1600 People, Virtual First: Scaling Without Chaos

Every single person in the company is responsible for culture. Everybody has to take some ownership to foster and evolve culture around them. The culture is built through action, so it's, it's really by virtue of acting in accordance with cultural values, like you naturally create that culture around you. So it's definitely, you know, something that we demand from our leadership team through a set of leadership principles. We hold ourselves very strictly accountable to how we operate and set the example for the company that we want everybody else to mimic.

Welcome to the Startup CEO Show. I'm your host, Mark MacLeod. In this episode, I sit down with Vitaly Pechersky, co-founder and CEO of StackAdapt. Vitaly and his team have built their company over the last 11 years to have over $500 million in revenue, and they 10x their headcount in the last 5 years. On this episode, he walks us through that journey, their decision that was kind of forced on them to not raise venture early and how that benefited them, how they went through that hypergrowth, how he transitioned from COO to CEO, the importance of core values and culture and how to live them inside your company. And then we ended with his thoughts on, you know, advice for marketers, which was counterintuitive but so powerful. I want to leave that insight for you. It's at the end. I really hope you enjoy this episode. Vitaly, welcome to the Startup CEO Show. It's a true pleasure to have you here. How you doing today?

Another day in paradise. Thanks for having me, Mark.

Canada in the winter. I don't know if we refer to that as paradise or not, but I love the outlook.

I love the cold, so it's okay.

I was trying to think of the last time I spoke with you, and I honestly feel like it was 2013 or '14. It was like very shortly after I started SurePath Capital. So it's been amazing. To see your progress, and I'm hoping we can dig into that today. Maybe for folks who don't know, just tell us what StackAdapt does.

So what we do now is, you know, interestingly, what we do now, I think in so many ways is exactly what we set out to do 11 years ago, except it's just gotten way more complex than I ever imagined it would be. But at our core, we build an enterprise software platform that used by marketing teams within agencies or brands to, to run advertising and increasingly more like larger marketing orchestration campaigns across the internet to drive, retain, expand customers.

I love it. And so do you make a distinction between marketing and advertising? Are those kind of separate functions to you? And are there specific verticals, like I'm guessing like e-commerce merchants, but are there other kind of sweet spots for you?

Yeah, so when it comes to verticals, I think pretty much every vertical imaginable from financial services to e-commerce, automotive, education, travel, you name it. When it comes to distinction between marketing and advertising, I think it's— some of these lines are not perfect. I mean, advertising, as I see it, is just a subset of marketing. And we, as a platform, want to increasingly become a larger marketing platform. So that means expanding beyond advertising, even though advertising is still our core business and the largest segment of our business. But we just see that to, like, growing businesses is so hard and we know that advertising is not the only thing you need to do to be successful. So what are all the things that a business needs to do to be successful? And we're trying to increasingly increase the footprint of our platform so we can connect it all in an intelligent way. To drive business growth for customers.

That makes sense. And maybe last question and then let's dig into the journey, but are you running media spend through your platform as well, or it's strictly a software layer that then plugs into how your marketers place and run their advertising?

It's a software platform. You can buy advertising through it. You can ingest, you can connect it to your Shopify or HubSpot. You can, push the data into StackAdapt. Off of this data, you can segment it, you can orchestrate so a sequence of campaigns, you can deliver an email, they didn't open email, you can deliver them connected TV ad. So you can, you could build orchestration connecting the fragmented ecosystems between customer engagement and programmatic. So parts of the platform are definitely transaction around buying advertising and parts of it are more like a, like a classic SaaS product.

Hmm.

Cool.

That's great. So my understanding, you talked about, hey, we're over 11 years in. My understanding is you've crossed $500 million in revenue, which is amazing. Uh, I'm wondering if you could just talk about the big milestones or inflection points along the way. Just walk us through that journey because most folks never get anywhere close to that scale.

