iGaming Daily

In this episode, Leo Judkins shares insights on decision-making, the importance of confidants in leadership, and managing pressures in the fast-paced iGaming industry. Discover practical advice for leaders to navigate challenges and build trusted relationships.

Key Topics
  • The role of confidants in decision-making
  • Industry pressures and regulatory challenges in iGaming
  • Building trusted relationships for leadership success

Host: Charlie Horner
Guests: Leo Judkins
Producer: Anaya McDonald
Editor: Anaya McDonald

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What is iGaming Daily?

A daily podcast delving into the biggest stories of the day throughout the sports betting and igaming sector.

Charlie Horner (00:01.259)
iGaming is a fast-paced, highly competitive industry where high stakes decisions must be made at regular intervals. New market entries, product launches, compliance checks and staffing decisions can all add up, and it's not always certain whether a decision is right until months afterwards. So how can leaders in iGaming talk about decisions before making them, and who can they trust to be a close confidant? Welcome back to iGaming Daily, supported by Optimove, the creator of positionless marketing,

and the number one player engagement solution for sports betting and iGaming operators. I'm Charlie Horner and today I'm joined by iGaming leader, CEO and founder Leo Judkins. Leo, it's great to have you back on the show. How's things?

Leo Judkins (00:46.446)
great mates doing really well. So first time I've been called CEO, I the ring of that. That's good. Yeah, doing really well. you been?

Charlie Horner (00:53.46)
There you go, you... Very well, I'm glad that I've just promoted you, but there you go. Congratulations!

Leo Judkins (01:00.174)
Cheers.

Charlie Horner (01:03.831)
All right, let's dive into this because I think there's a lot of lessons for people in this one because I'm sure there's lots of decision makers in the industry who have to take their time with those decisions and maybe want to bounce ideas off people, but they're not entirely sure where to go for that. So first of all, have there been times in your career where you've had a confidant? And if so, what were the main benefits of that?

Leo Judkins (01:33.144)
Yeah, great question. So thank you for asking. just a bit of background. I have been in the industry for 17 years now. I started in poker and poker affiliate, biggest affiliates, poker affiliate anywhere in the world at the time before it all collapsed. Then I moved into sports betting and casino operator side. I was a director there at 33 and it was all great. I got along really well with the CEO.

Andreas and that was at the time that was my confidante. I felt really comfortable just talking about, you know, whatever insecurities even and I think, I mean, maybe that's normal for maybe that's not a normal thing. I don't know. Maybe that's not true for everybody in a role. I know you kind of have that Charlie with Martin, I think, but I think that's not true for everybody. But what happens is

As you kind of grow higher and higher in your career, at some point you're at the top, right? You're at the top of the pyramid. And that's when it becomes really hard to have confidence. I noticed it when I resigned and started my own business because by default you're by yourself. You don't really have anybody around you. And yeah, I didn't have Andreas there, right? And it's the same at the top. It disappears. arguably that's probably the

the most expensive problem to have because at the top you're making the most expensive decisions, right? And if you then don't have anybody to challenge you anymore or that pushes back or that helps you see different viewpoints, it means that first of all, decisions might be going around in your head forever and you don't necessarily take that decision because you're weighing the pros and cons. And then secondly, I think it also

because you don't get that alternative viewpoint, it becomes really hard to go beyond your own biases and see things differently. And so you might make suboptimal decisions in that case, well, you very likely will. yeah, for me, when I started my own business, I basically got a business coach and it was a group coaching program with all sorts of other founders. I sat in this, like on these Zoom calls once a week where

Leo Judkins (03:48.502)
everybody was going through the same thing. And in our case, it was identifying your ideal clients, know, setting up your offer, deciding what that offer is going to be. And what I found is that actually when advising others, my peers, I got more out of it than when I was asking for help. And that's been crucial. I've been in business now for five years. The majority of people don't make it past five years, right? Starting their own business and having people around me to

trust and ask questions to and give advice to has been pivotal to all of that.

