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Google, Microsoft, Twitter and The Weather Network, Rory Capern has really done it all. But while he has built a career with some of the most exciting brands around, the art of the possible keeps drawing him back to the world of entrepreneurship.
An alum from Ivey’s HBA and MBA programs, Capern currently serves as the Chief Operations Officer at Redbrick, a B-Corp Certified firm that has built and acquired an impressive portfolio of companies to inspire innovation, encourage sustainable business, and support digital entrepreneurs.
In this fascinating discussion, Capern walks us through his career between start-ups and the world’s largest tech corporations, the importance of mentorship, and how his people-centric view of business has shaped his career.
The Entrepreneur Podcast is sponsored by Connie Clerici, QS ’08, and Closing the Gap Healthcare Group, Inc.
Transcript
Google, Microsoft, Twitter and The Weather Network, Rory Capern has really done it all. But while he has built a career with some of the most exciting brands around, the art of the possible keeps drawing him back to the world of entrepreneurship.
An alum from Ivey’s HBA and MBA programs, Capern currently serves as the Chief Operations Officer at Redbrick, a B-Corp Certified firm that has built and acquired an impressive portfolio of companies to inspire innovation, encourage sustainable business, and support digital entrepreneurs.
In this fascinating discussion, Capern walks us through his career between start-ups and the world’s largest tech corporations, the importance of mentorship, and how his people-centric view of business has shaped his career.
Eric Morse
Rory, great to see you. Thanks for coming in today.
Rory Capern
Great to be here. I really appreciate it.
Eric Morse
We're here in the digital maker space in the Schmeichel building here on campus.
Rory Capern
It is awesome here.
Eric Morse
Yeah, that's pretty cool.
Rory Capern
Really nice. Yeah.
Eric Morse
Well, hey, love having you here. And I start off every conversation with kind of the same question, what is it that drew you to entrepreneurship? Is this something, you know, you kind of knew as a kid? Hey, I want to kind of run my own thing someday. I know you've been in and out of kind of the biggest companies in the world. And you know, how did entrepreneurship play a role in that? And where did you get started? So
Rory Capern
So it starts at the kitchen table when I was really young. My family kind of forked in two. I had one half of the family were all entrepreneurs, driven to march to the beat of their own drum, some might say unemployable in some cases, and just working on their own because they had a dream and they wanted to make it happen themselves. And then I had another kind of half of the family that was very regimented military history, chain of command, do the job well, rise up the ranks. I sort of have this really interesting view of both models. And so I think that probably, if I get into the psychology of it explains why I've switched tracks a few times. But what drew me to entrepreneurship, and what continues to draw me to entrepreneurship, I think, is defining the art of the possible in your own context, right? So (awesome) the best entrepreneurs that I get this have the outrageous fortune of working with a bunch of them now. They are intent on bending reality to suit their vision, which means they have to be good at a lot of different things, and it's why when we're talking about the space that we're in right now as it relates to collision and multi threaded capabilities and lateral learning and all these different things. It's a real theme in the context of the work that I've done in entrepreneurial space. And it's, it's what makes it absolutely irresistible.
Eric Morse
Awesome. Well, let's talk about that lateral learning a little bit. You've been, you know, fortunate. I worked hard towards working in some of the biggest tech startups globally. You look at Microsoft and Google and Twitter and, you know, what were some of the experiences you had there that maybe you've taken into the entrepreneur realm? And you know, how is it that one has complimented the other perhaps?
