#9 - Haralabos Voulgaris: Being the Best at Sports Betting

24:42And I was like, okay, well, why don't we just bet against each other then? And he's like, I don't want to do that. You always win. I was like, okay, what? I was like, what? And I was just done. I couldn't take it anymore. I was just done with Floyd and the other. I was like, yeah, you guys can try to figure it out, but I'm done. my main thing was never doing anything wrong by anyone like my word was always so that was like a big thing for me as much as I was an asshole or director or whatever I would never screw anyone in a business deal or not pay someone or not pay someone on time or go back on my word or what I was going to do and I felt like by doing that it allowed me to have good relationships with people and it allowed me to be in situations where I was given an opportunity to work with someone like that I just want to dig into that a little bit more because would you say that your word was your bond and you wanted to act in high integrity was that always just purely the case because it had instrumental value or did you actually see it as something that you valued in and of itself as an innate goal that mattered or has that evolved over time for you?

25:51I think for me because like I mentioned earlier knowing that you can't necessarily trust the word of people and how hurtful that can be, like the word of whatever, like your caregivers or whatever, how hurtful that can be, I just was like, resolved myself to like, he was my anti-hero in some ways. So like being very different, like make sure that I follow through on things I was going to do, make sure I was followed through on things I've always been that way. So I think that was part of it. I don't think it was like, oh, this is going to get me ahead in business. I just think it's just something that, it didn't occur to me that, I mean, obviously you can, deceive people in different ways.

26:24There's business things where you can be cagey or in poker, you can bluff, you can do whatever. But in terms of if I tell you, and for sports betting, you would have several agents working for you and you would sometimes give them the wrong side. You just have to. Or you use a beard. There's certain degrees of deception that you were clearly very, very comfortable with. Yeah. Right? But why was that deception okay? I think because it's a game. It's almost like why is it okay to bluff in poker? It's like sports betting is a zero-sum game. The bookies are doing whatever they can in their favor to win.

27:01Even the guy that we had, the big outlaw bookmaker, we had a square account, so we would primarily bet overs with that account. Also because of the way the year was that year in the NBA, overs were more plus EV. It was post-strike year, so overs were more plus EV because the lines makers were using the lockout year's data, which was lower scoring. so they had a year's worth of data which was lower scoring the next year is not strikes, the players are in shape they're starting on a regular schedule so you're using this old data so my point is betting overs was profitable so we had an account with this guy to bet overs we would primarily bet overs with him but he would juice the lines up and make the over he knew we were betting overs so that's not a deceit the line's 180, 200 and a half everywhere and he's giving us 201 and a half because he thinks we're going to bet over That's not devious, it's just clever.

27:53And so sometimes we would fake the market or like you said, give people the wrong side, etc. So it sounds like, just inferring what you've said, it sounds like your thinking was if it's a zero-sum game,

28:11deception is acceptable provided it's within the rules of that game. Yeah, and I think also how is your reputation? What is your counterparty reputation? So with the guy I was betting with in Canada, his name was Dario with him, we had a close relationship. So I would never go back on my word with him. We were like effectively partners, but I might have someone else who is giving me accounts to bet, but he's giving me 10 accounts, but he's keeping 10 for himself just to see what I bet on the 10 accounts. And then he's betting them. So for a guy like that, or maybe he's giving me three accounts and he's got 15 and he wants to see what I'm betting.

28:42And then he's going to bet the 15, but he's telling me these are the accounts I have. A guy like that, I'll try to screw over because he's basically trying to take my information and not loop me in on the profit. And then the problem that's happened now with sports betting is you have so many poker players and former DFS guys who are all sports betting wizards now. And there is no honor among them. And they look at everything very binary. And so someone could be like, okay, I could bet$3 ,000. Let's say the three of us all want to bet the same game and the total market is$10 ,000. so we could each maybe get like, maybe you'd get five and Igor would get two and a half and I'd get two and a half.

29:23Someone else would be like, okay, but in the total market would be 10. Someone else would be like, well, maybe I could guarantee myself and maybe some days I wouldn't even get the full 2 ,500, but I can bet early and guarantee I'm the only one that gets it. And it just takes one person to defect, as you said, to start doing that. And now like Pinnacle opens their market at$500 on the overnight the night before and sharp guys who have very good models are betting the overnight market for$500. A, because their bankroll isn't that big. $500 might be enough for them to get down. Whereas back then, there was nobody who was sharp betting$500 that would move the market.

29:58Now$500 can literally move the market. That's why sports betting is just dust now. I'd love to just go into more the dark side of gambling, betting. Not so much for yourself, but I'm sure you've seen deep addiction. Did you ever have moments where you yourself felt like, oh, had to ask yourself, am I addicted to this? Yeah, I think certainly when I came back tree planting and I was losing money at the racetrack, I had a problem. I had no edge. I didn't know what I was doing. That's when I kind of resolved myself. I need an edge. I can't just be trying to win because I'm special. It doesn't work that way.

