Vitaly Pecherskiy on Building StackAdapt to $500M in Revenue and Why Great Marketing Starts With a Great Product

Vitaly Pecherskiy and his co-founders started StackAdapt with almost no money, no connections, and barely any history together. Eleven years later, the company has crossed $500 million in revenue and grown to 1,600 people across 20 countries.

In this episode, Vitaly sits down with Mark MacLeod to talk about how they bootstrapped early on after struggling to raise venture capital, how that constraint became a competitive advantage, what it took to 10x headcount in five years without everything falling apart, and why he believes the most underrated marketing strategy has nothing to do with marketing at all.

Let’s dive in.

Mark MacLeod:
In this episode, I sit down with Vitaly Pecherskiy, 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 five 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 hyper growth, 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 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 are you doing today?

Vitaly Pecherskiy:
Another day in paradise. Thanks for having me, Mark.

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

Vitaly Pecherskiy:
I love the cold, so it’s okay.

Mark MacLeod:
I was trying to think of the last time I spoke with you, and I honestly feel like it was 2013 or 2014. It was 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.

Vitaly Pecherskiy:
So what we do now is, interestingly, 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’s used by marketing teams within agencies or brands to run advertising and increasingly larger marketing orchestration campaigns across the internet to drive, retain, and expand customers.

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

Vitaly Pecherskiy:
Yeah, so when it comes to verticals, pretty much every vertical imaginable, from financial services to e-commerce, automotive, education, travel, you name it. When it comes to a distinction between marketing and advertising, I think 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, 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 increase the footprint of our platform so we can connect it all in an intelligent way to drive business growth for customers.

Mark MacLeod:
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 is it strictly a software layer that then plugs into how your marketers place and run their advertising?

Vitaly Pecherskiy:
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 did an open email, you can deliver them a connected TV ad. So you can 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 classic SaaS product.

Mark MacLeod:
Cool. That’s great. So, you talked about, hey, we’re over 11 years in. My understanding is you’ve crossed $500 million in revenue, which is amazing. 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.

Vitaly Pecherskiy:
There are a bunch of milestones that we’ve crossed throughout the years. I think, 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, 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 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 translate into more tactical decisions around product or business strategy.

If I can point to a couple of decisions, pretty early on, I think it will tie into a question of us raising not that much primary capital in earlier days. It’s when my two other co-founders and I started building, I’ve known one of them for five months, the other one matters of weeks. So we’ve had no history together.

We were taking a giant leap of faith, essentially dividing the company three ways and just going at it, even though we barely known each other. And 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 are you guys, like, you’re in your mid-twenties? 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 almost realized, expecting that somehow we’ll break through the noise, and we see that a lot of odds are stacked against us because on the surface, that story is not strong. So we said, you know what? Let’s own our own destiny. Let’s try to build a product and 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 an early milestone, but very foundational to the next decade of building. I can call out a couple more if there’s interest.

Mark MacLeod:
Yeah, I’d love to maybe just double-click on that first, and then let’s see, because that’s describing the origin. I’m sure some other things have happened since.

But first of all, on coming together with these relative strangers, Y Combinator ran a study where they looked back at their portfolio, which is, of course, vast, and tried to figure out what the predictors of success are. And the number one predictor of success was how long the founders knew each other. So your data point is not correlated with that. So I’m just curious, how have you made this collaboration work?

Vitaly Pecherskiy:
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. 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, where you find yourself 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 fractured friendships.

And 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, even though we don’t know each other, I could see their value system, their work ethic. The skill compatibility aligns very well with what I think would make a successful long-term.

Definitely, there’s still a bet. You still have to roll the dice. And that’s an element of luck, absolutely. But I think early on, there was a sense of very quick, we quickly built trust.

And what happened next is like, it’s a bit of a sequence of luck. And I think 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 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’re the best co-founders, for example. But for somebody, some accident in the family or some life event changes their ability to stay with the business, and that creates huge pressure on the business.

But 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, that’s rare, and that’s a bit of luck.

Mark MacLeod:
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 sex keeps several couples together, but you don’t have that remedy. So you just have to find other ways to make it work.

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 in terms of ownership, but this whole ethos that came out of, hey, we’re just going to 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 how have you thought about whether to get on the venture train or not?

Vitaly Pecherskiy:
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 one investors on a cap table.

Mark MacLeod:
I should 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?

