Lightspeed’s Dax Dasilva on 20 Years of Company Building, Strategic Acquisitions, and How Spirituality Shaped His Leadership Philosophy

In this candid conversation, Lightspeed Commerce co-founder and CEO Dax Dasilva opens up about the company’s remarkable 20-year journey from a bootstrapped startup in Montreal’s Gay Village to a billion-dollar public company.

Dasilva discusses how authentic workplace culture became Lightspeed’s competitive advantage, the strategic decisions behind major acquisitions, and the unexpected role that faith and spirituality played in his evolution from an introverted coder to a confident public company leader.

He also shares insights on navigating burnout, the importance of physical fitness for CEOs, and why he decided to return as CEO to lead the company’s profitable growth phase.

Here’s the full interview transcript…

Mark MacLeod:

In this episode, I sit down with Dax Dasilva, 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 when he was coding until 4 am, his decision seven years in to raise venture capital, his experience leading a public company, and the decision to come back and be CEO of the company.

An interesting and delightful tangent for me is the role that faith has played for him in this journey, giving him the resilience and the humility that he 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?

Dax Dasilva:

Great, thanks for having me.

Mark MacLeod:

Real pleasure. Yeah, I’ve looked 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 RealVentures.

And Lightspeed was very much under the radar, I would say until Excel 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, and I’d love to get to that initial funding journey.

But I’d love to start. You know, you’ve been very open about your background 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 the benefits you see from building a company that is counter to that environment.

Dax Dasilva:

Yeah. And I just sent some notes out to the team, like, this is a part of our DNA, right? Lightspeed was started by, there were four gay men who were the first employees of Lightspeed, including myself, in the Montreal Gay Village. And this was before DEI was even an acronym.

This is like 20 years ago. We’re celebrating our 20-year anniversary this week, actually. So 20 years ago I basically put together four people that I knew and trusted and thought were going to be great on the team and every person we added to the team thereafter, obviously they came from many different communities, but I think that the standard that we held for the company was 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: 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 selves 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 about the companies, I can be my authentic self at work.

Mark MacLeod:

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

Dax Dasilva:

I’m so proud of that because I can be too. You know, I’ve come back in the last year, and I appreciate that about the company, I can be my full self here. I can challenge myself in ways, and 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 who are also being their true selves.

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 everything, right?

Mark MacLeod:

Fake news, you name it.

Dax Dasilva:

People can sniff it, right? There’s a heightened sense, 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 DEI for me. It’s not a bunch of political polarities, and I think it’s sad that it’s become that kind of conversation because it’s about Lightspeeders being their authentic selves and bringing 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 gonna spend with us.

Mark MacLeod:

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 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, Lightspeed has gone through kind of some downs, perhaps not on its trajectory, but more in its share price. But that’s out of your control. But how does that show up for you? Are you willing to admit I don’t have the answers? I’m stressed. Like, how do you show up in meetings when being your authentic self?

Dax Dasilva:

The tone comes from the top, right? Company culture comes from the top. I think one of the things that I value the most and listening to a lot of people. There are a lot of new people here since I’ve come back. There were two years when I wasn’t in the office, right?

But what I love about this company is that people aren’t afraid to tell me things, you know? 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?

And that’s that old parable, right? The emperor has no clothes. I think the case for this company is that people feel comfortable telling me bad news and don’t sugarcoat things for me. And I think there’s also this idea that it doesn’t help anybody to create an alternative reality where everybody’s just cheering, right?

In the good times and in the bad times, right? It’s wrong. The way I look at things is I’m an instrument. You know, I’m an instrument, and I don’t claim all the successes, and I don’t bear all the failures. That’s just philosophically, spiritually, that’s how I look at things.

So we all need to be able to talk about the good and the bad, which happens multiple times daily. And so that is important. And when we’re not actually personally blaming each other, we’re all instruments trying to 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.

Mark MacLeod:

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?

Dax Dasilva:

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. And not try and not go on attack when things aren’t working. You know, I think that there are behaviors that can be learned if they’re portrayed and they’re negative. You, as the leader, have the ability to set the standard for how communication happens.

One thing I’ve noticed is that we’ve had execs over the years who 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. And I think 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.

And that’s sort of maybe a little bit of a Montreal thing too. Or maybe a Canadian thing where people aren’t so stuck on the levels. They’re interested in how we’re building something together. But that can be difficult for leaders. And so you do need to model the way that we want to work. And the way we want to communicate within the company.

Mark MacLeod:

I love that. Maybe let’s take a step back and talk about your funding journey, and what 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’re originally a desktop app and then moved to the web, mobile, etc.

