Christos Kalogirou: Wild Dogs: An Adventure In Adolescence | The Tyler Wagner Show #1019

In this episode of The Tyler Wagner Show, host Tyler Wagner interviews author Christos Kalogirou about his memoir Wild Dogs: An Adventure in Adolescence. Kalogirou recounts his tumultuous high‑school experience at a private boarding school in Saskatchewan, where he was the only student known to be expelled and later readmitted. He describes the culture of elaborate senior pranks, the infamous "He's Having a Seizure" incident, and the camaraderie among students. A major thread of the conversation is his teenage bootlegging operation: at age 16 he organized an alcohol‑distribution network that ran for months, evading school authorities until he was caught. He reflects on the moral lessons of those reckless years, emphasizing that high school can feel harder than adult life because of its lack of rules and the ease of escaping consequences. The interview also highlights the charitable aspect of the book: proceeds are donated to the Matty (Mandy) Schwartz Foundation, honoring a classmate who died of leukemia. Kalogirou speaks about the impact of supportive teachers, the alumni network, and the broader message that readers should value moments in real time and learn from youthful mistakes. The episode ends with a call to purchase the book (available at major retailers) and to support the foundation via an upcoming donation website.
Chapters
All right everyone, welcome back to another episode. This is the best way for it to start. This is real. Um, today we got Christos Kalogerou with us, so welcome to the show.
Thank you for smoothly pronouncing my name, Tyler Wagner. Really appreciate that, guys.
This is going to be a real treat for everybody listening. I'm really excited for this episode, truly. Um, so Christos, if you can start us off, just tell us a little bit more about you and what you do.
Yeah, so about the book or about my life, or—
yeah, yeah, I'd say, um, mostly I think we should talk about the book for this interview. So tell us a little bit more about the book and how it came to be.
Yeah, so I started writing it actually in 2006, and I, uh, you know, by the grace of God, miraculously graduated in 2005. And, you know, started writing it shortly after. And it was just a wild, interesting place. And I'm the only student in the school's history to be expelled and go back and graduate, as far as we know, because they never kept record of a lot of that stuff. I went to a private school in Saskatchewan known for athletics, hockey. A lot of draft picks have come out of there, and also doctors, lawyers, and whatever you may have. And It has certainly changed my life, but it was certainly a rocky road to get there.
So, and then what, um, can you give us a little background, like what's the book, uh, about? And like, what do you like, the, the overall premise of the book?
You know, coming of age as somebody in high school, you know, fitting in, um, wanting to make friends, and sometimes it's sacrifices that shouldn't have been met. Etc. We've gone from there, and it's— I try to make it, you know, in writing, I try to relate it to anyone who's ever been a teenager or individuals that are about to be a teenager and what you can expect, and certainly not to take the road that I took, as a lot of it's not necessary.
And, and this is tied to a charity, right? What's the charity?
So I went to school, uh, with a girl named Mandy Schwartz. Mandy was there when I— she was— so I was always one year ahead of her And it was, you know, I was screwing around the whole time and Manny was, you know, doing the complete opposite. Worked really hard, went on to Yale University, was an exceptional hockey player, and her life was, you know, just cut short. She got leukemia and they thought she was, you know, I think her second season into Yale and she started getting fatigued and tired and they didn't really know why. And they thought she had anemia, which is like, you know, common blood, you know, sleeping, related there. I'm not an expert. And they did the test and they found out that she had leukemia. So there was a huge push to get her a bone marrow match. And a lot of people don't really understand how easy it is. And you just swab your cheek and you get into a database. There's a lot of people and a lot of families that go through this, but you could actually save somebody's life just by getting in the system. So all the links, you know, will be up with the website that's getting created soon now. It's been overwhelming of how quickly all this has taken off, which is I just appreciate anybody out there listening who's bought it or is planning to. But yeah, all the profits go to the Matty Schwartz Foundation, which is something that I really believe in and I know a lot of other people do.
