Letter #299: Mark Miller and Hugh Chow (2025)
President & COO of Constellation Software & Executive Chairman of Volaris Group and CEO of VentureLab | VentureLab Chat
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Mark Miller is the President and Chief Operating Officer of Constellation Software, as well as the Executive Chairman of Volaris Group. Mark started his career as an intern working for the Canada Centre for Inland Waters, before joining the transit software provider SAGE full-time. SAGE was soon acquired by Teleride, and although Mark initially stayed on after the acquisition, left soon after to start Trapeze with one of SAGE’s cofounders. Trapeze went on to be the very first company Mark Leonard acquired for Constellation Software. Mark became the CEO of Trapeze Group, then assumed the role of Chief Operating Officer at Constellation, and then CEO of Volaris Group.
Hugh Chow is the CEO of VentureLab. Hugh started his career as a Process Integration Engineer/Test Engineer at Mosel Vitelic, before joining ATI Technologies, where he was an Engineering Director. He then started his own company, ViXS Systems, where he served as CEO and COO and took the company public. Next, he co-founded and served as Managing Partner of Pool Global Partners, and then served as CEO of ASTRI (Hong Kong Applied Science and Technology Research Institute).
This letter is the transcript of a conversation between Mark and Hugh. In this conversation, Mark shares the origins of Volaris Group and its ties to Constellation Software, transitioning from a technical engineer to management, learning by doing, advice for aspiring entrepreneurs, how to think about growth and market expansion, software vs hardware, advice for hardware founders, and the importance of community. Mark then shares what he was like as a kid, whether he remembers what all 200+ of his businesses do, if he is still learning in his job, the importance of finding a mentor, traveling, what gets him up in the morning, and much more!
I hope you enjoy this interview as much as I did! This was a fun interview not only because Mark would shortly be promoted to President of Constellation Software when Mark Leonard stepped down, but because he serves as a mentor to Hugh and Board Member at VentureLab. Also interestingly, there seems to be a lot of overlap in the way Mark thinks about businesses with Y Combinator in terms of talking to customers, the importance of community, and more.
[Transcript and any errors are mine.]
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Transcript
Hugh Chow: Good morning everyone. I am Hugh Chow, CEO of VentureLab. And today, we’re very fortunate to have Mark Miller. So thank you very much, Mark, for coming here and spending time with us.
Mark Miller: Good morning, Hugh. Great to be here. Happy to be here at VentureLab.
Hugh Chow: This is great to have you. So you just told me you have 250 companies under your management. How do you make time for that? Tell us a bit more about Volaris to start.
Mark Miller: Well, we started Volaris back in, really, 1995. And I was actually part of the first company that was acquired by its parent, which is Constellation Software. And I’m a programmer by background, and back in 1995, started to learn how to acquire businesses as well. And so we buy businesses and we hold them forever and focus our time on developing our management teams and have them learn from each other. And so we do that across the world. So we slowly, over couple of decades, have acquired a lot of businesses, and it continued to continue to grow the business.
Hugh Chow: That’s great. Great story. And in fact, if a lot of you guys haven’t heard the great story about Volaris Group, it is one of the best investment you could have ever made--other than Nvidia, obviously. And you beat pretty much everyone under the sun.
Mark Miller: Well, through our parent Constellation, yes. And we’re a large part of Constellation. It’s been just a really great, great group. And we hope to just keep on trying to do better. Learning.
Hugh Chow: Great. That’s great. Now I’m an engineer by training as well, and making that transition through from someone technical to someone in management, and you talk about M&A and all that, how hard was it for you?