Uh, there's a bunch of milestones that we've crossed throughout the years. I think what, in the moment when you cross them, they always seem maybe more significant than when you look back at them. And I think actually in retrospect, the most significant milestones were the ones that only looking back I could recognize that those were the most significant milestones, not necessarily in the moment because they're not necessarily tied to maybe specific like dollar amounts or specific product releases. A lot of it almost comes back to some kind of philosophical breakthrough or a new insight of how we think about the business. And those usually then translate into more tactical decisions around product or business strategy. If I can point probably to a couple decisions, so pretty early on, I think it will tie into a question of like us raising not that much primary capital in earlier days. It's, you know, when myself and my two other co-founders, we started building, I've known one of them for 5 months, the other one matters of, you know, weeks. So we've had no history together. We were taking a giant leap of faith, you know, essentially dividing the company 3 ways and just going at it, even though we've barely known each other. And, you know, going to the market and trying to raise money to fund product development and accelerate the build of the platform, Naturally, the first questions were like, well, why you guys? Like, you're in your mid-20s, you barely know each other, you have no history of working together. It doesn't look great when you try to present yourself that way. So at some point, we just almost realized like, you know, expecting that somehow we'll break through the noise and like, we see that a lot of odds are stacked against us because like on the surface, it doesn't like that story is not strong. So we said, you know what, like, let's own our own destiny. Let's try to build a product, get in the hands of customers as soon as possible. And this kind of own your own destiny has became in many ways like a core value of how we operate as a company, of just owning your own destiny, rely as much as possible on our inherent capabilities, our strength to control the future versus hoping that somebody comes in and rescues us or gives us something that will unlock the next stage of growth and really try to hone in on what is that we can do as a company that can propel us to the next phase of growth. So that's, you know, early milestone, but like very foundational, like to the next decade of building. I can call out a couple more if there's interest.

Yeah, I'd love to maybe just double-click on that first and then let's see, because that's describing the origin and I'm sure some things, I'm sure some other things have happened since, but like, First of all, on like coming together with these relative strangers, uh, Y Combinator ran a study where they looked back at kind of their portfolio, which is of course vast, and tried to figure out what are the predictors of success. And the number one predictor of success was how long the founders knew each other. So, so your data point is not correlated with that. So I'm just curious, like, uh, how have you made this collaboration work?

So I did not see that study, but it's interesting, and I can imagine that probably we're more on the exception side than the rule. You know, counter to this point is that I've tried starting businesses before with people that I've known for many years, and actually that didn't work because then you're— then where you find yourself is crossing this line. Well, we were always friends. Now we're trying to cross the line into being business partners. And that can be painful. And for many people that ends in, you know, fractured friendships. And I think, you know, when you— I think it's logical that you go in business with somebody that you know because you have a sense that, well, you can trust them, but you might be, in my view, overlooking some pretty important compatibility topics when it comes to actually running the business together. So even though when Ildar, myself, and Yang started, we didn't know each other for very long, but there were some values that I could very quickly see in them that I was like, these are— even though we don't know each other, I could see their value system, their work ethic, a lot of their, you know, the skill compatibility aligns very well to what I think would make a successful long term. Definitely there's still a bet, you know, like you still have to roll the dice and there's— that's an element of luck. Absolutely. But I think early on, you know, there was a sense of like very quick, we quickly built trust. And what happened next is like, it's a bit of sequence of luck. And I think, you know, where the luck really comes in is the fact that we were able to stick it out together for so many years. Nobody early on, a year into the business, had some unexpected unexpected life-changing event that forced them to step down, for example. That happens for so many businesses and you cannot control this. Even if you have perfect compatibility, you, you're the best co-founders, for example, but for somebody, some accident in the family or some life event changes their, their ability to stay, stay with the business. And that, that creates, um, um, a, a huge pressure on the business. But for, for us, even though we didn't know each other, we had this early compatibility that we knew. The fact that we're able to stick it out together and have gone through a decade plus with no drama, no conflicts, like that's rare and that's a bit of luck.

It sure is. It truly is rare. I often joke that, you know, co-founders, it's like you're married, but you don't get to have sex. So, and sex keeps several couples together, but you don't, you don't have that remedy. So you just, you have to other ways to make it work. This episode is brought to you by Linode.