Charlie Horner (04:25.465)
Yeah, no, it's a really valuable experience that you can bring to the table there. I think it's also, know, having your own businesses is one part of what offers one problem, but the other one is being a leader of an existing company. And the decisions that you make directly impact those people who you might see as your confidants, and that is another pressure in itself.

What are the unique pressures of making decisions in iGaming compared to maybe other industries? Because there's lots of video synchroses about this industry. I've mentioned some of them at the top, but what are the ones that maybe cause the most stress?

Leo Judkins (05:07.148)
Yeah, for sure. We all know it. We all say it, right? It's a very fast paced, really highly, fast paced and high pressure industry. And I actually asked in the mastermind in the group I run to some of our members, what were some of the biggest pressures and what most of them were saying is it's actually a speed of regulation, regulatory change, right? Because it affects the whole business.

It doesn't really matter if you're operator side or supplier side. When there's a regulatory change that happens, it basically stops the whole business, doesn't it? All of the projects get de-prioritized because of this regulatory change that you have to comply to. You need to make this pivot really, really quickly. That, I feel, is probably the pressure that is highest for most people because

It means that all of the good ideas that are commercial and are going to generate revenue, they have to be put on hold to avoid any sort of fines that you might get from the changes that you need to make. I think that combination of high stakes, fast change, and huge legal and financial consequences is what makes also isolation in your role so challenging because you have to make the best possible decisions when

when those changes start happening. And when you don't have confidence, every decision relies on you, right? On your own personal experiences, on your own personal biases. And that can get expensive really quickly.

Charlie Horner (06:50.611)
I'm sure there's plenty of people in the industry at the moment dealing with those kind of decisions, given everything that's going on regulatory-wise at the moment this year. So there could be a bit of a saturation point now where there is a lot of stress in the industry amongst decision makers who have to make those adjustments immediately. There's not often a huge grace period for some of these changes. So what happens when you reach that

point when you know you need support or you need a confidant in your decision-making process. You know, the struggles and challenges that people face when they sort of know, when that sort of light switches on, they know they need some support.

Leo Judkins (07:36.428)
Yeah, I think the hardest part isn't really admitting it. It's finding someone to talk to, right? Somebody that you can trust. Very often when you're in that position, the relationships that you might have, they all come with some sort of agenda, right? Whatever the agenda is. If it's somebody that works for you, there's usually some sort of financial motivation, career motivation. It's your husband or your wife.

They don't understand the pressure that you're, they see it, but they don't understand the pressure of the industry. Your friends don't really understand what maybe is like either. And then the people that you used to work with that perhaps at the same level as you are now, they've become your competitors. You know, it was such a small, small industry almost that we're all moving about, right?

think that's the really hard part because once you start noticing that you actually need that support, then trying to find someone just takes time. One of our members talked about how she felt really isolated and she's got a coach and gave her a clear head, but that didn't really solve the pressures necessarily that she was under. And by the time that...

Yeah, but some you know, you need someone, it's often too late. You often, you often, you know, you often don't have, you can't find that person. So one of the things that people often think is that the blocker is kind of people's ego in asking for help or asking for support. And it's not even about, you know, managing stress. It's also about great decision making. It's also about accelerating performance, right? It's not just kind of the negative side of that. It's also the positive side of it. Lots of people think that

It's about ego, it's not. think the blocker is usually that there's just no one kind of safe around you that you can talk to that doesn't have that agenda that has the same level of experience as you have and can actually challenge you on those big stake decisions that you have to make.

Charlie Horner (09:48.971)
That's a really interesting perspective because I must admit, I assumed that there would be a lot of ego involved in this and people could because you see on LinkedIn, see on Instagram, you see on earnings calls that some of these leaders, they are really successful, but they portray the story of there are no failures, there are no struggles, everything's brilliant all of the time. But it seems from what you're saying that that's not always the case and

There's a little bit of nuance in that. So do you think it is difficult for people in positions of power at companies to admit that they don't know an answer? And how do you kind of break down that barrier?

