SBC Leaders - The people behind betting and gaming's biggest brands

Discover the fascinating journey of Bryan Bailey, Casinomeister fouder and pioneer in the iGaming industry, as he shares insights on navigating the early days of online gaming, player advocacy, and the evolution of casino marketing.

Host: Sue Schneider
Guest: Bryan Bailey
Producer: Anaya McDonald
Editor: Anaya McDonald

What is SBC Leaders - The people behind betting and gaming's biggest brands?

SBC Leaders Podcast is a series of interviews with CEOs and decision makers at some of the betting and gaming industry's biggest, best and most innovative companies.

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Welcome to the Leaders podcast. I'm your host Sue Schneider and I'm very excited about today's guest, Brian Bailey, who many of you may know in the past from Casino Meister. um He truly is a veteran and um has been a tremendous leader for the industry in the past. So Brian, welcome. Really glad to have you on here. Yeah, it's great to be here. It's great sitting here chatting with you. Yeah, it's been a while. uh It has been a while. Yeah. um What I like to do is to start out just to give people context. What kind of things were you doing before you ever even jumped into the industry? I know you have a background in the military and other things, so talk a little bit about what life before iGaming was about. Yeah, well, when I got into iGaming, that was in 98, and I was already 40. So I had a pretty good bit of other things I'd been doing in my life before then. What was... I ended up in Alaska as a commercial fisherman, was a very young man. And then from 1980 or so, I was in the military for about 12 years. I was with the paratroopers, combat engineer at a Fort Bragg and I was stationed also in Germany and spent quite a few times, quite a bit abroad, different types of worldwide missions, lot of stuff. So I had done that. I got out and I was in a big push to get uh some degrees under my belt so I could actually get a job and support an ex-wife, three kids, and a new wife. So that was going on back in 1998, which I did. I got a Master of Fine Arts in Creative Writing from San Diego State University. Oh, really? I didn't know that. Oh, yeah. So you veered off dramatically then also. Well, actually, what I started doing, this is like in the mid-90s, I started getting involved with the internet. The main thing I was just really trying to have ideas, like how do you teach a college student a short story using hyperlinks and all these certain things. was like very beginning of the internet, we're just kind of experimenting how this could actually happen. And that was one of my main goals, missions, whatever, is to really... figure out how to teach short stories on the internet. And by doing that, honed my skills for uh HTML and graphics and stuff, skills that were good in the 1990s. But this all led to just really getting involved, really just building websites, web pages. Meanwhile, I was teaching in San Diego, was teaching at the community colleges, humanities, creative writing, and English, you know, your entry level English 101, uh, English Lit, same thing at San Diego State. And by this time I was also working at a translation company, those translating websites. And this is where I got started with Casino Meister. Yeah. So that's all that background stuff. Casino Meister was a completely new thing. Uh, this for me was really just a Bahabi website that I built. And there was, we had some clients at this um translation company that uh we translated their websites. They're all based in the Dominican Republic. Right. These guys. The Caribbean was a big thing there. Yeah. And so we had translated some websites, half the guys didn't pay us. And it was like, ah, what a joke. I just thought it was just like a, just a scam, you know? Yeah. And we were... approached by some owners of one of the land-based casinos down in Southern California, and they wanted us to build them a website that would be translated in five different languages, the European languages. And at same time, you know, we're giving a pitch about how much it's going to cost, all this stuff, and they go, well, that's, you know, it's a high price. And how do other, you how do people know that we're a good casino? And there's other bad casinos out there. How do people know this? And that's when I was like, wow, I'll build a website and call it Casino Meister and have a list of good casinos, like you guys and the bad ones, like the ones that didn't pay us. And that's really how the whole thing started. It was just uh like three or four pages of just some blah, blah, blah. This is what you can do. This you can't do. And I started getting news and stuff from like Rolling Rock. Yeah. with you guys and everything, and that was great. So we started kind of like putting that all together, but that's the very, very early days. Yeah, that's like 1998. Yeah, so that's really kind of the beginning. And you mentioned the good guys and the bad guys. You kind of kept that up as a feature throughout. uh Talk about that for a minute. I had forgotten about that. You had kind of a wall of shame there. We had, well, it's still there. I I sold Casino Meister back in... 2024 and uh yeah, we were really focused for quite a while on, you we had the awards every year and most of the