Limitless is an exclusive community of VC-backed CEOs who want to scale themselves and their companies without limits. The biggest outcomes in the startup world are founder-led. Meta, Amazon, Shopify, Airbnb, Canva, NVIDIA. Behind every one of these companies is a founding CEO who didn't just scale their business, they scaled themselves. They added one zero at a time and and today run companies with billions of dollars in revenue each. That's the goal of Limitless: to give you the tools, strategies, mindset, and community to lead at the highest level without sacrificing your health, relationships, or purpose. Through group calls, an elite peer network, a proprietary AI coaching bot, members-only library, and in-person experiences, Limitless gives its members everything they need to keep scaling themselves and their companies for as long as they want. Go to limitless.ceo to learn more.

I deeply believe that everything in life happens for you, not to you, even though it doesn't always feel that way in the moment. And seems pretty clear that your inability to raise capital early on ended up being a gift for you. A, in terms of ownership, but B, this whole ethos that came out of, hey, we're just gonna control our own destiny. Now, I'm guessing once you had some success, that question mark around, well, hey, they don't know each other, like that risk went away. Have you been tempted to raise money along the way? And, you know, yeah, how have you thought about, yeah, whether we get on the venture train or not?

Yeah, since then we've brought a number of investors, so that sort of in many ways our path became more average as time went on because we've been able to bring some tier 1 investors on a cap table, but—

And was that, I shouldn't know this, but was that like a typical Series A or did you kind of skip that stage and go more to growth stage investors?

Yeah, we skipped the Series, like very early stage financing and then we jumped at into growth stage 2022, so many years after their early stage rounds. But at that point, it was more about like the rationale for it was quite different than early days. Early days, it was all about how do we afford, you know, the next, bring the next team member. Now it's more about like how do we position ourselves towards become a category leader? How do we surround ourselves with a deep network of experts and people who, who can help us at the next stage of growth, like add credibility to the business, can support us through many years of as a private company or one day forever to be public. So really strategically building towards much bigger outcomes in the long run. So much, much less about short term.

A full half of my clients when I was running SurePath Capital were bootstrapped or had maybe raised some small amount of money at the beginning and then got profitable. And one of the main— they would often skip venture and go right to either growth equity or private equity. And one of their main motivations actually was to get some feedback and accountability. It's like they didn't have a real board of directors. Like, we're just doing stuff. We don't know. Nobody's pushing me. Like I can do whatever I want, I can go golf all day, like I need some accountability. Was that a thing for you?

I think we had always a pretty good sense of accountability. I think we always worked our butts off, but I think bringing on like really like institutional investors who've seen companies at real scale, building out a board to a much more mature board, having that level of accountability from like external communication, not just on execution on the business side, but also how do we, how do we communicate our plans with the board? How do we communicate with investors? All of that had to be matured because, you know, admittedly this is our first time doing it. So it's very hard to know what good looks like. And as we start surrounding ourselves with experts, you, you naturally are exposed to, you know, what are the best companies do? How can we leverage that, and I think we, in the last 3 years, we just, we have transformed into a much more mature organization from the way we plan our business, the way we understand our business, and it has translated into execution as well. That's probably the challenging part is that not often this type of effort translates into actually successful execution on the business side. But I think with us, it's, you know, we've seen that it helped us execute much better.

I love it. Bringing on those investors, how has that changed the company for you?

Well, I think it's, you know, naturally when it's just a few founders or a couple of founders, you know, you essentially do whatever you want to your point is, you know, nothing prevents from, some companies for their leadership team to be like, oh, you know what, it's, uh, we're gonna just go golfing every Thursday afternoon from now onwards. You know, the business is doing well, like we can afford taking a foot off the gas in some ways. Um, like we've never thought, we never thought like that. We always wanted to build something really big. And you understand that like to do that, you have to, you have to give up some degree of control because, you know, if we, if we draw a line from, um, founder-led, uh, you know, small, small business where they decide exactly everything that's happening to a large, large-cap public company where, uh, where the board of shareholders play a large role in the direction of the company and, um, election, election of the CEO and it becomes much more accountable. So I think, you know, the big transition is really happens around just giving up some degree of control, but understanding the way I think about it is that like this is just a normal course of action, but it's very hard to do it any other way. And like that should force us to build a business that could in theory function independently from us even so that like how do we build a business that's the most durable? And we know that the only way to do this is like if the whole business is not riding on decision on like one or several people, right? You want to build systems that are durable, that where you have many contingencies. And the price for that is some of that control that I think some founders at small scale are not willing to give up. But I think I've fully embraced that, you know, to scale into something really big. There are parts of that control that you have to surrender. And I think it's for the greater good of the company.

