain.” Now a lot of people were — yeah, go ahead.

John:

I was just like, I love that so much because I’m constantly telling the listeners, you must do your homework on the investors you are fortunate enough to pitch. What you just did was — this is also obviously how you got a job, but it’s that same — Look at the similarities because you want to make sure that who you’re even approaching for money has a lot of things in common with you, whether it’s background, experience, connections. So it’s what you just shared is gold. I love it. Keep going.

Lylan:

Then one of the investors I reached out to is a New York investor, Geoff Judge. Maybe we should check to see if it’s okay with him that we use his name, and in my conversation with him at the end of the call, he said, “Hey Lylan, I like you. I think you have some good potential. There’s no space at my firm to take on an intern, but let me introduce you to somebody.” So he introduced me to his friend, Mark Fernandes, and Mark’s admin wrote me back and said, “Mark would be happy to have a call,” and I did what you trained to do, why? “I very much would appreciate a call but I happened to actually be going to the Bay Area in a few weeks. Is Mark available to meet in person?” She said, “Yes.” Then I booked my flying ticket.

Then I met Mark in person, and Mark made it very clear to me at the beginning of the meeting, they had never hired an intern before, they had no desire too, and what I subsequently learned also is that the head of Sierra Ventures, the founder of Sierra Ventures is Peter Wendell, who actually teaches venture capital at Stanford GSB. So one can reason that if Sierra where to bring on an MBA intern, it would be from someone from GSB, but by the end of the call or by the end of the in-person meeting, Mark seemed interested. I think my technical background, combined with fact that I was already in my 30s, didn’t need to be overly coached had an impact. He knew that you could bring me on and I could run independently. I just owe so much to Mark for giving me that break. It was an absolute joy. From there, I had a great experience at Sierra, and then I applied for the Kauffman Fellows program.

John:

Let me just ask you to pause because there’s another gem there, the objections you got at Sierra. Most people would just say, “Oh well.” So, lying is not something we have ever propose people do, but, you were willing to go the extra mile, put your own money and spend your own money or own dime to get yourself there for that interview that didn’t look promising, but you still were willing to do it. So that’s that extra mile that a lot of people like, “I’m not going to do that unless I really think I have a good shot,” but you still went. You get there, all you do is hear a bunch of objections about why they never do it, and if they do do it, it’s going to be from somebody from some place else, and then you are able to turn that around. That’s the kind of tenacity and persuasive selling skills or storytelling that’s required to get someone like you now to say yes, correct?

Lylan:

Yeah, very much so. The idea of what you said earlier, of researching somebody, of understanding their background, understanding your commonalities if there are some, you don’t need to have some but at least show your research mean, and you didn’t just simply do a copy and paste, right? Maybe we’re drastically different about something and you want to talk about that. That’s fine. But just show me that you didn’t do a copy and paste and that you’re willing to do a little bit of effort just the way I continue to do.

John:

It can even be somewhat playful, right? I see you speak French, I eat french fries, does that count, right? It’s something that…

Lylan:

Yeah. I haven’t received that one but yeah, at least it would show some level of research.

John:

Right, and some playfulness and some human — Like if you want to stand up from the crowd, sometimes you have to do something a little out there like that. Alright. So you’re doing well there and then suddenly the Kauff, tell us about the Kauffman experience.

Lylan:

Yeah. So at Kellogg, Azeus Jelani was a year ahead of me, and he’d been in there for the Kauffman Fellows program. I learned about it, a little bit about it from him. I looked up the list of Kauffman Fellows who have history in the program and there are many fellows who are part of the who’s who of venture capital. The program is a two-year program where we meet once a quarter for three or four consecutive days, right? And in the times that we meet once a quarter, there is a fixed curriculum. The curriculum is specifically on how to make us a better technology investor. So the curriculum doesn’t relate to term sheets and financial terms, let’s assume that we learn that on the job or we’ve already learned it, and if we don’t then we can just ask.

Let me give you two of my favorite examples of the curriculum. One example was how to be a better board member, and so what Kauffman did is that they invited internationally recognized VC’s who are known as being exceptional board members.

