From Bootstrapped to Public: Lightspeed's 20-Year Evolution

That's why I love this current era of being able to work remote. You know, I just came back from spending a bit of time in Los Angeles. I didn't really take vacation. I was like working remote. It just helps you take perspective from the company and be able to be a better leader for the company. I love being in the office together. The energy is incredible. It's also great to be able to get perspective because being in the bubble is not always healthy for the company if you never leave the bubble.

Welcome to Startup CEO Show. I'm your host, Mark MacLeod. In this episode, I sit down with Dax Da Silva, co-founder and CEO of Lightspeed Commerce. Lightspeed is about to celebrate its 20th anniversary. And so in this discussion, we unpack that journey, the early days where he was coding to 4 AM, his decision 7 years in to raise venture capital, uh, his experience leading a public company, the decision to come back and be CEO of the company. And in an interesting and delightful tangent for me, the role that faith has played for him in all of this journey, giving him the resilience and the humility that he's needed to always be the best possible CEO for this company. I really enjoyed this conversation. I hope you do too. Dax, welcome to the Startup CEO Show. It's a true pleasure to have you here today. How are you doing?

Great. Thanks for having me.

Real pleasure. Yeah, someone here to look forward to having you on this show for a long time. I first heard about your company. I lived in Montreal for a long time and I was one of the original general partners at Real Ventures and Lightspeed was very much under the radar, I would say, until Accel seemingly swooped in out of nowhere and did a big round in your company. And then I was just like, man, why weren't the Canadian VCs all over this? So that's another story. Let's, I'd love to get to that initial funding journey, but I'd love to start, you know, you've been very open about, uh, you know, your, your backgrounds, uh, as a queer man and how you built diversity and inclusion into your culture from day one. And it seems like the world is going in the exact opposite direction these days. And so I know what you think about this, but it's an important topic and I think people should hear about it. So I'd love to hear your thoughts on the environment today and, and the benefits you seeing from building a company that is counter to that environment.

Yeah. And we just, um, I just sent, uh, uh, some notes out to the team. Like, this is a part of our DNA, right? We, Lightspeed was started by, um, there was 4 gay men at the, there were the first employees of Lightspeed, including myself in Montreal gay village. Uh, and this is before DEI was even an acronym, right? This is like 20 years ago. We're celebrating our 20-year anniversary this week, actually. So 20 years ago, you know, we, um, I basically put together 4 people that I, that I knew and trusted and thought were going to be, you know, great, uh, great on the team. Um, and, uh, and every, every person we added to the team thereafter, uh, obviously they came from many different communities, but I think that the standard that we held for the company was, you know, I would want a fair shot at opportunity if I was coming into a company and I wasn't like everybody else. And so that was the baseline for Lightspeed is everybody gets a fair shot at opportunity. And it didn't matter who you were. And I feel like even the folks that weren't part of the LGBT community, which was most people after a little while, always felt that they could be their most authentic self at Lightspeed. And that meant maybe they didn't have to put up as many masks or be somebody that they thought they needed to be at a particular company. And that's our highest ranking engagement on our engagement surveys. That's the highest ranking value. The thing that people feel the strongest at the company is I can be my authentic self at work.

I think I saw that on your LinkedIn today, like 89% of people feel that way.

I'm so proud of that because I can be too. You know, I've come back, I've come back in the last year and appreciate that about the company of, I feel really I can be my full self here. I can challenge myself in ways that aren't— there's no other— there are no bigger challenges. And I feel like people are able to do the best work of their lives. They're able to be who they truly are and also engage with people that are also being their true self. And I think that's a really high value in this social media era, this internet era where authenticity is very highly valued because there's a lot of fake. There's fake everything, right?

Fake news. Do you name it?

People can sniff it, right? They can, there's a, there's a, there's a heightened, especially in Gen Z and Gen Alpha, like there's a heightened ability to sniff out things that are not authentic. And so that's, that's DEI for me. It's, it's, it's, it's not, it's not a bunch of political polarities. And I think it's sad that it's, that it's become that kind of conversation because it's about Lightspeeders being their authentic selves. And bringing up their best, being able to do the best work of their lives and being able to be the best person at this time that they're going to spend with us.