That totally makes sense. Last question I have around the origin, because of course I think being at scale is far more interesting to folks, but I, you know, I believe like most startups raise capital too early. And, um, and when they do that, A, like, unless they had a, you know, they have a prior track record or they come from some big company that had great success. They're going to struggle and so not necessarily get the best investors. And then of course it's a one-way decision. There's nothing you can do about it. So again, practical terms, how did you guys bootstrap? Like, were you, was there a services component out of the gate? Was it an agency that became a software company? How did that work?

You know, we did some services in the very beginning where we essentially use third-party technology to just deliver services. And in parallel, we started building our own product. And then as soon as we got meaningful traction, which happened about 9 months into the company, we just said, you know, we'll— we're building towards being a product company. Like that first 9 months or so, that was really for us to validate some ideas using third-party technology and then very quickly pivot towards just just doing it with our own product. You were talking about founders raising money too early. Yeah. And so I think what I was going to comment on that is that I think quite a few founders, or like I see quite a few businesses maybe underestimate, like overestimate the opportunity and the total addressable market, or they look at some total addressable market and they think it has no ceiling. When in reality the math of how the total addressable market compresses down to something that they can realistically obtain, that math, I think a lot of them in some ways over— like they overestimate the size of their market. They raise money too early and then they hit the ceiling on growth and they're stuck in this no man's land where they raised a lot of money. Which the only way to return that capital is to continue growing. Growth is really hard to come by because the market is actually not as big as they thought it is. And it's really, really hard to get out of without some major pivots or some, you know, a lot of luck. So I think delaying raising money to me is just an opportunity to validate like, is there a real total addressable market? Is it so large and like you capture meaningful enough share realistically and raise money when you see like a true, you know, real continuous exponential growth that you, if additional capital can really continue driving it versus, you know, hoping that that additional capital will accelerate the growth that maybe it doesn't exist.

I agree with that. That's definitely a thing. I also think that separate from size of the addressable market, Many startups just raise too much capital relative to the revenue that they achieve for it. And so I've sold lots of companies where we got a great multiple of revenue, but the founder shares were worthless and they just got a carve-out. And the reason was what I just said, like they raised too much capital, the pref stack was too high, uh, strategic buyers don't like making VCs rich, they do it for the exceptional kind of truly shiny companies. But most exits are meat and potato, too small for buyers to even bother disclosing the purchase price. And on those ones, like there needs to be a very tight correlation between the amount of capital you raise and the amount of revenue you generate. And I think that's where a lot of companies shit the bed, frankly.

I think that the, it's that math is not very well understood because I think optically you say, oh, we raised at a huge valuation, big round, and we have been able to maintain big share. But then the question is like, well, what's going to happen next? How are you going to grow into that valuation? And we know that multiples tend to compress as you scale up. So then, so then you realize like, you know, your business needs to grow so significantly and it's so difficult. Then they find themselves in this situation. They just tap out. Um, and then people walk away with very little to show for it.

That's right. I mean, by definition, VCs have to overpay early on. Otherwise it would be like Shark Tank or Dragon's Den. Like, I'm going to take a third of your company for like some tiny amount of money because you have nothing right in those early stages. Right. And so to your point, you have to grow into this totally lofty, unrealistic valuation. And then of course, the more you raise, the more you have to grow. So it's tough.

Yeah, yeah. For us, when we raised our first round, it was the value, everything was so conservative. I mean, granted, this was very different. This was 10 years ago. This was a different world, but we never had that problem because we, I think because we were so, you know, humble about, you know, what we're trying to do that we're just happy to, that's, to have any additional boost, but, you know, we're lucky that, you know, we're lucky in some ways that we're not in the category where our egos were inflated maybe and our expectations were so inflated that we actually always took a fair valuation, but in the long run, actually it played out very well because I think it gave us a lot of room for, like, for a room for growth because we never had to live up to something really unrealistic.