And so you were well into that journey before you decided to raise venture capital. Could you talk us through what made you decide, okay, I’m going to go down that path?

Dax Dasilva:

Yeah. So we bootstrapped the company for seven years. We did seven years of VC. Started off with Excel and Inovia, then later Casadapo and investing in Quebec and others. But yeah, that first seven years, bootstrapping years, I actually feel like we’re sort of a little bit in that mentality today because we’re not growth at all costs. 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 the long term.

It feels a lot like the bootstrap days, where you’re keeping costs and you’re conscious of how everything balances, right? Of course, when you get VC funding, it’s to step into hyper-growth mode. We were, I think, in for more than a decade, 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 working on a transformation to make sure that Lightspeed’s set up is for the long term. That’s the reason that I’m back.

But the VC period, I think, helped us move from the on-premises Mac-based point of sale that I built originally, and move it to the cloud. That wasn’t actually the thesis behind the investment. The investment thesis for Excel is that Apple is ascendant in terms of business applications. This is 2005, when Apple’s really having its comeback, starting to open up retail stores. They’re starting to transform retail with their mobile experience. And also, payments were coming together with that Apple experience.

So, we were the intersection for a lot of investment theses at Excel, Apple, Mint, and business apps. But very quickly, we realized collectively with Excel that things are moving to the cloud very quickly and that in order to unlock the next levels for us, 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 the kernel of a cloud platform and then brought those teams together, and that was the first Lightspeed retail in the cloud.

And that’s where we really did a lot of scaling. A year later, we did a similar launch with Lightspeed 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 more established, that’s doing higher volumes. They’re not quite ERP users, but they have more sophisticated needs.

And so we extended that to hospitality as well, mostly in Europe. Now our user bases are North America retail and European hospitality customers, all these years later.

Mark MacLeod:

Yeah, I mean, that combination of the SaaS and payments is just so powerful, like chocolate and peanut butter. I saw that at Shopify and also at FreshBooks. And in both cases, the payments grew to become the largest single portion of the business over time. Just so powerful.

Can 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 hasn’t really worked out. Maybe let’s park that and just maybe talk generally about your thoughts on going public.

Dax Dasilva:

Yeah, I think it’s been a very positive experience for Lightspeed in terms of just graduating to another level of operating, another level of communicating your story. So yeah, 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 making.

But I think that even that shift, the market gives us immediate feedback, and whether you like it or not, it’s sort of a purifying and sort of a way to hone your story that’s useful for your employees, for your customers, for the market. And I think that when you get things right, you can reap rewards for all your stakeholders.

But it also helps you operate at a much higher level in terms of having a board with great governance, being able to track great employees, and being able to have the coverage of the company. And of course, raising capital. We were able to consolidate a lot of the complex SaaS players in retail and hospitality because of the money that we were able to raise in the public markets. There’s nothing like that kind the power and the resources you’re able to deploy because of capital markets.

Mark MacLeod:

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

Dax Dasilva:

I think it did. Like, I think that you’ve always spent a lot of time being the external and public face of the company. Obviously, there’s a lot more that you need to do in terms of interfacing with investors, doing investor conferences, and doing media. 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 are more obligations there, and then you have to supplement your team with great operators so that you can do everything. So yes, I think it does shift how CEOs spend their time. But I think for a net positive, what you can do as a company.

Mark MacLeod:

My understanding is that 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 become less introverted?

Dax Dasilva:

I think I started out as an introvert. You know, what I’ve said in the past, and it’s funny because, for the 20th anniversary, we’re looking at pictures of me sitting in front of the computer 20 years ago. This picture of me doing the programming thing as a 28-year-old kid.

And so I was an introvert back then. You know, I was coding till 4 in the morning for two years straight at the beginning, and I would come down, I was at a third-floor apartment in the gay village. The office was on the second floor, we walked down the back staircase, those spiral staircases, you got Montreal.

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 calling you about new versions of the software. But at some point, the team was growing. We were very successful very early on. Two or three hundred of the leading Mac dealers around the world that bought Lightspeed. And then, eventually, they went on to become our resellers, selling it everywhere.

We did two certification camps per year. So it scaled really quickly. And I think that the team needed to hear from me at some point. 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 who was comfortable with communicating.

And so I think it was Lightspeed that really forced me into being a leader and enjoying interacting with folks. Now I think that if people see me in a social setting, they would tend to think I might be an extrovert, but I think it’s an interesting question. There’s a professor, Carl Moore, who’s writing a really great book here at McGill, and I’ve traveled with him with a group to Ghana and Ivory Coast, and we talked about this book about introverts and extroverts, and ambiverts and the whole thing. And I think especially when you’ve had a career in business, there are many different parts to who you are.