30:40I thought I had an edge, but it was clear I didn't. I had a better idea of how deep the takeout was. In other words, the hold percentage. $100 was better at the racetrack. 30 % would just be going to the racetrack. 70 % is distributed amongst the betters. You've got to be really fucking good to overcome that. Some people have, but that wasn't me. Later on in life, I've had so many stressful situations. like when I was betting a large portion of my net worth times five or six on credit or through investments where I definitely take personal pride in thinking clearly in stressful situations. And so part of me is like when there isn't enough stress, I feel like my life isn't that exciting.

31:25So that's maybe the addiction is like, oh, I'm missing that part of me that makes me feel special where everyone else is freaking out or would be freaking out and I'm not. There's this really lovely analogy someone once gave which is like, I'm like one of those fish that lives at the bottom of the ocean where when there's tons of pressure on me and there's so much water pressure, it's fine. But if you bring me up to the surface and take that pressure away, I explode and die. Yeah. Does that? No, I don't explode and die. I just feel like a lack of purpose. I just feel like, okay, now what? It's almost like life is a little bit muted when there isn't that.

32:01It's not like that now because now I can enjoy vacations. but certainly in my late 20s, early 30s, if I didn't feel the constant pressure, I felt like life was just boring or stress. If you grow up in a, and I think it's like I've done a lot of work, whatever, with people in terms of therapy, et cetera, just knowing that when you don't know if someone's going to come in the room and start yelling and screaming at any moment, when you live with that as a young person, that feels familiar to you. And so you find ways to put yourself in that situation where chance or randomness can, it feels comfortable to you where something is out of your control.

32:38I can empathize with that a lot. Also having had a lot of yelling in the childhood. Yeah. And nowadays, I just feel it was very comfortable with... Me yelling at you? Well, actually, yes. But the gamble or like risking more is something that I'm seeking rather than avoid comfort. and it feeling that the pressure that it kind of gives is actually kind of like oh cool great now I now the situation matters is what it means it's like otherwise it kind of doesn't matter whereas like if now you're risking more like okay now it matters it means like this is I don't know just achieving something I still get like very like when people yell and scream like this also happened with the Mavericks like when someone yells and screams or like break something like I hadn't had that hadn't experienced that in a long time.

33:27But in the NBA, it's just right, you're literally like coach picked up a trash can, threw it across the room, broke something. And I thought, A, this is fucking silly. But B, something in me was almost like, I felt very, very uncomfortable. And I was like, what is this exactly that's making me uncomfortable? And then I kind of figured out like, oh. Can you explain who the Mavericks are and what your involvement was with them? Yeah, I worked for the Dallas Mavericks and NBA team owned by Mark Cuban. And my direct title was head of quantitative research and development, which Mark let me make up.

34:03So I was like, sounds good to me. It sounds fancy. I should have went with director of basketball strategy or something like that. It would have been a little bit more understandable. But I was like, quantitative research and development sounds interesting. What was my role? It depends on who you asked. Some people thought I was like the spook who was there to spy on behalf of the owner. Oh, interesting. Yeah. some people thought that I was like running everything um as like the gm of the team who's run literally running everything I think the truth was probably I definitely wasn't a spook I had a very early situation where I was in the coaches meetings all the time with the head coaches um I had a very good working relationship with with the head coach of the team and and several of the assistants not such a good relationship with some of the assistants um or one of the assistants.

34:45It wasn't bad, but it was just like I could tell like this guy's, he's scheming. And so, but anyways, what was it? It was like, you know, it's hard to describe. It was a gambler working in the NBA to help the team make better, smarter basketball decisions. And that involved everything from like what type of offensive philosophy should we be pursuing? What players should we be drafting? What players should we be trading for? Should we be putting like, it was a lot. I had a couple conversations with Coach Carlisle, who's like an NBA championship head coach. This is in 2000, not when I was an official team employee.

35:21And we got along fine. He liked me. He wants to win. And he would take anyone's opinion, who he thought would, not anyone's, but he would weigh the opinions of the staff equally in terms of who could help them win. And I think very early on, this might sound whatever arrogant, but I think very early on he recognized my opinion was giving him more of an ability to win games. And so he would use my opinion a lot more than maybe some of the people who are actually the assistant coaches. And so we redid our entire offense philosophy based on suggestions I made. And he can disagree with it if he wants, but I got the receipts.

36:00It's fine. But we went to a five-out offense because of me and the stuff that me and my team came up with. And he basically told me, I'm not fucking doing that. get the fuck out of here. And three weeks later, they went to a, like he would do that a lot. Like he would basically tell you to shut the fuck up. You don't know what the fuck you're talking about. And then implement the idea as though it organically sprouted from his own brain. But I think also because he wanted to understand it. And I don't know, the offensive thing was interesting because he, I don't think anyone really thought running a five out offense, which is like a specific offensive alignment.

36:32And so like I came up with it, by the way, like I just saw another NBA team doing it. And I was like, yeah, that's the way we should be playing. What was the state, their quantitative analysis before you came along? Like zero. Everyone thinks Mark was this super cutting-edge owner who has always begun in analytics, whatever. There's a couple guys working in the analytics office. One guy worked really, really hard, still works there. He's a good dude, works really hard, smart. I don't know how much people pay attention to him. I don't know how much they don't pay attention to him. I just know that in my mind, it was like nobody was...