Rory Capern
Sure, great question. I haven't, I don't think I've thought about it in that way before. The roles... like my path up the career ladder inside Microsoft and Google and Twitter was really in this business development capacity, which didn't mean much to very many people that's coming up. And I think it kind of works with this theme, which is the way that I tried to reduce a business development title to my parents, for example, was It's fancy sales. You got, you're selling a widget, or whatever you're selling. And then there's this other need for a lot of these companies to stick and mold and kind of bend into partnerships with other businesses, new channels. And it's not straightforward, right? There's there's different deals that have to be done. You really need to understand the economics of the unit that you're selling, or the business that you're in. And I always gravitated to those roles. I graduated from Ivey and went to the Boston Consulting Group, okay? Because I didn't know what I wanted to do, right, right? And stayed broad, and just literally did well, yeah. It went well, yeah, it was good. I just loved it, right? So I fell into biz school and couldn't pick a major. I just like everything, yeah. And I spoke to Mark Vandenbosch at the time, he said, well, that answer for that one is consulting. Just go see what you can do. And found my way into the Boston Consulting Group at the beginning of the web. Nice. They are their global headquarters for e-comm was in Toronto, yeah. And I just had a blast. Fantastic, very beginning of that wave. And so staying broad through the rest of my you know, post BCG, I went to Bell. They worked in the convergence group there, which was like putting all these different assets together to try and build online services that were innovative and made sense. And then as I kept going, I didn't want to just sort of straight up sell something. I wanted to stay in a space where strategy and sales kind of intersected. A lot of deal work, a lot of channel partnership work, and it allowed me to get a view into the machinery of the company, and usually the way that profit worked and how money was really made. That allowed me to keep that entrepreneurial edge and look for new opportunities all the time.
Eric Morse
And tremendous skills, like every entrepreneur has to be good at business development, or they don't last very long. And partnerships is such a key piece to success as well. Yeah, now I know we got to bump into each other a couple times when you were at Pelmorex, yeah, working for a common friend in Pierre Morrissette. (I did, exactly) So tell me about that a little bit.
Rory Capern
That was an incredible experience. So the story goes, when I was at Google, we found, found the Weather Network. Yeah, they were in Oakville. They've been there for a long time, doing just fine. Thank you very much. But what we didn't really realize from the outside looking in was, because of Pierre's entrepreneurial drive and vision really early for what the web was going to mean for weather, they were sitting on, at the time, the third largest community of online Canadians there was so in like 2012 it was. Yes, Google, and then Facebook and then Pierre, that was just an enormous asset, and there was a lot to be done. So my job at Google, no surprise, was partnerships and figuring out how we could sort of put together all the different assets that Google had around partners like that. And be honest, it took me a while to sort of ingratiate myself to Pierre in the beginning, but we made him a lot of money, right? Yeah, he understood the opportunity behind distribution, behind monetization, behind global expansion, and all these different aspects of what we could offer at Google just were a perfect fit for where they were at the time. So he was my star partner for a long time. They made each other a lot of money on the way through, all right, but then I had introduced my boss, Sam Sebastian from Google, who was running (I didn't know that). Yeah, the story, okay, so I introduced him to each other, because you do right, you introduce your best partner to your boss. Turned out they were almost neighbors, and the rest is history. They got to know each other really well. And when I had left Google, which was really hard to do, I really loved working with Sam in that first chapter, but Twitter came calling, and they kind of offered me the keys to run all of the Twitter business in Canada at a fascinating time. Turned out to be about a month before Trump took office. Really interesting after that, but leaving Google was hard, and Sam and I had decided we'll keep a monthly breakfast. Oh, okay. And for like two years, as I looked back in the rear view mirror, these monthly breakfasts seem to gravitate to the Weather Network a lot in the Pelmorex sort of portfolio, you know, what would you do with the TV business? What would you do with the mobile business, and what about global expansion? And we would just have these sort of conversations. And then when Sam decided that he was going to take the CEO role, we had been talking about getting off the intergalactic tech spaceship for a while. The awesome part about working for a company like Google is you just have access to all this incredible resource and thinking and smart people and but what it isn't, if you're running the Canadian operation, is the opportunity to get on the tools so finance, operations all the different aspects of the business. And so that was really what we wanted to do, okay? And when Sam called it was overwhelmingly obvious that that was the right thing to do. And so I joined him when he started, or just after he started.
Eric Morse
Yeah so the rest of the story, for you know, our listeners won't know, is that Sam actually went in as Pierre was retiring from the CEO role, right? And ran Pelmorex, and he had a good run there.
Rory Capern
That's it. He sure did, and we had a lot of fun together. Fantastic. That was a story about, you know, building a whole bunch of new capability inside this business, which focused on data in the very early days of AI, and understanding how important the weather data set was going to be to tuning new models, and really, kind of at the at the rock face of some really interesting new tech. And I think that combination of Pierre, who has created such an incredible business in Pelmorex as a private owner, and has done some incredible things to bring in outside talent like that and let us run. Was really wonderful. It was a great experience.
