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The Gamble & The Glory: Ep. 05 - Charles Gillespie & Kevin McCrystle, Gambling.com

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The Gamble & The Glory: Ep. 05 -  Charles Gillespie & Kevin McCrystle, Gambling.com

The episode features the co-founders of gambling.com, Charles Gillespie and Kevin Macrystal, who share their entrepreneurial journey. They started with affiliate sites, pivoted to the UK market and casino affiliates, and acquired the gambling.com domain for $2.5 million. After rebuilding the site, they found success in 2014. The company expanded with offices in Dublin and the US, focusing on corporate finance and raising funds. Their story showcases the challenges and successes of building a business in the online gambling industry over nearly 20 years, highlighting key decisions, partnerships, and the evolution of their strategies.

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10493 Words, 56096 Characters

Welcome to the Gamble in the Glory, where we here founders tell the story of growing their companies to become industry leaders within the sports betting fantasy and eye gaming industry. The Gamble in the Glory is presented by Sega of LLP, a full solutions law firm purpose built for the gaming and betting industry. Decades of experience and a truly global reach, Sega of LLP is your go to expert for legal solutions for all challenges commonly faced by companies from every industry vertical, including payments, blockchain, eSports, affiliates, data, and more. If you need help with private equity funding, public markets financing, licensing, intellectual property, mergers and acquisitions, commercial deals, or other business needs, this is your team and it's what they do. Whether you're just getting started or have already scaled to become a stalwart of the industry, discover how Sega of LLP can add value to your business and help you achieve your goals. Learn more at www.sagev.ca Alright, we are back with episode 5 of the Gamble in the Glory, where we talk to founders that have scaled their companies to become industry leaders. Through the first few episodes of this series, we've welcomed some of the most accomplished entrepreneurs in this space and I'm pumped that the trend continues with this one. I'm joined by Charles Gillespie and Kevin Macrystal, co-founders of gambling.com, who join me from Monaco and North Carolina, respectively. Guys, welcome to the Gamble in the Glory, how you doing today? Thanks, Jesse. We're very happy to be here and all good greetings from Sonny Vonaco. Yeah, greetings from Charlotte, North Carolina, glad to be here. Awesome. You guys have been on this journey for coming up on 20 years now and I have to say in preparing for today's discussion and doing a bit of research on your journey here. It really seems as though you guys have done and seen it all. In fact, I was thinking, if there was such a thing as an entrepreneurial bingo card, here's might be close to a full card. There's an early pivot in there, international expansion, M&A transactions. You've bought multiple category defining domain names, received countless industry awards and of course more recently completed an IPO in 2021. You've literally done almost everything and I think people are really going to enjoy hearing you share your perspectives and experiences over the next hour or so here. Let this get right into it and I want to start with the origin story because as origin stories go, I think you guys have quite an intriguing one. Charles, you were actually a recent guest on the next IO podcast and shared a bit about the origin story at a high level, but I'd love to just sort of pick up that thread from that conversation and for the benefit of folks listening to this episode. I'm wondering if you guys could sort of share the very beginning of all of this as I say almost 20 years ago, if you can get the delorean in the time machine, go back there, just tell us a little bit about kind of how this all started and then we'll kind of follow the arc of the journey closer to today. So it goes back to North Carolina, Kevin and I are both from Charlottes. We both went to the same middle school and high school together. We met on like a field trip on a bus one day when we were like, what, 12, 13, I would have been seventh grade. Well, yeah, randomly sat next to each other on a bus. That's my first memory of Charles at least. I remember Kevin was the first person that thought I was funny, that he immediately endeared himself with that. We were buddies growing up and then ended up going to the same university. We both went to UNC. We both studied politics, political science, I think, you know, I didn't really know what I wanted to do with my career or life at that point and UNC, you had to actually apply to get into the business school and as an undergrad, just a major in business applied to the business school and got denied, did not get into the business school at UNC. Not that I bitter about that at all or that I still think about that. But at the same time, they launched a, they had just gotten a hundred million from the Kaufman Foundation to create this thing called Carolina Entrepreneurship Initiative and a couple of enterprising professors which had been entrepreneurs themselves set up a program where kids could start to do a minor in entrepreneurship. So that's what I ended up doing during those years. Kevin, you got a double major, didn't you? Yeah, I was a philosophy in political science. I think at that time I thought I was going to be a lawyer, maybe even end up in politics. But every, every lawyer I talked to was extremely unhappy, so I was searching for something else to do. I was always interested in entrepreneurship but didn't really know how to get into it. It wasn't as accessible in those days. Charles had a vision for this early on, which was, it was interesting. Charles is ever since I can remember building websites, I mean, he was building flash sites probably in ninth grade in high school, so kind of before really anybody else I knew was into it. So it had always been kind of part of what he was into. I had some exposures to the industry during my university days. I started my first affiliate sites, 2003, registered start gambling online.com, built up an affiliate website. I had discovered an affiliate program. I read the term of conditions, you know, it sent us traffic and we'll send you money. And I thought, okay, I can probably have a go with that without, you know, it doesn't really cost anything to build a small, simple website, you know, we were kids, we didn't really have any money. So I took a shot at that and nothing happens. And then six, seven months later, I saw an extra couple hundred bucks in my bank account and I did not know where it had come from. I really just had no clue, took a few days for the penny to drop and I realized, wait a minute, somebody actually found that website. I made last summer, must have signed up for an online casino and I must have gotten a commission and they paid me. And in the great tradition of the online gambling industry, it came from some, no name company and some weird jurisdiction, you know, you would never be able to place. So that was kind of my first introduction to the industry and then I, I had some college roommates that played a lot of poker and did very, very well and teed with it, only kind of helped grow my love and curiosity for the industry. I really wanted to work in the industry, but again, coming out of school, we didn't have much money. So we, you know, I was thinking, okay, how do we get into this in the most kind of capital efficient way? And that seemed to be, be affiliates, you know, it's not, it'd be a lot cheaper than trying to be an operator and being a B2B supplier, that was over our heads. We weren't about to try to make enterprise software or games or anything like that. So I managed to talk a friend of a university professor into investing in the business early. The original business plan was, leave the states and go to the next biggest market