37:02I got there and I immediately started hiring people in my department, started doing stuff. were they just playing intuitively? yeah but they had skilled NBA coaches that were very good at what they were doing so it wasn't like they needed the analytics to help them get better but they would every team wants to pretend they're doing analysis without maybe actually doing it or maybe they have someone on staff but they don't listen to them and that's kind of the place where the Mavericks were where they had people who they weren't listening to and when I got there I was able to show them why there's just a lot of different scenarios like we'd be in an offensive meeting for instance and they're like this thing like the ball finds energy, all these euphemisms.

37:39We've got to make at least three to four passes before we take a shot. I just went and printed out a plot that showed your offensive efficiency, which is what you're solving for. Offensive efficiency, how many points you score every time you have the ball. Offensive efficiency declines with the number of passes you make. Because every pass is another opportunity for a turnover, which is bad. It sounds like there was almost a lot of old wives' tales, essentially. There was a lot of old wives tales. And there was a lot of like, I'm a guy where like, it became, the coaches meetings became very quiet.

38:12And even one of the assistants even said like, yeah, I don't want to stay in there because I know if I say something wrong, Bob's going to like have data like tell me to fuck off basically. So - Must have ruffled a lot of feathers. A little bit, yeah. But I was like an easygoing guy. Like I was never, I was just like having a good time, you know, I wasn't like life or death. Well, people don't like to hear their intuitions being challenged. Definitely not. And if they've got these deeply held intuitions that they've had a long time. And it's interesting because I bet some of them were born out of some truth.

38:36And some of them were good, by the way. Some of these guys had intuitions that were very good, but that doesn't mean every one of them was going to be good. And you should want to be able to... Right, you're able to come and razor blade the crappy ones. And I think the people I vibe with are the people who can accept the fact that they might be wrong and hear about it. And here's why. Here's my plot. Here's why you're wrong. Yeah, there's some actual data that shows. We would have coaches meetings sometimes. And then, by the way, after a short period of time, I was no longer in the coaches meeting, just to be clear, because it was just counterintuitive.

39:03of it because unless you were like, what do you think we should do here? And then you go around the room, not just because of me, but every person is going to impact the next person's choice. So like, unless you're writing like a sealed envelope, what you think, who we think should guard this person, it doesn't work. But we, you know, we used to go in there some mornings and there would be like, we'd look at shots and there'd be like a wide, this is like when that three point shot wasn't quite as like, I was pushing for more threes, more threes, more threes, more threes. In fact, they broke a franchise record in three point attempts.

39:31I think the second game or the third game of my time as an employee versus the Minnesota Timberwolves. They would see a guy with a wide open three, but three seconds into the shot clock. They'd go around and they'd freeze frame it. They'd go around the room like, is that a good shot or a bad shot? Wide open shot, three points from a great shooter. They'd be like, it just breaks the spirit of the team. If that doesn't go in, guys are going to feel like they create all these stories for why they think things are happening. I'd just be like, they get to me and I'd be like, what the actual fuck are you guys talking about?

40:05That's a wide open three point shot from a guy who shoots probably 43 % from there. So it's like, you're not getting any better than that. You're out of your fucking mind. Basically, let's move on. And now everyone wants to take early transition threes. Because we had data that showed like the earlier, you want to take early shots in the shot clock because you have a clock. You have to shoot within 24 seconds. So imagine knowing that you have to take a shot within 24 seconds. And someone thinking that an early good shot is bad. Do you know you're going to get a better shot than that later? And as the time keeps on ticking, it's like when you're playing chess with a timer.

40:38So I don't know. It's a lot of old wives' tale stuff. It's a lot of people who never really took, had the, you know, never really, the analytics weren't really a part of the game. Now it is and people think it's kind of ruined the game. Maybe it has. Do you think there's ever like a sort of tipping point of too much analysis? Yeah, for sure. And it's a culture war too. It's jocks versus nerds. Yeah. And me coming in there, it was almost like there was an immune response. This foreign body has come in to this ecosystem. And a lot of people had an actual physical immune response with me because it's just like, okay, if this is the way we're going, I can't compete in this environment.

41:14I don't have a place on this team if I can't do this. I'm not a statistician. Yeah, I don't know any of this stuff. Speaking of foreign language, essentially. Yeah, like one dude who was working there didn't even know how to use Excel. And I was like, how do you send emails? Like, who sends your emails for you? As a joke, I was like, bro, you got to learn how to use Excel. I can show you how to do it. It's easy. Drop down. It wasn't for any analysis. It was just for a simple task that we had because he was counting everything by hand. I was like, yo, I can show you. He's like, no, I just don't get that stuff.

41:39I'm not comfortable with that stuff. Super hardworking guy, super great guy, but wasn't comfortable with technology. Why did you leave? To be honest, when I was there, I'm the type of person who I signed a three-year contract and about six weeks in, I was heavily questioning what the fuck did I just do here? I had just had a broken engagement flew back from Greece direct to Dallas to meet with Mark agreed to a job contract that morning and then was like oh I'm moving to Dallas now every year like around December I'd be like yo I can't live in Dallas anymore like I want to go to Mexico I want to work for Mexico I'd rather like split my time between Mexico and LA or whatever Mexico and Europe mostly Mexico you can fire me you can let me out of my contract or I can work from Mexico but I'm cool with whatever you decide and they would be like okay no problem you can work from Mexico and there was like one point where it was very difficult because me and the coach actually got into an argument we always argued because that was just his style he was a very combative person and he was very good at it and he was also very like a master manipulator not in a bad way but just like mental mind games was his thing and so there was like one situation where we had our starting center got injured.