Got it, got it. So let's talk about a couple chapters. I have the book open here. There's some interesting titles here. So the first one, "He's Having a Seizure." What's up with that one?
I got busted with a dirty magazine and I didn't want to go down for it. So I, you know, You know, I didn't expect it to get to that point, but I was basically kind of getting armlocked and they were trying to bring me to the house parents' office. And this is the person that looks after all the boys in the dormitory. So it was a co-ed school, but the girls had their dorm and the guys had a few dorms. And I, you know, he had my back against the wall and I just started doing my, you know, best acting. And I just, I, it turned into I just wanted to act like I was unconscious, but someone yelled out he was having a seizure and I had to roll with it. And yeah, dude, that's awesome.
Yeah, I actually love, um, oh my God, we could talk about every— dude, your, uh, titles, uh, of chapters in here are amazing.
Thank you.
They perk a lot of curiosity because I'm like looking, I'm like, Jello, Lockdown the Hole, like, dude, I'm curious about all of them. Um, What, uh, what was the grad prank?
So we had some guys a few years above us, and I don't believe that they do this now because obviously this is so many years ago, but every year tried to outdo the year before them, and they would do like an ultimate grad prank. So I remember I woke up and, you know, you're going— you have to go to assembly every morning, and I came out of my dorm and I just couldn't believe what I was seeing. So these, the grade 12s, so your graduating year you do this, it's the grade 12 prank, right? They had taken, they had set up all the classrooms outside. So the exact classroom was set up outside. And I'm just like blown away with this because first of all, the amount of hours and coordination that this would take, they must have been, they must have been planning it for weeks.
if not longer.
So yeah, I just— there were— I remember there was a whole classroom set up on top of one of the buildings. Like, I just— I couldn't— I just couldn't, like, fathom what was going on. My mind and my eyes could see everything, but I couldn't process it.
Yeah, you're like, this is not real.
Yeah, this is a whole other level. Like, if you thought at that age, like, yeah, I'm a badass, and when you see what they have— like, you hear nothing. Compared to what you were— to what you're looking at. Yeah, and it wasn't just a group of guys or a group of girls. It was everybody working together, guys and girls. The coordination is like— yeah, they should have got an award, for God's sakes. It was the most incredible thing I had ever seen, um, for a prank at that school ever. And that was only my second year. Like, I know my grade 12 year, uh, that they— I don't really think that they did a prank, but it was nothing compared to to that.
So, so let's actually, let's go back a little bit. So in the description of your book, it says like high school was harder than real life for you. So what, uh, what does that mean? Like, what were you going through in high school overall?
Well, I think, I think in high school you want to be accepted like anybody else, and such is life. Yeah, I was away from home. Um, so, you know, you don't, you don't got mom and dad or brother to run home to. You're on your own and it's tough love and It was hard because there's nothing to compare it to. And there's— high school doesn't have like a manual, right, of how this is supposed to go. And just as a whole, I look back and it was a very positive time in my life, that place specifically. And I know for a lot of people out there, high school probably wasn't the greatest. And I hope that they can kind of see themselves in some of the things that I was doing and that everybody learns from it because that's what it is. It's not just, oh, here's the guy that did all this stuff. You know, here's the guy that learned from all this stuff that he did. Like many people, like I'm sure you did in high school, like half the people listening. And I mean, I'm trying to answer it in a simple, short version of high school is harder than real life. If something happens at your work, and someone runs up like I did and throw a pudding in your face, you know, there's consequences and repercussions for that. It's quite point blank. In high school, you can weasel out of anything if you're smart enough.
True. Yeah, yeah, that makes sense.
And people are casualties in that that don't deserve it.
Yeah.
And I would— a lot of the people, I don't want to say victimized, but a lot of the people involved in some of my pranks on the positive end or on the negative end We're forgiving, we're understanding. I don't have a bad relationship, I don't think, with anybody in my story. And I did some things that I should have got the shit beat out of me more than once.
