Rachel (00:00)
Thanks so much for joining us, Kirk. We're so excited to have you. Goal for this time is to delve into your story, better understand your founding journey and your views on building in Canada. So thanks again for joining us.

Kirk (00:36)
My pleasure. Thanks for having me.

Rachel (00:37)
First question is call it a basic one. Tell us about your backstory and what context should someone know to understand where you are now.

Kirk (00:45)
I guess most of it came from my journey with Wave. So James Lockery and I started the business in 2009, got serious about it in 2010 and had a really fun, crazy journey to selling the business in 2019. I stayed with it till 2022. I'm about three years removed from that journey, but I think for most people coming to this, that would be where they might've heard of Wave and myself. About 1200 people worked at Wave over the years. Some amazing people that have gone on to do remarkable things. And it was just a real highlight for me.

Rachel (01:25)
That's fantastic. And for those that don't know the founding story, what was a seed or why you guys started with

Kirk (01:30)
Yeah, I think James and I were both at a point in our lives where we were looking to do something entrepreneurial. We really didn't know which field we wanted to go into. He had a long background with small business tax and I had been a small business owner myself and felt the pain of sort of those back office tasks like accounting, tax, payroll, those kinds of things.

And so I came at it from a perspective of a potential customer, not wanting to do any of those things and feeling like those were getting in the way of most small business owners lives. He came at it with some domain expertise. Liked the space and between us came up with some ideas around the go-to market and the technology and those kinds of things. And as I mentioned before, it got serious about it in 2010, raised our first round in early 2011, which was a very different time in the Canadian tech ecosystem.

Was one of those first companies to get a lot of attention with Valley based VCs in 2012. And over the time raised about a hundred million dollars Canadian and got the business to about a hundred million dollars of revenue per year. And yeah, it was an amazing, fun, ridiculously crazy journey.

Rachel (02:41)
Such an incredible outcome. If you reflect back, many founders have the "oh my god it's all over" story — things that might've happened along the journey where it looked like things were going in a very different direction. Can you tell us about a time like that and how did you go about navigating some of the perhaps more challenging periods?

Kirk (02:59)
Yeah, I think like a lot of startups, had a couple of those. One in particular was very near death in 2015 where we were technically insolvent and in breach of our venture debt and probably about 10 days away from full sort of cash out. I would say, how did we navigate those times? You just fall hands on deck trying to make sure that doesn't happen. A lot of people had put their faith in us to really make Wave a place where they could build their career and rely on us to help pay their mortgage. And so there's a lot of stress through that period, but I think you try and put one foot in front of the other, try and make today better than yesterday. And if you string enough of those days together, good things start to happen.

And part of it is just fortuitous luck at different parts of the journey. And you can't really put it down to anything other than that. We had a strategic investment coming from ADP, the big payroll company. The whole board didn't think that there was any way that they would come through and we'd be able to close that deal. Thankfully, the president of small business was someone who did what he said he would do and came through in the clutch — and that saved us.

Rachel (04:09)
That's wild. I haven't heard many founders in their OMG moments describe being borderline insolvent. So it's pretty remarkable that you were able to pull that off and drive that turnaround situation. Switching gears slightly, building in 2025 — there's a lot of negative press out there, productivity issues in Canada, all of our great talent are leaving the country — and you chose to build here. So I'm curious: What are some key lessons that you learned about building in Canada and any thoughts you generally have on the topic given this hot button?

Kirk (04:43)
I think there's a couple of things that I would say about it. The first is that the pendulum has a tendency to swing too wildly in any given direction. I think for a while becoming a tech entrepreneur was so romanticized that people that were going into it without their eyes wide open to, I'm being honest, what at times painful life it can be in front of you. I like to describe the fact that being an entrepreneur — and really putting your all into it — despite having three kids, a lovely wife, great family, great friends, all of this kind of stuff...