42:58We had to revamp the way we were doing things. I was working remote, so I wasn't there. He calls me up and he's like, did you hear what we're doing? I was like, yeah, you guys are going with so-and-so starting. I wouldn't do that, but it's fine. I said, well, what would you do? I said, this is what I would do. We should go small. We should embrace the small thing. We'll play Dodo at the four. We probably were playing Portland that night. They already met with the team and told the team, this is what we're going to do after this injury. We're going to lean into this style of play. We're going to go big, lean into it.

43:30And so they presented it to the team. I think this is what happened. I don't know. This is like maybe too much of the spilling the tea, but whatever, who cares? And then he talked to me and I was like, yeah, that's a bad idea. I think you should do this. Like we're going to win games 130 to 120, but we're going to win games. No, he's going to be able to stop us. We'll be able to go full five out. That's what I would do personally. I think you're making a mistake. And I didn't realize like, okay, cool. Like we'll change it. I didn't realize it would be if he agreed with me and I could tell he was, that part is I could tell he was agreeing with me, but he was still hesitant to do it.

43:59And I didn't figure out why until I spoke to one of the assistants. He's like, well, yeah, because we just met with the team and explained to them what we're going to do. Now this guy's got to figure out a way. And the players are smart. Like they're going to think immediately, oh, it's that it's Bob. Like Bob, Bob's not something different. And that's why we're doing something different. And so, yeah, sure enough, he started yelling and screaming at me like what the fuck this is why we can't have you working remote like you've got to get like what does your contract say I was like my contract says that I have to answer to you and Mark and that I I'm working where does it say you have to work it says I have to work in Dallas like okay case closed I was like yeah no problem so you went why are you coming to Dallas no I'm not coming to Dallas I do not want to live in I didn't like it I didn't like it were there other teams at the time that had their token not token nerd but just like another nerd come in Now, I think there's more, but not in the role that I had.

44:51It was such an odd situation where there was no other team that would ever hire me. Because it was such a fucked up situation, I had to appreciate the fact that it had to have been fucked up in order for me to be there. Because if it wasn't fucked up, you had to have a guy like Mark to want to do something as crazy and out of the box as that. have a dude who was a former gambler around all the time, coming up with ideas in coaches' meetings, providing reports. I had to CC Mark on every email. And so Mark would chime in with some ideas too in playoff series. It was just a different environment.

45:26Mark gets up in the middle of the huddles during playoff games and talks to the, he's on the court. That doesn't happen. That just doesn't happen. That surprises me because you clearly added value to the team. 100%. So why are other teams not emulating that? I mean, I don't know. I think that maybe I was better. I don't know. I studied the game for 20 years, gambling at the highest, highest level. I've had tons of bad ideas. But when you gamble, all your bad ideas are gone. Or you go broke. So there's survivorship of ideas. Things that are predictive are left behind. It strips you of all delusion.

46:03There's a lot of delusional gamblers. Everyone hears this. I have a friend who never loses at blackjack. There's always that. But if you have a 20-year career where you're winning money and you're doing it in an analytical way using very, very strict, not just record-keeping, but model building, you have good ideas. Do you start introducing probabilistic thinking into the organization? Sure. We added something called XPPS, which is expected points per shot. and the coach was like, what was the XPPS last night? It couldn't have been bad. It couldn't have been good. I was like, no, it wasn't that bad.

46:39Like quantified metrics that they didn't have before. In other words, you're reducing, you're removing the luck of the shot going in. Like what was the quality of the shot? Were we supposed to win the game via shot luck? Shot luck is not a great proxy for that because basketball, there's a lot more nuance than that, but it's decent. It's not like football where it's like XG is the big thing, expected goals. But in football, soccer, we call it football. Now that I'm a football guy. XG is like the gold standard in some ways. And I don't think XPPS, expected points per shot, is quite the gold standard in the NBA.

47:11So you left the Mavericks a few years ago. And then last year, you bought a football team, a soccer team. I did. Almost a year. We're doing this on the 19th. I believe it's a year to the day, actually. Wow. July 19th, 2022. I think on the 20th, we bought the team on the 20th. And they are... When I say we, I mean me and Oscar, by the way. I don't know why I keep on using we. Oscar for those who don't know but at the time it was just me Oscar is Bob's dog and love of his life he's not the love of my life are you sure? seems like he is no he's been described in the Spanish newspapers using Google Translate as my most faithful squire and I'm going with that either way there's a very symbiotic it's a great bond there's a lot of love there so yeah you bought C.D.

48:04Castellon Spanish team currently in the third division historic team was not always in the third division last in La Liga in 91 they were in the second division like four years ago I don't know how that happened three years ago three or four it seems to an outsider like me an absolutely crazy undertaking why and what's your goal with it? the goal is to get the team to La Liga that's the goal the equivalent of the Premier League in the UK yeah it's like you're playing Barcelona, Real Madrid those teams. It's not that unrealistic. It really isn't. Going into it, we had soccer models, football. We had models already for the sport.