I love that. And I can't see why anybody wouldn't want that. And so let's talk about how that kind of shows up for you, right? So I only coach CEOs. The CEO role tends to get lonelier, you know, the higher up you go. And often I'm encouraging CEOs like, dude, just take your armor off. Like, be vulnerable, be open. And so I'm wondering, like, you know, Lightspeed has gone through kind of some ups and downs, perhaps not on its trajectory, but more in its share price, but that's out of your control. But like, um, like, how does that show up for you? Are you willing to admit like, I don't have the answers, I'm stressed, I don't know, like, yeah, like, like, how do you show up in meetings when being your authentic self?

The tone comes from the top, right? Company culture comes from the top. Uh, I think one of the things that I value the most, uh, and listen, a lot of people, there's a lot of new people here since I, since I've come back, those 2 years where I wasn't in the office, right? Where I was there. But what I love about this company is that, um, people aren't afraid to tell me things, you know? And I, and I think that once you get into this place where people can't tell you the truth or people can't bring you the reality, then you're all in trouble. Right. So, and that is that old parable, right?

The emperor has no clothes.

That's, that is always, always been, I think the case for this company is that people feel comfortable telling me bad news and don't sugarcoat things for me. And, and I think there's, there's also this idea that, that, that, that doesn't, doesn't, that doesn't help anybody, right? To, to, to create an alternative reality where everybody's just cheering, right? Uh, in the good times and in the bad times, right? That's, there's, there's a, it's, it's wrong. I think the way I look at the, the way I look at things is I'm an instrument, you know, I'm, I'm an instrument and, uh, I don't claim all the successes and I don't bear all the failures. Right. That's just philosophically, spiritually, that's how I look at things. Right. And so we all need to be able to talk about the good and the bad, which happens in multiples daily. Right. And so that is, that's, that's important. And when, when, when we're not actually personally blaming each other, we're all instruments trying to do, you know, be conduits for what's going to be good for us here at the company and good for us collectively and good for our customers. That's less personal and it's like, let's try to solve or celebrate what we have in front of us. I love that.

When you bring in leaders from the outside who presumably haven't operated that way before, how do you get them to unlearn the previous habits and then learn to actually let their guard down and be open?

I think it's showing it. I think it's the interactions, it's the listening to one another. It's being able to have vibrant conversations and still be real, right? Uh, and, and not try and not go on attack, uh, when things aren't working. You know, I think that that's— there's, there's behaviors that can be learned if, if they're, you know, if they're portrayed and they're negative, right? That's— it's, it's you as, you as the leader have the ability to set the standard for how, for how communication happens. One thing, one thing I've noticed is that, you know, we've had execs over the years that have come from a lot of companies in the US that have been much more hierarchical than Lightspeed, maybe people don't talk across levels, right? And I think that that's part of the reason why people feel okay to talk to me is because I'm not particularly hierarchical. I think it's an easy thing to unlearn. I think it's beneficial that you're talking to everybody no matter what layers you are in the company. That is only a construct so that we can scale, right? It's, um, and, and that's, that's sort of maybe a little bit of a Montreal thing too, right? Or maybe a Canadian thing where people aren't so stuck on the levels. Um, they're, they're interested in, um, and how we're building something together, right? And, but that can be difficult for leaders. And so you do need to model, um, uh, the way that we want to work, right? And the way we want to communicate, uh, within the company.

I love that. Maybe let's take a step back and talk about your funding journey. And you've been through, like you said, you're about to celebrate your 20th anniversary. So you've been through different platforms. I think maybe you were originally a desktop app and then, you know, moved to the web, mobile, et cetera. Um, and so you were well into that journey before you decided to raise venture capital. Could you talk us through like what was, what made you decide, okay, I'm going to go down that path?