full of people that love to gamble because the US is almost certainly not going to regulate any time soon. You know, I'd send a few letters to my congressman in North Carolina. I got a few responses. I got a lecture from one of them about how online gambling is responsible for terrorist financing. You know, that was the tone of the conversation in 2006 and that very quickly led me to believe that this was going nowhere fast in the US. And obviously, fast forward 20 years is a very different situation, but it took decades to get there. And I had secured this investment and I called Kevin. I said, look, I've got, I've talked this guy into backing me with a couple hundred thousand bucks to move to China to build a sports betting information website. Will you come with me? Like, let's do this and Kevin had a few terms and conditions. Well, yeah, the sighted at time, I think, was dragon bets. That was the opportunity. And I said, I'd do it, but we have to rename it to something else. So we landed on a WSN.com, which is now owned by another affiliate, which long story we ended up selling that. But you know, it was just a short domain name was, it was really, really the key there. And at that point in time too, I was super into fantasy more than you know, trolls came from the gambling. I was in 525, 30 fantasy leagues into the sports analytics side, you know, the first opportunity was there like a sports stat site, basically, which we, you know, we're able to kind of add on gambling information to so it was nice marriage in that sense. And you know, we're young. So moving to China wasn't scary, there's little loose. It seemed like a fun adventure where whatever, 23, however old we were at that point. It was an extremely fun adventure. We managed to connect with a couple of very successful American internet executives that had been in the, in the sea suite of the largest Chinese internet companies. They opened up their role at X's to us. And so we, we really kind of hit the ground running with all the right people in the startup scene in Shanghai, which was at the time, incredibly vibrant. Yeah, it was, it felt like maybe Silicon Valley in its prime because there was so much excitement. There was this sense that the Chinese pie was so big that nobody needed but a tiny morsel of it to have a really interesting outcome. And there was incredible amount of cooperation between everyone out there and was, you know, I think it 180 degrees different than the way it is today fast forward two decades and the relationships between the US and China now very different. You know, China is a, it's a very difficult place to operate as a foreigner now. Not that it was easy back then, but it was, it was certainly more accepted and, and easier. And you know, our whole kind of thesis in the beginning was China will regulate and will be in a little bit early. We'll have this interesting American sort of approach to things and, you know, we'll do very well. After a couple of years on the ground in Shanghai, we realized, okay, China is not regulating any time soon. And even if they did regulate, two dudes from North Carolina are probably not best placed to end up with the top of the scrum on who's going to make the most money in Chinese online gambling. So maybe we can deploy our, our limited time and resources in a different way and turn this around. You know, we basically had a broken start up after four years on the ground in China. But what we had done with WSN is we built an English language version of it as, as kind of a plan B. And it was also how we kind of did quality control on the Chinese version because we didn't speak Chinese. The site was mostly sports data and stats that would help you with, with gambling. And the content was automated. So it was pretty easy to do a multi-lingual site. And eventually the UK site also just started making money more than the Chinese site. We're like, well, let's just kind of, why make this difficult? Let's do that and it's bad and we learned a lot there too, you know, one of the throughlines through this business has been SEO. I think during that period, really on this like massive scale site learning how to do that properly, you know, that was always kind of a main part of the thesis, but really figuring out how to get it ranking this huge, huge asset and even to build it for SEO. Once you kind of figure that out, we're like, okay, we can, we can take this and do lots of things with the SEO angle. It's just WSN in the UK market. But back then too, we were looking at the UK and we're like, are we too late? You know, maybe this is 2008, 2011. We thought we might maybe miss the boat. Of course, we haven't or we didn't still growing in the UK to this day. And it's been a great lesson in front of markets for us. You're rarely too late for these markets. At some point around 2009 and 2010, we started to realize, okay, casino is actually from an affiliate perspective, maybe a more interesting opportunity than sports betting, you know, there's not as many players, but the players are more valuable and they're hover for the operators to get. So they're basically willing to pay more for the players. And then on the content side, it's not, it's just not as complicated to build the content for a casino affiliate site than it is to build the content for a first class sports betting affiliate site. The SEO is harbor. It's a lot, however, but that is where we thought we had our edge and we made two really key pivots at that time. So we pivoted away from China toward where the world's largest regulated market at the time, which was the UK and the UK's obviously been the world post mature and long-giss regulated market up in the largest until very recently and away from sports to casino. So we started building out casino affiliate sites. The first one of those was casino source, which was around and had a very good run. It was probably a 15 year run for that, but we just rolled it into casinos.com last year. But that was our first pure play casino site. The first market we targeted was the UK and that started to work. It was not an overnight success. It was a hard grind. I remember innumerable late nights and tedious projects to get that thing working, but it did work eventually. And around the same time, I got a phone call. We had started working with Mark Blanford in 2008. He originally invested in us when we were still in China and I think he described that ambitions in China is quite brave, which at the time I thought was the compliment and that I think I learned more about British nuance and that that was compliment but own in certain ways. Anyways, we've still been working with Mark ever since. Mark's a fantastic partner of ours. We would not be where we are today without Mark and in 2011, we got a phone call. Mark had been contacted about the gambling.com domain name, which was at the time owned by Media Corporation, a formerly UK listed company, which owned a great many fantastic domain names. They had bought gambling.com in 2006, a couple of months before Euega. They paid, I think, 20 million for it. At the time, allegedly, he was making a million dollars a month or something like that. It was a highly successful affiliate site in the US market in 2006, but then you had Euega, the market closed overnight unexpectedly, last day of the congressional session, big disruption, and it went from apparently doing very well to basically not even making money. It wasn't even profitable once they had to pull out of the US market. The guys that had it were not SEOs or digital marketers. They were more on the finance side and they didn't pivot it to the UK, which we thought was kind of the obvious thing to do with it. It basically withered on the vine for about five years until they needed money. They went around the industry and said they're going to auction the domain name. I think they said they had a reserve price of nine million bucks. We had seen these headlines and thought, "Okay, well, not that we have nine million bucks, but even if we did, that's too much for that domain name." That's not what