Mark Miller: I think it’s a really good question, because the startup I was involved with, we started in about ‘88, ‘89, we were developing software for helping to run transit agencies, ultimately, around the world. And I was lucky, because got to learn a lot about business by actually doing it. When you’re developing software for customers, you’re listening to them, you’re trying to understand what their needs are, you’re having to sell it, you’re having to implement it, you’re having to support it. So you get to work through all the various functions of a business. And I sort of did it by rolling up your sleeves and working with a couple of founders and we worked really hard to learn from our customers and learn through making mistakes, which I think is a great way to learn. But as far as learning how to do mergers and acquisitions and acquire businesses, that was something pretty new for me. Because when you’re a software developer, a programmer, you really like to believe you can just build it. And this sometimes it makes sense to also acquire businesses and expand your business that way. So it allowed the business that I started to move into various countries around the world, expand globally, and move into different areas of the customer that if we tried to develop software to do would have taken far, far longer. And you also pick up a lot of talent when you when you acquire businesses like that as well, which can help you expand what you’re trying to do. So it was kind of an interesting skill. So as a technical person, which was really the question, I think, as a developer, you break everything down into sort of problem solving, and you go, if this, then that. So whether it’s business, whether it’s developing software, whether it’s--you sort of think about logical sequence of how to make things happen, and you consider multiple options. If you’re writing code, it would be if this, then that, else--whatever. And I think that helped me a lot, that sort of developers mentality, to move into business and learn business the other way, I would say.
Hugh Chow: Well, Mark, I think you’re a little too humble. I think what you’ve done is just a lot of great work over two and a half decades now. You touched on a number of great points. I’m gonna poke you a little further later on, about talent, about global expansion and all that. But I want to go back to your transition from a technical person, a programmer, to a business person. So are you saying to a lot of the young kids nowadays, say, Hey, skip the business school. Just get your hand dirty, make your mistake. According to you, that’s the fastest way to learn.
Mark Miller: I agree. I think it does. I think you can learn the business by either reading or experimenting and trying. I think there’s a lot of great content out there. I think it’s important you know how to do something that’s unique and matters to whatever target market you’re you’d like to provide your products to, or your services to. I think it’s really all about that. And you’ll learn about the business. Business is a tool to help you do what you’re trying to do with a target group of customers in a market. It’s not the reason to be--it’s really just another tool in your kit that makes you better. And it is important, and you do need to understand it. The first business course I took was probably in ‘96, believe it or not. So seven or eight years after my startup. And it was only a six day course, and it was about strategic marketing. It was understanding how you segment customer bases, or segment markets, and understand how you think about those markets. For example, I think I used an example at the Hard Deck Summit the other day, which was General Electric was building aircraft motors, and the engineers thought they could build one that was twice as good as the previous one. But the question is, are people going to pay to fly twice as fast across the ocean, enough to support developing a multi-billion dollar aircraft engine? And I thought it was--it seems like a small point, Hugh, but as a developer, it was really good learning to think, yeah, you need to think about these things, you can’t just go build better products. You need to make sure the market can support what you’re doing, you’re solving a real pain point that people are willing to pay for in order to create a business.
Hugh Chow: Right. Product-market fit. At VentureLab, we have a lot of aspiring entrepreneurs. They have big dreams. They have a lot of determination in them, a lot of commitment. They believe deeply in what they do. And we all know that not everyone’s gonna make it all the way, let alone be as successful as you are, but even surviving under this kind of economic environment. So what do you say to them? Hey, your chance isn’t that great--to keep them motivated? So as someone who right, been there, done it before?
Mark Miller: Right, I think my best advice is to really study your customers very closely and to don’t assume that you know better than they do, that you have an idea that that market needs, that is clear to you, but maybe isn’t going to be as clear to your customers when you actually complete developing your product. So I think being very close to them, any time you can get early adopter customers, there’s a great book I love to read called Crossing the Chasm by Geoffrey Moore, and getting those innovators and early adopter customers to actually think about using your product and maybe even put a little bit of money into making it happen is really, really important. And also it’s important not to just study the end user of your product, it’s important to study the organization that they work for, and what the leaders in the organization care about. And you can somehow disconnect what the actual end users need from the actual leaders of those organizations, and they need to intersect you to build something that really matters. So my advice would be to really study the target market you’re going after by being right there and observing the customers live, but also understanding what the leaders of the organization really care about. And if you can bring those two together, I think your chances are higher. But failure is is always a potential outcome. And I think that’s important. I also think it’s very important to make sure that your shareholders, your investors, are in it for the long run. It takes longer than everybody wants to get to where they would like to be. It’s great to have that level of optimism, or you wouldn’t even be able to start doing something. But you also need to make sure you surround yourself with people who are in for the long run and are patient, because businesses don’t happen overnight, unless you’re very fortunate. You don’t build businesses overnight. It takes sometimes years to do it, and nobody can see the future, Hugh. If you could, it would be a wonderful thing, but you can never see what what’s ahead. So you need to be working with some people who are going to be in it for you and the long haul after you’ve listened to your customers and observed your customers as well.