Speaker 1
For me, running into Pierre, career wise at that chapter, was I couldn't have asked for a better transition out of big tech. What I what I learned from him was risk taking. Okay, he invested in the web a lot earlier than most would have. For sure, a lot of folks rung their hands and weren't sure what they were going to do, and Pierre just jumped at it. And he was right. He was rewarded. Yeah, right. So he had amass this giant community. And when you get to that kind of scale, your ability to experiment and try new things just goes way beyond what a new start in that space would have been at the time. And he's been enjoying a leg up on the rest of the market for a long time I think.
Eric Morse
Yeah, and a testament to him, I think just last thing on Pierre is that he was always aware early days that these new mediums were going to be important to the Weather Network. So really early to web, really early to mobile, really early to understand that the data was, you know, the key asset that he had. And I think, you know, finding people like yourself and Sam who understood the digital tech world better, you know, was absolutely the path that he needed to take. And for sure, and lucky to find you guys, which was great.
Speaker 1
Well, you know, you've, you've hit on this a little bit already, but I'm gonna, you know, let you maybe pull, pull some strings together. Here is that, wow, you're working for some great companies. Like, why leave that for the entrepreneurial path?
Rory Capern
So I started to get a lot of calls, usually from venture capital, saying we've just put five, 10 million bucks in a new business. The typical profile is the 25-30, something set of founders who haven't really done it before. And it's a in the beginning, it was, we just need you to help you go and please go in there and help them de risk all these decisions that they have to make. And there's a really fascinating dynamic I find of new founders. Yep, when they first get funded, they found they've been super scrappy, and then find product market fit. But once you get a big check and the pressure goes up quite a bit. The problem is that there's a there's a communication issue, which is usually a founder, if they admit that they don't know what to do to their board, triggers a whole bunch of concern, yeah, and if they talk to their team, triggers a whole bunch of fear. The leader doesn't know what to do absolutely and so. What I found my kind of entry into that space was the ability to be that call, do I turn left? Do I turn right? How do we think about these things? What are some of the common pitfalls that anybody would make for the first time? Don't fall in the hole, don't touch the hot stove, that kind of stuff. Absolutely, it originally started with a real focus on revenue. Most of these companies have a really hard time splitting up a revenue, engine, marketing, lead gen, sales, all that stuff. That's an area that I've got a lot of depth in. So I was able to apply quite a bit quickly to get them up the ramp fast, but it quickly morphed into broader topics as it relates to scaling up teams and hiring the right people, and defining culture and all the things that you have to do early and well, to get right down the line, to really be able to successfully grow, and it's kind of taken off from there. It's been about five years. I've been gravitating more and more to this company I was talking about earlier, called Redbrick...
Eric Morse
Well, tell me more about Redbrick. What a your Chief Operating Officer?
Rory Capern
COO, there, I lead the M and A function. So we've been acquiring quite a bit, but it's kind of a dream gig. If I'm honest. I love the deal. As I said before, it's just fascinating.
Eric Morse
Well, what do they do? Tell us what they do.
Rory Capern
So, Redbrick... It's a business that's there to empower digital entrepreneurs, okay? So the company has invested in a series of different companies. It's a holding company, and we believe that there's just this massive opportunity, really, in the SaaS business, okay? To make to sort of power the ability for entrepreneurs to drive their companies online and do it successfully and continue to make it easier. So we bought a company called LeadPages, which is landing pages like four years ago, bought a company called Delivra, which is an email service provider. And most recently, we bought a company called Animoto, which is Video Production online. They built a browser internally about 13 years ago, incredibly successful. It's the biggest browser you've never heard of called Shift, super interesting. There's a whole other talk track around that. Given the experiences that I've had both with Internet Explorer and then with Chrome at Google, fascinating business that they've done really well with, and we've been sort of leveraging the success from that company to acquire other ones in the service of the digital entrepreneur. Fantastic. So my gig there is gig there is buying the next asset, sometimes selling, we don't sell very much, and then working with the CEOs of the acquired businesses to help them hit the plans that we agreed to on the way through. So it's this great mix of M and A and operations and an amazing team right in Victoria, where I've very close to where I've moved. (Fantastic) So the ability to find this tech hub in Vic, I was saying earlier, I had no idea what was going on when I was living in Toronto, sure. And the conditions just got right all of a sudden. And I made this move serendipitously for family, and was introduced to this incredible community. (Fantastic) Tobyn Sowden, who's the CEO, CMOs name is Marco Pimentel. We just got along quickly. And I started advising, and then sort of worked my way through these additional roles and find myself as the COO, which has been amazing.
