Podcast Episode 18: Drowning the voices of Imposter Syndrome with Simon Pilkington

Leo Judkins: Hey, welcome to the iGaming Leader Podcast. I'm here with Simon Kinson, former CEO of KaFe Rocks, leading iGaming  affiliate that most of you will know. 

I'm really excited to talk to you, Simon, because, you've been through such a transformative journey both in your career and in your wellbeing, and I can't wait to uncover it all together with you. 

Welcome to the podcast.

Simon Pilkington: Yeah, thanks so, so much for having me on. I'm, I'm, I'm thrilled to be on here. 

There's been some pretty, pretty big players in the industry on this, so I, maybe the imposter syndrome's gonna come back whilst we're talking.  But no, absolutely thrilled to be on and, and chat to you.

Leo Judkins: [00:02:00] Yeah. Fantastic mate. And the first thing I'd love to talk about is, you joining KaFe Rock as the CEO. well, You took over from a founder's team. Can you talk me through that journey and some of the things that were going on, your head as you were taking over, how that went and how that went for you personally and professionally, please. 

Simon Pilkington: as a little bit of context, I, I joined KaFe Rocks two years prior, actually taking the role on, so I joined as the head of International Markets. I'd actually worked with Fed McCann, who was one of the owners, back in my lab Brook days, which was my very first interaction in iGaming almost 17 years ago now. 

I'd then gone onto stats, perform, well now, but then perform group. And I was made redundant and it was a really pivotal part of my sort of career. Not so much the redundancy.  I'm a big enough and ugly enough guy to sort of understand it, that happens and you, you can take that and you can move on.

But just how it happened, how it came about and how cold it was, as a sort of action in a company I'd been with for a long time

 And knew the management very well. I found that really interesting and it put a little bit of a chip on my shoulder and actually managed to use that in a good way. 

[00:03:00] Went to ICE that year in the February of 18, caught up with Fred McCann again, by May I joined,  KaFe Rocks as the head of International Markets. So focusing on all English language content sites and assets. Starting with a very small team and sort of building that out as the company grew.

I think I was in employee 15 maybe. And then. Did a nice job, obviously, hopefully. And the comp watched the company grow alongside and managed to play a good part in how that culture sort of framed. And then on a, on a. A cold night in New York on a conference with Tim to pass the incumbent CEO and one of the other owners alongside Kai and Ger. He actually offered me the promotion, which if I wanted to stay in the uk, was gonna be up towards sort of the VP level and, sort of sit on the C level. But if I was happy of move the family over to Malta and take the position fully and fully commit, then yeah, it was gonna be the CEO role. Which honestly from my side and from my family side was just too good an opportunity to take. It was a surprise. I thought I was doing a good job, of course, but I thought there was certainly other people in the hat and I wasn't totally aware that Tim was looking to fully step back either.

[00:04:00]  But Tim was very grateful. He was ready to move back to Berlin anyway. at first, the overriding feeling was just pure excitement. One of like, wow, this is exceptional, you know? That preconceived idea of what a CEO is, this big rigid box that, you're the leader.

You're gonna be in charge, you're gonna take things on, you're gonna be do great. And everything, you know, from that point went pretty smoothly and sort of within a. Two months of taking over Covid hit,

 Which absolutely skewered the sort of moving over plans for a little bit.

And it was later that year in 2020 that I managed to get across to Malta. But it involved my wife who is a lifetime NHSF in cystic fibrosis physio. So real tough job and one that she's highly passionate about. Leaving that taking a big sort of career break to, to help support us

and moving her, two children over two and four into a new country. I mean, the 2-year-old had no idea what was going on.

We could have been anywhere but the 4-year-old, you know, highly impressionable at that age.

[00:05:00] And having to move to a country where she's now having to go from a little cottage style nursery into a comprehensive school. School

at four years old, face mask on. All of a sudden the pressures. Jumped massively. So it went from pure excitement to almost the fear of like, oh God, what am I doing here? That came down on me quite, quite hard on top of the fact that yes, we are a successful business and it's going great, but Tim, in as the last CEO, has been responsible for the majority of that up till now. and I've now got really big bloody boots to fill

To make sure that I keep that moving and keep what has been built is a beautiful and fantastic cultured company, moving in the right direction as we no doubt we're going to scale.

So yeah, it was fantastic, but it became very clear you know, imposter syndrome had had set in massively. I was trying to be the CEO that I thought you had to be, rather than realizing that actually. A CEO or a C level or a leader can be whatever you want it to be. 

[00:06:00] And it should be you dictating that and putting your personality into the business and your leadership style. And if that just happens not to be a match for the company, then alright, obviously, so be it down the line. But I never saw that and I was very blinkered to the fact I was always trying to be Tim and trying to be an

extension of Tim, which obviously big compliments to him, which, you know, I'm sure he'll be sitting at home enjoying. But yeah, I, I really had to sort of. Make changes quite quickly into that journey, and I don't think it's unfair to say that Tim being one of the owners alongside the other two owners, it was their baby.