Mark MacLeod:

You know, I think we have this stereotypical definition of a CEO. Broad-shouldered, 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 talk about that hyper-growth, the only way to get through it is self-awareness. 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, as a result, they’re highly self-aware. So I see it as positive.

Dax Dasilva:

Yeah, I think the reflective nature of introverts is a part of growing.

Mark MacLeod:

I do want to carve out some time on your leadership philosophy, but this seems like a natural place to ask this. So, that kid who was coding till 4 am is not naturally communicative. Other than just putting in the reps and putting one foot in front of the other, what have you done? What tools, resources, support, 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?

Dax Dasilva:

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. Like, for example, I don’t have a design background. You know, there are a lot of artists in my family, a lot of creativity. That’s why the original version of Lightspeed was such a hit, because of the user experience. I was an okay coder. But those are two things that I got a lot of satisfaction out of.

Fast forward, and you have me in the finance world, running a public company. No background in that. It’s like there were many moments between me being a designer coder and me being a public company CEO where I’d throw 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.

And so that I think is something you’ve got to show people at the company that you’re willing to do, and you might need to ask them to do to push the company forward. So you need to be able to do that and not hang on to things because you like doing them. Or you’re good at them. You have to do that.

And I think that comes from, I would say, what my tools are, I would say it’s that I’ve made a lot of investment in spirituality in terms of my journey. I mean, my journey as a startup CEO coincided with my conversion to Judaism. It was the same year, 2004, 2005. We’re a very spiritually inclined and also creatively inclined family, and we were drawn to that.

And so my whole journey, 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 so that ability to remain calm and remain centered and be able to react and to be able to be humble and be able to throw away my job description and also to have a greater faith that everybody could draw on whether they knew about my own journey or not. That’s, I would say, a central piece of what has allowed me to lead this company. That’s what I think is the most important thing compared to any book or any mentor. It’s the most important thing.

Mark MacLeod:

Wow, I love that. Not the answer I expected. So we’re going to have to go into it. And so 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. But first of all, I don’t know if you agree with that distinction or not.

Dax Dasilva:

I do agree with it. And I would never say that my journey, which was a very specific path that opened for me, wouldn’t be something I would say that I would prescribe for anybody.

I mean, everybody’s going to have their own spiritual path that has its own characteristics. I feel very fortunate. I was raised Catholic. I never expected or had a connection to Judaism growing up. It was just at university that a path opened 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.

But yeah, I do think that there’s a depth of things you can learn from some of the older religions. People might feel like, oh, there’s nothing there for me anymore, we’re so modern. I do think that there’s a tremendous amount to benefit from, but of course, some of these are 6,000 years old.

So 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 personally, I’m not ready to throw away religion because it is a different context than we live in. You just have to keep that in mind.

Mark MacLeod:

Even though those religions may be, as you say, thousands of years old, there’s maybe a little translation that needs to happen. But I think those teachings are timeless. And, certainly on my end, I took Buddhist vows in 2019, and what I 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 all the religions are actually saying the same thing in different ways. I think these are universal truths.

Dax Dasilva:

You know, I think especially as you get into the mystical parts of each of those faiths, you go into the higher truths. It’s different legends for the same truths. And I think a lot of it is dictated by the landscape. There are the Abrahamic religions. And it was a shepherding culture, it’s in a very arid landscape, and therefore patriarchal. And there are a lot of aspects where the Abrahamic religions would never have developed the same way in the Amazon, where there’s bounty, and you have a lot more matriarchal-led religions because maybe nature’s considered in a different way than it would be in the Levant.

So there’s context, and there’s all just beautiful different human legends to get to the same truths. And you can enjoy those legends 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. But there’s no one truth because there are so many different human experiences.

Mark MacLeod:

Amen. Yeah, absolutely. And when I think about humans as spirits, we’re going to move on because I don’t think the CEOs showed up for this conversation, but because we are spirits, we all have infinite potential. And I would argue you are living proof of that. That same guy who was coding till 4 am in his apartment now leads a large public company. And you’ve transformed yourself many times, right?

So you have this capability, and you could keep doing this for as long as you wanted because you have infinite potential. So I love that. And I do think, just maybe to put a pin in this, where we lose the infinite potential is when we lose humility. You know, ego is death.

Dax Dasilva:

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

Mark MacLeod:

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

Dax Dasilva:

Yeah, I think the acquisitions 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 Venns, the Gastrofix, and 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 best products we’ve ever had in the company’s history. X Series, which is based on the Vend foundation for retail, where we brought a lot of the other pieces, technology pieces together, and re-engineered an amazing retail platform, and K Series, which is a leading restaurant platform in Europe, also bringing together all the best technologies, re-engineering.