48:46We thought they were decent. We got some help from some other people who have some very good models that we believed in. You have been working to try to improve our models. We're doing a real data. The one thing I didn't like about the Mavericks was it was half-end data, but not really. and I wasn't able to set the culture. I wasn't able to really define who I wanted to work with and why I want to work with people who have high integrity, who work hard, who can handle criticism, who can give me criticism without worrying about offending me, who are just honorable, good, hardworking, smart people.

49:21That's been my recipe for success is finding people that are smarter than me in certain areas and leaning on them and partnering with them. I wanted to do that but with a real analytic bent for football. I really wanted to lean into the data because I think it is I think there's an edge there I really do Spain is a wonderful country there's a great culture there's great history but one of the jokes I had is we lost a playoff game to a coach wearing skinny jeans and I'm just like I can't handle this anymore if we can't beat the guy coaching against us in skinny jeans What's wrong with skinny jeans?

49:58I don't know there's nothing wrong with skinny jeans but it was just like it was just endemic to like how what the reality is of third division football like we played a game where the sprinklers turned on in the middle of the but in the middle of the game and then yeah we got beat by a coach wearing skinny jeans and so it's like my point is is not you know this is a culture that loves football it's very passionate it's very emotional they have a deep history they play a style of football which is not the same as they're playing in England in the Premier League which is not to say that it's backwards but it's certainly not cutting edge.

50:36And I feel like there's a lot of room to play. Maybe their style is better. Let's just say that. Maybe the style of Spain is better. But if every team in Spain is playing a similar possession-based or let's say a cautious style of football and you come in there and you're the only team playing a really aggressive front foot, play on the front foot style of football, you have a competitive advantage. That's my belief. And so that was part of it. I really wanted to define the cultural workplace. Also, I fell in love with the city and the people. They really love the football team. I didn't really get that when I first bought the team.

51:09How much did you pay? We paid somewhere in the neighborhood of$4.5 million immediately, plus assuming another much larger amount in debt, plus guaranteeing payments that hadn't been made, pass payments for payroll, social security, money that's owed to the government. There's also we didn't have a training facility. So when people say how much a team costs, it's like, okay, it's not how much a team costs, how much does it cost to get the team up to a level that needed to compete? And so we have a six-year plan to get to La Liga and we're spending as if we're already in second division. So we're burning quite a bit of money in the third division.

51:51And what's your expected revenue stream? How do you monetize a team? You get them to the second division, you don't lose as much money. Second division, you break even or make a little bit of money or lose a little bit of money in the second division absent player trading. You can make money through player trading. So I think in the second division it will be profitable for sure. So the way I looked at it was we're buying a team in the third division at about, let's call it, let's say maybe like 8 % of the price of a second division team. Do I think I have a better chance of getting a team than 8 % to getting up the second division?

52:30Yes, I do. In fact, we came within one goal of getting promoted in the first year of owning the team. What roles do you have at the team? It sounds like a lot of different roles. You're doing transfers. You have a better GM role as well. This is funny because when I bought the team, all the people who were dismissive of me were like, he's going to fire four coaches in his first year. and I was just like, get out of here. These people, I'm not that awful a people person where I'm just going to fire all the coaches. But I'm on my third coach. But to be fair, I inherited one coach. He was already hired a week before I bought the team.

53:02He was not the guy, just to be clear, not the guy. I couldn't vibe with him. His personality type was a top personality I was not going to vibe with, could not handle criticism, was not facts-based, was very into his feelings, and in my opinion, operated in a manner of integrity that did not fit the way I wanted to run my football team. And the coach really does represent your football team. It's not the owner and his doodle, it's the coach. So the second coach was an amazing human being, like really good person, high integrity, worked very hard, very smart, but maybe just didn't have the experience necessary to get the job done.

53:39So we let him go. We were going to let him go whether we won or lost our promotion game. third coach we hired someone from the Dutch league and he is like I think this is the guy we have so much in common in terms of the way we see the game the way we see being aggressive and taking chances my thing is we played in our playoff game as though we were hoping to get lucky and win the game that's not my lifestyle I've never been the type of person I'm not going to be taking any chances and just hope I get lucky like, oh, I'll just play it safe and then maybe I'll ladder up. So this style of football that I think we're going to play is going to be much different and much better.

54:21So to answer your question, what is my role? My role was to find a coach who played a style that I jived with and just let him do his thing. I think I found that. We did that through analysis. We determined which styles of play we thought were the most effective to impact winning, what coaches approximate that style of play most, whether through their own analysis or just by blind luck. You know, like, just rant, you know, Durr got really, really good at poker, probably just got a blind luck. The style just kind of worked. He just randomly lucked into a style that was very, very successful for the time.