Stepping back and actually giving control to someone else, which was a big punt on their behalf.

Someone internal with no leadership experience. And obviously a big punt on my behalf, moving everyone over and, taking this big risk on something that may not pan out well. 

I think we both realized that we needed to get a handle on it a little bit. And we both worked with a career coach and an executive coach. A lovely little funny German guy called Ralph. He was fantastic for both of us. We tried out a few coaches before getting to that point, and we both settled on Ralph. And actually he played a really big part in helping, I think, Tim. 

[00:07:00]Give up a little bit more control while still being able to have an influence in the business and how to communicate that better into me, whilst actually dealing massively with my imposter syndrome but you know, it was largely a. 

A successful three years, I believe in, in the role we all left very amicably with each other, which was one of my number one things going into the role is a, I wanna leave the company as, best the place I can leaving it, but I also don't wanna leave on bad terms with the guys that have given me the opportunity and, love and trust.

So that all went very well. But, reflecting afterwards as you get a chance to it, it just made me realize how much imposter syndrome's actually probably played a part throughout my life, let alone. My career,

I think as a, goes a bit deep and I get sometimes get a bit emotional about it, to be honest.

But I look back and I'm, you know, I'm a, I'm young for my year group at school and I'm an August baby, so I was right at the bottom end of it. And when you go through school, you don't know what that feeling is, but especially as someone who's actually falls more on the introverted side of things. 

[00:08:00]You're a bit more shy, you're a bit more shy around groups, and you're almost a year younger than most people.

You're playing rugby, but you're a year younger than most people. And it wasn't small, but you just, you felt small. And actually, I never realized how big a thing it's actually played throughout my life. In that regard, you know, I come from a very working class background, but I got very lucky that I got put into a private education in North Devon through assisted places at the time.

So everyone else there sort of deserved their place there. And I, I always felt a little bit that I, that I never did.  and it was very similar at university, but it, funnily enough it was leaving KaFe Rocks and all that coming to a head that really made me realize all of this.

Leo Judkins: Thank you for sharing that, Simon. What a journey, man. I love it.  is around that moment when you realized I. Or where you started thinking and that feeling started creeping in of, oh my God, what have I done here?

What was that like? What, what, when did that start happening? Is that, was that a specific moment? Did it slowly start happening? And, and what was some of the things that you did as a, as a result of that? How did you kind of live with it, if that makes sense.

Simon Pilkington: [00:09:00] Yeah, I, I think so what I, I have a number of non-negotiables.  one of which, and the primary one is that I'm family first. I think if you spoke to anyone at KaFe, they, they, they'd say the same thing about me. So if ever I thought something completely wasn't right, the family would always become number one. And with that in mind and with that non-negotiable there, you know, I think seeing. Emma's reaction, my wife's reaction to the move and how hard it kind of hit her having to leave being quite a home bird. That was probably the first moment of like, oh, bugger, have I, is this the right thing? Is this the right decision?

Have we done the right thing? But I think outside of that, it was probably a bit more of a slow burning. came underneath that, that actually I wasn't really realizing I was necessarily that stressed, but all of a sudden you realize you're juggling a lot of different places. You are trying to be, you're trying to find your way as a leader.

[00:10:00] You're trying to understand what that is. You're trying to keep a family unit happy in a new country where you can't make friends because of. Infectious disease has taken over the world. You are eating terribly and you are, you're not worried about your yourself and you're not thinking about yourself 'cause you're trying to keep so many other things happening.

You are worried about decisions you're making, affecting all of a sudden a lot of people when having been used to making decisions and it affecting a few people.

So all of these little moments, all these little pieces started adding up and accumulating into a much bigger sort of manifestation.

If, if that makes sense. And I think, it totally affected my health and that journey. you mentioned it earlier, sort of transformative career in, in that regard. And, and it, it went very quickly. Hockey sticked up to that CEO level. 

But my sort of life journey alongside that has been very similar, especially around the health side of things, which coincided massively with the stress of, of KaFe. And when I say stress of KaFe, that's with no. Sort of disrespect or insult to the owners for putting stress on me.

[00:11:00] This is internal stress I put on myself. Too worried about what people were thinking of how

I'm doing and, and how I was coping with things. But,  you know, the first thing to go was, was the health and was the eating and being fair.

Malta is not totally conducive to the most healthy eating all the time. It can, you know, a lot of Fs and a lot of,  pastries going around, a lot of pastas and pizzas.

And. I indulged and I wasn't doing as much exercise. I was trying to make sure that everyone was happy. And I ballooned from about 80 kilos to 105 kilos, over a relatively short period of time, but without even realizing it.  

The moment that everything changed massively was November 27th, 2021. And I remember it very clearly. I just looked at myself in the mirror and I was. Absolutely crest fallen with what I was looking at and like not just physically, but mentally and emotionally wrecked. I was making absolutely shoddy decisions from a family perspective.