John:

Wow, and now are these advisory board members or a board member of directors?

Lylan:

The board of directors, because generally as a venture capitalist —

John:

Yeah, they’re on the board. Just want to clarify for the listeners.

Lylan:

Yeah, absolutely. That training was outstanding, and then there was another session on…

John:

Before I let you jump off of that, do you have one or two takeaways that what makes a great — or how can you become a better board of director?

Lylan:

Well, everything that happens in Kauffman is Kauffman confidential.

John:

Oh sorry, okay.

Lylan:

No, no, but what I can say, because a friend of mine actually recently published this, and so he leaked the information first if you will.

John:

Fair enough. Yes.

Lylan:

In addition to having great board members coming to speak to us, we had an entrepreneur coming and speak to us. A well-recognized CEO, and at one point the question was asked if he know about his board and his level of appreciation for the board, and there are many of his board members who he felt did not contribute as much as they’re capable of, they were not as helpful, and he thought that all those individuals had the networks, had the skills, had the intelligence, had all the attributes required to be helpful, but just had never invested enough time and effort and mental energy. When we asked him which of these people would you want in your board, again, the answer was surprising or was disappointingly low. So the key takeaways, they were often about some of the simple stuff John. Simple, read the deck, as a board member, read the deck a week in advance assuming it’s the CEO’s, so the two week in advance. And if you have questions start asking those questions in advance so that you’re not staling the board meeting unnecessarily.

John:

We’re going to tweet that out. “Time, effort, and mental energy. Those are the three key elements to be successful in anything, whether it’s pitching for funding, being a good board member.” It’s all, like you said, simple things, but putting your time, putting the effort, and not just effort of being busy, but mental energy. I love that. That’s such a great line.

Lylan:

If you just do what intuitively feels like the right thing, and you make your portfolio coming a priority, that should naturally occur. There’s a lot of the small things too, so your behavior in the board meeting. How often are you checking your cellphone or for email? Are you writing down notes for yourself about what’s been discussed, and about your follow up and your action, and as how to be helpful. That’s important stuff.

John:

Sure. Well, it shows you care, right?

Lylan:

Yeah it does and we should care, right? Because our job is on the line, our personal income is on the line, our reputation is on the line, and in the life of most companies out there, the CEO is a CEO that was driving the company, but there can be one or two seminal moments where an outsider, as in a board member will observe something that the operational team, the CEO, the C-levels, the VP’s, will not observe because they’re stuck in the wheats. And it takes an attentive board member to recognize a seminal moment and to make a certain recommendation or to even ask the intelligent question allows the CEO or the team to reach a certain conclusion.

John:

Well, I love that. That’s so great because it works both ways, doesn’t it right? When you’re pitching someone like you to get funding, you better be sure your phone’s turned off. You better be sure you’re listening to what you say and maybe even taking a note during the pitch meeting, right? So you show that you’re engaged.

Lylan:

Yeah absolutely, and it’s fine to have your laptop open the whole time if it’s clear that you’re taking notes, and you’re not overly multitasking. Or if there is something urgent in your life going on and you’re expecting a certain phone call, just say so. One little thing that I try to do, and I think I do more often than not, is when I do have a meeting with someone I know, I have another meeting coming up thereafter, instead of being the guy who is always checking his cellphone for the time or checking his watch, I set myself an alarm. So in that way there, I’m not rudely checking the time, I trust that my alarm will notify me when it’s time to start wrapping up the meeting.

John:

Right. Nice. That’s very helpful. Alright. So you’re meeting once a quarter, obviously it’s a huge commitment: how to learn to be a better board member. Is there anything else you can share from those confidential quarterly meetings that’s what you’ve learned or no?

Lylan:

Well, there was another session on how to best define your personal brand and your firm’s brand. You can imagine that the VC’s that we invited to speak on the branding side were different than the board member’s side. Because some people are much better at one than the other, and so for us we ought to pick and choose and learn from the best at each part of the curriculum, is key to Kauffman. On the branding, it’s all the normal stuff that we talked about just applied to venture. So branding is specially difficult for VC’s who are considered generalist, and a generalist is defined as a VC who invest in many different categories.