54:53But I think this guy looks at the game very analytically. He's very, very smart, and he's got a good track record. He's promoted his team to the first division in Holland. In that final game of the last season. where you're one goal off from making it into the next division. Surely if there was anything that gave you this emotional... You had the feelings on the line then. Actually, it's funny because I don't normally fist pump or clap. And I'm pretty sure I did when we scored 2-0. I'm pretty sure I gave someone a high five. And then after the game... You came to regret that fist pump. I did. yeah it didn't serve me no and then after the game I was like okay we didn't play good enough to win we weren't ready let's get back to work did you have any moment did you like have you ever kicked a trash can or like cried into the mirror I don't know cried into the mirror is a little like definitely not into the mirror I've definitely cried before that's happened not into the mirror that would have to be that's not a thing I do either before people think I've never done that no of course yeah but like my thing is like sports isn't it like yeah I've had emotions with girlfriends or people I love and care.

56:06Not where I've yelled or screamed because I just don't do that. But where I've been sad and I've cried and I've tried to plead my case. It hasn't worked. Whatever. I've definitely done that. But sports, this ain't life and death. It's a fucking sporting event. I want to win very, very badly, but I don't. I know. I did. I got excited when we scored. And then we lost. I was very, very quick. Not even when we lost. By the way, as soon as we went to a completely defensive game plan, I was resigned. I was like yeah this is probably we're not going to protect the lead for 70 minutes it's just not happening um and so but after the game I did almost cry I probably could have cried if I allowed if I was just like a little bit more like sad but it was because you know what it was it was everyone around me was crying like the players were like in tears the dude who runs our social media and and graphics the nicest kid ever like lives in the same time he was like he was inconsolable and I saw that and I was just like I gave him a hug and I was just like okay I feel so so I was sad yeah I was like really hard like there's a picture of me like one of my players and the players is like crying and I'm just like consoling him it's just but to me I was just like it's okay like we're gonna get back like we're gonna on the bus ride back I was just like remember how this feels like I'm proud of you and like next year we're gonna win I don't know what to say like work hard use it as fuel so yeah this makes me feel because I was never that into sports um you know i i loved it playing i love playing sports always very competitive person but as i've gotten older i've never quite gotten the sports bug like i've never had a team that i love and i root for and so on but so i want to understand like what is it about certain sports that you know what is it why does society well this love it so much this this this town this team is so important to this town like you know we had more people watching the game on a TV in our stadium on TV versus the other team had live because our fan base is so big.

58:04And we had like three or 4 ,000 people like see the bus off or see the bus in before the game, just come early. Like it is a religion. They love the sport. They're so passionate. They can be entitled at sometimes, which that's okay. But they're definitely like, it's something that's actually really, to me, it's actually quite beautiful how much they love this team and that you can be someone who brings joy assuming you succeed. Now the flip side of that is when you don't succeed they're going to be coming for you. And I'm not sure I'm ready for that. Not if I'm losing five million a year I can promise you.

58:37I'm going to be like if I'm losing five million a year to get yelled at by some fans that's like okay you can run this team if you want. But for now it's been very beautiful. Everywhere I go people are very positive. You can see they love the team. We've already sold more season tickets for next year. more commitments than any other team in our league by almost two, I think. What is this hole in people's hearts that you think it's filling? I don't know. It's a working-class city, and I think it's the connection between fathers and sons and daughters, and some of the kids play in the foundation, and they play in the youth team.

59:15I don't know, because I've only been in it for a year, and I haven't even spent that much time there. I've been spending a lot of time recently, but I didn't in the beginning, because I didn't really like the people that were working there at the time. But now that I brought in my own people, I enjoy the environment more. It's hard to describe unless you can kind of see it. Like you go to the stadium and they're singing and chanting. They're crying after the game. The fans are crying. And you know, it's, yeah, it's a lot. I don't know either. Like for me, I just, it's, I wouldn't like, I own the team or I run the team, whatever.

59:49Like I'm the custodian of the team. so I have a more but I don't get it because I've never been that passionate about some other sport I think you touched upon it though it gives people a community a real community in Dortmund where at the time it was a population of 580 ,000 people while we had a stadium that fit 82 ,000 out of which let's say I don't know what the actual number is but probably like 40 ,000 to 60 ,000 people come out of Dortmund So it's about up to 10 % of the whole town congregating every two weeks in the stadium together and half of the rest probably watching the game. It's just like this, we're all doing something together.

1:00:33It's kind of the same reason why public holidays or all of these things are unifying and great. It's like you're just, I don't want to say it's a replacement for religion, but in a way it is. People do have similar rituals and all sorts around it as well. Yeah, it bonds the community together. It gives them something that they can... And I think also it's a working class town. And I think maybe, especially post-COVID or during COVID, I think it was already like this before. But this team's been through a lot. This is what people told me. Okay, we lost this promotion game and now we feel okay. Because we know you have a plan.

1:01:10Because before it was life and death. Because for a lot of these teams, they can't afford the next year of losses if they don't get promoted. Oh, wow. So then the town wouldn't have had a team at all. Yeah, or the team goes bankrupt or it gets relegated because they can't afford to make payroll. And so now they go down to the fourth division or they have to sell more players and now the team's guaranteed to get relegated the next year. So yeah, I don't know. I think it's just a shared familial, cultural. It's a beautiful thing. Like watching, even like driving to the stadium on the day of like the first playoff, the last playoff game we had and seeing like all the people wearing like their jerseys, like their kits and little kids with the black and white and I go around, people ask me for my selfie.