[00:12:00] Shoddy decisions from a personal perspective, probably shoddy decisions from a. Business perspective, but thankfully with the support of a, a great team around me to sort of keep things moving in the right direction, which is very important. And yeah, but physically as well, I, I just thought, this is you.

This isn't you, this isn't great. You're mentally in a bad place. You've gotta do something

And I signed up to Noom, which is, they're

Leo Judkins: Yeah, I know them quite well. Yeah. 

Simon Pilkington: app. And I think, you know, that probably changed my life. Dramatically, and I, I, I've always been good with nutrition generally, and health and fitness.

But just doing that and actually taking an action and starting to do 10 minutes exercise a day, 15, 25, 6 days a week until I could start seeing difference and making it a habit.

You know, I love, love seeing the whole habit rewire behind you. Like those little habits that turn into big, big things.  that changed my life again and dropped the 25 kilos. Everything became much more mentally clear. The action we took to actually work with the coach to, to help remove or manage is probably better. 

[00:13:00] The, the imposter syndrome, those things all combined just put me in such a better place overall, and I have no doubt in my mind that it made me a better person, but also a better leader for the company whilst also being a better person away from the company and, and for the people around me who, who cared about me.

Leo Judkins: Yeah. Love it. What a, what a pivotal moment, Simon. And, I think we started talking not much after that, right? When you, when you created some of those big changes and, those pivotal moments, they always need to happen for us to take, like the consistent action that needs to happen for us to, to see the results.

Right. So before that, you were saying that you hadn't even noticed kind of the, weight gain and the changes that were happening. What made that moment different? When you were looking in the mirror and you were thinking, oh my God, I'm making all these shoddy decisions. Why did that happen, you think?

Simon Pilkington: I, I don't know. I mean, I must have subconsciously seen that I was ballooning, but I think it's probably something that you, you're shoveling to the back of your mind because again, like

[00:14:00] I wanted to make sure that the business was. Going, you know, I wanted to make sure people knew I was good at what I was doing and, and that the company was moving in the right direction. And, and again, if I'd rather deal with my child being upset than worried about me getting bigger

or whatever it may be like, or the, the fact that my wife couldn't make friends in that first year because there was no way to get in front of people during covid times like that, all was much more important to me.

So I think. I mean, subconsciously, I could clearly see that it was probably happening, but it was just a point when I was, I dunno what it was, but it was just something that said like, if I don't, I'm actually gonna be worse for them and for, for every single one of those parties. And I think part of your job as a, as a leader, you have a certain set of stakeholders, right?

And I don't just mean owners of the company, but you, you know, they are one of the stakeholders that your, your employees are another stakeholder. Your family. Family is a stakeholder. You are a stakeholder. And all of these parties need to, you know, as best as your ability as a leader, you need to make as many of those happy in as many of the [00:15:00] decisions as possible.

And if you can go through on each decision and go, right, that one ticked, that one ticked, that one ticked that one not. But next time they'll get, you know, that will be ticked as well.

And I think you're in a really good place. And I was doing all of it apart from me all the

time. And finally I was like, well, actually, if I tick the one for me. It's gonna ensure that the others are ticked much more often, and it's gonna put every other part of it in a better 

place.

Leo Judkins: That is amazing, Simon, because it's so true, right? When you are in that 

moment of. You know, struggling to prioritize yourself not seeing the solution to any of it because you're so involved in the business and because you're already so business busy and you've got a family that you are worried about, It's impossible in your head to find time for it. And then 

suddenly when you start doing that and you start prioritizing yourself, you see that suddenly there's time becomes available, right? So 

Simon Pilkington: well, you realize how much time you're wasting as well, because, you know, you're, you get into such a great style of procrastination or you know, you're telling, you're telling yourself busy when actually. 

[00:16:00] The actual bits of being busy, were, were much smaller than you think, or, I mean, a big part of it was delegation as well. It made a very good decision business wise to sort of build out the

C level a bit stronger and brought in a very strong COO. He, I mean Justin was a very experienced guy. He came in, did a fantastic job and, and actually helped me work. less in the business and more on the

business and, and be, be able to act more between the founders and be between the C level and act as that filter of information. And also, I guess a bit of a, a protective filter as well from, from, from any other ideas that maybe didn't need to come through. And once you could delegate more out, you realize how much more time you actually did have. And actually that, you know, leaving 20 minutes earlier in the morning has no impact on. The, the family side or the family unit, but it gets you half an hour, 45 minutes in the gym or in the swimming pool, which is, or swimming in the sea, which was fantastic out there. 

[00:17:00] Something that I could just do to get my, my calorie burnout for the day up. Get that mental clarity in place, a little bit of reflection along the way. And actually you've still got what you've got. You've got 20 minutes less in the day to, to crack on, but you've delegated enough out To not worry about that. 