it's worth. As the clock was ticking down on them and they became more and more eager to find a buyer, to raise some cash. They rang around the industry called us and we thought this is very interesting. At a more reasonable price, this is something we need to take seriously, so there was a whole series of discussions over a long weekend with Mark and with media corporation about, "Are we going to put in a bit at what level and obviously we're going to have to find the money?" Nobody doesn't have that sort of cash line around, so that would entail some extra push from the back from existing investors. All of that happened. We put in a bit of two and a half million bucks on a Friday and they said, "If you raise your bid to three million, we'll end it early. The auction early and you can take it home. You'll be the winner." We did not buy it on that and they called us on Monday and said, "You won the auction for two and a half million." You saved yourself a half million dollars there in the process. I dusted off some of the gambling.com business plan we made in 2011 and a lot of great ideas in there that we haven't even gotten to yet. I think Casino's.com is going to inherit some of these great ideas. I think there's a lot of the vision we light out there is what we executed and it's interesting to look back on that. Well, I'll try to fill in the blanks and just finish this story and then we can go on to more just topics to sure. We got the gambling.com domain name we had to rebuild it. It was basically a broken affiliate site. It produced one new deposit and customer in the first two months that we had it. Officially, we just bought the domain name. We didn't really buy a website. There was no people in the process, no revenue. They kind of let us just keep the old website for a couple of months while we built a new one. Then I think it was 2012 by the time we launched a new one and then it took a couple of years to really get some traction with it. There was an incredible number of late nights. We built our own publishing platform for that website. We didn't use WordPress. We've always been kind of tech first. That's my background as a geek. Let's build proprietary technology that gives us an advantage. Otherwise, what value are we really adding here and it took time. But by 2014, it was going pretty well. Team was growing. We had a small team in the US. We've had an office in the US since 2011. I'd been in Europe since 2011. By 2014, we realized, okay, this is going pretty well. We need to get a bit more serious. We need a proper headquarters. It definitely needs to be in Europe. So where are we going to put it? Okay. Malta, London, Dublin, the debate really came down to God of so long ago. I can't remember what the number two was, but in the end, we picked Dublin. And that was absolutely the right choice. Had we gone with London, we would have been affected severely by Brexit, but an industry like this where we operate in so many of these European markets, that would have been an incredible headwind. But we opened our office in Dublin in 2015, started with the first couple of hires. And now we've got over 150 in Ireland. And there's nearly 500 people across the entire group. I think we've got over 150 now in the US, so the US would be our biggest jurisdiction in terms of headcount, but most of the senior team intellectual property and lots of, you know, the for all intensive purposes are our large operating entity is still in Ireland. And then the US really runs just the US business for the metaphor. Kevin, you came over, you much to my surprise and the way you volunteered to move to Dublin at the beginning of our Irish chapter. Yes. Right. I was in New York at the time. I had a kid who was six months old at that point in time and was ready to leave the York. So the idea of Dublin came up figure why not is interesting opportunities there for four or five years, fast forwarding a bit when it passed by happened and then I'm moving back to the US. But I think I'm on my fifth city now within the group. So from 2015 to 2020, Kevin lived in Dublin. I spent a lot of time in Dublin. You know, I've been based in Monaco since 2011, but you know, spent a lot of time on the road traveling for work and had been very happy to spend a lot of time in Ireland. 2016 and 2017 is really where we got serious from a corporate finance perspective. That's what we brought on our first and only CFO, Mr. Elias Mark, who's been a fantastic member of the team. Elias came on and helped us raise 16 million from some Swedish investors in a convertible bonds because we thought we, at the time, we thought we would take the company public in Sweden, because that's just what you did with a European online gambling performance marketing company. You know, we had a couple of peers already listed on that as ex-soccom and those investors had had a lot of sessions with those companies. So they understood the space, they understood the affiliate part of the space. Nobody had listed a company like this in the US. You did have Excel media listed in London, but there was a bit of a hub in Sweden. At the time and it seemed clear to us that that was the path to go. And so Elias, even though he's married to an English rose and went to university in Scotland, he is originally from Sweden and obviously speaks Swedish and so he was kind of the perfect hybrid for us. It helped us get taken seriously in Sweden, but it's also very easy to work with and relate to from our own past experiences. So we raised that convertible bond in 2016, we did four relatively small acquisitions. We got bookies.com out of that. We got some apps out of that, which could have continued to do well a few other smaller sites. It wasn't, they were not landmark transactions that made huge headlines, but it helped us scale up a bit. And we thought that we wanted to demonstrate our ability to do M&A prior to taking the company public in Sweden because continuing to do M&A would have been a big part of that strategy. And then past bad, that was 2018. And we all, you know, we were well on our way with the Swedish IPO. We had what we thought was the best investment bank in the Nordics engaged to do the IPO. We were some ways down the path and then we all had to kind of sit down and look each other in the eye and say, wait a minute, hold on here, the facts on the ground have changed. The strategy needs to change. Why would we IPO this company in Sweden when clearly the future of this industry is now in the United States? And we're the only people that run one of these companies that are actually American. So it was a 180 move at the time, which fell quite painful because we, you know, we would have been pushing so hard in a certain direction, but it was, it was the obvious thing to do. I then had the distinct pleasure of ringing 80 Swedish bondholders and telling them that we were not actually going to IPO the company in Sweden. You were going to raise some additional capital and repay them as quickly as we possibly could because that was the fair thing to do. And also, you know, those, those investors had come into a convertible bond because they wanted equity eventually. And so we offered them the opportunity to convert to equity if they wanted to. And I think ten of them did and they got in it like, I don't know, two bucks a share. I can't remember exactly what the figure is. But if you translate it out to today, it's two, two, two, fifty a share, something like that. You know, so they've obviously done incredibly well. The ones that converted to equity. Then, you know, we started a series of conversations to figure out how we're actually going to IPO this company in the US. At the time, we were a multi-s company, had an office in Malta for many years, and for a long time, the top co was a, was a multi-s company for those of you out there that have dealt with certain things in Malta, you know, it's not always the most efficient jurisdiction for some things and when we looked at it, when we looked at taking a multi-s company public in the United States, we realized very quickly that