I remember on specific days going for a walk during some of those high pressure moments and looking around and the blue sky isn't as blue and the green leaves aren't as green because your business isn't doing what you need it to be doing. And there's a lot of people who are relying on you and customers relying on you, etc. And it really shouldn't, in my opinion, be diminished how it takes away from other aspects of your life at times. And of course it's gratifying in so many other ways, but I guess my point is it really shouldn't, in my opinion, be fully romanticized. It should be a path for people who want to pursue it, but it's not a path we all need to go on. It's not a path all of us should go on.

So I think the pendulum has swung from that to a place now of negativity around building in Canada, etc. And if I'm honest, I look back on the time that we were building Wave — and this might not be the case for everyone — but I really honestly, for the most part, didn't care what was going on in politics in Canada. I didn't care about whether or not the government was investing in startup incubators or whatever. I was focused on building the business. And as long as we had a safe place to live with rules that were consistent, that was producing great talent, then I felt like it's the entrepreneur's responsibility to take from that and build upon it and not expect any handouts or that someone's got to pave the way. Like you got to pave it yourself, and you and the team just need to be better than the other people that are working on this challenge.

I look at the situation and I think to myself, I don't think the fundamentals have changed. I think if smart people, young people who are graduating today believe that there are companies here that they can learn at an accelerated pace, that they can have lots of opportunities, that they can raise their families here if they choose to do so, that they've got a good quality of life — all of those kinds of things — then we can attract the best to stay in Canada and build.

Rachel (07:47)
So refreshing. It's almost like it's just noise. Focus on the problem, focus on the customers, put your head down, build a great team and get after it. That's super refreshing.

Kirk (07:56)
And in some ways the companies that are comfortable with more remote work can pull talents in from anywhere in a way that was very difficult to do in the early 2010s as an example, and certainly before that. And I remember we had this one executive who was so good that it didn't matter where he was or how much we had to move the way that we worked around him because he was more remote. That is so much easier to do now than it was back then. And the tools were hard to use and clunky and the person felt alienated and all those kinds of things. That doesn't have to be the case now. So there's even less reason why we can't just get down to it and build great companies.

Rachel (08:39)
And that really resonates. So it's a good segue into — you've been known to give back to the community, having had impact in your past team and many other folks. And so curious to hear: you've done some mentoring, what drives you to mentor others? And can you maybe share a story of a founder or a leader that maybe had an impact on you from a mentorship perspective in your building journey?

Kirk (09:00)
Yeah, so I think as you said — and I think this is cliche because it's true — everybody got to where they are by people helping them. And what more should somebody do or how to look at it any other way than of course it's your responsibility to do the same as best you can. I had many formative people in my life. I'll quickly tell the story of this woman, Carolyn Meacher, who...

I had my first failed .com startup in like 1997 to 2000 and I had dropped out of university twice. I was now saddled with all sorts of personal debt coming out of this. I was whatever — however old I was — 25 or something like that. And I really didn't know what I was going to do because people who are entrepreneurs, especially early on in their career, know that you very rarely get the opportunity to focus a lot of your attention on a given area of the business. In the early days, you really got to spread yourself across many different aspects of the business. Quite frankly, whatever needed to get done, you got to roll up your sleeves and try and do it.

And so as I was out of a job, no university degree, no real signs of any sort of momentum in my career — this woman by the name of Carolyn Meacher not only gave me my first job, but really believed in me. And one of the things that I think was really formative was in the early days when I started working at Keymedia and we would go to meetings, she would tell the story of the startup that I had done and why they were quote-unquote lucky to have me join. And I tell you, there's nothing like building confidence in somebody — of course in an authentic way — but building them up so that they can grow into what you believe is possible for that person.

And I think she just exemplified that for me. And it was something that really stuck with me because it was so formative to my career to have somebody at that stage believe in me, give me lots of opportunities, show me where I wasn't living up to the standard, and show me how I could live up to the standard. All of those kinds of things were so formative.