And so I, I think as I, as I got stronger in delegation, I got stronger in sort of other skills around, around being a leader. I think that really just, just helped me create the time to actually focus on myself.

Leo Judkins: Okay. I love that. One of the things that I see a lot with people in our mastermind is that when you actually start taking care of your wellbeing and you start noticing some of those physical benefits, right? Where you perhaps losing some weight or, mentally you're feeling more clarity, that delegation and time management and productivity actually becomes the effect 

of you. It's not just the skills, right? It's, it's your. Like how you feel makes such a difference in winning time back. What, what are some of the big benefits that you've experienced in, in those areas? From taking charge of your health and wellbeing,

Simon Pilkington: it was just that clarity of judgment, I think was the biggest thing. 

[00:18:00] I could sit back and reflect and actually make proper decisions rather than telling me stuff. I'm so busy, so I've gotta make rush decisions, realizing that you've got time to do things and this might just have been part of the evolution of becoming, you know, being in the role for longer and, and actually having time to realize that being a CEO isn't what someone else tells you.

It's what you want to be. But without doubt, the, the, the benefit off the back of the, the health. Side of things was just having that clarity of mind to make better judgment calls and a better judgment call Is delegating something out to someone? 

A better judgment call is saying no. When you would've just said yes. Just because you're too tired to think about it or too cloudy to think about it properly, you can get a lot deeper into the weeds without getting tired or getting fatigued 'cause you've got a bit more energy about you there. 

There are so many little incremental and sort of almost butterfly wing style effects that come out of it, that compound down the line to actually much better outcomes.

Leo Judkins: One of the things you mentioned earlier is that when you think back of having had that, imposter syndrome actually for far longer than, than that CEO position that you first, when you first got in there, how did that turn up in your life before that? 

Simon Pilkington: [00:19:00] It kind of makes me more emotional to think back about it because I probably, I never really knew what it was or understood it.

Back then, and actually if you could take the equivalent of a career or exec coach now knowing what you know now and take it back to when you were at school or whichever part of your age that it was, and affect some change there and manage it in a different way and understand what it was. 

And I guess this is the same with any sort of neurodiversity or, or, any type of thing. Like you, if you understand it, you can manage it better. You can use it to your advantage. So I think when I look back, you know, you just, you don't want to regret things and you don't wanna dwell on things.

But actually I look back and think, well actually. Never used to be very curious or ask too many questions 'cause I always thought people would judge me you know, I'd never be the first person being quite introverted. I'd never be the first person to go up and, you know, swing from the chandeliers of the party or, you know, go fully go and introduce myself to everybody who knows me. 

[00:20:00] And so, actually I probably missed out on opportunity along the way. Now at the same time, I've been lucky enough to have plenty of opportunity and I've made my own luck as well, which is great. And I've had to really sort of . Retrain how, I think a bit to push myself more to go and be, go and introduce myself at things like that. 

Or go and actually, be a bit more open and a bit more out there. But just know that it's fine to take yourself away and just. Have a moment back to yourself again. 

So I think when I look back and reflect on all that, I can now use that experience knowing it now to actually help frame how I go forwards as well.'cause I don't want to continue, you know, I don't wanna get to 80 and think, well shit Simon, you should have asked more questions. 

Or you could have done more there or you should could have done less, less there. I think knowing what I know now, you can really use that to sort of hopefully help propel you forward.

Leo Judkins: It's so true, right? We are our own worst enemies, so not asking questions because you think you're gonna be found out. 

[00:21:00] Like I had it as well. I was, I was promoted as the youngest director. I remember not,  not knowing how bonus costs were calculated, you know, if it came off,  GGR or if it's, if it actually happened on staking or on winnings, you know, it's just an accounting issue.

It's very normal question to ask if you, if you're running your p and l for the first time. But I thought if I'm gonna ask that. They, they're gonna find out that they've promoted the wrong guy. You know, like, who's this director that doesn't even know how, how bonus costs work? 

And that must have been so much worse for you as a CEO, where you have all of these areas that you're managing that you're not necessarily sure about, and you have nobody to ask, except for the guys that you kind of just came in for.

Simon Pilkington: Whilst you're in that imposter syndrome moment, it's, it's completely like that. You're thinking like, oh my God, I've got tech, I've got product, I've got

SEO, I've got content, I've got hr. And actually, I, I really had HR for a large part of the business as well.

Like, I sort of sat, sat over that side whilst we, we had different people moving in and out, but,  and you're like. How can I do all this? I don't, you know, how they, they're gonna know, like, I'm not, I haven't got the depth of knowledge that some of these guys and girls have. 

[00:22:00] Once you've got a hold of it, and once you actually could get that management and you realize how broad your knowledge base actually is through 30 at the time, what 14 years of experience and you know where your weaknesses are as well.