Vitaly Pecherskiy:
Yeah, we skipped the very early stage financing. And then we jumped into growth stage 2022. So many years after the early-stage rounds. But at that point, the rationale for it was quite different than early days.

In the early days, it was all about how do we afford bringing the next team member. Now, it’s more about how do we position ourselves to become a category leader? How do we surround ourselves with a deep network of experts and people who can help us at the next stage of growth, add credibility to the business, can support us through many years 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 of a short term.

Mark MacLeod:
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. 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. I can do whatever I want. I can go golf all day, like, I need some accountability. Was that a thing for you?

Vitaly Pecherskiy:
I think we always had a pretty good sense of accountability. I think we always worked our butts off. But I think bringing on institutional investors who see in companies a 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 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 naturally are exposed to, you know, what the best companies do? How can we leverage that?

And I think we in the last three years, 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. I think with us, you know, we’ve seen that it helped us execute much better.

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

Vitaly Pecherskiy:
Well, I think, naturally, when it’s just a few founders or a couple of founders, you essentially do whatever you want, to your point. You know, nothing prevents some companies for their leadership team be like, oh, you know what? We’re gonna just go golfing every Thursday afternoon from now on. You know, the business is doing well, so we can afford to take a foot off the gas in some ways.

Like we’ve never thought like that. We always wanted to build something really big. And you understand that to do that, you have to give up some degree of control. Because, you know, if we draw a line from a founder-led small business, where they decide exactly everything that’s happening, to a large-cap public company where the board of shareholders plays a large role in the direction of the company and election of the CEO, it becomes much more accountable.

So I think, you know, the big transition really happens around just giving up some degree of control. But understanding the way I think about it is that 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, if the whole business is not riding on a decision, like one or several people, right, you want to build systems that are durable, 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, 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.

Mark MacLeod:
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, you know, I believe most startups raise capital too early. And when they do that, unless 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 of course, it’s a one-way decision; there’s nothing you can do about it.

So again, in practical terms, how did you guys bootstrap? Like, was there a services component out of the gate? Was it an agency that became a software company? How did that work?

Vitaly Pecherskiy:
Oh, you know, we did some services in the very beginning, where we essentially used 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 nine months into the company, we just said, you know, we’re building towards being a product company, that first nine months or so, that was really for us to validate some ideas using third-party technology.

And then very quickly pivot towards just doing it with our own product. You were talking about founders raising money too early. And so I think what I was going to comment on that is I see quite a few businesses overestimate the opportunity and the total addressable market, or they look at some total addressable market, and they think it has no ceiling.

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, 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 raise a lot of money, so 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 hard to get out of without some major pivots or a lot of luck.

So I think delaying raising money, to me, it’s 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 I’ll raise money when you see real, continuous, exponential growth if additional capital can really continue driving it, versus hoping that that additional capital will accelerate the growth that maybe doesn’t exist.

Mark MacLeod:
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. 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 potatoes, too small for buyers to even bother disclosing the purchase price. And on those ones, 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.

Vitaly Pecherskiy:
I think 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 a 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 you realize your business needs to grow so significantly. And it’s so difficult, then they find themselves in this situation, they just tap out. And then people walk away with very little to show for.

Mark MacLeod:
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.

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.

Vitaly Pecherskiy:
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, I think, because we were so humble about what we’re trying to do that we’re just happy to have any additional boost.

But, you know, we’re lucky in some ways that we’re not in the category where our egos 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 growth, because we never had to live up to something really unrealistic.

Mark MacLeod:
Yep. I love it. So, going back to your journey, you know, I often tell my CEOs, the single biggest thing you can do to grow yourself as a CEO is unlock revenue growth and then hang on for dear life. And it sounds like your revenue traction happened early, you’ve got like a meaningful amount of revenue now. So 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?

Vitaly Pecherskiy:
Yeah, I mean, to address your first question, every year feels, in some ways, like we’re a bit of a different company with a different set of requirements. And even though it feels like we’ve been around for 10 years, and for all intents and purposes, it was a fairly long time. We were a team of 170 people when COVID happened. And now we’re a team of 1600 people. So we have almost 10x our team in the last five years.

So every year is so different. So it naturally leads to a lot of need for evolution for the leadership team, myself included. And I think, you know, I feel personally, I have to do a lot of growth this year to set myself up for 2026.