Yep. I love it. So going back to your journey, you know, I often tell my CEOs, like, the single biggest thing you can do to grow yourself a CEO is unlock revenue growth and then hang on for dear life. And, you know, it sounds like you, you know, your revenue traction happened early. You've got like a meaningful amount of revenue now. So you've, you've been on this virtuous cycle of like, The bigger the company gets, the better you get, the better you get, the bigger the company gets. Like it's genuinely a virtuous cycle, but I'm curious, what else have you done? First of all, do you agree with that theory or not? Feel free to throw up on it, but also what else have you done to make sure that you are always the CEO that StackAdapt needs?

Yeah, I mean, you know, to address your first question, yeah, every year feels in some ways, like, we're a bit of a different company with different set of requirements. And even though it feels like we've been around for 10 years and it, you know, for all intents and purposes, it was a fairly long time. You know, we were a team of 170 people when COVID happened and now we're a team of 1,600 people. So we almost 10x our team in the last 5 years. So it's like every year is so different. So it, it naturally leads to a lot of need for evolution for the leadership team, myself included. And I think, you know, we had to do, I feel personally I had to do a lot of growth this year to set myself up for 2026. How do I know? So to your question earlier, so my co-founder Ildar was the CEO of the company for the first 9 years and I've been in the COC for the last 2 years. So I only have, 2 years in the CEO seat. So, well, and some months anticipating the transition. So that was a bit of a scramble that I had to do a little bit of a catch up. So the question is like, how do I know that I'm the right CEO? How did you frame this question? Just, I wanna—

Yeah, how do you, what do you do? Like you just said, you've gone through almost 10x growth in 5 years. Which means if you were leading it this whole 5 years, you would need to 10x. But the point is like, whatever your growth rate is this year, like you need to grow by that amount or you start to fall behind and you become the weak link. So like, how do you personally grow faster than this business?

There's probably many things I can think of. Maybe one way in which I've grown this year is I've been just trying to proportionally drive the focus of our business around key things that I really believe will be the driving force for our growth. So maybe my growth this year was by virtue of just forcing the company to regain a lot of focus around key, very few but very important aspects of our product or our execution. And probably, you know, there's an element of continuous growth around, like the way I'm thinking about this year and next year, there's literally 5 things that I wrote on our company's priorities and said like, we just have to nail these things. And I myself trying to develop as much expertise and as much understanding about what's happening in the business, how it all comes together from a very minute pieces of within execution or form a very strong opinion about what that should look like, you know, 12 months from now, really work closely with the team to execute on those items. So maybe I look at my personal growth in a, from a perspective of increased focus and increased understanding about just a few key areas within our business that I believe will be the main drivers for us in the next 3 to 5 years. And I think in the past, counter to that, I think some of my attention was maybe spread a little bit too thin, thinking that, you know, we need to almost always expand into new areas to drive growth. This year thematically was more around regaining focus and much more defining much tightly, like, what is our philosophy around expansion to new areas? How do we think about them in relation to our core business? And how do we, how do we put this all together into some universal framework that we can live and breathe by that we think that it's what's going to take us to through the next 10x growth, right?

Many CEOs I speak with, they have like a coach, they're part of a peer group, maybe they have some mentors or advisors. Do you do any of those things?

I have a bit of that. To be honest, I never had a specific point in time that I was like, I have to join specific group or I have to, like a lot of these things happen very organically and there was just a point in time whether maybe I was introduced to somebody that I just felt really good chemistry with and suddenly I found myself either being part of the group or working with somebody. So I have a CEO coach, I'm part of one group of entrepreneurs, and a lot of them are just not structured. I just have made friends along the years that, you know, they're doing their own thing, I'm doing my own thing, we talk about business. And I have, you know, a few, few acquaintances that sometimes pick their brain on some, you know, topics that are, you know, that bigger companies, you know, dealing with just to anticipate, you know, what kind of set of problems we should expect. How do we build towards that next bigger stage of our business? But yeah, I would say that support system is super important. And I think one of the challenging parts for me in earlier days of the business was that, you know, I was in my mid-20s. I had almost no connections to anybody who's done, built a successful business that I could like realistically sit down and pick their brain. So I think we probably wasted a bunch of time figuring a lot of things out from scratch when in reality, like we could have probably saved years of our lives if we had the right mentors and the right advice. It's always a bit tricky. Like it always has to be taken with a bit of grain of salt because A lot of things that we've done, you know, a lot of people were telling us like our approaches were wrong and we went and did them despite those, counter to those, that conventional advice. And I think that's what allowed us to do something that's somewhat unconventional. And we broke out from, you know, challenging industry, you know, against a lot of odds. So some of that advice has to be taken with a grain of salt, but at the same time, I think we could have saved some years if we had somebody really experienced, really strong that was able to lay out like exactly how we should be at least thinking about the business and like make our, form our decisions. Like there are some playbooks for sure.