And I think being able to identify where your weaknesses are, so, you everyone at KaFe would've known that tech and sort of technical seo, that that was never my strongest suit. You know, I'd have a base level understanding, but across commercial product marketing content, I could at least hold my own.

And I made sure that we identified great talent to come in underneath, so that they were the experts. They, they were the sort of the, the, specialist in each vertical.

And I was there with a broad knowledge to help them. Guide, therefore it's helped them guide themselves throughout the, throughout the business better as well. So I think it hugely comes down to how you, how you go about hiring and how you actually form that team around you or form that sort of advisory board around you as well. I.

[00:23:00] And that can be from above and beyond that, that advisory board, I think too many people are, are too obsessed about actually having a, that sort of personal advisory board of people who are in higher ranked positions than them or, you know, can offer really advice when actually some of the best conversations I've ever had are with much more junior people and It is one of the rules we tried to install KaFe and I tried to push heavily was that. 

Knowing that I went through my life not trying to ask stupid questions, it was like, you have to ask stupid questions. I want you to tell me what's wrong with the business. I want you to have an absolute path to me, and I blocked off every Friday afternoon for anyone to book a session in with me at any point. I tried to make myself as accessible as possible so I could understand the business in the same way. I still think, you know, the customer support. 

Crew in operators, it's one of the best roles to have a grounding in iGaming because you really truly understand customers and you understand the problems.

And I just wanted to, embrace that and make sure that everyone knew they could come to me and tell me what the heck was wrong with the business and what the heck was I doing wrong,

because I'm sure there was stuff and plenty of people did, and that was fantastic. And it helped foster a really sort of trusting experience and culture within the business.

Leo Judkins: [00:24:00] Yeah. Yeah. I love it.  if you would go back to that moment now, what were some of the things that you would've told yourself, to help you get out of that isolation of your own head and. And overthinking and feeling like an impostor.

What would've been some things that would've helped you to kind of getting over that?

Simon Pilkington: I think, and it probably applies to most of my life, but like if I could truly drum it into my head that. Not many people actually care what you're doing, and I mean that in the most positive way. 

Like no one's really judging you Like the only people judging me back then realistically were Tim Federer and Kai. And they are more than forthright enough and outspoken enough to tell me when things were, when the, when the proverbial was hitting the fan.

Things are probably a lot better than you think they are. And I think if I have drummed that in from a very much earlier position. That would've been a great, great thing for me, and I think it would probably be a great thing for everybody.

'cause just by human nature, we're all very worried about what other people think of us. And, and even more so in a, in a much more socially driven environment now.

Leo Judkins: [00:25:00] Yeah, it's,  it's called the Spotlight Effect.  it's a natural bias that we all have where we think the spotlight is on top of us and everybody's judging us. And it's because we obviously think about ourselves all the time and how we're perceived that obviously. Nobody else does that. Nobody else thinks about you continuously unless they have some sort of weird obsession.

Simon Pilkington: I've tried really, I mean, I've tried to make, I actually do it in my running to be honest, but like I've tried really hard and had to really train myself not to judge others as well, and not because I was, I was a horribly judgy person, but like just my natural cynicism and my natural worry about what people think about me is actually then influencing my thoughts about, you know, 

I mean, full admiration of the person can go in and hold a room through whichever means necessary at whatever level necessary. But I'm probably also there judging them, saying, well, you're brassy, you're cocky, or, you know, you're this, you're that. And I've had to really be like, no, they're, they're just them.

And they're, they're doing what they, they're they're playing to their skill set and they're playing to their strengths and they will be as fragile in other areas or have issues in other areas as I do in, in my areas.

[00:26:00] And it's, you know, it's the same in all walks of life. I, I've really had to push myself hard to like. Even when I have judged internally, like to say, like, stop being a dick at the end of the day. And, and you know that that person's out there doing it. They've had the discipline to show up and, you know, whatever they're doing, you don't have to judge 'em for it.

Leo Judkins: And I think for you as an introvert, that's even harder, right? Because you're gonna be stuck in your head a lot more than somebody that's maybe a little bit more extroverted and talks about these things. So what were some of the lessons that you've learned from that, perhaps working with your coach or just being introspective about it?

Simon Pilkington: it's almost sort of being in a compartmentalize a little bit. That internal monologue, like I, never understood people who don't have an internal monologue.

Leo Judkins: Yeah, I don't think they exist. I think 

Simon Pilkington: No, I, I'd really like to think they don't, 'cause they'd be the people I'd be most worried about.

 I'm back to judging.  but yeah, I, I, mine is an ongoing, constantly internal monologue of sometime absolute loopy stuff, sometimes very thoughtful stuff. 

[00:27:00] But some of the best outcomes I've had is when I've had a lot of time to really. Just chat to myself, which helps with the exercise because I, you know, I don't, I don't listen to music.