awards that we had were awards for the worst casino, the worst casino group, stupidest named casino, stupid casino tricks, the worst player experience, all this stuff. So yeah, there's just so much. Now there are a lot of cricket sites and everything. Right. And this is mostly, you know, you Russian mafia and all that stuff like that. Um, but back then he just had everybody and their brother trying to start up an online casino in their, in their, know, in their, you know, basement or their garage or something. It could be done. It was easily done back then. Just get a laptop, throw on some software and try to get players to come in. And, uh, yeah, we had a lot of folks, no licenses, no nothing. Yeah. Yeah. A lot of. crazy things back in the early days. Yeah. Well, you're alluding to the lack of regulation, was, it truly was the Wild West at that point in time. How were you able to navigate through that given that it really was a situation, again, a lot of these operators that were out there at that point, I won't say a lot, but some of the operators that were out there at that point really were trying to make a quick buck and were not really the long-term businesses as some of them have turned out to be and have worked their way through the whole coming of regulation cycle. And it was an interesting time. So I mean, as an affiliate marketer at that point in time, that really was working kind of on behalf of the players, to be honest. I mean, that was really a lot of your focus. So how did you navigate through that part of it? Well, when we're going back to like 98, 99, early 2000s, there wasn't really any regulation at all. And this is the industry and this is what was so cool about the industry back then, really. Cause you had more good apples than bad. You did. And it was self regulated because a of these people coming into it, they wanted to do the right thing. They wanted to do the right thing for players, for their advertisers, because they want to... have a clean slate and be the honest ones. And so that's why a lot of these people, they meet up with me and they'd be scrutinized and everything and figure them out. And you could tell who was like trying to pull your leg and who wasn't. And then you could tell the baddies and you could. You could just look at the websites, try to figure out where they're based, what kind of communications they have going on, how willing it would be to like meet me at a conference or something like that. uh The self-regulation period, and this goes up to around 2000, probably 2006 or something, right before the Ouija around there. this is, yeah, this, it was a good time, except there were a lot of issues with players uh that could be ripped off. And there was a lot of issues with um operators. uh being ripped off by players. this was another, it was a big challenge back then, because you get groups of players that would come in like a gang and uh start pounding some of these casinos for these bonuses and stuff. And this is the early days, people didn't know how to write a bonus, know, term and condition. They'll just give out, you know, free five bucks and that would be it, free five bucks in your account. You could cash it out, no questions asked. That lasted about a month. Right. And you know, it's interesting in terms of where some of those have, where some of those went. mean, again, you mentioned, you know, before I got into River City Group, we had Rolling Good Times online and looking back, it was probably one of the first affiliate sites because we did advertising for, it was a consumer site and yours and other ones came along. There was gambling.com and other ones that really ended up having, there was no mechanism for a dispute. between a player and an online casino or sports book. So, I mean, that was a whole nother role that you took on, gambling.com took on. I know we did a little bit of that before we switched over to B2B. But how important was that side of it? It wasn't necessarily the advocacy side, because as you said, some of the players were scamming also. So it was a matter of having to sort through that. And I know uh a good friend of ours who has passed on, Mickey Ostrand did that on behalf of the Mohawks as a licensing jurisdiction. That whole interaction between the player and the casino when something went bad was a real critical role. So how did you kind of stumble into doing that on a regular basis? It really started with uh the forum back in the early, early days when Julie Sidwell that worked for a casino. Yeah, right. And she was doing the player advocacy for a bit and unfortunately she passed away. And when she did, there was a void and people were like in my forum and there, know, was right. So when I said, okay, this is what I should be, you know, I should be picking up the ball for this. So that's when we started up a service for players to, uh you know, uh pitch a complaint. We called it pitch a bitch. uh They come in there, pitch their bitch and yeah, we try to help them out. And that was, yeah, in the very early days in 2000, 2001. And, you know, I felt that that was really a responsibility, you know, of myself. I mean, this, you know, for my website, Casino Meister, I never really considered myself an affiliate because I wasn't really involved with any of the affiliate stuff in the early days. I had media buys, but I wasn't