first of all, it had never been done before. We would have been the first, you know, there had been some struggles with some bureaucracy. And we said, okay, that's, we don't need to get an award for blazing a new trail here. Let's make this more simple on ourselves and read out a style of the top company to a jurisdiction which will clay nice with the Americans and is somewhere that the plumbing already exists in order to do a US listing. So we settled on the Channel Island of Jersey, transferred our top-coded Jersey, started doing board meetings in Jersey and, you know, all the work that goes into a US IPO. That is probably worth its own podcast, but what you quickly learn when you try to take company public in the United States is that it's all about the audit. That is the most complicated thing by a country mile. Companies which are listed in the US are, have to be audited to a special standard. The PCAOB standard, which is uniquely onerous in terms of how thorough the auditors go. The auditors themselves then get audited by the PCAOB to make sure that they did it correctly and you don't really know what that means until you go through it yourself. But we had to get, you know, re-audited for a couple of years, even though we already had PWC malt as our auditors. That was not good enough because they didn't have that special accreditation you needed for the US. So we did all that and got the company listed in July of 2021. I think we got about 40 odd million in proceeds from the IPO and we probably used that to do two deals at the beginning of 2022. So we bought RotoWire, which is the, for fantasy folks out there, like Kevin, you know, it's the original authority in fantasy sports in the United States. So we saw this as a really obvious opportunity to buy a company which has a 25-year-old well-known American sports website that's not doing sports betting. I mean, it was a kind of perfect setup. So we went in and essentially added on a new business model to RotoWire. This performance marketing model that we do and do so well. And that added on an additional revenue stream for that that didn't exist previously. But it also didn't conflict in any way with their existing business in terms of that premium content subscription that they sell and the other work that they do supplying content and news feeds to sports companies around the United States. So that has gone very well and we're very happy with that acquisition of the next one was Bonus Finder. Kevin, you want to go over that one? Yeah. I think Bonus Finder was the one other business we've come across or website or group of sites that most reminded us of gambling.com, both the team, the way they work, the way they think about entering markets, their growth trajectory, margins, the whole thing. So made a lot of sense to scoop it up, you know, when we start thinking about other businesses that were maybe stealing ideas from it, often a good time to target them with M&A. They had a great team as well and it's gotten spectacular I think with them continue to grow lots more on the tableware too. Since the Bonus Finder deal, we haven't done another acquisition, but the big kind of development in the business over the past two years has been our push into media partnerships. So a little credit to some of our peers, our friends at Copenhagen, kind of pioneered this model, but we've tried to take a little bit of a different angle on it and partner with large media organizations in the US that have an entire portfolio of newspapers rather than just one individual newspaper. We did a deal with McClatchee at the beginning of 2022 and then we did a deal with Gennett beginning of 2023 and that's proven to be a really interesting new driver of the business for us. Gennett in particular has got the USA Today, which is really the only truly national non-business newspaper in the United States and if you go to USA Today.com/Betting, that's basically all loss. We help them monetize force betting across the United States. They also have hundreds of local in-market papers which we also support and work with in addition to the papers that are owned by McClatchee and that brings us all the way up to present. So now the next big date on the calendar is March 11th when sports betting goes live in North Carolina. We've got betcarolina.com in addition to all of our other more well-known brands but we've also got the two major North Carolina newspapers between the Charlotte Observer and the News and Observer. Thanks to the partnership with McClatchee so Kevin will be directing those troops from the Queen City and I'm sure the North Carolina will be another successful new state launch for us. Well guys, I have to say it's a hell of a journey you've been on and the arc of it is truly fascinating. I'm going to resist temptation to pull the thread on a number of the points you've raised over the last 20-ish minutes here because I do want to shift some of the time to focus on more contemporary topics but I do want to just maybe take a couple minutes here and just get a bit of perspective on a few things that came out of that for me anyway. And I talk to a lot of founders through the podcast that are on their quest to find product market fit. I'm just kind of hearing the arc of your journey with gambling.com. I'm just curious to hear like as you reflect back on your own journey towards product market fit. I mean there was a few like pivotal moments it sounds like obviously exiting China and focusing on the UK pivoting away from sports to casino. I mean this sound like obviously you know key moments in time in the story but I think more like on you know for yourselves as the entrepreneurs driving all of this like what was it like for you to sort of reach product market fit and I guess what I'm curious about is like how did things change and you know mentally and just like for the business going from start up to scale up and like what does that mean when you talk about sort of crossing that chasm from start up scale up and Charles you mentioned a few times in that story about things kind of growing up and getting a bit more mature for the business like just what's that meant I guess or what does that look like in practical terms kind of just getting a bit more you know structure and operational cadence and all these sorts of things that you would associate with the more well-eiled machine and sort of a startup at the earlier stages wondering to the forest trying to find itself like just talk a little bit about I guess that for for you guys if you don't mind. For us obviously you know Charles went through the depth there we pivoted a few times with different types of assets different markets. I think for us the proper product market fit was about a year and a half or so into gambling dot com. I mean we're profitable which is a huge step and so you can kind of keep going but then you feel like you have a model that can scale up to then you know we had a lot of good ideas we understood we needed to do we hadn't hit the beach had yet that we thought we could grow from and so once you're there obviously that's exciting but scaling is hard especially when you know the early days of when you're thinking about it it's you don't want to put too much resource into it right you want to stay fairly efficient but think about this business the finding product market fit in a scale up or two just totally different phases right finding product market fit you're just kind of wandering around until you get there this scale ups intense though and it's just as hard but for for totally different reasons you know the hardest part with scaling up is the people finding the right people learning how to kind of manage them having the right processes or structures all of that and that has continued right through through different phases you see a lot of teams fail you know once they get past whatever the 25 people are so mark and then similarly around the 100 people mark for ever reason communication just starts to to break down for us a big part of that was that moving to Dublin meaning to properly scale you