So on the two platforms, we’ve got very modern platforms where we can build rapidly. In two quarters, we shipped 160 features across these two platforms. So I’ve never seen that before Lightspeed, so very exciting. Lots of new modules, and shipping too.

And then the other thing is just we have a huge base to monetize Payments across. So that’s how we’re now on a trailing twelve-month basis as of like last quarter at a billion in revenue. And we’re about 40% penetrated in terms of payments because we’re a bit later in the journey than other companies. But yeah, that has allowed us to really get to scale in terms of revenue, and because of the payments and lending, we’ve been able to have four or five quarters of adjusted EBITDA.

So 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 really move into this profit growth phase and be more and more profitable quarter after quarter. So it set us up, but obviously, there are things that have been brought back; we’ve been trying to overcome with all the acquisitions.

There is a lot of duplication and redundancy that we’ve been trying to find operational efficiency, and that’s our strategic pivot where we’re going to focus our go-to-market dollars, our R&D dollars on those two core growth engines, North America retail, and European hospitality. Not try to grow everywhere where we had an acquisition, which is what I think we were doing before. Very expensive and has 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 have brought a lot of positive, but we also now have to balance that with profitability.

Mark MacLeod:

I’m curious, 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 is that what happens?

Dax Dasilva:

Yeah, so I think really we have two platforms, the retail and the hospitality platform. And what we’ve discovered is, one of the things I was wrestling with when I came back is, what do we do with all these other platforms that aren’t the two flagships? You know, there are several hospitality and retail platforms that we have customers on. The reality is that people are pretty happy on those platforms.

You know, when we upgrade our core omnichannel engine, our core supply chain engine, or our financial services engine, all of the non-flagship platforms benefit from those updates. Plus, they get their own updates, and some of those customers have been on those platforms for more than five years. So they don’t need a lot of tech support. The platforms are stable, so rather than do mass migrations, we let people move through the flagships when they feel like they’re scaling their business and need to move.

But other than that, all of those people on all those platforms are contributing very meaningfully to our growing EBITDA. And so we have three ways of looking at the business. There are these two growth engines and everything else that we’re optimizing for profitability and keeping those customers happy, and making sure that those customers are still recommending Lightspeed. As opposed to doing mass migrations, I think that doesn’t make a lot of sense.

Mark MacLeod:

Yeah. It’s obviously that’s something that’s in your interest versus the customer’s interest. When I was at FreshBooks, we did a massive re-platforming. And the original FreshBooks was this million-code monolith. It’s not flexible at all. But 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 in SMB, like nobody starts a business to run a back office. And we were trying to make that simpler, but we didn’t want to give them homework, so we incurred tons of extra costs. Maintaining two platforms for years was tough.

Maybe let’s switch gears and just talk about your leadership philosophy a bit. 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, 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?

Dax Dasilva:

Yeah, I think it’s. We did touch on it earlier. Like, I think that I do think of myself as an instrument. And I do think I’m not taking on all of the burden of the good and the bad. Although you have to remind myself about that sometimes, because you do as a leader, you do feel the challenges the company’s facing, and you take it on.

But when you’re at your best as a leader is when you unshackle yourself from that and you become just this instrument that can channel something positive into the company, try and help everybody do their best, and focus.

Because I think taking it all on a personal level, it’s just unsustainable. And everybody’s going to burn out, right? Everybody’s going to burn out. They won’t be able to do their best work. And that’s an important frame in which to look at your work at Lightspeed.

Mark MacLeod:

Let’s talk about burnout for a second. I’ve done over a billion worth of exits as either an operator or a banker. And when I set aside situations 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, have you encountered burnout along the way, and how did you get through that?

Dax Dasilva:

I think there have been moments where, I mean, in a 20-year history, there are 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 in 2017, like two years before it went public. There are so many things, 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.

And as good as you can be at thinking of yourself as an instrument, not taking on the burden, sometimes the body can’t. It gets too weak. It can’t resist some of the incoming viruses, sicknesses, all those things; that’s what happened to me.

And so that I always felt like, mentally, I never burned out. But sometimes the body does have its consequences. Like, I remember when doing diligence for the Excel investment, which could be transformational for us, was stomach acid up until the moment we signed the deal.

So even if I feel like mentally I can handle almost anything, you’ve got to be conscious of the body because there are limits, right? And I think once you lose your health, then you’re very compromised. 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 for actually feeling like the intensity and the companies mentally burning you out, I think it’s good to get perspective, and that’s why I love this current era of being able to work remotely from a different place.