Rachel (11:07)
I think we've all had folks like that. But I think the way you framed it — around believing in what you can grow into and just relentlessly supporting you to do that — it's fantastic. We've been so fortunate to have your input and mentorship at Simple Ventures as a sounding board for new ideas and in some cases helping us vet and interview CEO candidates. What attributes do you believe make a fantastic CEO — specifically early stage from a founding journey perspective?

Kirk (11:34)
You're too kind in the description. It's been a pleasure and it's always... I think the thing that makes the world go round as it relates to the working aspect of your world is just getting to interact with smart, driven, passionate people. And I really had that feeling at Wave and quite frankly, you need to be careful what you wish for because obviously we were excited about the exit and gratified for the results and all those kinds of things — but I definitely missed that feeling back in those early days of just being in the trenches with amazingly smart, driven, compassionate, fantastic people.

And so we've got that at GoConfirm now, but my work with Simple Ventures is just a good reflection of — it's just great to be around folks like yourself and the team members who are really trying to build. And we all know it's really tough building. And the people who want to throw themselves at that and have that as their life's work — it's a joy to be around.

Back to the question — can you remind me of the question?

Rachel (12:36)
Thank you for those kind words. What are attributes that you believe make a fantastic early stage CEO?

Kirk (12:41)
What are the attributes... If I were to have to sum it up in three or four:

I think the danger is you have a mental model of what it means to you. And I think it's important that I try and expand that out to other examples that I've seen. Because for me, I'm a highly competitive person. And so for me, that trait of competitiveness or wanting to compete — not necessarily in the sports metaphor — but more from the perspective of...

I think you have to have a grit and a resilience. Going again through the journey with GoConfirm has shown me — especially in the early days — it takes so much to get any sort of escape velocity on your idea. And the ability to continue to stay positive and stay committed and stay focused as you're seeing a lot of negative signals is really difficult. And so I think a level of compete, resilience, grit — whatever you want to call it — is really important. And I don't think it goes away.

Because once you get to the next stage, it's a new resilience to an organization getting complacent or these kinds of things. It's just a constant need to reflect and to stay on the path and stay committed to the goal and all of those kinds of things. So that's one.

The second is — and again, I might not be using the best words, but hopefully a description makes up for a lack of word — but something related to charisma and an ability to sell an idea. The reason for that is because — especially in my mental model, which is tech startups — you have so many people you need to sell the vision to. Whether that be investors, employees, customers — you are constantly describing this new world that hopefully your product can provide. And your ability to do that in a concise, positive, forward-facing, exciting way is really important. So that ability to inspire is really important.

And then I think the third — related, but not the same — is the people side of the business. The ability to be both empathetic but also hard-driving. The ability to connect with someone while also pushing them to levels that they didn’t think were even possible. I think all of those things together are what I look for.

Rachel (15:18)
The last one is such an art — and it’s key. You summed up the crux of leadership, right? And it’s so hard to find exceptional leaders that have that innately and that have the track record of doing it. So all three really resonated — but that last one, that last one hit. A bonus question for you and then we’ll wrap. Is there something that you’ve read or a podcast that you’ve listened to that you’ve learned something from that you’d recommend to any listeners?

Kirk (15:43)
Oh, interesting. I have a tendency to just read and digest a lot and then take nuggets from different places. I'm not sure that there's one in particular that really struck me — or that's at least coming to mind. I think what I've tried to do, especially over the last 12 to 24 months given this new world that we live in, is just try and not be pigeonholed into what I read, what I listen to, etc., that feeds my own sort of bias. But instead try to understand the world through other people's lens so that I can at least understand what's happening.

And so whether that be in tech or politics or anything, I just find I'm trying to widen my reading and listening list to just try and get more ideas from different sources and be a little bit more discerning about what I'm trying to glean from it — versus being fed purposefully myself in the selections that I make, only listening to certain voices.

Rachel (16:45)
Fantastic. Thank you so much for taking the time, Kirk. Really appreciate it.

Kirk (16:49)
Thanks so much for having me.