know we've historically been a remote first group Charles and I have only lived together in the same city for like four years this whole journey which is wild but it's worked you know in Dublin during the initial kind of proper scale up phase we were all in the same office which was helpful but it's yeah totally different process and you know you look at Silicon Valley just as an example everybody thinks it's tech cove it's really a growth in scale hub that's the expertise and it's a different set rather than just knowing how to find that thing that got us product market fit and how do we deliver that across our wider group of people is its own challenge yeah I just add on you know in terms of the key breakthroughs yes it was a pivot out of China to the UK it was dependent from sports spending takes a scene out and then it took some time for us to really understand the value of the traffic and how much we could actually sell it for you know I think for a period of time we had achieved some level of scale in terms of traffic and NBC's but had not yet kind of really fully appreciated the pricing power that we had and once that became more clear everything started to move a lot faster yeah a lot of that initial product market fit is learning just where the where the money is in the monetization funnel once you figure that out it kind of all clicks some will we're going to come back towards the end here with a few again just more like actionable insights based on all your experience but let's shift here for the next little bit talk about a couple more contemporary topics given that you are one of the category leaders within the industry when it comes to performance marketing you know I'd love to get your perspective on a few aspects to that business model and I guess generally the role of affiliates within this space you know I mean look to call it what it is my my read and my sense right now is that the particularly for me US perspective I guess I'll qualify it by isolating it to the US but it really seems to me that the operator affiliate relationship is a contentious one of times and you know a lot of the operators I talk to like take the position that affiliates are almost like a quote unquote necessary evil and I guess I'm just curious from your guys perspective again as one of the largest performance marketing companies in the industry and and really supporting these operators like does this sentiment actually align to your experience like is it actually truth in this or like what's your perspective I guess on just this overall vibe right now on just that relationship between the obviously very key stakeholders in the ecosystem look there's a lot of operators that are begging us for traffic as well that side just doesn't get as much publicity there's always going to be probably some brands that view it that way oftentimes especially if they're smaller brands those are the ones that that don't last yeah the affiliates can deliver a more cost effective acquisition strategy then they'll see elsewhere especially with brand marketing our sweet spot it always has been and we'll likely continue to be challenger brands that's where we can deliver and what they need overlaps the most but I think a couple different groups of affiliates perhaps there's those that maybe aren't delivering as much value a lot of small ones that are small affiliates that are perhaps very needy I can see why you know maybe some operators would be less interested in working with them but you know we've always really strive to deliver high value players and to be an easy partner to work with a preferable partner you know one that can be all compliance and this kind of thing and that really helps and for us to especially brands that want to expand globally when we can help them in many markets there's always going to be points in time where there's something contentious happening but I don't think that's the rule I think that's the exception I agree with all that's an necessary evil isn't the most flattering phrase but I think it's pretty accurate the operators big operator affiliate relationships they could be paying an individual affiliate multiple millions a month which if you're you know in the operators shoes that's a lot of money but at the end of the day when they do the math they understand that they're making an incredible return on that investment so they come back every single month and make that investment and it hasn't changed in 20 years the value that affiliates can provide for these operators it's been a remarkably consistent since the inception of the industry you know this kind of affiliate everybody loves to ask all how's the affiliate operator relationship evolving well if you just zoom out a little bit it kind of fundamentally hasn't changed at all in 20 years to be honest and the operators more than ever have better business intelligence so they can actually calculate the value of this traffic in a fairly sophisticated way and therefore they know what they're getting and they're even more confident than ever to buy it yeah 15 years ago there was the same conversation right and we're still here and if anything the industry and the affiliate operator relationship has all grown since then it is one of the oldest businesses on the internet do you affiliate business and another topic that I think is quite again relevant right now is responsible gaming and again from a US perspective it really strikes me that like things are becoming more and more under the microscope when it comes to responsible gaming I mean look five and a half years now coming up on six years post pass by repeal obviously there's a bit of a land rush here and you know we all know how it's played out and what it's led to is is a bit of a saturation I suppose in in marketing messages out there and just the general proliferation of betting content into sort of like the mainstream consciousness and now you know we're starting to see a little bit of like what people call the inevitable backlash towards some of that and gambling.com I think in November last year a few months ago I guess you were a founding member of a new trade association called the responsible gambling affiliate association so through that land and I guess just given the backdrop of sort of this increasing conversation around RG within the US market you guys just share a little bit about your perspective on it and maybe what was the catalyst for you guys to be one of the founding members of this new trade association. Yeah sure the RGA was formed amongst ourselves and some of the other major affiliates in the US really in response to this idea that affiliate marketing in various states should be limited in any way. There was a bit of a situation in Massachusetts you know there was a proposal that there should not be marketing affiliates so ourselves and the other members of that group swung into action before the group was formed and brought the facts and the full context of the situation to the policymakers and helped them understand that if they didn't have affiliate marketing they're going to have even more TV radio outdoor and all this stuff which is actually more in the face of the average Joe because it's being pushed at them or as most of these affiliate marketing companies really run with a search model which is the opposite the only way you see gambling.com if you go to the website that's an argument everyone has always come around to that argument when they get all the facts so that it's not a you know we're fortunate to have a highly defensible position on this but yeah it's not you know responsible gambling is a critical aspect of the entire industry problem gambling is everyone's problem you know we've got a very substantial problem gambling resource center on gambling.com but the RGA itself is more of a is not directly about responsible gambling it's more about ensuring that the affiliates in the United States market are represented and not discriminated against. Interesting and I guess just sort of through that lens and just to continue on the theme for a moment what are