John:

Right. You don’t specialize, yeah. Like we only do medical or we only do fintech, then people will say, “Okay, that’s your brand.” But there’s still so much branding that can be defined and I can’t wait to talk about White Star’s branding in a second, but please keep going about what is it that the — I”m really curious about what they might have told you about how important it is to have your own personal brand?

Lylan:

Yeah. Your personal brand and your firm brand need to be very complimentary, I certainly hope so, but at the same time, we are each individuals, and we each have our own way of being memorable within the firm. That’s why it is, I hope with all firms. So be it that you organize events, be it that you wear some kind of a kick off to use a term, right? But at the end of the day those are great hooks into what is the core of you and your firm, right? So it’s fine to have that little memorable thing that gives someone a reason to remember you, but then they also have to remember you for the key two things which are being really really nice, or being incredibly helpful or useful. Because a nice person who’s not helpful is just not all that valuable, right?

John:

We’re going to tweet that out. “You must be nice and helpful, not just nice.”

Lylan:

Yeah, it’s absolutely critical and there’s some people out there who are known as the nice guys or the nice women. It’s important to be nice but the buck does not stop there.

John:

I also like this concept of your personal brand is defined by what can you do to be memorable. That’s another great tweet. It’s so important, so is it something you wear, a certain hairstyle, colored socks, or you’re known as the go-to guy for events, or you’re known as a go-to guy for being able to help people with their pitch or whatever it is, right?

Lylan:

Yeah, and it’s like there’s also — that stuff is a little bit kitschy but it works as long as it’s seen effectively. Then there’s just the core fundamental parts of branding. One of the firms that I admire the most in the whole wide world is Emergence Capital. Emergence is truly a top tensile firm, a fantastic portfolio. The people I know there are — I can’t speak highly enough of, and at Emergence, they define themselves early on as the firm that invests in SaaS, before people even knew what a SaaS was. They use a couple of other terms around SaaS because they started investing in SaaS before the term SaaS, I think, was even defined. Then they invested early on in sales for Stockholm, and so that’s a strong form of branding.

All the other stuff helps, right? First on capital. What do they invest in, right? There’s something nice about either by your name or just how you define yourself externally, that people know you for something important and as applicable to many entrepreneurs.

John:

Well, let’s talk about the branding of White Star Capital. Before the show started, you told me a little story about how they came up with that name White Star for the VC.

Lylan:

Yes, so White Star fundamentally, we are transatlantic firm. We have investments in many parts of western Europe including London, Paris, Berlin, Stockholm, and also in North America including New York, Montreal, Toronto, Ottawa. We even have some investments in LA and San Francisco, and looking at the history of what brings both sides of the Atlantic together, well, White Star Cruise Line, I may not have the exact details straight here, but it’s effectively the first cruise line, commercial cruise line across the Atlantic.

John:

Perfect. That said it all, right there, and even the little logo has a white star obviously. It instantly brands you as a place that is international and cutting edge, if you bring the first and all that other great stuff. Now in your bio, I talked that you live San Francisco as a VC and now you’re in New York as a VC. I rarely get the chance to talk to people who’ve done both coast and they’re so different. What would you say are some of the differences about being a VC based in New York versus San Francisco?

Lylan:

Yeah. The differences are shrinking, I must say that because New York is becoming very much more focus on all the industries of technology. It’s no longer so strongly focus on ad tech and fintech, and fashion media and so on. That being said, the competitive dynamics in the west coast historically in the last few years, even though it is slowing down a little bit now, are different. The time it takes to make an investment at the area has shrunk because of competitive situation. So my friends who are their investors, in order to make the best investments, some of them have learned to be more proactive at creating investment theses or mini theses if you will. So identifying some sub sector tech and researching it in advance, so that when it comes time to actually speak with a certain company that’s trying to raise the amount of money that you generally invest, that you already have your market knowledge and so you don’t need to do catch up. So the reliance of a lot of VC’s have an investing companies that’s introduced to them, that’s decreasing. It still exist so very strong, but the proactive investors who go out there and say, “Here’s what we invest in. Here’s where we have established in thought leadership. Here’s where we have strong knowledge.” That allows you to make investment decisions a lot more quickly.