Hugh Chow: Well, great advice there. Surround yourself with great people and be the ultimate optimist. I remember when I went through my entrepreneurship journey, and that really kept me up every day. Now, you talked about listening to your customers and really get to understand it. We here at Canada has somewhat of a disadvantage. We are a country known for resources, we got a lot of things. One thing we don’t have is a lot of people. And when you want to build up a business that is large enough of a scale, or to give you enough growth potential, you really have to go global. And a lot of Canadian Founders, what I find out is that they are very--their growth strategy is, Hey, let’s get my province under control first. And then if my business does well enough, in five years, I’ll try to US market. What will you say to them with your global experience? I mean, you have 18,000 people across--
Mark Miller: Yeah. We’re in over 60 countries, I think, now. But in starting a business, I’d get my first customer in the US, if I had the choice to do that, just because of the larger adjustable market. It depends, obviously, what sector you’re in. If you are selling in the natural resource sector, there’s things to do in Canada. There’s lots of different ways we do things in Canada. But ultimately, getting to the US sooner would be better--go south of the border. And you’re right, I do meet a lot of founders who feel they’d like to make sure that things are working well close to home. One of the things I’ve learned in traveling around the world and visiting our different businesses is, even though a market appears to be similar, it really, on the surface, it really isn’t, when you really observe what’s happening. And so starting a company here that is selling to, for example, Canadian customers, there’s a risk that your product that you design won’t work as well in other countries, namely the US, which is again such a large addressable market. So you need to be very wary of that. And I think it’s an important choice to make. You can build a lot of momentum. I also think generally the US market, they are early adopters of technology. It’s depending on the sector right, which is also helpful for you as a startup, to get involved with customers who are willing to take chances on maybe some new way to approach a problem, and we’ll buy into it and try it. I think it’s a little harder in Canada--not impossible, but it is harder in certain sectors in Canada to do that. And plus you have a larger adjustable market, so the chances of finding early adopters and innovators inside of a larger market like the US or elsewhere probably gives you a better chance of success.
Hugh Chow: I see. Now, Volaris mostly in software, right?
Mark Miller: We do have some hardware. We do have hardware. We do a lot of in-vehicle devices for tracking busses around the world and various large urban centers. We have software that weighs--determines how much grain you would put into a truck or a rail car in the Midwest of the US. But I think the hardware side of it is--and semiconductor side--is very important. I think having unique, proprietary hardware is something that is of great value to a business to do it. So it is harder, though, because you’re developing software, obviously, inside that hardware, as well as the back-office to connect to it. So there’s a lot of work in doing it, and it takes a lot longer to get there. Anyway, I jumped ahead, and didn’t answer what you asked.
Hugh Chow: No, no. I was just about to ask you that I understand that their are hardware components in your group holding as well, and given that at VentureLab, we do have majority of our founders in HardTech--HardTech is what we consider as something that’s difficult, but having some--a prototype, something related to hardware--it makes it difficult to start. Verticals that we focus on are semiconductor, AI, and medical technologies, which is about ask you, Any special advice that you would give to a HardTech founder as opposed to someone just started out having a SaaS idea and get up in the morning and start coding? What would be your best advice to the HardTech founders?