Leo Judkins (10:28.984)
Yeah, we were talking about this before the recording, right? So I think it's so interesting. We all know that LinkedIn and conferences and, you know, being on panels and standing on stage, all this portrayal of success, right? And what we see as consumers of that is we see, we are looking at somebody else's highlight reel, right? All the successes that are being pitched off stage and the news articles and all that. We see the massive dramas in the news, but it's not...

It's never the day-to-day mundane boring challenges that somebody goes, that's not what gets talked about because it's not really interesting. But everybody has that. Everybody has those challenges. Everybody has uncertainties, goes through periods where decision-making is really tough. You know, just simple examples.

I have this with our members all the time, but I remember it myself when I had to make a huge group of people redundant. And this is very current for many businesses now, right? Where they're talking about AI being the reason why they're making a huge amount of stuff redundant. I've gone through the exact same thing many years ago, not with AI, but the period in between you knowing that you have to make that stuff, that group of people redundant and actually doing it, that is...

Super difficult, right? Because you can't talk to anybody about it. You know who's going to be affected. There people that you've worked with for a long time. You've created a personal connection with them and you know you've got to let them go. But you also know the business needs to keep ticking over. So it's very, very hard period. And yeah, it's not so much, I think it's not so much about that people in power don't want to show that vulnerability. It's just they can't, right?

In that situation, you can't. And I was talking to Ramiro about this. don't know if you know, but Ramiro was, he was saying, it's a bit like being the captain on a ship. know, imagine you're on a ship. I thought it was such a brilliant example. He said, imagine on the ship, you're on a ship. And the captain says, no, I actually don't know what we're doing. I'm pretty, pretty uncertain where we're going and how to do it. You don't jump, we don't jump off, wouldn't we? You know, so I think that's the issue in leadership.

Leo Judkins (12:50.508)
is that you have to betray this certainty and otherwise everybody freaks out.

Charlie Horner (12:58.603)
Yeah, that's a great example. yeah, I mean, I remember actually being on a flight once and there was a particularly bad bit of turbulence and the flight attendants actually looked worried and I thought, this is quite bad. So yeah, maybe you don't want to offer that sort of vibe to your teams. Maybe that's a good idea to keep that internal.

Leo Judkins (13:20.846)
Yeah, but that's the thing, Charlie, right? This is what we were talking about beforehand. So like I said, I'm talking to Raz about doing some stuff for SBC leaders and we'll facilitate that there as well. But that's the thing. Once you have a CEO that actually talks about openly, feels that they're confident and comfortable enough in an environment where they can openly talk about day-to-day challenges and something that's going on in their business and...

like open that, start that domino, everybody else around them will do the same thing. So it's just about having a trusted environment of peers at your level who understand the challenges that you go through and then being able to relate to that. And once somebody opens up, know, it's like, that's when it goes, it'll be fine.

Charlie Horner (14:08.709)
Well, Leo, let's take a short break and then we'll come back and we'll talk about what those conversations might look like with a confidant.

Welcome back to iGaming Daily. Now, Leo, we've identified that we were struggling. Let's paint the picture. We're in a market that's recently re-regulated. Maybe there's affordability checks. Maybe taxes have just gone up. I'm not picking any specific market. I've just made it up. Maybe people are experiencing that right now.

Leo Judkins (14:38.337)
Sounds very UK heavy.

Leo Judkins (14:43.426)
haha

Charlie Horner (14:47.635)
And we've realized that we need some support. We need a confidant. If you're looking to get a confidant, how do you ensure that you're protecting some of your company information, your data, your internal strategies? Because I think some people might be hesitant to share too much because some of these confidants might be competitors, for example.