John:

Now, one of the pride and glories of your portfolio is the Dollar Shave Club, which is such a success story. Can you share with us where you got involved? Was it seed into series A or how did you get involved with Dollar Shave Club?

Lylan:

Yes, so we are investors in a company called Science. Science is also located in LA as a Dollar Shave Club, and Science is effectively a startup incubator. They call themselves a studio, and that’s what really what they are as a startup studio. So one of the startup studio companies that came out of Science was Dollar Shave Club, and by being an investor in Science, the head of Science is very good at letting his investors know when there’s something good coming from his program from a studio. That’s when we learned about Dollar Shave Club and this was before the video came out. So it was very good timing.

A funny story with Dollar Shave Club. I was having coffee with a friend of mine in venture capital  a couple of months ago, and he had taken a deep look at Dollar Shave Club, but he ended the past thing and his reasons were very sound at the time, right? No product, no traction, they’re still are creating some video has going to go viral. Yeah right, and then of course they do the video, it goes viral, and all his friends who didn’t even know that he had even looked at Dollar Shave Club are now sending him the video.

John:

It kind of like rubbing it in your face, right? You can’t predict what’s going to viral or not. That’s for sure.

Lylan:

Yeah, and they didn’t know that they were rubbing it in his face as you put it, but yeah, and he was like, “Darn it!” But looking back at his notes, his logic was sound.

John:

Sure, but somehow you still did get involved with that, and it’s been a huge success.

Lylan:

Yeah, and it worked out really really well. The most recent round of financing was quite large, and the number of products that the company now has, it’s a lot more than just shaving products.

John:

Oh I know, I’m a customer. Everyday, from what to wipe your butt with to — I mean, it’s hilarious branding but it stays consistent. It’s as all funny.

Lylan:

It is.

John:

It’s great, and talk about disruptive, I just love it. Now, can you share with our audience since it’s called The Successful Pitch, what you think makes a good pitch?

Lylan:

Yeah, ultimately, giving a good pitch, I liken it to the word “story”. I assume some other VC’s have told you the same thing. It has to be a story that gets an investor excited. Now, don’t get me wrong. Some of the best stories for me are really unsexy boring businesses, but at the end of the day, money is sexy.

John:

There’s a good tweet, yup.

Lylan:

And that can be misinterpreted by some people. But people who understand the crux of what I’m saying, the genesis of what I’m saying, is that now you can be doing a startup on some improving database, server, something something, right? You tell your friends about, your non-geek friends, about improving something at database, and tell your parents if your parents are not technically inclined about improving something on database stuff. That doesn’t sound all that glamorous in a way, right? It’s not like working on a social media startup, but still, a company that’s working on massively improving a database in some form or doing some artificial intelligence product for the enterprise. Those can often also be really really a compelling businesses. They’ll generate meaningful revenue and meaningful recurring revenue.

John:

It’s great, and do you often have people come to you at seed, and then you’re there for their second rounds? Is that a common experience?

Lylan:

Yes, so there are times where we are the first institutional investor. Sometimes that’s often a seed round, and there are times where there are already great seed investors and it’s time for the company to raise an A, and those seed investors, they don’t have the capital, the check size is too big for them, and we’re there for the A. Ultimately, that’s a core part of the White Star strategy, is to do the late seed and the series A, and it helped our companies get to the B. That’s very important to the help and get to that next step.

John:

What would you say is, besides growth and traction and hitting the milestones are some of the things that are so important to help somebody get from series A to series B?

Lylan:

Yeah, the quality of the team, right?

John:

Because back — just of the same as a seed, it’s amazing how that never goes away, does it?

Lylan:

Yeah, but you know, suddenly when you’re trying to raise your — for every round, every subsequent round, there are higher expectations on the team. So, one of my colleagues, Christian Hernandez out of London, one of the founders of White Star, he blogged about this recently, how it’s important to be leading a company that is today’s company, not yesterday’s company. So today’s company, the CEO may have been also historically doing most of the finance, or heading a product. But at some point, the company should get big enough, that the CEO should not have time to do both. So you need to bring in a head of finance or the head of product, et cetera et cetera. It’s fine to go dabble a little bit in those areas and to coach on those areas, but ultimately at the end of the day, as your company continues to scale, you need to bring on leaders in each of those job functions.