Mark Miller: I think they need a longer term horizon. I think thinking that you’re going to get there really fast, and so you need to prepare for the long haul. And again, get customers engaged early on in what you’re doing, and hopefully putting some money on the table to support you--not entirely--you need investors, you need angels, or private companies to support you. But find those early adopter, innovative customers. So I think it comes back to that. And also realize it’s going to take longer. It’s going to take a lot longer. But when you get there, you’re going to have something very special. But if you get there and you find out that nobody cares, that what you’ve built doesn’t matter to them, and you’ve spent all that time. And that’s that’s tragic. So I think that would be the best advice I could give, which I would give to a SaaS company or a software company too. But I just think the time frames are longer to get there than it would if you were just building a software product. But again, it depends. If you’re building a multi-departmental software--it can be also very hard building software. It can be decades or algorithms you’re building. So it really depends on the industry, but time. You need time. Good long term investors and customers who care about what you’re doing, not a false sense of belief that your product is going to work independent of them caring.
Hugh Chow: That’s great advice. In fact, I would say that every startup is admirable. So you can’t say software is any easier, just hardware, it takes a bit more capital. As you put it many times, it’s a longer horizon. You really need to get some investor who who see eye to eye with you, to have the patience and willing to go all the way with you. It’s great advice, Mark, and I think that--let’s take a break, and let’s--
Mark Miller: One quick thing to add before we take the break, though, just sort of to wrap up that point, is you need a VentureLab. You need a VentureLab. Because you need a community who supports you, who surrounds you, who’s been there, who has the equipment to make it happen. This is a very important organization. And people need to realize that it can make a big difference, being part of community that is going through the same challenges as you have. And so I think that’s just an important thing to add to what you said, Hugh. Very, very important.
Hugh Chow: Well, thank you very much, Mark. And a slight disclaimer: Mark’s also my board member, so he’s doing a bit of commercial for VentureLab. Understandable.
Mark Miller: No, it’s not a commercial, it’s not a commercial. Where do you find a lab like this? You just don’t find them just anywhere around. There’s not many of them, and we’re very fortunate to have it here in Canada, and I hope people realize that.
Hugh Chow: That’s great. So we all know Mark as a very, very successful business person. But what is that kids inside of Mark that really power the entire Volaris Group, and even the Constellation Software company, which is really one of the best performing public company in North America, in general. So what is that little kid inside Mark that drive you every day, that get you up every day. Tell us a bit more them.
Mark Miller: I think I probably--I liked to disassemble things when I was a kid, so take it apart, and didn’t always put it back together again, but it was always fun taking it apart and trying to put it back together. So maybe a bit of a natural curiosity to try to understand what’s inside, how something actually works. I was saying to you to the other day, it’s hard to take apart a cell phone right now. Whereas when I was a kid, I’ve been trying to do that. How can I dismantle that? So I think that’s, that’s important. I really also believe that--I think I really enjoyed solving technical problems at a young age, just figuring out technology, and I love gadgets and just trying different things. So that’s it. I’m also like to maybe argue with myself in how to do something. I’m very happy to look at the absolute opposite view of how you could look at something. And I think that’s pretty helpful to me today. And I think probably when I was young too, I would never say, Well, this is the only way to do something, there’s a whole bunch of ways to do that. And I think I’ve continued to do that through through business. So always questioning basic beliefs and suggesting, Well, maybe we should try doing it this way or this other way, which can be interesting for people, because it can be a little disruptive for people who have a plan. Some people love to plan and follow a very specific strategy, and a very specific strategy in life, or in business. And I think being able to take a very hard right turn or left turn that is off that path might be the appropriate thing to do. So it’s that curiosity and sort of challenge. Challenge yourself to believe that there might be another way to do something than you currently think. If that makes sense.
Hugh Chow: Those are all great quality for a very successful entrepreneur. Don’t take no for an answer. Challenge the status quo. I either learn something, or I succeed, I’ll never fail. I think these are tremendous quality. As you’re growing up, as you’re growing your business into this, I mean, I can’t imagine the most ever I have people working for me at like 500, and you have, what, 18,000 in over 100 countries. Do you remember all these companies, what they do? I mean, at some point becomes numbers, or every one is actually story behind them?