Leo Judkins (15:11.278)
Yeah, I actually coach listed companies as well. So it's an obvious issue there too, right? They're listed, so it will affect share prices when too much information comes out. And so you can't have that. But then, like I also think on the other hand, when you talk about private business, I think in general,

There's nothing that is that somebody hasn't invented before or hasn't done before or hasn't, you know, there's no, a lot of it is actually speed to market, right timing.

But that doesn't really answer your question. The big thing really is that you want to, when you want to have peers that you want to be able to talk to somebody, a confidant that you want to be able to talk to through these regulatory changes or these tax impacts and implications that they might have on your business and your strategy and your overall structure. There's a few things that are important. It has to be someone that has no stake in your business, In your, like that has no agenda, that has no...

financial benefit from you going one way or the other. I think that's really important. There can't be any conflict and it can't be a competitor. Those are probably the three key things I'd say. You have to have a trusted relationship with someone where somebody turns up for you. But you're also willing for somebody to challenge you and to honestly tell you when you're wrong, when you're drifting, when you're making wrong decisions.

Because if you just want somebody to encourage you, that's pointless. It might feel good, but it doesn't help at all. So I think the confidence is key. No political interest or no agenda is really key. I think just making sure that you're really ruthless about who you use or who you have as a confidant is truly important.

Leo Judkins (17:12.75)
When I first started my business, I did it with Ashley Lang. He's the CEO of Pragmatic Solutions. He's a good friend of ours. There's no involvement whatsoever with my business. There's no agenda. He doesn't benefit from it whatsoever. We regular lunches with him to talk about decisions. It made all the difference. I think that's the key, just being able to...

to talk to someone and that doesn't have to be a heavy conversation. It could be just that, right? It could be just a lunch that you treat somebody to just to pick their brains or just to offload.

Charlie Horner (17:49.241)
I guess there's just a bit of independence and a bit of trust and that can go a long way. Let's flip the switch a little bit. What about being the confidant? Because you said earlier that if you give out advice or you offer some support to someone else, that can help your own internal way of thinking. How do you go about telling a leader or someone who...

again like we said earlier, seem so successful all of the time. How do you tell them that what they're doing is wrong? They're about to make a bad decision. What they're doing is not necessarily the best thing for them or their business. That must be quite tough.

Leo Judkins (18:30.914)
Yeah. Well, I don't know. I'm Dutch, so we're quite direct. No, but I get it. I think there's two, we've got to look at it from two different angles. Right? So if you're somebody's confident, then that by default also means that you've kind of been given permission to be direct and to be open and honest to someone. Right? So I think that shouldn't be an issue. If that's the relationship that you've got, then that shouldn't be an issue. And if that's not the relationship that you've got, then you're clearly not there confident.

Right? Because then you're some sort of, I don't know, some sort of person that just encourages them and makes them feel good. That's like fine if that's the way it is, but that's not the relationship that we're talking about here. I think what you're asking is maybe more about how do you manage upwards when you disagree with a decision that's being made or you see that somebody's, you know, in isolation making decisions from their own biases, like we were talking about before and...

And you know that it's the wrong decision. Well, that's difficult. And that really depends on the type of leader that you've got. Some people, don't want to be challenged in public. Some CEOs or leaders don't want to be challenged in public, do it in private. I think the key is always, and this is true in coaching as well, is you've got to ask permission to give somebody feedback. If you would say something, Charlie, and you'd go, and you know, doesn't really...

matter if we've got some sort of business relationship and you'd be my boss or you'd be a mate or you'd be a client, whatever that is, I'd still ask you, hey Charlie, do mind if I give you some feedback on something I've just seen you say? And I'm going to be a bit challenging with you. Is that all right? And then once you say yes, it changes the whole dynamic because you've just been given permission to be open and honest and direct about the thing that you're going to say. And very often,

That's what it's about. Because we feel good about the things that we say when we can complain about something or we can encourage someone. If you feel good about the things that we say, but it's not about what you say, it's about what somebody hears. It's big difference between those two. so laying that up, like in basketball, like a layup, I think that's really important.