1:01:48For me, it's foreign to me. I don't like it. I don't like the fact that I am recognizable to that level, but I like the fact that people have appreciated what we're bringing to the team, if that makes sense. This whole podcast is about competition. Sport is arguably the healthiest manifestation of competition in civilization. Again, it's like bringing people together. That or mating. That or what? Mating. Mating. Mating? I'm just kidding. Clearly you've never been. I mean, there's been a lot of jilted lovers who've done bad things. That's not healthy at all. It can be. It can be. It can make people strive, you know, to work harder.

1:02:28No, you've never been like on a trip where three dudes like the same girl. It's like not a fun thing at all. Right. How do we, you know, from what you've seen of competition throughout your career, When do you think competition is most likely to be healthy and how do we manifest more forms of that in society? I think separating yourself from the outcome in a manner that's understanding that it's competitive but it's not personal and separating yourself from a life and death. My thing is avoiding the life and death manifestation of some of these outcomes. I think once you've separated yourself from the fact that it's going to be okay if you lose, you can have healthy competition and do your best.

1:03:07But think about if it's life and death, now you're starting to talk about people cheating people doing whatever it takes to win I think um I don't know I think sport's beautiful in that regard because it you know most people most people can appreciate the fact the beauty of the fact that you start at a young age in a given sport and so it's like it all becomes part of your part of your identity as you move up into your into your life and I think like the innocence of when you start playing a sport when you're younger I think people keep that purity with them as they go up which I think is quite is quite evident in athletics.

1:03:39Everyone who's made the top of their field in athletics, even like a third division player, they're not the top player in the world, but these guys are still very, very good. It's a great form of soccer. They all started at a young age for the most part, and I think they've kept that purity of the game with them along the way, and I think that's why in some ways, professional sports can still be quite beautiful, even though the stakes are so high. How do the players react to having a foreigner run the team who's got this very analytical approach to the game. They're a beautiful game. Yeah, and who traipses around with his doodle everywhere.

1:04:14He comes into film session. And his flowery shirts. Yeah, the flowery shirts are only boat wear, so to be fair. How do they, you know, it's interesting. I think a little skeptical in the beginning. I think also a little bit like, oh, this is kind of cool. This guy's kind of well-known in some ways about like in some field. But I don't know, it's interesting. I think the culture is so deferential in some ways that the fact that you're the president of the team means a lot. Even if you were someone that they didn't respect, they would still respect you because you're the president. Some players will call me Prezi or El Presidente or Jefe.

1:04:50But they're all really good people. I don't pretend to know all of their intimate details, familial backgrounds, and their interpersonal relationships with their opposite members. but I can see what I see in terms of how they conduct themselves and I'm very proud to have every player who's on our team but there's some funny things too I thought like wow I was going around we have a promotion bonus when we get promoted so I went to a bunch of games and for a while every game I went to we won so every time I would be around them I would hear prima, prima, prima and I wasn't so sophisticated I'm still learning Spanish so I thought they were saying I was number one They would say Prima at me, and I was like, hey, I'm number one, I'm prime, I'm whatever.

1:05:31It's got to be good, right? And then I was like, let me look this up. And it just meant bonus. That's all it meant was bonus. So maybe I'm just like the guy who cuts a check for them. And that's cool too, because that's good enough. But yeah. In general, in football, what do the leagues do to try and keep the spirit of competition alive? Keep things fair? Because I could imagine the game could easily devolve into just basically which teams have the most money to throw at buying the best players. Yeah, that was the one thing that was attractive about Spain in some ways was that there is a real financial guardrail system in place where you can't spend more than you make.

1:06:07So in third division, our division, you can spend whatever the fuck you want because you're not part of La Liga yet. So it's like kind of a competitive advantage to be willing to spend. But I'm trying to buy expensive players or sign expensive players. They just don't want to come to the third division. Like I would pay a lot for some of these players. they just don't want to come because it's worth it to me to avoid the massive if I think they can meaningfully impact our chances of getting promoted. La Liga has very strict rules where they determine what your revenue is, they tell you what your revenue is, and you're allowed to spend X amount of that on players, coaches, and front office people.

1:06:38When I think back of, I used to follow football quite a lot, and I remember this odd time when just like video as evidence was starting to become a thing that was possible and was already used in many other sports football was quite against and very many people and reporters would write about how no no no no we want the randomness of the referee basically oh you mean like these close moments where it's like oh was that offside or not yeah or like the ball goal go in or not and like you can just look at the camera and find out or you go with whatever the referee decided And people just thought it was against the spirit of the game to have camera evidence be used, which now seems obviously insane.

1:07:23But I suppose maybe they wanted the randomness, didn't want it to be touched. But anyway, what I wonder from there is it seems like they were even further behind of the kind of quantitative data-driven approach than other sports. and then you come in there with just like a fully quantitative approach to a team with a lot of history. Yeah, it's interesting. It's different. I mean, I think the one thing that's to our advantage a little bit is I have a history of doing well at this predict whatever. And then there's other people that are much better. They've done it already in football. Like the most successful football teams in the world relative to what they're spending and what they can spend on players and what their results are.