Mark Miller: No, it’s not all. Yeah, there’s a story behind them. And sometimes, like--I was an event recently we had, we had 1300 of our employees there, and we did a lot of 12 person breakout sessions for 45 minutes. And it sort of surprised me that when you’d hear them talk a little bit about their business, that a bunch of it would come back to me that when we either thought about making acquiring their business, and so you don’t remember it all, for sure. You do remember--and it’s hard to remember all the people as well, and there’s some people I’ve known for years, but it sort of comes back to you. And I think what you remember, if you remember, what you remember is what you learn in your career incrementally. It’s a tough question. When I see them, do I remember all the businesses? No. But I do have this sense, when you’re with someone, that you remember challenges they have in their business. For example, maybe a highly concentrated customer base where they have a few very, very large customers, or they have a lot of small customers, or they have a large geographical span to their business. So I kind of probably remember some of the big picture things, so I hadn’t thought about this, about them, and I try to also remember the lessons I’ve learned from them, so I can tell those stories to other business leaders who are faced with those situations. It’s always interesting coaching other business leaders, because you spend a lot of time coaching, I’d say. Most of my career the last couple of decades has been thinking about how to coach people and how to help leaders get better at what they’re doing. A lot of people, even though you can tell them this is what’s likely going to happen if you do this, still push ahead and do it. And they really need to learn by mistakes as well. And you have to give them that opportunity to do that, and do your best to help them through that. It’s interesting. And I know you weren’t asking me about that, but it just, it kind of fits in with that, because you remember the stories of these business, you try to tell them to other people. Because I think storytelling and telling people different situations that you’ve seen is really helpful in business.
Hugh Chow: That’s a very good point, Mark, is that sometimes we all like to think that we know it all, but at the same time, we live in a innovative world, and we have to give people the room and space they need to take the ideas to whatever height it is. And again, they succeed or they learn. So that’s great philosophy that you have with your team, as big as it is. And you also talked about sharing story with your team, and learning. And do you feel like you’re learning every day as well? Like I can’t imagine, in your position, you’re still learning?
Mark Miller: Yeah, it’s important. I am. Oh, for sure you’re learning. My business has changed. It changes. And each country you’re dealing with has unique challenges. So we try to suggest that we’re a culture of cultures, and understanding how to succeed in a different place in the world. It could even be a different region in a country as well. You can’t use a country as a label for a market either, you need to think about different regions inside of that country, and different sized customers as well, because very large customers operate sometimes very different than small, local, family owned businesses. So I’m always learning. Always learning. My best advice on learning, though, is to find a few mentors in life. And those mentors won’t last you your whole career--you’re going to need to change them as you find areas that you need to learn more about, but the best is to find mentors--who are usually peers. They’re not necessarily extremely successful business leaders who have grown great businesses. A lot of people think those are the people that they should listen to. And I think there’s something to that, but I think to really have someone that you can pick up the phone or connect through Teams or Zoom or Google Meet or whatever technology and talk to them about some challenge you have, whether it’s around marketing, sales, developing some new product. I think finding those mentors and doing that is the best thing you can do. And those mentors might not look like you. They might be someone who’s different, from a different part of the world, with a different area of expertise than you have. And people sometimes like to hang out with people that look like them or seem like them. So I think the best thing you could do as a leader, and I didn’t give that advice earlier, in developing a business, is to find those mentors, especially if you’re a single founder of a business. Generally, having a few founders is a bit better, because you have offsetting skills, and you you can build them. But if you’re a single founder, you really need to have that mentor network. And they need to trust you. And they don’t need to be given to you, mentors. You need to find your mentors. And they’re all out there. They’re all out there. They’re here at VentureLab, they’re here around the world. But if you can go find a mentor, a few mentors, and keep them going. If you don’t, I think your chances of success drop dramatically.
Hugh Chow: Well, I’m pretty fortunate that I have you. I call you--may I call you my mentor?
Mark Miller: We’re peers. We’re peers.
Hugh Chow: I have this great board. What comes with all walks of life. Very successful politicians, business person like myself, and so on. So really, really grateful to have you as a person whom I can call upon once in a while. You have to travel around the world a lot, and I was told that you also take your bike with you when you travel the world. Just came back from a big bike trip in Spain.