Charlie Horner (20:41.529)
Mm-hmm.

Charlie Horner (20:51.257)
There's something off the back of that that I'd love to explore, which is how do know that maybe the relationship that you're having with your confidant or someone who you thought might be your confidant isn't necessarily working? And how do you go about maybe changing that situation? Because I'm sure that not every relationship works. So if you say, I had a confidant, we had a few chats, and it just wasn't clicking.

Leo Judkins (21:08.184)
Do you mean?

Charlie Horner (21:20.819)
wasn't working, that I didn't find that necessarily valuable. How do you go about navigating that?

Leo Judkins (21:29.08)
Yeah, you've to find somebody else for sure. because it's the foundation of it, right? If you do, it's got to be, we often talk about safe space and all of these things have a, I think they have really bad PR behind them. I can't remember who I was talking to about this, but maybe Michael Baker Moseley or something about that. Some of these things have a PR issue, right? Safe space and all that. But the definition of it is correct where

you have to be able to just be able to talk about the things that are on your mind that are bothering you and you shouldn't be feeling that there's going to be some sort of weird consequence based on what you're saying. And as soon as you feel that that relationship is off and you feel uncomfortable, or there's just not a click between two people, it's not that it doesn't work anymore. And actually the same is true everywhere. The same is true with coaching, the same is true with a psychologist, the same...

Right, I've burnt out twice and I've gone through four different psychologists because the first three, there wasn't a click and then it doesn't matter how good they are, it's just not going to work because you've got to be able to talk about the things that actually got you to where you are. The same is true with confidence, exactly the same thing.

Charlie Horner (22:45.539)
Sure, yeah, you could have a great relationship with somebody, but it might just not click in that specific scenario, and I guess that's fine. We're coming towards the end of our time, Leo, and I'm sure everyone's taken at least something away from this and have really enjoyed the conversation. I guess just final question really is, if there's someone in the audience who is finding themselves in the sort of situation that we've described today.

Leo Judkins (22:52.726)
Exactly. Yep.

Charlie Horner (23:15.245)
What's the first step that they should take to find and vet their own trusted confidant? What's the one bit of advice that you would offer?

Leo Judkins (23:24.45)
Yeah. Great question. So as a takeaway, think, I think the first step is actually not necessarily to find a confidence straight away. The first step is to be honest about why you haven't got that yet. Right. So, and that might be because you're isolated at the top. anyway, that doesn't really matter, but the first step is to find out why you haven't got that yet. And most people think it's some sort of personal failing, you know, they

can't open up or maybe they've lost all their mates because they've been too focused on work or whatever it is. But more often than not, it's actually not a personal failing. It's a structural issue. And so once you've identified what the, you know, what the kind of the why that currently is that you don't have that person that you trust that you can talk to about things then I think really important is just to look for one person who passes three specific tests. They have to be at your level.

or beyond, right? So they have to have done what you're currently doing or they have to be doing what you're currently doing. They have to have no stake or no agenda in the decisions that you're making. And they have to be willing to disagree with you. They have to have all those three things, not two, not one, all those three things. So at your level of beyond, no stake in your decision, I have to be able to disagree with you. And yeah, you shouldn't settle for pleasant and available. I think that really fails. It's about thinking.

about who is that person. yeah, what I would encourage listeners to do this week is to think about, you know, what's the hardest decision in the back of your head that you haven't said out loud yet? You know, so, you know, who could you talk to about that without any consequences? And if the answer is no one, then that's where there's a gap. And that's when you should try and find somebody that you can talk to about.

Charlie Horner (25:14.937)
fantastic. Leo, really appreciate your time and expertise today. Fantastic as always. And looking forward to having you on the show again in a few weeks. So Leo Judkins of iGaming Leader, thanks a lot for your time. Thanks to Optimu for the support as always and to our listeners. Thanks ever so much for tuning in to today's episode of iGaming Daily and come back tomorrow to keep up to date with all the latest global gambling news.