Eric Morse
Yeah, well, I, you know, I think this is something that we've chatted about in the past, but you've been part of all these tech companies, and I think been able to bring to them, you know, the importance of the people side, right relationships, partnerships, and even critical in what you're doing now in M and A Right. Is this going to be a good fit for us? And, yeah, and who are the people involved in that? Can you talk to us a little bit more about the importance of people, even in, you know, the tech side of things?
Rory Capern
Sure. So the mantra that I, you know, my teams are always sick of hearing it, but I believe that business is about people before it's about anything else. We are here to unlock the potential of employees and people on our teams, but we're also here to meet needs for customers and consumers, and that's a highly human thing. So I start there, usually because the great work, the the awesome deal, the incredible unlock inside of a business, comes from an insight that comes from a human and so building the conditions to have that happen. The idea is to spark, but also the collaboration that's required to make ideas come to life. This is all about teamwork. It's all about understanding how to define a culture early, how to hire for it, how to keep it, how to defend it. I just don't think business is successful without a solid investment early in humans.
Eric Morse
I couldn't agree more, and I think it's even it's always been important. But I think today, with kind of revised work platforms and some at work, some off and building a culture is maybe more complicated than ever, but I think more important than ever.
Rory Capern
Yeah, I think so. I talk a lot about people understanding what their deal with your company is.
Eric Morse
Tell me more.
Rory Capern
It's not a paycheck only, right? There's a lot of companies that can pay the same amount of money. Yeah. What I think people need to understand is how they're connected to the business and what's in it for them, (right, sure) if they stick around. So the personal development plan, the career track discussions, the idea of training and learning and parallel learning, and all the stuff that you can open up if you really understand somebody that you're working with, and you have that conversation in the right way, you build a plan that is the deal for that person inside the business. And most companies don't have this right so my view and experience over the last 30 years almost is, if you don't know, if your team doesn't know what their deal is, they're poachable, because there's always a company that will pay more Absolutely, and we need to find ways to retain that culture without just having to pay or battle on a paycheck. And I
Eric Morse
tell that to entrepreneurs all the time, if I say it a little differently than you would do, but I say, Look, if it's all about the paycheck, we're going to lose because we don't have the resources absolutely to compete with the Googles and the Twitters and all those people that will poach really good talent, right? So I love that the deal. I'll try to remember that I know you're here as entrepreneur in residence. You help out a lot of our teams. You know, off and on throughout the year and every fall, and you keep coming back. So what is it about mentoring students, or mentoring in general, that keeps you coming back.
Rory Capern
So part of it is entirely selfish. I get a head full of ideas coming back and speaking to students. There's a, I don't mean to make this sound negative, it's absolutely not. But there's a, there's a benefit in naivety, right? Like having been in the in the market for the last chunk, I sort of pre cancel a bunch of ideas because I have, I've seen them not work before. But when people that haven't had that experience come to the table and articulate a thought or a new idea that I would probably otherwise not listen to, I learn a lot. I learn from fresh eyes. And so I love that aspect of it. It's very selfish. The less selfish part is I benefited enormously from a bunch of Ivey alumni who were only too willing to pick up a phone or help when I was running a really small company, and with a couple of other Ivey grads getting that off the ground, there was just this incredible support network. And when I was going through that, especially as an entrepreneur, understanding the value of that and how important it is to be able to build a strong tech ecosystem, which is really what motivates me today, to be able to do it from here is just been incredible. It's a constant source of inspiration, but it's also an immediate impact.You can kind of poke the world. When you come back and talk to a fresh eyed student about something they want to do, and help them do it. It's just very rewarding.
Eric Morse
Yeah, absolutely. I you know, do you still have mentors, still people that you reach out to?