Yeah. So we did, we bootstrapped the company for 7 years, the first 7 years. Uh, we did 7 years of VC, started off with Accel and Inovia, then later Casadepo and, uh, um, Investissement Québec and others. But yeah, that first 7 years, um, the bootstrapping years, I actually feel like we're, I feel like we're sort of a little bit in that, in that, in that mentality today because we're not growth at all costs. We're, we're in a profitable growth phase. That's why I came back to lead us to this more balanced period of growing, but profitably. And that's, uh, and sort of it's the long term. It feels a lot like the bootstrap days, right? Where you're, where you're keeping costs and, and you're, you're conscious of, of how everything, how everything balances, right? Of course, when you, when you, when you get VC funding, uh, it's to, it's to step into hypergrowth mode. We were, I think, in for, you know, more than a decade. Uh, and then I think all of the acquisitions, all of the things that we did have led us to a point where we are now, you know, you're working on a transformation to make sure that Lightspeed's set up for the long term. That's a little, that's the reason I've, that I'm back. But the, but the VC period, I think, um, helped us move from the on-premise Mac-based point of sale that, uh, that I built originally and moved it to the cloud. That wasn't actually the thesis behind the investment. The investment thesis for Accel was, you know, Apple is ascendant in, in, uh, in terms of business application. Um, this is, this is like track, this is 2005 where Apple's really having its comeback, starting to open retail stores. They're trying to, they're starting to transform retail with their mobile experience. Uh, and so we were and also payments was coming together with that Apple experience. So we kind of, we were the intersection for a lot of investment thesis at Accel. Apple, payments, business apps. And so, but very quickly we realized collectively with Accel that things were moving to the cloud very quickly. And then we were going to in order to unlock the next levels for us, that we didn't want to pour gas on the fire of the current on-prem platform and just build out a huge user base. We wanted to bring our developers to a cloud platform. We acquired, you know, the kernel of a cloud platform and then, you know, brought those teams together. And that was the first Lightspeed Retail in the cloud. And that's where, that's where we really did a lot of scaling. A year later we did a similar launch with Light Street Restaurant because we're helping all the complex retailers on the street. And now we thought, okay, you know what, we have a very similar go-to-market, a very similar sort of thought process around this type of more complex merchant that's doing, that's more established, that's doing higher volumes, has, they're not quite ERP users, but they're, you know, they're They're, they're, they have more sophisticated needs. And so we extended that, that, uh, that to hospitality as well, mostly in Europe. Uh, our user bases are that Noam retail and that European hospitality customer, you know, all these years later.

Yeah. I mean, that combination of the SaaS and payments, right? Just so powerful, right? Like chocolate and peanut butter. I saw that at Shopify and, and also at FreshBooks. And in both cases, payments grew to become the largest single portion of the business over time. Just so, so powerful. You talk us through, I guess, your decision to go public and any advice you might have for CEOs who are considering going public. You know, the recent cohort of Canadian IPOs haven't really worked out. Maybe let's park that and just maybe talk generally about Yeah. Your thoughts on going public.

Yeah, I think it was like a very, it's been a very positive experience for Lightspeed in terms of just the graduation, you know, to another, another level of operating, another level of communicating your story. So yeah, you know, for sure there's been challenges for Lightspeed as interest rates fell and we were very oriented towards grow, grow, grow. And now to be a company in its profitable growth stage requires some shifts that we've been doing. But I think that even that shift, the market gives us immediate feedback. Uh, and it gives us whether you like it or not, whether you like it or not. It's, it's, uh, it's sort of a purifying and sort of a, um, uh, a way to hone your story for that. That's useful for your employees, for your, for your customers, for the market. And I think that when you get things right, um, you know, you, you can, you can reap rewards for all your stakeholders, right? Uh, but it also, it also helps you operate at, uh, uh, at a much higher level in terms of, you know, having, uh, a board with great governance, um, you know, being able to attract great employees, uh, being able to, you know, have the coverage of the company. Uh, so there's, and, and of course, you know, raising capital, right? We were able to do, able to consolidate a lot of the complex SaaS players, uh, in retail and hospitality because of the because of, you know, the money that we were able to raise in the public markets. There's nothing like that kind of the power that you're able to, and the resources you're able to deploy because of capital markets, right?

Did going public change your day-to-day life a lot? Like as an example, did you find spending more time communicating versus operating, or is it, was it actually manageable?

I think it did. Like I don't, um, I I think that, uh, you're always, always have spent a lot of time being the external and public face of the company. Uh, obviously there's a lot more, uh, there's a lot more that you need to do as a public company, uh, in terms of interfacing with, uh, with investors, doing investor conferences, uh, doing media. Uh, but I do enjoy all of that because I love talking about the company and I love talking about what we're doing and what's exciting. But yeah, there's more obligations there. And then you have to supplement your team with great operators so that you can do everything. So yes, yeah, I think it does shift how a CEO spends their time. But I think for net positive, you know, in terms of what you can do as a company.

My understanding is you describe yourself as an introvert. So I was a little surprised to hear you say you enjoy that. Have you, I don't know, come out of your shell over time and been less introverted?