getting any kind of profiting from. like a percentage of people making their deposits. I tried to steer away from that because I thought that was, it just didn't ring right with me. I'd rather have people pay to be on the site and if they're good, they're good. And if they're bad, I just take them off the site. I don't have to worry about it. um So starting the PAB bit, uh That was probably one of the best things I did because I did already have a lot of experience counseling and everything. I've used to counseling troops and soldiers and figuring out problems that people are trying to solve for themselves and everything. with the connections I had in the industry, um and this is from the very early years, you know, I had a newsletter that most everybody, know, most of the C level people were, uh, subscribing to. So I go to a conference, they had more people knowing me than I would know them. And so I had a lot of connections in talking with, you know, the CEOs, know, C-level people, people who actually developed the software for all these casinos. I had a lot of the, the, the, the main people, the owners of casinos and software companies, you know, standing by their phones, waiting for me to call them up and tell them what problems I was having. You know, I even had a CEO from a Microsoft every time I meet him he said okay, who's giving you grief not talking about the players But talking about his operators, you know, which ones are you having problems with because we'll sort them out. Yeah micro game interesting Well as as marketing whether you want to you know term it as affiliate marketing or you know some variation um That sort of really began to blossom as entry point for somebody that wants to come into the industry, but yet not be an operator so When you see the growth of that side of the sector growing and beginning to kind of organize itself and things like that because you had other peers that you know you would get together you were kind of known for your You know your various parties at some of the industry events, but yeah Organizing that side of the business is something, whether you did it consciously or not, you really were involved with that and knew who the really solid uh marketers were and who maybe didn't do things quite as they should. And again, regulation didn't exist really at all for that side of the business at that point as it grew. No, yeah. And there were some movements to get, uh, you know, have the affiliates get together and make some kind of group. GPWA was one, APCW was another one, I think. You get all my acronyms all messed up. It's been a while since I've been talking about the industry, but yeah, there was a few attempts to, to ban affiliates together, but it's like herding cats. Yeah. Yeah. Just can't do it. Yeah. Um. Actually, there are a couple that exist now probably since you've been out of the business. So it's long overdue, but that does exist at this point. um What kind of things did you learn from those earlier years as you got in the business? What were some of your learnings that you can share? um You a lot of my, yeah, you're always learning something, you know, and I think a lot of it was really about the human behavior. Right. And I think what I learned a lot was about the behavior of people who gamble. uh Before getting into business, I wasn't a gambler. uh I'd go to Vegas to go to the buffets. I just couldn't, I could not care less about it. But what I did care about was creating something, right. And uh like with Casino Meister, my first priority was really to have the site working and then the images. things were working in an actual functioning website. So learning a lot of technical stuff, at the same time learning about how players react to different casinos. was really, it was interesting. I thought this whole bonus thing was going to be a short-lived kind of flash in the pan because for me it just didn't make any sense. whatsoever. Why would you play with somebody, you know, a bonus money that's going to have all sorts of terms and conditions in it, like how much you can win, what games you can play. And they're all set up really for you to make a mistake. You make a mistake, you get nothing. And so, playing without a bonus, I used to really advocate that that's the way you should be playing. You should not be playing with bonuses because they tie you into things. You play with your money, you cash out, you know, whenever you want. So yeah, I have learned a lot really about the way players behave. Well, and the bonus issue is an interesting one because it's, think a lot of operators are very reliant on that at this point. I mean, I've seen it in the US as states have come in, it's like, that's what they're using. And there are bonus hunters out there on the player side. That's what they do. And it just blew my mind, know, like, God, it's idiocy to be playing like that, but that's what they did. And it was just like they created this Frankenstein's monster. It just never went away. You know, and I remember we got Virgil Casino on the site, you know, at one point and I was going, oh, thank God, you know, because they could actually insensitize, you know, bring in players with things other than a bonus, because they had ulcers in deep pockets. Virgin Airlines, could send people on vacations, they could send them down to the Virgin