I don't listen to pods. I don't, don't do anything. I just talk to myself. I, I work through problems that I'm having, whether it's small ones, big ones, life problems, life admin work, whatever it is that goes through my head. And by the time I come out the other side, I, I'm in a much, much better place from it. I'm much much more in control of it now, so when the sort of demons start showing and sort of saying, well. You've not done this, you're failing here. You haven't done this in your life admin. You're pathetic or whatever. You can actually be like, shut up. Like, what are, you know, what are you doing? You just sit over there in your head and let's actually just work through the problem and see how badly you are failing.

These are the things you've achieved this week. These are the things you have done. You've met all this target, you know, I worked for myself now, so there's a lot more of it going on in my head. Bad stuff over there. Good stuff here. Let's work, let's find a happy place in the middle and, and work it for you together.

Leo Judkins: I love that mate, because that's one of the biggest things, right? I think when, like for all of us, when we are stuck in our head and you have that constant negative voice, right? 

[00:28:00] That's judging and saying. It's not good enough. It's gotta be better. You are already moving onto the next thing.

You're not even celebrating the thing that you've achieved today, which is maybe a big thing for everybody else. Small thing for you, because you are, you've already moved on to the next thing. You are setting a bar so high for yourself that nobody else would, and that may be makes you a high achieve, but it also makes you, it creates that imposter syndrome because.

It's never good enough in your head. Right? And it's this constant talk, which is not filtered. 

So how have you managed to turn that around and not being too judgmental getting over, you know, the. The failures that happen through life and, and, and not, lingering on it too much and, and actually making progress through that.

Simon Pilkington: Yeah, I mean, okay, so my life is relatively varied, work-wise anyway, and I. It's very varied family wise, just 'cause it's absolute chaos, usual with a 5-year-old and an 8-year-old and a dog.

[00:29:00] And I've sort of put more of a system in place that on a weekly basis I have a ses. A bit like the Friday afternoons I used to put away for other people. I sort of put it away for myself now, and it might not necessarily be a full afternoon, but there'll be a bit of time where I actually sort of look down, actually reflect on what's happened the previous week, actually reflect on what we've.

Got ahead of us and you know, I've just become a lot more rational with age. I've always prided myself in actually been a, a good problem solver and a good listener for other people, but I've probably not always applied it. 

You know, it's amazing how sometimes we're brilliant for other people and then don't apply those skills to, to yourselves and, and treat, treat yourself with the same respect that you, you do to other people. 

And so actually by taking that time and actually having a, a set session to sort of work it through and actually rationalize a little bit and, if something has gone badly, like, take it, own it, realize that it hasn't gone well, and then put out a plan to actually how you're gonna change that or how you're gonna move forwards with that if you can. 

[00:30:00] And if you can't. Own it, take it, swallow it, and try to move on and, and find the next thing that you are moving on to.

There's always gonna be more to do no matter what. You're always gonna keep reaching for more. I think that's, again, human nature. But at the end of the day, remind yourself, you are good enough.

You know how to do this. You've done a lot of this already in your life. You are just pushing onto another level now. And if it isn't scary or a little bit. Not understandable, then that's just, it wouldn't be challenging, right? Like, you, you want this and knowing when to be able to take a break from that and sort of step back, if it's getting too on top of you, that's a great skill in itself. 

Generally I think I want it and I want to move forwards. I like the challenge, I like the scary bits, but I still need to, you know, I've got better at dealing with them as well.

Leo Judkins: Yeah. Love it. I had love to hear from you,  what were some of the biggest challenges moving into your current business and, you know, having such a change of size and, and like that must have been so difficult, right?

[00:31:00]Where you have team and you've learned, finally learned to delegate, you're finally offloading and now buck, buck starts, stops where it starts and stops with you. And so 

Simon Pilkington: yeah. 

Leo Judkins: what, did that look like?

Simon Pilkington: So I'm fortunate in that it's not the only time. It's not the first time I've had a, a business interest in myself, so I've sort of been through it before. So I've got a little bit of muscle memory there I mean, part of the reason I left other than maybe sort of. Different views on where strategies on strategies should lead to and how we were doing, you know?

But part of it was the fact that at that point, every decision I was now making was affecting 200 lives.

And That's cool. That's fine. Up until a point, but it gets on top of you and you, you really, I. Don't realize how stressed you are about some of those things until you leave and the weight comes off your shoulders and everything, all of a sudden you feel light again and you're like, and that's not because I thought the place was negative or there was no toxicity. It wasn't negative. It was a very happy place to work.

[00:32:00] The best place I've ever worked and the people were fantastic, but the weight that came off my shoulders when I left was, was unreal. The challenges I have now are very different challenges. Obviously there's fewer people to talk to. I, I mean, the majority of my businesses are either one or two man sort of directors or one or two person directors and a couple of freelancers.