Uh, I think I started out as an introvert, you know, that I, I, if I, uh, what I've said in the past is, and it's funny because we're, we're like looking at, uh, for the 20th anniversary, we're looking at pictures of me sitting in front of the computer 20 years ago. Uh, with this picture of me, like, you know, doing the programming thing., as like a 28-year-old kid, right? And so I was an introvert back then, you know, I think that I was coding till 4 in the morning for 2 years straight at the beginning. Uh, and I would come down, uh, I was like, I was a 3rd floor apartment in the gay village. The, the office that was the 2nd floor, I walked down the back staircase, those spiral staircases you got Montreal. Uh, and honestly, the team didn't really hear from me for a while. I had it all in my head. I spoke and visited with customers. Deploying new versions of the software. But at some point the team was growing. We were very successful very early on. Uh, 200 or 300 of the leading Mac dealers in the, around the planet, around the whole world that bought Lightspeed. And then eventually they went on to become our resellers and sell it everywhere. We did 2 certification camps per year. So it really scaled really, really quickly. Uh, and I think that the team needed to hear from me at some point. We needed, they needed to understand what the vision was. They needed to understand what was in my head. And that's where I think I ventured into being more of an extrovert, being more of somebody that was comfortable with communicating. And so I think it was Lightspeed that really forced me into considering being a leader, right? And enjoying interacting with folks and And now I think that like if people will see me on a, in a social setting, they would tend to think I might be an extrovert, you know, but, but I think that's, I think it's, it's, um, it's an interesting question. Uh, there's a professor, um, Professor, uh, Carl Moore that's writing a really great book here at McGill. And I've traveled with him with a group, with a group to, uh, to Ghana and Ivory Coast. And we talked about this book. About introverts and extroverts and, uh, and ambiverts and, and the whole thing. And I think especially when you've had a career in business, um, it's, there, there becomes many different parts, you know, to, uh, to, to who you are.

You know, I think we have this stereotypical definition of a CEO, broad shouldered. Okay, check. You've got broad shoulders, male, unfortunately, check, you know, charismatic, makes it rain. We don't often think about the CEO being introverted, but in my experience, I've been in the startup world since 1999. I actually think that introversion is a superpower because, you know, you talk about that hypergrowth. The only way to get through it is self-awareness, right? If you think your shit doesn't stink and you start believing your own hype, and let's face it, startups are full of hype, you stop seeing the signals and you stop learning. And so the CEOs that I've seen thrive the most are actually quite introverted. And so as a result, they're highly self-aware. So I don't know, I see it as positive.

Yeah, I think the reflective nature of introverts. Yeah, I totally agree that helps. It's a part of growing, right?

I'm curious. I do want to carve out some time on your leadership philosophy, but this seems like a natural place to ask this, you know. So that, that kid who was coding till 4:00 AM, not naturally communicative, other than just putting in the reps and putting one foot in front of the other, what have you done? Like what, I don't know, tools, resources, support, like whatever comes to mind, have you surrounded yourself with to always be the CEO that this company needs and to kind of stay one step ahead of the company?

Yeah, I think it's definitely a little bit of a philosophy of let's throw away your job description every year and what does the company need from me this year? And also then that means stepping away from things that you're really good at and really love. Like for example, you know, have a design background. You know, there's a lot of artists in my family. There's a lot of creativity. That's why the original version of Lightspeed was such a hit was Um, the, the user experience, user experience, and I was an okay coder, but those are two things that I got a lot of satisfaction out of. Uh, fast forward and you're, and you have me, you know, in the, in the finance world, running a public company, no background in that. It's like, there's been, there was many moments between me being a designer coder and me being a public company CEO where I'd throw out my job description so many times., and I had to step into something I was super uncomfortable with and didn't know how to do it, you know. And so that, I think, is something you've got to show people, uh, at the company that you're willing to do, uh, and that you're gonna— might need to ask them to do, uh, to push the company forward, right? So you need to be able to do that and not hang on to, uh, things because you like doing them or you're, you're, you're or you're good at them. You have to, you have to do that. So, and I think that comes from, you know, I would say, what are my tools, Mark? I would say it's, I've made a lot of investment in spirituality in terms of, in terms of my journey. I mean, my journey as a, as a startup CEO, I did it, my, it coincided with my conversion to Judaism. It was the same year, 2004, 2005. And that, that journey, um, they were very spiritually inclined and also creatively inclined family. And I was drawn to that. And so my whole journey as, you know, as of my conversion mirrored my journey with Lightspeed. And so the more I invested and the more I deepened my faith, the more I was a foundation for Lightspeed through everything that could happen. And right. And so that, that ability to remain calm and remain centered and, and, um, and be able to, to react, uh, and to be able to be humble and be able to throw away my job description, uh, and also to, to have a greater faith that everybody could draw on, whether they knew about my own journey or not. That's like, that's, that is a, I would say, a central piece of what has allowed me to lead this company. Right. So that's, that I think is the most important thing compared to any book or any mentor. That's the most important thing.