shop in London or something, buy all the CDs, DVDs that you want, whatever. They had so many other things besides bonuses. The first thing they do, bonuses. Okay. Yeah. What did you find the most rewarding about your time in the industry? Oh gosh, there's so much. mean, mostly just the forum. you uh know, dealing with all the people that the forum would bring in. And that was really, really, it was, was good, especially when we were do, you know, do something good, like somebody paid that was owed a lot of money. And each year we'd have like some windfall, you know, and it was just really good. But I think a lot of it was, you know, seeing some of earlier operators who were really focused on their players. And I think one of like, for instance, Ed Ware from 32 Red. Um, we had one, one of his players, he was a, uh, was a um disabled vet, um, in, the UK from Afghanistan. So I'm broken to his apartment and stole his TV. And yeah, 32 red turned around and they, they sent him a new TV. He had one delivered by Amazon, you know, stuff like that, you know, and these, and knowing that these people wouldn't have met or wouldn't have been connected. without my forum, without the website. then it's another thing, like with the Meister meetings, we had this every year, always people getting together and just sitting around looking at everybody thinking, wow, this is really cool. Yeah. It's all because of me. No, but it's like, you know, it's very satisfying seeing these people that this time had been friends for decades and they met through the forum. Right. Yeah. Yeah, that's true. mean, when you look back, first of all, it was very global from the outset. And you make friends in South Africa or Australia or all over the place. that's been very, very gratifying. I think you've been like me in some ways and that you enjoy the community building part of it. And that's really what it was. Oh yeah, definitely. Looking at your peers out there and bringing them together. Did you, uh and again, Granted you've been out of it a bit for like two years now, I guess. um How have you seen the marketing side of the industry grow and evolve? has it turned out the way you had hoped? Are there things that you think, you know, oh, I wish we, as a group, had done it this way instead of this? has it really kind of turned out in a way that you're pretty satisfied with at this point? Well, I think the industry has evolved into what it was going to end up being, you know, and it's all about the suits. It's all about the corporate groups and everything. And this is with any industry really that started online back in the 90s. You you can look at any of them today and see that it's changed into completely, you know, completely corporate. You can sit there and reminisce about the good old days, about anything, but you know, it wasn't safe for players. They'd have to rely on certain things like, you know, going to website, you know, it's... but they'd always go there to get the information after the problems. Weird, it's ugly head. But yeah, it's a different internet now. Yeah, it's evolved to what it is now. Back then it was mom and pop organizations. Most of the companies weren't even publicly traded. And it was very, you knew the people you were dealing with. Now you're dealing with people that is just either revolving doors. um I think one big problem now is they've lost a lot of the knowledge. from a lot of your middle managers and people who've been pushed out of the business in the last maybe five, 10 years. lot of these people like affiliate managers and these people who've been in the business for the very beginning. I think it'd be very difficult to find anyone really, maybe a few handfuls of people that we had known back then, they're actually still actively working. It's a new face now. And so I think that's a big mistake as well because the new corporate folks they don't have that street knowledge. I could use Casino Meister as an example. I I had everything set up on that site when they sold it, with the newsletters, podcasts, uh sections for the players get involved with analyzing uh casino games and this sort of thing. A lot of stuff all set up for this. is it be like features, know, things would help out, you know, assist players for their own knowledge and everything, but there's no interest from that, from from corporate side. It's really about numbers. It is about, and I get it, it's bottom line. They got it, you got to, you know, pursue, you know, you know, the, the Benjamins, they have to, because that's just the nature of the beast. But I've seen a lot of things has faulted away side. And I think it's, it's, it's very unfortunate. Yeah. Well, and I, you know, I don't want to paint a broad brush with all the companies that have gone public, but my observation, at least with some, is that it becomes more about share price. And that's where, again, a lot of that has been lost in terms of what that relationship is between the company and em the player themselves. And if we didn't have the players, none of us would be here. it is an issue as... The industry has evolved overall. I always found that frustrating to keep reminding everyone at these conferences, you know, it's all about the player. You do know that, you know, Oh, yeah, yeah, you wouldn't have a job. It wasn't for players, but they look at players as