Right. That totally makes sense. So you talked about you were, you know, you've been CEO for 2 years. You were COO before. I'm curious, 2 things. How did you, prepare yourself for CEO and did it actually work or did you just have to be CEO and figure it out?

I think, yeah, you, you probably just have to be and figure it out. Yeah, I think so because I was a co-founder alongside Ildar, who was the CEO for the first 9 years. You know, I, I think, and, and our relationship was always very unique because we shared responsibilities, probably unlike any other CEO, COO, like our working relationship was very flexible around who took care of what. And so he took care of some maybe COO-like work. I took care of some CEO work. So it was not a total switch from something, you know, parts of the job were net new. So for example, managing the board or fundraising was net new, but a lot of work that I was doing previously, I was already doing it, so I just kept on doing it. So there was not much of a change. Well, I'll say generally, I think I called him about 6 months ago and I said, you know, I just now that I've been in the seat for like about 18 months, I've got to tell you that I have a different appreciation for you, for what you've been doing for the first 9 years. Like, that's awesome. Like, I thank you for, for doing it for so long because like, this is way harder than I, I, what I expected.

It truly is. Honestly, when I was operating, I was offered the CEO gig twice and I turned it down flat both times. I was very happy being a number 2 or number 3 exec in an org. And, and, you know, the CEO, the bigger you get, just like everybody wants a piece of you. Like it's, it's just a super demanding role, rewarding. And I only coach CEOs now, but I do that because it's the toughest role. And then with founding CEOs specifically, like all the biggest outcomes are founder-led, right? So how do we enable those founders to keep growing faster than their companies year after year after year, right? Just totally obsessed with that question. But yeah, to your point, really demanding role.

Yeah, but I'm also having just the most fun. It's just hard to imagine doing anything else now, now that, you know, having done this job for 2 years, like I can't imagine doing anything else.

I love it. 10x-ing growth, 10x-ing headcount in 5 years. Like, first of all, sounds like a nightmare, but also a nightmare that everyone listening or watching would love to have. Like, that would be a champagne problem. Looking back, how did you make that happen without it being total chaos? Or was it just total chaos?

I was gonna say it was total chaos. But it was, you know, because, so what happened is COVID hit and we all went virtual. And that was basically when we were like, we're building out of Canada, everybody's in Toronto. A lot of our business is increasingly global. Why would we be doing— being just in Toronto? Let's unlock all these networks of people and talent globally. So we started hiring in the US, UK. And so because of that, a lot of this growth happened virtually. You never were, you know, actually facing this, this size of the organization until we had our company-wide event for the first time since COVID last January, and we walk in the room with like 1,000 people, you're like, oh my gosh, this is what it looks like. You never see this many people on Slack, so it kind of doesn't even connect that it's so big. So I think that virtual component was huge for us because being able to just ship laptops, add a user on within our software, And, you know, we had like one thing we did well, I think, is we always have pretty robust onboarding programs. So we, when COVID hit, we already had sort of a very solid framework for how do we onboard people and how do we make them successful. So I think that's why we were able to rapidly start adding a lot of people to the organization and it didn't break. I think there, you know, some things could have worked better, but in retrospect, I think if they work smoother, we probably didn't hire fast enough. So, you know, I would say by 2022, 2022, yeah, ballpark when we were about 900 people, I think that's, you know, a lot of the fears of recession start hitting. That's when we're like, okay, let, you know, we added so many people, let's pump the brakes a little bit and like really tighten up our, internal operations, make sure that all the systems mature, catch up with our headcount. And so for the past like 3 years, we've, I mean, we've now at 1,600 people. So we've kept on growing, especially over the last 12 to 18 months. But now that all the systems, all the processes have kind of entered this new chapter of maturity, like right now, next year, we're probably planning to add another 500 people and you know, it feels like it's going to be more or less like business as usual, which is good. Like it's going to put some strain on the organization, but I don't really think that there's something that should break because I think a lot of what we have now is like should scale, you know, by 30%. Like we're not 10x-ing it anymore. At this scale, it's like a question, well, can we add 30, 40% a year? And the answer is yes.