some of the the tangible activities that the association is doing I mean is it lobbying is it just having conversation and opening dialogue with policymakers like what is what is the actual I guess sort of like functional remit of the association. A lot of the goal is just to have a unified presence what's happening prior to this you know we always thought kind of all regulations good regulation for gaming we just wanted to move gaming forward it got to the point where that wasn't necessarily the case but it wasn't obvious for whether it's a regulator or legislators to anybody interested in the process especially on the affiliates I've who to talk to so we want to create a unified voice on that and just make it obvious who the leader is there you know we strive to be kind of inclusive within the affiliate space but we're focused on is overall more than anything else the proper regulation that is a little bit different in the US than other Geos we are not licensed in most countries around the world there are a few but in the US that that's a part of it so we need to make sure that a us as affiliates from the same page and that be that we can communicate that effectively to our partners at the state level the responsible gaming is super essential and that is a key piece of it I mean we want to show that we are being responsible as trolls noted you know without affiliates you're going to get more generic brand marketing we always target high intent users that are kind of seeking out information rather than pushing information to those users you know I think there probably is too many or too many ads on TV and that's sort of thing so you know wanting to limit that's totally reasonable but that's not an affiliate issue and I think at times many legislators and regulators don't totally appreciate what the line is on that that's kind of not us so just explaining kind of how our business model works is a big piece of education awesome the one thing that also really strikes me about your story is your guys as co-founder relationship and I'd love to spend a couple of minutes to talking about that if you're willing to look I mean you know co-founding a company is is hard at the best of times and for co-founders it's often likened to being a marriage right I mean it has its ups and its downs and it's on a roller coaster and just like the sheer amount of time you spend together I mean probably other than your spouse with your co-founding of business you're probably spending the most amount of time with your co-founder and in some cases maybe even more time with your co-founder than your spouse right so I guess I'm curious to hear from you guys over the arc of this 20 year journey I mean really dating back to when you met on the school bus back in the day like how have you both been able to maintain such a strong partnership and really like what have the keys to success been for you guys maintaining that partnership and obviously kind of going through the evolution of the business together and evolving yourself as individuals and entrepreneurs and just staying and sink through the entire arc of that journey just like talk a bit about that I guess and share you know maybe a bit of wisdom for other founders that might be earlier on in their journey. At the very beginning we lived in the same apartment and worked together all the time and we realized pretty quickly that was not a sustainable strategy so we fixed that but as Kevin said we had to live in the same city actually but for a couple of years on this journey you know but we're on the phone all the time we're on slack all the time we're at board meeting I feel like I see Kevin all the time even though we don't live in the same city I've got different areas of interest and different strengths I think then Kevin and Kevin's strengths and areas of interest are quite complimentary to mine but I think that's been incredibly helpful for all this you know I don't mind dealing with investors and capital markets and the finance side of the business and I think Kevin probably gratefully doesn't have to do some of that yeah I think we do have you know complimentary skill sets not just more good up but also interested in but we also do think about the world much in the same way which is important I could easily I think this probably wouldn't have worked if that wasn't the case we've always had a healthy openness to debate topics as well kind of find the route issue and answer and think about it from like first principles perspective and you know I remember early on people think we're arguing we're just debating the topic trying to find what's the actual truth here that's served as well as we continually as we grow think through what we're actually doing in the why why behind it but we're not afraid to have a kind of real discussions on those and I think that's totally essential if you don't have the healthy debate that I think the relationship will fall apart awesome and like to do a bit of a rapid fire on a few questions again more in service of providing a little bit of experience sharing and insight through your journey Charles earlier on you made reference to the investors that are you know that have backed you from the earliest stages and certainly sounds as though your experience with your investors has been nothing but positive and a lot of value add and based on that experience I'm just curious what you can maybe share with other founders as they're out there maybe looking for their first investor maybe assessing different investors like how you know you often talk about due diligence that investors do on founders and opportunities and deals but let's talk about I think is like the reverse due diligence of founders really taking the time to find the right fit for an investor because that really is a partner you're bringing to your business and for better for worse you're going to be stuck with this person for the duration of your business so I guess I'm just curious again given that the tone of your experience is very positive like what can you share with other people as they go out there and assess potential new capital partners in their businesses I think we were probably more lucky than smart to be honest but we found two great entrepreneurs that had made their money and we're looking to back the next round of entrepreneurs I think entrepreneurs backing entrepreneurs is it's a good fit they understand the business plan is irrelevant the second you've finished writing it you know and that you're going to get punched in the face and things are going to change you know I remember when we called Mark and said look we're going to lead China you know I was expecting to get it in the neck and he said if that's the right thing to do then let's do it and I was kind of shocked but only an entrepreneur would have the poise to handle a situation like that later in the development of the company we have worked with a private equity fund in the US and that's been a positive experience they have brought added financial discipline and rigor to some of our process which was a little foreign to us I suppose at the time when they came in but it was you know in retrospect they were right about all of those things and you can always debate strategy and direction and it was the best next move but fundamentally having people that have done it before I think is is the safest bet in terms of taking on outside capital but we always say one bad apple can ruin the whole barrel you know from just the people perspective and the same is true for investors you know if you get one wrong person on your cap table that decides to stew everyone or make everyone's a life and nightmare that's pretty much the end of a startup because people aren't going to want to stick around and deal with that where they could just leave and get clean slate so entrepreneurs have got to be careful about who they're getting in bed with I add to that I think it's important especially these days and over the past couple of years we've seen a lot of examples of this to make sure that you have the same long-term interests