just, Ooh, going to churn out some, you know, some money out of them. Yeah. That is really true. And, and it's been interesting being in the event production side of things, how, you know, I tried in many instances to bring in like a player's panel. what are you looking for, what works for you, that sort of thing. Whether it's a recreational player or whether it's professional player. it's, you know, a lot of times that they really are forgotten in the whole equation. So I think you bring up a good point there. you, uh let me ask you this. If you had someone coming to you today and said, oh, I'm interested in getting into the industry or want to explore it. I mean, what... What sort of advice would you have for them? Um, really, I think that the best thing that anybody could do is to go to really as many conferences. I'm not really trying to push conferences, but you know, it's the networking because a networking will, will underscore everything that you do on. You got to know people, you know, you can't go in it alone and think you're going to go ahead and. and do whatever you're to do. And I think it's really difficult for just a single, I don't even know it's even possible for somebody who's just on their own building a website to get involved, you know, or they can get involved, but I'm just wondering how far that would go because it is very difficult. mean, you know, the search engines are just flooded with, know, all, you know, all the websites you could possibly imagine. um But there's a lot to gain from, you know, networking, meeting people. And yeah, and keeping your mind open, because there's always a niche, you know? And that's one thing I always told people, you know, find your niche, you know? And, you know, for a while I had no competition. No one was doing any kind of like player resolution, because they knew they couldn't compete with me, because I knew everybody in the industry, that sort of thing. So I didn't have any competition for a while, but that was the old internet. You just can't do that anymore, you know? Well, and I really do buy that again. I'm working more with startups now and we say the same thing. It's like, you know, if you have a site that's aimed at women's sports or, know, pick a subspecialty in there and you can make a decent living at that sort of thing. Oh yeah. To your point about picking a niche. Yeah. Well, that's the most important, picking niche that you're going to be confused with somebody else. Yeah. Not being all things to all people. Yeah, yeah, so it's a matter of, yeah. You you brought up about one of the things that I think has been a challenge to, know, that side of the industry and continues today is sort of staying ahead of the technology that's out there that, you know, I know there's a lot related to SEO and all that for affiliate marketers and yet, you know, they're constantly having to adapt and make changes to stay ahead of Google or. or whatever, and that's been an issue for a long time. do um you see that, historically, how was that dealt with? Because it seems like it's just a matter of trying to share information among yourselves. It's like, well, I did it this way and that worked. But how have you dealt with the things related to the search engines and all that so that you get some visibility from players? Well, know, I'm talking about, Back when I was like starting, well, when we started, but actually getting started, had what was called a friendly competition. All All the webmasters pretty much, we stuck together as a good, probably five of us that shared a lot of information about, you know, how to build things in your website, this sort of thing. So it was actually bringing in our own kind of group that would, we would assist each other with different sorts of things like technical issues. you're always going to need somebody smarter than yourself. And there's going to be other things, other things that other people, you know, are able to do better than you. And so we were able to do this with amongst ourselves as peers, because as a webmaster you're learning and you have webmaster bodies who are learning sort of the same thing. you know, bringing that up to now, I think it'd be really important to find some kind of like groups of people that can assist you in getting through a lot of this, like SEO for one thing. mean, you could hire as many SEO consultants as you want and still, it's a new science. You're gonna have a lot of like, oh, this work, does that work or what? So yeah, I think a lot of that has to do with getting other people like yourself involved. And now if we fast forward to today, There are licenses in many jurisdictions for affiliate marketers and that sort of thing. I mean, if you look forward as best you can, uh what sorts of things, I mean, is there a way that you think people can kind of prepare themselves to try to stay ahead of the curve on the increasing regulation that's happening on that side of the business? Oh, God, that's tough because... the more it's, that is really difficult because the more regulation you have, it's in other words, you're going to have, there's more hands in that pie. So what's happening is for the affiliates and marketers who are like focused primarily only on uh regulated markets, right? uh I think there will be some difficulty at one point actually, you know, earning a living off