So implied in what you said there, like obviously in COVID, many companies were forced to go to remote, but then more and more, a lot of CEOs have been demanding people come back into office. You made a decision, you are now just remote. Is that correct or are you hybrid?

We call it virtual first. We have two hubs that which we call are in Toronto and London. So people can come in, but it's entirely voluntary. And, you know, we, we call AirSalt virtual first.

What, if anything, did you do to make sure that culture and values remained strong as you made that transition?

Uh, a lot of repetition. Um, I think we've always taken, um, great, great care of our culture, uh, because we just wanted to have an environment where people feel like they can belong. They they can actually form friendships, have a place where they can be productive and successful. And culture was always top of mind for us. I think two critical sort of key areas that we've been focusing on especially is just reinforcing the fact that every single person in the company is responsible for culture. And it's not something that, that can be only pushed down by the CEO and everybody else just, you know, expects it magically to happen across the organization. Everybody has to take some ownership to foster and evolve culture around them. And the second point is that like it all is, the culture is built through action. So it's really, you know, by virtue of acting in accordance with cultural values, like you naturally create that culture around you. So it's definitely, you know, something that we demand from our leadership team, through a set of leadership principles. We hold ourselves very strictly accountable to how we operate and set the example for the company that we want everybody else to mimic. So it definitely starts from the top, and I really hope I live our culture through action. Like, that's where I think it's the most important for me is that, you know, am I acting in accordance with our values?

Mm-hmm.

I hope I do.

That culture flows down from the top. That's for sure.

Yeah. For accountability, number one is me. Accountability number two, leadership team. Um, and then hopefully the rest of the organization will, will follow. Um, yeah. So yeah, those two, two principles of like how the company culture is built and, uh, and that's why we're, we're prescriptive about some areas of like how we want people to operate. But a lot of the times we. I think we were more focused on this idea of like just understanding of how company culture forms. And subconsciously, I think everybody can very easily distinguish what is a good company culture, what is a bad company culture. So I don't have to go and tell everybody, you know, line by line, it's like, what is good and what is bad? Everybody already knows it. Everybody can sense it on almost a, you know, subconscious level. So how do we bring it top of mind for everybody that, you know, you already know what it is, you are empowered to shape that company culture around you and you do it through action. So if you act in accordance with those, that good company culture, you should see it shaped like that around you. Obviously it doesn't happen all the time, but you know, being virtual first at 1,600 people across 20 different countries, I think like there's something to it that seems to work and I like, I'm not, I'm not looking to change it going into new year.

Yep. No, it's clearly working. That's for sure. So, you know, some very famous CEOs write an annual letter. Warren Buffett's done one forever. Jeff Bezos did, like a bunch of people do. My understanding is you do as well. And if so, could you just tell us about that?

No, I don't, unfortunately. Oh, you don't? Oh, wait.

Well, it showed up in my research, but I can get rid of that.

So I do a bunch of, you know, these, so annually on my birthday I write a letter, but it's like in a personal capacity.

Oh, okay.

Every week, every week I write a letter, like an email to our team, which I call Memento Weekly. And I talk about all things Top of Mind for me. So every single week, on Monday at 4 AM Eastern time, it lands in everybody's inbox. And so far since I started, I haven't skipped a week.

That's great.

And then at the end of the year, I've been doing a mix of, in early days it was like a, I call it top 40, which is just summary of all the things we accomplished this year. The last like 3 or 4 years, it was more like the videos where I recorded specific key messages. But I don't have a letter that I write as like a shareholder letter. That's how the famous CEOs, right?

Yeah, I wasn't thinking of it as a shareholder letter per se, but more like an annual thing. I'm curious if you're willing to share. That letter you write to yourself on a personal front every year? What kind of, what, yeah, what, what, uh, I guess, what are you trying to achieve with that? Is it a retrospective? Is it looking to next year? Like, what's that all about? Because, you know, the number one thing for CEOs is self-awareness, and, and that kind of letter feels like it would promote self-awareness. So I'm very curious.