as your investors this isn't something we've seen but we see this throughout the market especially a lot of companies are looking at with M&A where maybe they raised that a little bit of too high of a level too high of evaluation and expectations little to be reset and that's very challenging I think everybody wants to put the kind of biggest number on the table or worth X and we raised Y and that can kind of shoot them in the foot down a line and a lot of these businesses that we see are not really kind of venture capital style businesses but there's expectations going to grow like that and so you really need to understand what the profile of the business is and does that align with the investors and if you do do a deal you know what are what does that mean for your future options down a line because it can become a limiting factor for sure all right next rapid fire topic here for you guys obviously over the arc of a 20-year journey lots of lessons I'm sure you've learned the hard way through experience is there one that stands out for each of you that really serves as a case study that you would dispense as advice to others and help them avoid making the same mistake or anything like that jumping out for you in terms of just lessons learned in my case we we touched on this when we pivoted from doing the Swedish IPO to playing a long game and IPOing the company in the US I did have to call 80 pissed off Swedish bondholders and I personally grew a lot through that experience I realized I've had always been quite focused on pleasing everyone and it was the first really point in my life where I realized the right thing to do is going to piss a lot of people off and it's all fair and it's all correct no one's behaving unethically but the correct course of action now involves telling a bunch of people know that thought they were going to hear yes and you know we did everything we could at the time to make that right and as we said you know it came very right for a lot of those investors but yeah it's something that really has then gone on to affect other things in my life I've become more comfortable disappointing people which it sounds like a kind of a strange skill but it's something I think is necessary for an entrepreneur. For my end I think a lot of people can focus too much on strategy sometimes especially in early days when you see to focus on execution execution is the hard part you know we're constantly turning down good ideas because we're worried we maybe can't execute on it and we want to execute properly and everything we do executing is much harder than than coming up with an idea we're right now executing is all about having right people and that has its own but I think a lot of teams just don't spend enough time on execution in general they just you know maybe hire one person and assume it's going to be solved or whatever but it's really challenging and it takes a lot of effort from everybody. We're very good at saying no to things and focus is always front of mind anything we're doing needs to be adequately resourced with the right people and the right amount of investment to ensure it has a credible path to success otherwise don't even bother. Awesome and then my next question here is a bit more philosophical and I mean look zooming out a little bit I'm just curious like how do you think about ambition and just like what drives I guess humans generally speaking like you guys have created something with I think a nine figure market cap now and continuing to push right and what pushes you to keep you know showing up every day keep grinding when you know ostensibly like you probably don't you know air quotes need to like what keeps you going and just sort of like how would you I guess think about ambition in that broader lens for me it's the competitive dynamic I see other companies out there that do what we do that are good at what they do that our respect and it's what what drives me is being able to put a better growth figures than every one of those companies every time we report you know it's a bit of an intellectual game but it's like a giant complex 3d pucker game or something you know obviously the money is a big part of it but I think we're at this stage is clearly about a lot more than just the money we've also got a great and loyal team and we've got an incredible number of very talented people that have bet on Kevin and I with their time over the past 10 years in some cases and they're very loyal to us and I think we're very loyal to them it's a beautiful thing when you've got a committed group of smart people that are all pulling exactly in the right direction and you never want to let them down and you want to deliver the best results you can yeah look we're still relatively on wordy and I'm going to go sit on a beach for the next 30 40 years so you have to do something we built this thing we expect this this business we have to continue to work we built it in a way then it's a place we'd want to work at with people we want to work with and so it makes a lot more sense to be here than somewhere else where you have to try to recreate that or however you want to think about it you know we first got started we're always very ambitious we got humbled a few times along the way but you know I remember thinking I would be if I wasn't retired by the time I was 30 I was like a failure but kind of learned long ago that it's it's going to play out a little different than that and you know expectations have changed as well and I think yeah no matter how big you get you always realize how there's this other goal out there wouldn't it be fun to get there that keeps growing just as we grow awesome I guess just looking ahead to the future now I mean you know as you alluded to Charles you have the North Carolina launch coming up shortly here and and no doubt a bunch of other initiatives that we'll hear about in due time but like zooming out and maybe over like a five to 10 year time horizon let's say like what do you think the world looks like for yourselves and the gambling.com group in that time and kind of where's the puck headed as it relates to the future of the business and I guess your respective involvement in it. Well in 10 years a long time if you just say kind of five years I would hope that we are heading shoulders above the competition as the undisputed clear number one largest most influential online gambling affiliate in the world that is our mission if you go 10 years out you know I think it's probably fairly likely that we'll be doing more than just the variety of gambling affiliation that we're doing today you know maybe we're selling other services to our 200 plus online gambling operator clients but I would think it's some point before 10 years we'd probably look to expand the TAM if you will and add on additional business models but for the foreseeable future there's a very high ceiling just in terms of what we're doing we with the business model we have now so there's no short term focus on that but you know 10 years of long time and I would think that we'd be doing more than just what we're doing now in 10 years awesome guys well I think that takes us to the finish line for today the hour flew by for me and it was extremely insightful and as I said a hell of a story and it's been fantastic to get a bit of a deeper window into it so thank you both for giving us a time here today and giving the audience your time and just a quick plug for anybody that's looking to learn more about the gambling dot com group and or get in touch with yourselves or your teams can you quickly shout out where people can go do all of that yeah gambling dot com slash corporate is our corporate website so that's got all the corporate information including contact us forums Kevin and I see anything that comes through on those forums so if anybody wants to get in touch just drop us a line there awesome guys appreciate it once again wishing you all the best and yeah that wraps up this episode of the gamble in the glory thanks to everybody for tuning in bye for now thank you jessie thanks a lot jessie