So, to your question earlier, my co-founder, Ildar, was the CEO of the company for the first nine years, and I’ve been in the CEO seat for the last two years. So I only have two years in the CEO seat and some months anticipating the transition, so that was a bit of a scramble, and I had to do a little bit of catch-up.

So that’s your question, like, how do I know that I’m the right CEO? How did you frame this question?

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

Vitaly Pecherskiy:
There are 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 very few, but very important aspects of our product or our execution.

And probably, you know, there’s an element of continuous growth around the way I’m thinking about this year and next year. There are literally five things that I wrote on our company’s priorities and said, like, we just have to nail these things.

And I myself am trying to develop as much expertise and as much understanding about what’s happening in the business, how it all comes together from very minute pieces of within execution, or form a very strong opinion about what that should look like 12 months from now, really work closely with the team to execute on those items.

So maybe I look at my personal growth 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 three to five 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 defining much more 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 put this all together into some universal framework that we can live and breathe by, that we think is what’s going to take us through the next 10x growth?

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

Vitaly Pecherskiy:
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 a specific group, or I have to. A lot of these things happen very organically. And there was just a point in time where 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 have made friends over the years who are doing their own thing. I’m doing my own thing. We talk about business.

And I have, you know, a few acquaintances that sometimes pick their brains on some topics that bigger companies are dealing with, just to anticipate 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-twenties. I had almost no connections to anybody who’s built a successful business that I could, like, realistically sit down and pick their brain.

So I think we’ve probably wasted a bunch of time figuring a lot of things out from scratch when, in reality, 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 a grain of salt because a lot of things that we’ve done, a lot of people were telling us our approaches were wrong. And we went and did them despite those counter to that conventional advice. And I think that’s what allowed us to do something that’s somewhat unconventional. And we broke out from a challenging industry 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, who was able to lay out exactly how we should be at least thinking about the business and make or form our decisions. Like, there are some playbooks for sure.

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

Vitaly Pecherskiy:
I think, yeah, 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 nine years. I think our relationship was always very unique because we share responsibilities, probably unlike any other CEO.

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 the work that I was doing previously, I was already doing it. So I just kept on doing it. So there was not much we changed.

Well, I’ll say generally, I think I called him about six months ago, and I said, you know, now that I’ve been in the seat for 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 nine years. Like, I thank you for doing it for so long, because this is way harder than what I expected.

Mark MacLeod:
That’s awesome. 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 two or number three exec in an org. And, you know, the CEO, the bigger you get, everybody wants a piece of you. It’s rewarding, but just a super demanding role.

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. So how do we enable those founders to keep growing faster than their companies year after year after year? Just totally obsessed with that question.

But yeah, to your point, really demanding role.

Vitaly Pecherskiy:
Yeah. But I’m also having just the most fun. It’s just hard to imagine doing anything else now. You know, having done this job for two years, I can’t imagine doing anything else.

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

Vitaly Pecherskiy:
I was going to 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 building out of Canada. Everybody’s in Toronto. A lot of our business is increasingly global. Why would we be doing 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 actually faced 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 a thousand people, you’re like, oh, my gosh, this is what it looks like. You know, you never see this many people on Slack, so it kind of doesn’t even connect that it’s so big.

So I think, you know, that virtual component was huge for us because being able to just ship laptops to a user within our software. You know, we had like one thing we did well, I think, is we always have pretty robust onboarding programs. So when COVID hit, we already had sort of a very solid framework for how to onboard people and how to 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 some things could have worked better. But in retrospect, I think if they were smoother, we probably didn’t hire fast enough.

So, you know, I would say by 2022 ballpark, when we were about 900 people. I think, you know, a lot of the fears of recession started hitting. That’s when we’re like, OK, you know, we added so many people. Let’s pump the brakes a little bit and really tighten up our internal operations, make sure that all the systems mature, catch up with our headcount.

And so for the past three years, I mean, we’re 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 should scale, you know, by 30 percent. Like we’re not 10x-ing it anymore. At this scale, it’s like, can we add 30-40% a year? And the answer is yes.

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

Vitaly Pecherskiy:
We call it virtual first. We have two hubs, which are in Toronto and London. So people can come in, but it’s entirely voluntary. And, you know, we call ourselves virtual first.

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

Vitaly Pecherskiy:
A lot of repetition. I think we’ve always taken great care of our culture, because we just wanted to have an environment where people feel like they can belong, 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. It’s not something that can be pushed down by the CEO, and everybody else just expects it to happen across the organization. Everybody has to take some ownership to foster and evolve culture around them.