Wow. I love that. Not the answer I expected. So, you know, we're going to have to go into it. And so you, you label this as spirituality and I would make a distinction between spirituality and religion. You know, religion is perhaps man-made, divisive in some ways. Okay. You're Jewish. I'm Muslim or I'm Christian. You know, like there's a separation, whereas spirituality is universal. Um, but first of all, I don't know if you agree with that distinction or not, but second, like I do, I do agree with it.

And, you know, I would never say that my journey, which, which was a very specific path that opened for me. Wouldn't be something I would say that I would prescribe for anybody, right? I mean, it's— everybody's going to have their own spiritual path that, that, uh, has its own characteristics. I feel very fortunate. Um, I was raised Catholic. Uh, I never expected or had a connection to Judaism growing up. It just, um, it, uh, in university, uh, a path opened and, and I followed it and it's been incredibly enriching, but that could be something completely different for somebody else, whether it's religious or non-religious. Um, but, uh, but yeah, I, I do think that, um, there are incredible depth. There's a, there's a depth of, of, um, things you can learn from some of the, the older religions, right? Where, where, where people might feel like, oh, there's nothing there for me anymore. We're so modern. I do think that there's tremendous amount, um, to be, to benefit from, you know, but of course, these are some of these, you know, some of these faiths are 6,000 years old, right? So you've got to bring it, you've got to think about the context and therefore learn from it in a particular way. So yeah, I think that they are distinct spirituality and religion, but me personally, I'm not ready to throw away religion because, because it is a different context than we live in. You just have to keep that in mind. Yeah.

Even though those religions may be, like you say, thousands of years old, there's maybe a little translation that needs to happen, but I think those teachings are timeless. And, you know, for certainly on my end, you know, I took Buddhist vows in 2019. And what I had discovered along that path over the years is really come to experience this notion that we are spiritual beings living in a physical human casing. We're not this human, we're not separate. I think a lot of the teachings that you see in, in all the religions actually have, they're actually saying the same thing in different ways.

I think these are universal truths, you know, I think especially as you get into the mystical parts of each, of each of those faiths, you go into the higher truths. It's, it's, um, it's different, it's different legends for the same truths, right? And I think a lot of it is dictated by landscape, right? There's, you know, the, the Abrahamic religions.

Now we're going off into all this, but this is why all the CEOs are here. It's for this conversation.

It's, it's, uh, it was a shepherding culture, right? It's in a very arid landscape. Uh, and so therefore patriarchal, and there's a lot of aspects where The Abrahamic religions would never have developed the same way in the Amazon where there's bounty and there's, you know, you have a lot of more, you have a lot more matriarchal-led religions because of maybe nature's considered in a different way than, than it would be in, in the, in the Levant, right? So there's context and there's all, it's just beautiful different human legends to get to the same truths and you can enjoy those legends, uh, and understand where they were created in the context and maybe some of the why. If you just think about where they grew up and appreciate them for where they come from, right? But there's no one truth, right? There's just, because there's so much different human experience.

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And that's like, you know, going back to the, you know, the hierarchical nature and the fact that people will tell me things in the company and it's It's because I think people can read that, especially in a place where authenticity is a truth, right? We all act with humility. You know, of course we're proud of what we're accomplishing, but people will, you know, people can be open in this environment. And that's like something I'm proud of about here.

All right. This is going to be a hard pivot. If you referenced some acquisitions kind of in your journey and they were pretty sizable. You know, I was actually an advisor to the board of Bend when you bought them. Oh, right. Yeah. And maybe just talk us through that, you know, like kind of relative to your size at the time, they were bigger deals. They were geographically dispersed. Like, how do you kind of, I guess, summarize your, your acquisition strategy? And are you able to talk about what your acquisition strategy is? Kind of going forward?