Podcast Summary

Key Points:

  1. The transcription is from an episode of "Gamble in the Glory" featuring Charles Gillespie and Kevin Macrystal, co-founders of gambling.com.
  2. The co-founders share their journey from building affiliate sites to acquiring the domain gambling.com.
  3. The story includes pivots from China to the UK market and from sports betting to casino affiliate sites.
  4. They bought the gambling.com domain for $2.5 million and rebuilt the site, achieving success in 201
  5. The company expanded with offices in Dublin and the US, focusing on corporate finance and raising funds.

Summary:

com, Charles Gillespie and Kevin Macrystal, who share their entrepreneurial journey. 5 million. After rebuilding the site, they found success in 2014.

The company expanded with offices in Dublin and the US, focusing on corporate finance and raising funds. Their story showcases the challenges and successes of building a business in the online gambling industry over nearly 20 years, highlighting key decisions, partnerships, and the evolution of their strategies.

FAQs

Gamble in the Glory tells the story of founders growing their companies in the sports betting, fantasy, and iGaming industry.

Gamble in the Glory is presented by Sega of LLP, a law firm specialized in the gaming and betting industry.

Sega of LLP provides legal solutions for challenges faced by companies in various industry verticals, including payments, blockchain, eSports, affiliates, and more.

The co-founders of gambling.com are Charles Gillespie and Kevin Macrystal.

Charles and Kevin started gambling.com as an affiliate site after pivoting from their initial plan to operate in China's online gambling market.

In 2011, gambling.com acquired the domain name from Media Corporation and started rebuilding the broken affiliate site.

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