Yeah, I think that's so interesting is in high school, at least I'll speak to my own experiences, I feel like, well, me and a lot of people, it seems like that's your whole life at that time. And then once you get older and you're like out of high school for like 6, 7, 8 years. Like, now I've been out of high school for 12 years now, and it's just like, I still have my core group of friends, but like, things that happened in that high school, they were not as serious as I had, as I had anticipated they would be now in my life, you know? Because that's kind of like your little economy. Like, you're just like, everything that goes on, like you were saying, so somebody threw a pudding at you in the cafeteria Dude, you, you could be like upset about that for weeks and people could still be—
but I threw the pudding, Tyler.
Oh, you threw the pudding?
I threw the pudding at a girl, and if somebody would have done that to me, I'd have killed them. But I did it to this person, and as you'll read about, she defended me.
Oh really?
I was like, no, like these other guys put him up to it, which was true, but they didn't put a gun to my head. I did it to you. And just, I didn't deserve some of the, some of the outcomes. I deserve to get in a lot more trouble than I did. But as you'll read about, it all caught up to me and rightfully so.
So yeah, let's talk about that. And I want to make sure, because I don't know if we actually said this. So the title of the book is Wild Dogs, and then the subtitle is An Adventure in Adolescence. So then you say here, by 16, You started your own business venture, you know, went well, and then like it cost you everything. So what's that story? What happened there?
So I was in my grade 9 year, like, oh, there was alcohol on campus, you know, as there were with many private schools. I mean, I think it's a lot different now, but back in these days, there was like a code amongst the kids, right? You didn't typically You weren't able to get alcohol if you were in the grade 9 dorm. Like some of us were like 120 pounds or less. So it's dangerous, you know, you don't know. I had never been drunk in my life at the time, or I don't even think I had even sipped beer at the time. And when I got in my grade 10 dorm, I learned how there was these guys running things. And because we used to do pizza runs, right? So you'd go around with a list and you'd say, oh, you want to, what kind of pizza do you want? And the pizza back then would cost $8, but you'd give them $10. So they'd make a $2 profit. And it wasn't always profit. There was tax or something that we weren't adding up when we were that age, right? Like you're learning the hard way on a lot of things. Well, there were guys that were doing this with alcohol. So you'd go around and you'd take alcohol orders. And these guys were like making hand over fist. They were like, yeah, if you get us 15 orders or whatever it was, we'll give you a flask for free. Yeah. I was like, I'm a hustler. So I'm like, yeah, hell yeah. So I was drinking for free every fricking Friday and Saturday. And these guys had it made with me because they didn't have to do So they had their crew, but I had like a whole dorm of guys were coming to me like, hey, I need to get me this, so let's try this. So this weekend it was like writing it down, and then, you know, the delivery would come. And they had their setup, like they would get an older student to go to another town or city, and he either had a fake ID or was of age. I don't know, we had one guy whose mom was the art teacher, really good dude, and I know he ran it for a long time. So, in my grade 10 year, I was doing this and the guys I was working for were in grade 12. So, I knew that the next year they were gone. And I didn't really know who else was going to, I don't want to say take it over because I'm sure there were other kids doing it, but I didn't know about them, right? And I remember I was working at our restaurant when I was back home in Alberta with my brother and I was telling him how much they pay for and this and that, and we came up with this bright idea that he was going to ship me the alcohol and water bottles and I would sell it to the students. So I'm reducing the amount of steps. I had more, I had, I could charge more money, I had more availability, and I did. Yeah. And that's how that all started. And it got out of hand quickly. But in retrospect, you know, you go to school there for how many months a year? This went on for 2 full months. And it got to the point where every day or every other day I was getting searched, my locker, my belongings, to try to find the alcohol. The staff knew what I was doing but they couldn't catch me because I had a system. I had people tipping me off. It got deep, you know. I look back now and it's funny but at the time, it was very nerve-wracking because like I was in over my head.