Yeah, I think the acquisitions, you know, I think we were definitely a moment where we wanted to consolidate all of the best players in SaaS, in retail and hospitality, all the complex players like the Vens, the Gastrofixes, the Upserves. It was a lot to take on. I think we were quite bullish on bringing this all together. And I think that what we got out of it is a couple of key things. We have the two 2 best products, uh, that we ever, ever had in the company's history. X-Series, which is based on the Venn Foundation for retail, where we've brought a lot of the other pieces, technology pieces together, re-engineered an amazing retail platform. And K-Series, which is, you know, a leading restaurant platform in Europe, uh, also bringing together all the best technologies, re-engineering. So on the 2 platforms, we've got very modern platforms where we can build rapidly, you know, in 2 quarters we shipped 160 features across these 2 platforms. So I've never seen that before, right, Steve? So very exciting. Lots of new modules shipping too. And then the other thing is just, we have a huge base to monetize payments across, right? So that's how we're now on a trailing 12-month basis as of like last quarter at a billion in revenue. Uh, and we're, we're about 40% penetrated, uh, in terms of payments. We're a bit later in the journey than, than other companies. Um, but yeah, that's like, that has allowed us to, to really get to, to scale in terms of, in terms of revenue. Uh, and, and because of the, because of the payments and, and, uh, and lending, uh, we've, we've been able to, uh, have, you know, 4 or 5 quarters of adjusted EBITDA. So all of that's All of the acquisitions contributed to the platforms, but also to the scale and size of the revenue of the company, which allows us to, uh, uh, to really move into this profitable growth phase and be more and more profitable quarter after quarter. So it set us up, but obviously there is, there is, um, things that Stubbenbach, we've been trying to overcome with all the acquisitions. There is a lot of duplication redundancy that, that, uh, that we've been trying to find operational efficiency. And that's our new, our strategic pivot where we're gonna focus our go-to-market dollars, our R&D dollars on those two core growth engines, you know, North America retail and then meal hospital, not try to grow everywhere where we had an acquisition, which is I think what we were doing before, right? Very expensive and a lot of low ROI prospects in some markets. So moving from that growth at all costs to profitable growth. And I think the acquisitions brought some, a lot of the positive, but we also now have to, you know, balance that with profitability.

I'm curious, you know, when you buy things that are too big really to kind of rebuild on your own stack, do you end up having these sort of islands of platforms over time and you just connect them or That's how it happens.

Um, yeah. So I think really we have two platforms, uh, the, the retail and the hospitality platform. And what we've discovered is, and one of the things I was wrestling with when I came back is like, what do we do with all these other platforms that aren't the two flagships? You know, there's lots of other, there's several hospitality and several retail platforms that they have, we have customers on. The reality is that people are pretty happy on those platforms. You know, they do, they do receive, you know, when we upgrade our core, our core, um, uh, uh, uh, supply chain engine or, uh, or our financial services engine. We, all of the non-flagship platforms benefit from those, from those updates. Plus they get their own updates. And, you know, some of those customers have been on those platforms like more than 5 years. So they don't, they don't need a lot of tech support. The, the platforms are stable. So rather than do mass migrations, you know, we let people move to the flagships. When they feel like they're scaling their business and need to move. But other than that, those, those, all of those people on all those platforms are contributing very meaningfully to our growing EBITDA. Right. And so we have 3 ways of looking at the business. There's these 2 growth engines and everything else that we're, that we're, that we're optimizing for profitability and keeping those customers happy and make sure that those customers are still recommending Lightspeed.

A lot of it.

Yeah. As opposed to doing mass migrations. I think that's just not, doesn't make a lot of sense.

Yeah. It's, it's obviously that's something that's in your interest versus the customer's interest, right? We saw this, we did a, when I was at FreshBooks, we did a, a massive replatforming and the original FreshBooks was this million code monolith. Just not flexible at all. But we, we kept them running in parallel for years. Because just to your point, we knew customers didn't want to switch and we were dealing with the smallest of the small, like truly the S and SMB. Like they, A, nobody starts a business to run back office. And we were trying to make that simpler, but we don't want to give them homework, you know? So we incurred tons of extra costs maintaining two platforms for years. You know, it was tough. Maybe let's switch gears and just talk about your leadership philosophy a bit. And I relied on ChatGPT for some of this background research. So it may or not, may or may not be true because it has this tendency to be a fictional writer. But it said along the way, one quote attributed to you is that a leader sometimes has to be a philosopher. And so I'm wondering, A, did you think that? And if so, maybe we covered this a little bit when we were talking about Judaism, but what are your leadership philosophies?