And the second point is that the culture is built through action. So it’s really by virtue of acting in accordance with cultural values that you naturally create that culture around you. So it’s definitely something that we demand from our leadership team through a set of leadership principles.

We hold ourselves very strictly accountable for 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. That’s where I think it’s the most important for me is that, you know, am I acting in accordance with our values? I hope I do.

Mark MacLeod:
Culture flows down from the top. That’s for sure.

Vitaly Pecherskiy:
Yeah. Accountability number one is me. Accountability number two, leadership team. And then hopefully the rest of the organization will follow. So, yeah, those two principles of how the company culture is built. And that’s why we’re prescriptive about some areas, like how we want people to operate. But a lot of the time, I think we’re more focused on this idea of just understanding how a company culture forms.

And subconsciously, I think everybody can very easily distinguish what a good company culture is, what a bad company culture is. So I don’t have to go and tell everybody line by line what is good and what is bad. Everybody already knows it. Everybody can sense it on almost a subconscious level. So how do we bring it top of mind for everybody that 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 a good company culture, you should see it shape 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 there’s something to it that seems to work, and I’m not looking to change it going into the New Year.

Mark MacLeod:
Yep, it’s clearly working. That’s for sure. So, you know, some very famous CEOs write an annual letter. Warren Buffett has 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?

Vitaly Pecherskiy:
No, I don’t. Unfortunately.

Mark MacLeod:
Oh, wait. Well, it showed up in my research, but I can get rid of that.

Vitaly Pecherskiy:
So I do a bunch of these, you know, annually on my birthday, I write a letter, but it’s like in a personal capacity. Every week, I write a letter, like an email to our team, which I call Memento Weekly. And I talk about all the things top of mind for me. So every single week on Monday at 4 a.m. Eastern Time, it lands in everybody’s inbox. And so far, since I started, I haven’t skipped a week.

And then at the end of the year, in early days, it was like a I call it top 40, just a summary of all the things we accomplished this year. The last three or four years, it was more like the videos where I recorded specific key messages. But I don’t have a letter that I wrote as a shareholder letter that some of the famous CEOs write.

Mark MacLeod:
Yeah, I wasn’t thinking of it as a shareholder 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 are you trying to achieve with that? Is it a retrospective? Is it look into it next year? Like, what’s that all about?

Because, you know, the number one thing for CEOs is self-awareness. And that kind of letter feels like it would promote self-awareness. So I’m very curious.

Vitaly Pecherskiy:
So I actually publish them publicly on my blog. So I’ve been writing it for nine 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 want to write about things that are top of mind for me.

And they cover all kinds of random things, some of it introspective, some of it lessons learned. But it’s because I’m writing for myself mainly to look back on and force myself to reflect on the years past, 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.

It started with something more structured. I think I started my blog. This was like nine years ago, when I wanted to write more and share some early lessons of building the company with early-stage entrepreneurs. And over the years kind of mainly transitioned to 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 six months. But I do like writing, and hopefully in the future I’ll write more.

Mark MacLeod:
I love it. I think writing’s so powerful. It’s certainly for me; it clarifies my thinking. I learn when I write. So it’s 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, 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?

Vitaly Pecherskiy:
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 talk about today, like what I think, maybe the way I’ll answer your question is that I think in the topic 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 marketing teams sometimes are stuck promoting what they have. But I would say if I were a marketing leader, I would insert myself much closer to the product and find a way 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 maybe is not talked about enough in the marketing world because it all starts with a great product.

And I think, of course, marketing can make the same product perform better. But a good product with great marketing will work even better. So I’d say maybe my sort of two senses 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.

Mark MacLeod:
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 it’s funny. When a product is not great, it impacts many areas. So some will turn to customer support as a band-aid or more operations, right? We’ll do more duct tape and apply more band aids to get the result.

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 a really powerful asset to work with. So I love that.

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 as an IPO, something that you’re thinking about?

Vitaly Pecherskiy:
Maybe one day. I haven’t worn a suit since my wedding day, so I’ll have to bring it to the dry cleaners.

Mark MacLeod:
So good. Well, congrats on all your success. Like I said at the beginning, honestly, it’s rare. Sometimes 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 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.

Vitaly Pecherskiy:
Yeah. Thanks. A huge kudos to our team and thanks a lot for having me. Hopefully, the next update I’ll give it in a suit.

Mark MacLeod:
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 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!