Yeah, no, that's an amazing story, dude. Oh my God, I love that. So does that lead, um, do you talk about this or is it something completely different, the Liquid Courage chapter, or is this something completely different?
No, it's so the lead that my book is a lead up to, you know, the main meat and potatoes of my book is, is the operation what I was doing. I don't, I certainly don't want to give too much away for sure. A lot of lessons in there. It's not just, hey, I was selling booze and I got caught, or I was selling booze and I gave the whole jig up.
But I feel that there's a lot of people that do things when they're younger and they feel like they can't come back from them. And I want them to know this is probably about as bad as it gets. So, and I came back from that and I had some people that really went to bat for me and really looked out for me. And, you know, we talk about business and I think that A teacher is the— sometimes it's the most patient return you can have on an investment because you invest all this time in a student that you know has potential, but he's just not quite there yet. And sometimes they don't see that return for 15 or 20 years when that individual that they taught is all grown up. And that's kind of how I feel with most of the staff there. I knew I had staff that I frustrated that had had enough of me, but I truly didn't have a teacher that ever gave up on me. And I'm, you know, you can never repay that.
Yeah. No, no, I agree. Teaching is really an interesting job. I've always kind of thought that because like you're saying, in a lot of cases, you don't even get to see what they become, you know? Like if I was a teacher, say like a 7th, 8th grade teacher or something, I would, as long as it was okay with like the parents and the faculty, I guess, I would want to like stay in contact, you know, with my student, or like at least follow them on social media or something, just to see. Not to see where they're at one grade from now, but to see where they're at like 15 years. And just, you know, that would be really cool.
Well, one blessing that we have from all being, if you went to Notre Dame or any other private school, is that you have this alumni that can communicate with one another. And it's very easy to get in touch with anybody. And I've had people reach out with me from the book that have congratulated me, people that I expected. One guy, and you know, as you'll read about, was involved in my operation, and I kind of at the time felt like he burnt me, and he kind of reached out and was like, I'm, you know, happy for you. This is amazing. And you just never know who's going to come around and be like, you know, people get married and they have kids and they get older and your perspective on life changes. And we're so blessed that I can go back to that school and a lot of the teachers that educated me they're there for me to say, hey, I really appreciate you and a lot of the reasons why I am the way I am is because of your guidance. And maybe I didn't show it then, but it hit me.
For sure.
And I owe it to me is like, no matter what I accomplish in my life, there's no honorable job than these people because they make such a great sacrifice for themselves and their own family to move there and to devote their life to the student body. And I know I speak for a lot of people when I say that, when I have that outlook of how great some of those people were, because I went to a charter school system and believe me, I had teachers that like outright did not like me. Like it wasn't a secret. I was very hard to like when I went to high school. And I know there were teachers inside that were probably like, I'm gonna get this, like I'm gonna get this son of a bitch. But like they just were so patient. And they didn't have to be. Like, I was shit. I should have got kicked out in grade 9. I got kicked out in grade 11. So that in itself is a—
So wait, actually, how did that work? Like, so you got expelled and then came back. Like, how were you allowed back?
That doesn't—
I had a husband and a wife that were like parents to me on campus, and incredibly patient with me. And when I got kicked out, I think the husband had told me, you know, Christos, if you can meet these requirements, we will get you back in here. So he put it on the line for me and I did meet those requirements, which was probably when I got— so when I got kicked out, I had to go back and do high school at home.
Yeah.
And it's so much harder to have good grades in high school for me than it was in private school because you have all this help at at your disposal. It's just, it's right there. And they're monitoring you. And miraculously, I got my grades good enough that I could go back. And yeah, I don't want to, you know, I'm already giving too much away, but it wasn't for them, I wouldn't have went, I wouldn't have been able to, and I don't know where I would be. Because I wasn't the smartest, like I was doing intricate things, but I was always close to danger, you know. I never wanted to burn myself, but I always put my hand near the fire, you know. And sometimes with that you get burned, as a lot of people do. And I don't think my— I don't think I have the best stories from that place, but at least I wrote them down.