You know, I just came back from spending a bit of time in Los Angeles. I didn’t really take a vacation. I was working remotely. Obviously, it’s a three-hour difference, so everything’s earlier. But, yeah, 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. The other energy is incredible. It’s also great to be able to get perspective because, being in the bubble, it’s not always healthy for the company if you never leave the bubble.

Mark MacLeod:

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

Dax Dasilva:

You have to pull inspiration right from somewhere. And by living and experiencing and by absorbing.

Mark MacLeod:

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

Dax Dasilva:

I do a ton of working out. I mean, I work out five days a week, and jump rope every day. That’s also, I think, a big part of being able to have mental health in order to do this job. I don’t think that I would have the energy. There’s just no way.

You could be a spiritual guru, and still, if I didn’t have the working out and I didn’t push that hard, I think I’m actually working out more than I ever have in my life. I have been doing bodybuilding since I was 16. It’s a huge, important part. And it will help your body with some of those things that I’ve had as challenges where your body is physically weak. And in a weakened state, you’re susceptible to having those challenges.

Mark MacLeod:

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, it will create the energy for you. It’s like the person who tells me, oh, I don’t have five minutes to meditate. I’m like, great, then you need to take an hour. You need to make the time.

Dax Dasilva:

At some point, coffee doesn’t do much. Like, if you try 10 minutes of jump rope, you’ll have a lot of energy.

Mark MacLeod:

Going back to these inevitable ups and downs, 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. But I’m wondering about faith as well.

Just tell me if this resonates, what I’ve come to experience over the years. My beard is a different color from yours. I’m older. I didn’t have this perspective when I was younger, is that everything happens for me, not to me, even the shitty thing, even 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?

Dax Dasilva:

I totally resonate with that. And you know what? One of the interesting things is that I’m a few years behind in this, but I usually write down what the big highs of the year were and what the lows were. What were the difficult moments? And it’s so funny because you go back and read what you think was a low in the moment, and was for you, almost without exception, they were all for you. For me, for the company, for my development, for my growth.

Like, none of those things have felt so difficult in the moment, but they were all so important for them to have happened. And writing them down and looking back actually makes you realize that. So, actually, you approach a low moment in the present very differently. Like, what is this going to really feel like in 12 months or two years or three years? I’m probably not going to. I can actually feel more centered about that. I can feel more like an instrument navigating this moment without taking it on in such a negative way and having it take you down because you’ve got perspective on things like that felt like this before.

Mark MacLeod:

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. I mean, that was a big part of what reinforced. Oh, shit. All of that was for me, all of that was a gift.

Maybe final question, Dax. 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, and he’s still involved. You’ve always had these kinds 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 struggle with motivation? Just walk us through that.

Dax Dasilva:

Yeah, I think it’s a different stage of the company, the profitable growth phase. And I think the founder is an important person to come and lead that shift. There are a lot of shifts happening at Lightspeed, and not all of them are easy. In the two years that I was away as exec chair, I realized that you are quite far and distant from the operation of the company when you’re on the board. Even as exec chair.

And coming back to lead this phase, I actually had a new appreciation for the company because, having been in the seat for 17 years, you kind of lose perspective on it. And coming back, I really appreciated it a lot more. Also cognizant that a lot of stuff had to be done, but also without, with humility, and with no sacred cows.

Came up with the new strategic plan, doing all of the things that were necessary. And I think that to do such a big transformation at our 20-year mark, where yeah, we’re at a billion in revenue, but we’re not profitable to the degree that the market would like to see. We’re getting there.

And not all of the things are oriented in a way that is going to build us long-term success. That’s a moment where I’m excited to be back to do that for the company. The company is a source of so much goodness for people who have come through the company. Growing up with the company myself from Montreal for Canada, it’s an important company, and so it’s a privilege to be back.

You know, I also am able to do some of the other things that I’ve been working on, but Lightspeed is especially in this like 20-year birthday, it’s a part of me. And so, why would you not want to help your company exit its teens and step into its 20th year confident about who it’s going to be? I think that there have been lots of different paths in the past 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 Canadian company in its twenties.

So, for me, that was not expected for me to come back, not until a day 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 gonna step into this moment and I’m gonna enjoy it.

Mark MacLeod:

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 that was just a fascinating conversation, and I think listeners and watchers are going to get a lot from it. So thank you so much.

Dax Dasilva:

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 at markmacLeod.me, or follow me on LinkedIn at The Mark MacLeod, or X account @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!