My, my affiliate business is very much being bootstrapped at the moment, so we, you know, I'm very hands-on and back to very. Deep into the weeds there at the moment, which I, but I'm, I'm loving that and really thriving on sort of being back there whilst being able to balance the leadership side by having a, a small group of people that work for us, either on a freelance or sort of contracts type basis, which I can be on top of and

Not to compare us to KaFe Rocks, but it feels like what KaFe was at the very, very beginning when, you know, when we first joined and that that. Amazing chaos that you have and that amazing, any day won't be the same. 

[00:33:00] And I love that. I've realized I really enjoy that. And it's not to say I'd never go back into work For another Employer again. But I think if I did, probably it would be more likely to be at the smaller sized company again, that's sort of 30 40. And knowing what I know now, I'd be able to really put my stamp on it from a personality perspective and culture perspective, which I, I really believe heavily in. 

But yeah, the challenge is, I mean, my biggest challenge is trying to get clients to pay me on time, to be honest now, and chase chasing invoices.

I'm sure You sure you have that problem as well? And it, it's. You know, it's little admin things that become more of the problem, and now I wish I had people to delegate to that.

That would be, that would be fantastic.

Leo Judkins: Yeah. Yeah. It's,  I hear you.

Leo Judkins: Hey Simon. I want to talk a little bit about all of the charity work that you've done.

So Tell me a little bit more about how, what inspired that and also what it looked like and, and the outcome of that and what you're doing today. So, can you, can you talk us about that please?

Simon Pilkington: So I'd already lost the weight, essentially back down to 80 ish kilos. I was in a much better place and obviously I was very aware of the SBC boxing event, have it had ran the, the year prior and I saw a call by Dan Beard on, on LinkedIn to where anybody interested to get in touch

[00:35:00] I've always liked the sport. I've always been interested to know what it would be like to do it.

I've never thrown a punch at that point when I put my hat in the ring and I had a good chat with one of the sort of. Boxers from the year before. Luke Cousins who were sort of helping vet people going forwards and for some reason they did choose me. And at that point I literally, you know, I can, I can be quite, when I commit, I commit.

And the day they told me, I literally signed up for boxing classes and started training with personal trainers every week. And for eight months I taught myself how to box and. Absolutely busted myself to make sure that I was in as best shape possible going forwards, which was a really nice. Extension to sort of the, the health journey that I'd just been on as well to sort of say like, you know, I've not just gone up and gone down.

I've, I've then really solidified this by doing something pretty, pretty cool with it. And honestly, the boxing was probably, it was one of the best, most, the best event outside of sort of the, the deeper family stuff. Just to caveat that in case Emma's listening. 

[00:36:00] But yeah, by far one of the best events of my life, like it, it's the closest I'll ever be to being a professional sports person.

550 people in black tie in a hotel in London. You've got walkout music, you've got the ring walks, you've got celebrities like, wishing you luck. It's, it was bonkers. Like, and I, I, I never knew what I was getting into really. And sometimes I didn't know, 'cause I've been punched too hard in the head and, and just forgot it.

But that night, that night was special and I think. Oliver's Wish Foundation is the charity which is set up by Robert, Rob Dowling and his wife. They lost their son Oliver, four years old to sudden unexpected death in children. I can't genuinely think of much worse and the feeling that someone would go through in that situation at the time, my own son was four.

And. I'd worked with Rob's brother, ed Dowling and his cousin Jimmy at Perform Group. So I had a connection there and I know that one of the other charities they gave to outside of SUDC was cystic fibrosis. My wife works in cystic fibrosis, so she, I've had a sort of 13 year. Secondary connection there. So it just felt like it was the right, the right thing to do and a great charity to do it for. 

[00:37:00] And through the, through the training, the group become a real group and we got to know each other. And I've got some great friends come out of that. And it's amazing that even the, you know, the people you're fighting, you, you're still friends with and we're all industry people. we all love each other really. And just for those six minutes, we, we wanted to knock each other's heads off. But Mark tla, who I thought is one of the, is probably one of the best people I've ever had a chance to sort of sit down and speak to in the industry, some of the stories he's got from his life.

And if you're looking for transformative change in a, in a person, that, that man is a. Incredible person and incredible human. He did scare me quite a lot by having, I had lunch with him before the boxing and he was telling me about his, some of the darker stories and I was just like, oh my God, I don't have anything like this.

[00:38:00] I, you know, imposter syndrome coming back in again just before the fight. I did win, which you know, was great. My cardio was in really good shape. It was unreal. 

I couldn't sleep for about a week afterwards. The adrenaline was just flowing and I think, we raised about 152,000 pounds through that event for the, for the charity, which is just a phenomenal amount of money.

And moving on from that, I realized that last year it didn't happen. For various reasons. And not that the charities got a hole in the. Finances, but I, I was very aware they didn't have a flagship event to sort of raise money for the foundation. 

1. Had been to a few fighters, concert in Cardiff and got very drunk, and the next day I always go in for the ballot at the London Marathon mostly to try and make myself convince myself I'm a good person by donating the fee I never expect to get in and very hung over. 