Mark Miller: I do. I love to travel. Yeah, I was in Spain. It was great. Yeah, I mean, last year I did one in New Zealand. I like to go cycling. It’s just been good for me. It gives me a chance to--it clears your mind. Because when you’re cycling on a trip like that, you’re spending hours on your bike, and you’re not on your phone, you’re not on your computer, you’re disconnected, in a way. Depending on where you are, I remember New Zealand last year, there’s a lot of places where there was no cellular coverage, so it didn’t even matter if you had your phone, you weren’t going to connect. And I think that’s really good for you, and it keeps you in shape too. So it’s just something that lets you clear your mind and you come off of a trip like that feeling a lot better. I wish I could travel more with my bike. It is a bit harder, because I’m a carry-on traveler. I’ve flown millions of miles around the world, and I find--I try to make sure that I’m not waiting for something to arrive when I land at the airport, because it just might not, or I might have to wait an hour, hour and a half, for my bike to come out. But when I can, I bring it with me, Hugh.
Hugh Chow: Wow. You’re not just successful in business, I think you’re successful in life too. Great shape, good health, great family. I know that today’s your birthday, Mark. Today’s your birthday. So what more do you want to accomplish? What additional success you are you after? What gets you up in the morning?
Mark Miller: It’s a great question. Well, my greatest satisfaction in life, because if--when we started, I guess Volaris is part of Constellation--was probably the first operating group in it. I mean, what I had to learn how to do to grow the business was to give things up, let other people do things, and other people make mistakes, and try to coach them along the way. So I really love the opportunity to develop leaders and allow them to be successful. So that’s something I’d love to continue to do. I am getting also interested in areas outside of our traditional areas, for example, bioengineering and other areas, although it isn’t really my background, I think there’s a lot to learn, a lot to to understand in in other fields, to give back a bit as well, and try to use some of those skills. But we’ll see. In the meantime, just really make sure that I can help some people learn and get better. And I’d love, obviously, to see the VentureLab and Canada doing better in--and definitely in the semiconductor space, and what have you. I think there’s a lot of potential here, and I think--I hope I can help. But it’s a good question. I find my path, I guess, as always. You never know. Through my career, it’s been a bit of a you just never knew where you’d end up. You just kind of keep going and we’ll see what the future holds. But I’m just looking forward to it, and really positive about it, and hope I get a chance to to add some value. And time will tell if I can.
Hugh Chow: Oh, you definitely adding value at VentureLab here. So what I would summarize what is it that still getting Mark up in the morning? There are three things, if I summarize correctly: 1) is that you like to learn. There’s still a lot more for Mark to learn--I can’t imagine that. 2) is that you like to pay it forward. I think that watching other people becoming successful and pursuing their dreams are satisfying. 3) I think that--Oh, I lost my train of thought. Oh, actually, I know what number three is. It is your birthday, and we have some little surprise for you. All right, let’s bring it out.
Mark Miller: Oh, no, that’s so nice of you, Hugh. Thank you so much for spending the time with me. It’s really been a pleasure chatting with you. Could chat with you for hours, I enjoy it.
Hugh Chow: Such a pleasure. Oh, there you go! How many candles do we need?
Mark Miller: No, I’d say a lot. It’d probably be a fire hazard in here. Would be a problem here.
Hugh Chow: So, I know that I mentioned about Mark, you being a kid inside. So--
Mark Miller: Yeah, there you go. Donuts.
Hugh Chow: Every kids love a little bit of a donut.
Mark Miller: And if you’re cycling, Hugh, like having one of these, doing 100km ride is probably not a problem.
Hugh Chow: There you go. So you make a wish. And to be honest, my wish is that--even though it’s not my birthday, my wish is that every founder at VentureLab, at some points, you get a mentor like yourself. I do have you as my board members is really my privilege. So I’ll let it to you to make your wish.
Mark Miller: I’ll wish for us to rock and roll with semiconductors here in Canada, with VentureLab leading the way. I think it’s entirely possible. Let’s make it happen. Everybody can pull together: governments and private industry to make VentureLab a tremendous success. But thank you so much, Hugh. A pleasure speaking with you and incredible event at HardTech, and hopefully we can keep on building this organization out that it becomes better and stronger every year.
Hugh Chow: Thank you very much. Let’s do it together.
Mark Miller: Okay, thank you. Bye, bye. There we go.
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