Rory Capern
Yeah, I was told early in my career that you should always have a personal board, and I do. These are the folks that I turn to when the path isn't clear, and sometimes just for a beer and to catch up, absolutely. But I think it's critical the ability to get that fresh perspective comes from mentors for me, and I've got them all over the place, in different disciplines, some business mentors, some personal mentors, and then a whole bunch in between. But I just think it's a critical element of being able to live a happy life. At the beginning of the journey. I guess that's for me, the really interesting part. I talk a lot to the NVP (New Venture Project) students that I work with about sales, yeah, I just don't, I didn't really learn that much about it while I was here, and it's absolutely critical importance. And whether I'm dealing with somebody who's just totally into finance, I try and use that opportunity from a business perspective to show how important the rest of the analysis is. Yes, your numbers are tight, and that's great, but how are you going to actually sell this thing? How do you get it to market? Like those kinds of questions are the ones that usually open up fascinating conversations and and I watch students think about things from a new lens for the first time, (absolutely). And if there isn't, if that's not inspiring, then I don't know what is
Eric Morse
Yeah, I agree. You know, not to quote Ted Lasso, but staying curious, yeah, is really important. And you know, it's so much fun when you are mentoring a young person, however you want to define that, but you know, up to in their mid 30s, sometimes, probably more about my age than anything else. But anyways, I digress, when they're still curious, when they know they don't have all the answers, and they just want to learn, and they know that you may not even have the lesson that they're looking for, but they're looking for that one piece, that one gem. And, wow, that's so much fun. And I, you know, I certainly try and maintain that myself as I look to people that I consider my mentors, is, you know, what's the one thing, two things I'm going to take away from this meeting and this, this opportunity that I have in front of me, and, you know, just, it's, it's magic when you get to the chance to meet with some of our students and young people that have that curious edge to them still and really want to learn. Well, and we, you know, I my last question I always ask, and maybe it's sales, although I think we finally are doing a little bit on that in that regard, teaching sales. What would you recommend that that we're doing for our students to help prepare them for career and entrepreneurship that maybe we're not doing or, you know, just in general.
Rory Capern
So not as close to the rock face I used to be in terms of what's going on in the classroom. So I don't want to misspeak, but there's two things that I talk about a lot, yeah, just what?
Eric Morse
What's important to you? Yeah?
Rory Capern
One is the value of lateral learning. So don't fall into the business hole. There's a lot of things to understand, human psychology, economics. (Stay curious) Exactly. And I think the strength of that comes out in two different ways. One is, I think you can build a better product if you understand the world from a bunch of different perspectives. But two is in the ability to relate others, right? So those who might not look through the lens of business all the time, yeah, that the ability to find a common bond is usually a very important unlock in the context of finding consumers, finding a market that sort of, absolutely, that's thing, one that sort of lateral approach that, yes, we're getting, you're getting a great education in business, I will defend as the finest in all the land. But how that education intersects with other parts of the economy, right? Is actually where the business is, yeah, right. So you need the engineer, you need the musician, you need the writer, you need the politician or whatever to be able to put business into work most of the time. And understanding how those connections happen is something that I think often gets overlooked. (Great) Second is sales, right? So I think in large part because my experience didn't involve it very much while I was here, and it became such a critical element to succeeding in any facet, whether I was consulting or working for any of these tech companies or running my own thing or working inside another business, right? You know, it's such a cliched thing to say Eric Janssen is a good follow on LinkedIn if your listeners don't, but I'm so happy to see him doing what he's doing in the context of the content that he's bringing forward, because I think these kids need to go into the world armed with an understanding of how to communicate, how to connect, how to articulate value, how to understand needs, all the things that you learn well, you don't have a business till you make a sale. Revenue is a really important part of the equation.
Eric Morse
For sure, yeah, for sure. And it's been missing from business schools globally for so long. It is nice to see it finding a place.
Rory Capern
Yeah, absolutely. And there's a lot, there's a lot of openness to it, yeah, but it takes a while to like, crack through that.
Eric Morse
It does. So great to see you again. If you were to leave our listeners with one last thought, what might that be?
Rory Capern
I think I'll go back to the quote business is about people before it's about anything else.
Eric Morse
Yeah, fantastic. Great to see you, and thanks so much for joining us.
Rory Capern
Thanks for having me. Great to be here.
Eric Morse
Awesome.
Outro
The Entrepreneur Podcast is sponsored by Quantumshift, 2008 alum, Connie Clerici and Closing the Gap Healthcare Group. To ensure you never miss an episode, subscribe to the show on your favorite podcast player or visit entrepreneurship.uwo.ca/podcast. Thank you so much for listening until next time.