John:

Including, I would assume, a more impressive board of advisors that you might have in the seed round, correct?

Lylan:

The board of advisors can be helpful. When an entrepreneur tells me that here she has an extraordinary board of advisors, I look at the name, the titles and all that, but then what matters most to me is okay, these are great names and all, but what have they done for you lately? How active are they? Are they people that you — that are in the office regularly or are they people that you have a call with one hour a week? Are they people who say, “Yeah, call me up, I’ll try to help you,” and at the end of the day, they end up calling me once or twice a year.

John:

Yeah, very different levels of involvement.

Lylan:

Yeah, and that’s critical because at the end of the day, the people who are working the greatest number of hours on average in the company, are often, not always, but often the most influential.

John:

Interesting. Now is there a book that you would recommend founders read about life or funding, or anything you just think is important to them to know as people?

Lylan:

Yes, so I’m going to avoid a lot of the obvious books, of that written by Mark Henry’s and all those kinds of, fabulous books by the way, Brad Felix’s et cetera. I’ll go a little bit off a beaten path. There is one book that I still remember something from, even though I read it in 2009, and the book is called The Trusted Advisor. In The Trusted Advisor they talked about the formula for being a trusted advisor, and really it’s not about being a trusted advisor, it’s a formula for trust.

John:

I love it.

Lylan:

And the formula, I call it the CRIS formula, and you’ll see why. To develop trust, you must have a high level of credibility, reliability, intimacy, and then a controlled level of self-interest. CRIS, C-R-I-S. I try to break this rule. I try to find errors in this and ultimately, really to come down to those four: credibility, reliability, intimacy, and just don’t have too much self-interest.

John:

Wow, control self-interest, that is a really tough one for a lot of people and it all goes back to have a little empathy for your customer, and a little empathy for the investor, right?

Lylan:

Yeah. Absolutely.

John:

Nice. It’s been such a pleasure having you on, Lylan. Is there a way that people can follow you on social media? What’s your twitter and all that good stuff?

Lylan:

Yes, so just a quick correction, my name is Lylan.

John:

Oh I’m sorry.

Lylan:

It’s alright. Yes, so my twitter handle is @lylanm. I don’t publish much on LinkedIn, actually LinkedIn, I think I’m also lyanm. Then I have a specific blogging strategy that I haven’t launched yet, but stay tuned. Ultimately through the White Star network, I’ll be publishing through there probably on medium. Who knows?

John:

Oh that’s great. Well it’s interesting because I take the podcast and transcribe it to a medium as well so we’ll be able to do that as well for you. Well thanks again, it’s been a pleasure. You’ve given us so many. I love this trusted advisor criteria and how important it is for the team to continue to evolve as the funding gets bigger. Those are incredible takeaways.

Lylan:

I appreciate it. Thanks John.

Thanks for listening to The Successful Pitch Podcast. If you liked the show, please go to iTunes and write a review, and encourage your friends to write reviews too. It really helps get the word out.

You know, people say that the longest distance is between someone’s mouth and their wallet. People can tell you they’re going to invest but when it comes time to write the check, they don’t do it. So, how do you get people to say yes and then follow through? Visualize yourself on the left side of a riverbank and you have to cross the river and on the other side of the river is where the funding happens.

So, first, you make up your idea and then you make it real and then you make it reoccur. Once you start dipping your toe into the water to get to funding, that’s where I can help. I get you across that river faster than you would on your own with a lot less frustration than you will get when you hear a bunch of no’s and you don’t know why. So, if you want some help getting funded faster with less frustration, go to my free funding webinar, sellingsecretsforfunding.com/webinar and sign up and get in depth information on how you can get funded fast. Thanks.

TSP076 | Dan Weinfurter – Transcription
TSP074 | Laura Rittenhouse – Transcription
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