So I actually publish them publicly on my blog. Yeah. Uh, so I've been writing it for 9 years now. And it's taken so many shapes and sizes and it's not been consistent around the theme of it. It's just been, this is my birthday and I wanna write about things that are top of mind for me. And they covered all kinds of random things, some with introspective, some with lesson learned. But it's because I'm writing for myself mainly. To look back on and like force myself to reflect on the years past. You know, I don't hold myself to like, I don't feel pressure that it has to resemble something. It's just, that's why I think it just comes out however it comes out. Love it.

It's a great practice.

I started with something more structured. Like I think I started my blog, this was like 9 years ago when I tried to like I think I wanted to write more and share some early lessons of building the company with early-stage entrepreneurs. And I kind of over the years kind of mainly transitioned to, you know, write whenever I feel like. It's just something that I have, but I don't commit to any timeline. Sometimes I write every quarter, sometimes every 6 months, but I do like writing and hopefully in the future I'll write more.

I love it. I think writing's so powerful. It's certainly for me, it clarifies my thinking, right? I learn when I write. So it's, yeah, super, super useful. Maybe as we start to wrap up here, you know, when I talk to many of my companies about marketing at large, and advertising is a subset of that, they feel like there's just lots of moving pieces, you know, algorithms changing, you know, iPhone platform causing changes to advertising, now people searching for products or merchants inside ChatGPT, etc. So I'm curious, like, what's the state of the union? What's working, what's not, and what's the future of advertising in your mind?

Maybe I'll take a slightly different approach, and maybe because I just talk so much about this topic that I'm a little fatigued by it, but I think what I'll I will. What I'll talk about today, like what I think maybe the way I'll answer your question is that I think in the topic of, in the subject of marketing, what is not talked enough is the subject of product. And I think it's way easier to make good marketing when you have a good product. And I understand, you know, marketing teams sometimes are stuck promoting what they have. Yes. But I would say if I was a marketing leader, I would insert myself much closer to the product and find ways to influence that in some ways. I know this is easier said than done, but I would say making the product continuously better, you get to a stage where product is just so good that it's just, marketing is easy because people come back, they talk about it. And I think, you know, this is a subject that's that, you know, maybe is not talked enough in the marketing world because it all starts with a great product. And I think, of course, good marketing can make any, like a same product with better marketing will perform better, but a good product with great marketing will work even better. So So I'd say maybe my sort of two cents is that marketing teams should sit much closer to product and potentially even influence the direction the product should go because great product should make marketing much easier.

I really, really love that answer. I'm glad you didn't give me the usual whatever state of advertising. But it's such a good insight. You're absolutely right. And I think, yeah, a lot of CEOs will turn to— it's funny, it's funny, like, uh, the, when a product is not great, it impacts many areas. So some will turn to customer support as a bandaid or more operations, right? We'll do more duct tape and apply more band-aids to get the result. Uh, or in the extreme, we'll add. A managed service around the product. All of this masks that the product isn't best in class, where if it was, to your point, truly disruptive, it's not that it would sell itself, but then marketing's got, you know, a really powerful asset to work with. So I love that.

Yeah.

Well, thank you so much for spending the time. I'm curious, are we going to see you with a suit ringing the bell someday? Is an IPO something that you're thinking about?

Uh, maybe one day, maybe one day. Oh, I haven't wore a suit since my wedding day. So I'll have to, I'll have to bring it to the dry cleaners.

So good. Well, congrats on all your success. Like I said at the beginning, honestly, it's, it's rare. We seem sometimes, you know, you read TechCrunch all the time and you think that these billion dollar outcomes and billion dollar valuations are common, but they're not, they're like statistically very improbable. So even though you're still going, you're mid-flight, like you're already in very rare air. And so yeah, it's great to see it. I really appreciate you making time to come on the show.

Yeah, thanks. Huge kudos to our team and, and thanks a lot for having me. Hopefully next update I'll give it in a, in a suit.

I love it. 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 @TheMarkMacLeod or Twitter @MarkMacLeod_. And if you wanna 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.