Yeah, I think it's, um, we did touch on it earlier. Like, I think that, that I do think of myself as an instrument, right? And I do think of myself as, as, um, I'm not taking on all of the burden of good and the bad, although you have to remind myself about that sometimes because you do, you know, as a leader, you do, you feel, you feel, uh, the challenges the company's facing, you, you take it on. Uh, but when you're, when you're at your best as a leader is when you Um, when you, when you unshackle yourself from that, right? And you become just this instrument that can, that can, uh, channel something positive into the company, uh, try, uh, and help everybody do their best and, and, and, uh, and focus, right? Uh, because I think some of the taking it all on, uh, on a personal level, it's just unsustainable. And everybody's going to burn out, right? Everybody's going to burn out. Everybody's going to, they won't be able to do their best work. And that is, that's an important way, important frame in which to look at your work at Lightspeed.

Let's talk about burnout for a second. I've done over a billion of exits as either an operator or a banker, and when I set aside situations, right, where a buyer came inbound and I just isolate situations where a CEO said, I want to sell. The number one reason is they're burnt out. They just can't go on anymore. And I'm curious, like, have you encountered burnout along the way? And, uh, yeah, how did you get through that?

I think there's been moments, um, where I mean, in a 20-year history, there's often moments where you feel like you've run very fast for a long time, especially during the VC era. I had a facial paralysis at one point, Bell's palsy, in 2017, like 2 years before it went public. And it's just, it's just, there's so many things. And I, and I feel like as much as you can have a spiritual foundation and invest in it, sometimes your body can't take multiple crises. Uh, and as good as you can be at thinking of yourself as an instrument, not taking on the burden, sometimes the body can't, um, it gets too weak. You can't resist some incoming viruses, sicknesses, all those things. That's what happened to me, right? And so that, that, um, I always felt like mentally I never burnt out, but sometimes the body does have— it has consequences. Like, I remember when being in diligence for, um, for the Accel investment, which was, you know, super— could be transformational for us, was— it's stomach acid up until the moment we signed the deal, right? So even, even if mentally you can— and I feel like mentally I can handle almost anything, you've got to be conscious of the body because there's limits, right? And yeah, I think once you lose your health, then you're very compromised, right? Like, it's really beyond your control. The body is such a mysterious thing that you have to treasure. So I've experienced that. And I think, like, for actually feeling like the intensity of the company's mentally burning you out, I think it's good to get perspective. Uh, and that's why, that's why I love this current era of being able to work remote, you know, from a different place. You know, I just came back from spending a bit of time in Los Angeles. I didn't really take vacation. I was like, uh, working remote for obviously it's 3 hours difference. So everything's earlier, but, uh, but yeah, it just, it just helps you take perspective from the company, uh, and be able to be a better leader for the company to be able to, um, I love being in the office. Yeah, the energy is incredible. It's also great to be able to get perspective because being in the bubble, um, it's not always healthy for the company if you're, if you never leave the bubble, you know.

I think that's particularly important for a CEO, right? You know, part of your job is to live in the future. Uh, and so getting out of the building, so to speak, helps you get that perspective.

You got to pull inspiration. Right from, from somewhere. That's, and that's like by living and by experiencing and by absorbing.

And I love you brought up the importance of the physical body and health. You know, I think a healthy person has 100 priorities and a sick person has one priority, which is to be healthy. So that puts it in perspective.

I do a ton of working out. I mean, I work out 5 days a week, jump rope every day like that. That's also, I think, a big part of being able to have the mental health in order to do this job. I, I, I don't think it's at, I don't think without that I would have the energy. There's just no way, you know, like you could be a spiritual guru and still, if I didn't have the working out and I didn't push that hard, and I think I'm actually working out more than I ever have in my life. And I did bodybuilding since I was 16. It's a huge important part, right? And it will help your body with some of those things that I've had as challenges where your body is physically weak, right? Weak in a weakened state and you're susceptible to, um, to having those challenges, right?

Yeah. It makes you so resilient. You know, lots of founders tell me, I don't have the energy to work out. I'm like, dude, you'll get it. It will create the energy for you. It's like the person who tells me, oh, I don't have, 5 minutes to meditate. I'm like, great, then you need to take an hour. You need to make the time.

At some point, coffee doesn't do much. Like, if you, it's like, try 10 minutes of jump rope, right? You'll, you'll have a lot of energy.