Yeah. And it seems like you would kind of— and actually Jordan Peterson, we've talked about him I think before.
Oh yeah, yeah.
He kind of talks about that where it's just kind of— you kind of like flirt with the line, you know, like you And you kind of have to do that in life.
I wasn't just flirting with the lion. We were in a serious relationship for many years.
Yeah, yeah, you and the lion. Well, yeah, and I mean, obviously you don't necessarily want to do it with, you know, bad things. But I mean, as far as like pushing yourself to limits and stuff, you do, you want to kind of put your hand close to the fire. And like you said, sometimes you get burnt. Like, that's just the way it is. But the point is learning from it and then, you know, you keep increasing.
This one individual that was a major reason that I went back to school, we actually went for beers years later. And I remember sitting down with him and we just had like an adult conversation. And he said something to me that I'll remember for the rest of my life. He said, when you're that age, you think that the sun rises and sets around you. And it summed it up perfectly for me because I didn't care who I burned. Or who got the shit end of the stick as long as I got what I wanted. And he kind of let me know like, hey, you're not the only one here. Like, you know, there's a lot of that. And he probably, they probably saw so much worse than I thought that I was at the time. Not to say that what I did was okay, but a lot of people—
I know exactly what you mean.
Yeah, I would hope that a lot of people went through what I went through. Maybe it's worse, maybe it's not so worse. And then just kind of a switch went off and went, hey, Like, you got to start doing this the right way, uh, you know.
Yeah, no, when you're younger, I feel like that is what it's like, and you really don't— like, your brain doesn't see. And actually, your brain isn't fully developed till 25 anyway, apparently. Um, but like, you're— it doesn't see the ripple effect. Like, if you do this one negative thing to this person, then that also not only affects them, but then they go home right, and then it affects the family. It can, like, that's how it can.
Of course, you know, all that, those things we don't see.
Exactly.
And when you go and you have to be aware of— and I know that what was very important with my book was that it was never about money to me. It was like, these are really cool stories, and I hope that everybody can see themselves in my stories. They're not— they're through my eyes, but everyone can relate. And to be able to give it all back to Maddie's Foundation And for her family to be so on board was, uh, was just so humbling for me. And I'm so appreciative that it kind of came full circle like that.
100%. So here's what I want to do is I feel like we've, we've definitely teased it enough that if people don't want to read this now, then, you know, I don't know. So what I wanted to like tell people, if there's anything else you want to share, please do. But also tell people, um, there's a website being built now that they'll be able to donate. Should be live soon.
Right now, the best way to get a hold of me or Or if you want to get the book, even more important is you can get it on, I mean, Target, Barnes Noble, Amazon obviously, and it all goes to charity. I don't, I seriously do not take any profits for this. And I hope you see a little bit of yourself in it and have a good laugh. And I think that's what we all need in this year and a half and more that's been difficult is people need to laugh more.
Yeah, I agree. So what are, we'll wrap up here, like what are some of the biggest lessons you think that people get from reading it?
Oh, it's evaluating your time, I would say, is— would be the flagship.
Okay. Is it's so rarely do we value things when they're happening in real time. It's when we look back and cherish those moments, and which I have very— I have a lot of, too many to talk about. And I know so many people that I went to school with have them as well in their own right. And it's just such a valued time when you're young, and don't beat yourself up too much, but also you know, get the lessons that are— people aren't grinding lessons at you because they're doing it for their own good. They're doing it for you. And if you can just pick up a fraction of them, it'll really help you down the road.
Yeah, no, 100%. Um, well, listen, dude, thanks for coming on. And for everybody listening, um, definitely stay in contact with Christos. And again, the, the, uh, the title of the book is Wild Dogs: An Adventure in Adolescence. So Thanks again, brother.
Thanks for having me, Tyler Wagner.
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