I opened the email and it sort of spat confetti at me and I was like. That's not good. That's not, that's not a good sign, is it? but I've done it before about 12 years ago, and I, I figured, like asking for money for that I'd, I'd make a little bit for the charity, but it wouldn't go that far. 

[00:39:00] And actually, do I really wanna run it fast to try and beat my PB again? So the next charity event will be I'm running the London Marathon and then running home to Bristol, via the canal paths and river paths, which is gonna work out at 180 miles over six days.

So 30 miles a day for six days, with a guy who hasn't ran. For 10 years at long distance and is 12 years older

and is having to get up at 5:00 AM to do most of his training in the freezing cold to make sure, but he still gets back for the school run.  The boxing was tough and like, but in a great way.

This, this is. Unreal. Like in terms of how much training I'm having to do, like I've, I've literally finished a 15 miler run this morning. I did 15 miles yesterday morning. Last week I did three half marathons back to back. I'm a bit broken, to be honest. 

But at the same time trying to balance that getting fit enough and being to cope with the pain and mentally be there for the pain without actually breaking my body.

[00:40:00] We're trying to get as many people from the iGaming industry involved. Whether that's sponsorship, or whether that's just media contacts, whatever it is, that'd be fantastic. But more importantly, why not come and join me on part of the run? 

I mean, I, I know no one can come and join during London Marathon, although Rob has actually got a charity place that he's gonna be running it with me, which is fantastic. But days two through six and we finish at a pub in Bristol. So it's a nice, nice, nice, unsurprisingly, most people are doing day six so far.

So yeah, if anybody wants to run, even if you've never ran before, but wanna do your first mile, I. Perfect. Come and do it.

If you've, if you wanna run 5K, 10 k, if you wanna run a 30 30 miler with me, we'll be going slowly. Come and do it, and let's try and let's try and get the iGaming industry mobile.

Let's go try and get the, let get it moving and let's try and raise as much money as we possibly can for an amazing course. 

The gaming industry's just got so much about it and I love the industry. I've been in it for so long now. I really love it. I've tried to leave. I found it really boring leaving.

[00:41:00] I love being in the industry. I think there's a lot more good in the industry than probably externally. I just Think there can be more of a sort of centralized version of CSR within the industry that just does some good, or some events that just pulls the whole industry together and gets people. 

Doing things and I, you know, if I can be a, if even a tiny, tiny part of a catalyst to, to get towards that, I'd be thrilled.

That would be, that would be a real nice part of my legacy in iGaming.

Leo Judkins: I love it, Simon. Okay, so what can people do if they wanna personally sponsor, do 

corporate sponsorship, stand on the side and cheer you on, or with you? What do they need to do?

Simon Pilkington: I, I'd recommend that job rather than stand on the side and cheer. It is gonna, it is gonna be April by a canal path. It might, I, I can't guarantee a nice, a nice area. But I, I think that, I mean, if anyone wants to run, that would be amazing. 

Obviously, personally sponsor if, if you can afford to and whatever you can afford.

Fantastic. It's not about people throwing in huge amounts. It's about lots of people putting in. Little bits. 

[00:42:00] It really genuinely makes me run, like I was pretty tired and not looking forward to 15 miles yesterday. And literally the day before one of the school parents sponsored me 180 quid, a pound a mile, which I thought was, you know, for a school parent, I don't know, very well, I thought was unbelievably generous and it just made me get out there and do it. 

And so whatever you can throw in, I'd love to go past the 20 grand marker. I, I think we can do a lot more if, if we pull it all together Well,  and I think a lot of people are probably holding on until I actually complete it, maybe, which is absolutely fair as well.  I mean, I've had, I mean, Ben Robinson's been fantastic and pledged a thousand pounds.

If, if we can. Finish it and he'll be the first, first one in Bristol buying me a pint. He says, 'cause he's this way as well. If your companies are looking for a great cause or a great thing to get involved with, I'm willing to run in whatever costume people want me to. 

So if you've got a new slot game coming out and you want me to run as the character. I'll do it. As long as I'm not carrying a fridge or a wardrobe or something on my back, then I'm, I, I'll, I've got no shame in that side of things.

[00:43:00] If people want me to get involved and, you know, do some consulting for free alongside it, I'll happily do it to, to make this work. You know, what, what, whatever it is. Just get in touch and see what you can do. If you've got contact the news or media outlets even inside or outside of iGaming, let us know. look out for me or Brooks Peterson or Rob, Rob Dowling himself from

Patis. And yeah, all the details are in there, so. 

Leo Judkins: We'll make sure that it's in the show notes as well. If you're 

watching, it'll be in the YouTube description. If you're listening to this on Apple or wherever, Spotify, you'll find it in the, in the description as well. 

Simon, fantastic. 

Thank you very much for sharing your story. It's been,  been really wonderful talking to you.

Thank you.

Simon Pilkington: I'm glad I didn't cry. It's all good. Thank you.