of that because so much has cut back. I don't know what's going on right now, but I remember before I left there was talk of like higher taxes and stuff for affiliates and this sort of thing like in the UK or what have you. And yeah, I get it. It's great because it's probably there just to help assist players and make things safer. But you're going to start looking at affiliates that can't cut it that way. Same thing with operators, can't cut it that way. So they start looking at other. uh properties to promote and some of these properties are, you know, in places where it's, know, it's weak, you know, weak jurisdictions. But speaking from my own experience, I can tell you for a fact, some of our best operators were, uh had their casinos, their RTG casinos running out of, know, Costa Rica, which isn't really a uh gambling license, it's a business license. It's not a casino license. I honestly, some of those guys were the best in the business and been in the business for decades. Hardly ever complain. When there was a complaint, it'd be like that. It'd be taken care of right away. And I do see, you know, affiliates that do fall into things. Well, I'm not going to mean any, I won't be making any money off of Betfair because they're so saturated. There's no freaking way you're going to do it. William Hill and all that. Oh, I'll go, you know. I'll start promoting, you know, know, bingo Bitcoin. don't know. Right. Yeah. Something more gray market, black market. Yeah. Yeah. And unfortunately that's where affiliates can make a lot of money. Uh, but there's a lot of caveats there. Who are you dealing with? You know, who, who, are the people who would be supposed to be sending those, those paychecks, know, mostly Russian mafia guys and stuff. mean, anything Bitcoin. Not throwing anybody under the bus, but yeah. Well, um, just, and I know, I think I mentioned to you that I had Martin Sack on and he talked about some of his health issues that he's dealt with recently and we had you kind of worried about you at one point. So just to make sure, how's everything going? Are you, are you okay? And advice would you have? Cause I know you like to talk about prevention at this point. Yeah. Oh, for those of you don't know, I was diagnosed with prostate cancer back in August, August, 2024. And I, they caught it early. And the only way they caught it early is cause I was, very adamant about, you know, watching my health and having regular checkups and stuff. And it was just a routine checkup that, know, I do every year. And they told me, oh, wow. looks like your prostate's a bit enlarged. We need to test that, you know, have it checked out. So, okay, so they had more tests. The thing was, I had zero symptoms of anything to be worried about. So, okay, so they did more tests and said, oh, wow, we need to do some more, do a biopsy. Oh, shoot, there we go. And so they did the biopsy. And then after that, you know, week later, they brought me in and said, okay, you need to sit down. Oh, shit, here we go. And yeah, that was it. So I had prostate cancer and they said, you know, the thing is you're lucky you're young relatively long. I'm in my late sixties. I'm not young. Yeah, but it's relative. Yeah. But for them, yeah, that's, that's, it's, it's young. they said, you know, uh, we would recommend doing the surgery and say, Oh, okay. I'm still, yeah, I'm not going to do any chemo and that weird shit. No. Um, unless I really had to, but it was still early stage. It hadn't spread yet. So. Yeah. So January, 2025, I had the surgery done and took everything out and it's been a year and a half, I'm pretty much all pretty much all the way recovered. get 95, 97 % but still, still looking for the cancer. Didn't find any, which is great. And so I'm cancer free, but if I hadn't had checkups, I would still be sitting around not having a clue because I tell you there are no symptoms. So I'd sometimes tell any guy over the age of 45, 50, if you haven't had your PSA checked out, check it out. Yeah, because you just don't know. You just don't know. And I didn't know, and I found out. Well, and I'm happy that you're always willing to talk about that and to put that out there because people do need that kind of nudge. Periodically, we have the same thing with women that are getting mammography and mammograms and stuff. And it uh is important to stay ahead of that because if it gets too far along, then it's a whole different ball game. So, appreciate that. um It's time for us to wrap up. So, I wanna thank you for being on. It's great to catch up and kind of, as you said, take a walk down memory lane and talk a little bit about what the history is. So, appreciate you doing that. Yeah. Sorry, he's a little scattered, but you had so many years. mean, gosh. Yeah. And there's so many things have happened and you know, Sue, we've had such a great time, you know, in this industry and so many people, so many faces. And really it's a people industry and I hate that they even really counted away because, you know, there was so many great people, but at the same time, but to say, lot of these people are gone. They've all moved on elsewhere. I mean, you go to conference. If I went there now and the people are, who the hell are you? Right? How quickly we forget. So anyway, thank you all for being on, Brian. And thank you all for watching. Appreciate it.