Going back, you know, these inevitable ups and downs, you know, just connecting some dots here. I would think, first of all, your commitment to physical fitness provided some resilience to get through that because you've got the energy, the optimism that comes from like, I just did a workout, like I can crush the day. Like, But I'm wondering about faith as well. Like what I have, just tell me if this resonates, what I've come to experience over the years. My beard is a different color than yours. I'm older. Means I didn't have this perspective when I was younger, is that everything happens for me, not to me. Even the shitty things, even like the hardest moments, I realized that, that has happened for me. And I'm wondering, is that the perspective that you've brought to this as well through faith?

I totally, I totally resonate with that. Yeah. And you know what, one of the, one of the interesting things, and I'm, I'm a little bit, I'm a few years behind in this, but I usually write down what, what were What were the big highs of the year and what were the, and actually throughout the year, and what were the lows? Uh, what were the difficult moments? And it's so funny because you, you, you go back and read that and you, what you think was a low in the moment was for you almost, almost in almost without exception, they were all for you, for me, for the company, for, uh, my development, for my growth. Like none of them, none of those things have felt so difficult in the moment. Were, um, like, they were all so important for them to have had. And in writing them down or, and looking back actually makes you realize that. So actually, you approach a low moment in the, in the present very differently. You're like, what is this going to really feel like in 12 months or 2 years or 3 years? I'm probably not gonna— I can actually feel more centered about that. I can feel more like an instrument navigating this moment without taking it on, right? In such a negative and having it take you down because you've got perspective on things like that felt like this before.

Yeah, I love it. I mean, I journaled for most of my adult life, and as I go back and read those journals, you're right, those— that, I mean, that was a big part of what reinforced, oh shit, all of that was for me. Like, all of that was a gift, you know. A final question, Dax, you know, I I saw in the news when you stepped away and kind of moved to exec chair and I was like, the guy's made it, you know, he took the company public, he's created personal wealth, he's still involved, but now I, you've always had these kind of causes and now he gets to focus on that. And I'm curious, how did you find the motivation? Was it difficult to come back? Did you, was it, did you struggle with motivation? Just walk us through that.

Yeah, I think it's, it's a, it's a different stage., of the company, uh, the profitable growth phase. And I think the founder is an important person to come and lead that shift. There's a lot of shifts happening at Lightsweep and not all of them are easy, you know. And I think, uh, I never, in the 2 years that I was away as a chair, I, I, I did realize that you are quite far, uh, and distant from the, the operating of the company when you're on the board. Even as exec chair. Um, and, and I, and coming back to lead this phase, I actually had a new appreciation for the company because having been in seat for 17 years, um, you kind of lose perspective on it. And coming back after being away for 2 years, I really appreciated it a lot more. Um, also, you know, cognizant that, that a lot of stuff had to be done., but also without, with, with humility and, and with, with no sacred cows, right? Came up with a new, the new strategic plan, doing all of the things that, that were necessary. And I think that to do such a big transformation, um, at our 20-year mark where, yeah, we're at a billion in revenue, but we're not, we aren't profitable to the degree that the market would like to see. We're getting there, right? Uh, and not all of the things are oriented the way that it's going to build us the long-term success. That's, that's a moment where I'm like excited to be back to do that for the company, right? That's, um, the company is a source of so much goodness for, um, people that have come through the company, grown up with the company, myself, uh, from Montreal, you know, for Canada. It's, it's an important company. Uh, and, uh, so it's a privilege to be back, you know, it's, I also am able to do some of the other things, continue some of the other things that I've been working on. But Lightspeed is, you know, especially in this like 20-year birthday, it's a part of me, right? And so why would you not want to help your company exit its teens, you know, and step into its 20th year confident about who it's going to be, you know? And I think that there's been lots of different paths in the 20 years. Everything from the bootstrapping days to a lot of acquisitions to a lot of things that need to evolve for us to be a great, great Canadian company in its 20s. Right. So for me, that was not expected for me to come back, not until like a day until before I decided to. But yeah, I mean, this is just one of those things in life where you're like, you know what, I'm the instrument. I'm going to, I'm gonna step into this moment and, and I'm gonna enjoy it.

Well, I'm a proud Canadian and Lightspeed is a very important part of our Canadian ecosystem. So I'm definitely cheering you on from the sidelines and I'm really grateful that you made time for this. I think it was just fascinating conversation and I think listeners and watchers are, are gonna get a lot from it. So thank you so much.

Thanks, Mark. Great to join you here.

Hey, thanks for listening to the Startup CEO Show. If you'd like to connect with me, be sure to visit my website, site at markmacleod.me or follow me on LinkedIn at The Mark MacLeod or Twitter @MarkMacLeod_. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.