1:08:09are, you know, one of them is run by like the most successful soccer better in the world or the former soccer player in the world. And so like people can be like, okay, maybe he's not as good as that guy. But if we, if I'm like, you know, 2D Tony Bloom, that's not like a bad thing. Like two dimensional Tony Bloom is not bad for the third division of Spain, you know, or like, you know, of Brighton. And then there's the owner of Brentford also uses like a data heavy approach from former gambling. And so while I've never was like a super successful football better, we do have the ability to make models based on data that's available and I think we can use that approach I don't know AI to me is like I don't know machine learning regression analysis is machine learning and that's essentially like a large language model but using the language of mathematics versus iteration so when you're doing a regression analysis you're kind of doing AI but like I don't know I don't know what AI means for when people think about AI like I'm certainly not going to like upload my videos to chat GPT and ask to tell me what we were doing wrong that's for sure Have you seen this video of a boxing match being tracked by AI Vision?

1:09:19Yeah I've seen that There already is that for football Oh okay It seems like it would just give you more items like more fine-grained information There's a couple different problems there isn't a large enough repository of video. All these AI things, they're large language models. In other words, you need a ton of fucking inputs to make things happen. And there just isn't enough recorded football that you could plug in or bits of data. Surely, there's so many recorded games. There is, but it's like the processing power to process recorded video versus words is completely different. You're analyzing every second of every football match that you want to upload.

1:10:01And then you've got to do that over and over. And then also, at what cost? You could also do that, or you could take financial data and try to build a model that could beat the stock market. Like, oh, I'm probably going to do the stock market. I'll probably go towards finance. And so I think it's there, but it's not quite there in terms of it's just not applicable. Let's say, though, in the hypothetical, it is possible to develop some kind of system that could create such accurate predictions. Well, that's what the Brighton model is. I mean, Brighton, I don't know personally, like intimately how they operate, but I feel like I have an idea.

1:10:38They charted data early, really early on. They were the first ones to hire like remote, like, you know, basically remote workers in a different country to watch games and record data. And so these two groups, they did that. In fact, the owners of Brighton and Brentford used to be, not partners, but the Brentford guy used to work for the Brighton guy. But they charted their own data, so they had a massive advantage where they were the only ones with the level of data that they knew was required and they built their models based on that and they were able to predict outcomes, which then allows them to also predict which players are going to be valuable and they make a lot of money on player trading.

1:11:16And they both play the game very differently also, which is interesting. The way their coaches approach the game is very differently. Let's say we get to artificial general intelligence whereby by almost anything a human can do, an AI can do. It feels like sports is one of the few sectors of human life that may be left relatively unmolested by it, right? Yeah, it's like the last vestige of humanity in some ways is these types of competitions where humans can actually still. Now in the background, the machines could be informing people on what decisions they should be making strategically that the human should be making or the coach should be making.

1:11:53but at the end of the day it's still a game like even you know we look at like you know there's certain things like high certain things in football are like plus EV or negative EV like a high cross you know from far outside the pitch across the you know across the center of the penalty area is pretty low EV versus like a low on the ground cross but like if you're a player and you're barreling down like you have to practice in such a way that you can understand like we had a player who was crossing the ball way too much and we were just like hey this isn't a plus cv play like like sometimes you're crossing the ball and there's no players in the box like what's the point of that but you know he has taught at some point that i'm a right back and i have to learn how to cross the ball yeah and so like you know we tried to show him some stuff and he was like yeah but i'm playing and it's a game it's and you have to respect that that they're playing and it's a game and they can't they're not robots but you can still improve and you can still get better and you can still make better decisions and so we're trying to identify what is and isn't the proper strategy and reinforce that through practice.

1:12:53I think that's the coach. I spent quite a bit of time with the coach. I think that's his approach and he has full reign to run his practice and do his thing in any manner which he see fits. And I think they do such a good job of making the practices geared towards making good decisions in games because you're iterating it over and over and over again. And so the machines, yeah, they're going to leave probably sports alone. That's kind of nice. What about sports betting? Yeah, sports betting is dust. There's ways where you can still make, but in terms of the scale that I would want to support where I'm going to spend my time and get the most utility, it's just certainly AIs can beat sports betting.

1:13:31The same way that I expect online poker, high stakes online poker is already basically dead, right? Yeah, the machines are just better. And whoever has the capital to build and deploy those machines. The owners could be run out by machines too. The machines could be making better decisions than the owners, for sure, but we try to use the machines and at least have some control. Do you think that will happen? I don't know how that would happen. How does a machine buy a football team? If we can figure that out. I just have to presume that anything that AI can be used for that has an economic incentive, it will be used for.

1:14:00Perhaps. I'm just the type of guy, though, where it's like, I plan, but I don't worry. Does that make sense? If it happens, it happens. I'll figure something out. I don't know. Okay, great. to me the worrying is the part that's unnecessary so I'm not in control we've had these conversations about other things and they're like you could certainly make an impact on this but I was like maybe I could, maybe I couldn't I just want to live my life and enjoy my life and spend time with people I care about so if AI ruins something then it ruins something and I don't want to spend the next 10 years worrying about what's going to happen I want to enjoy the time I have left and I think that in as many ways as it can make the world worse in a lot of ways.

1:14:42I think it can make the world better in a lot of ways too. And I think it's just something that I'm a big believer. I'm not super into Buddhism, but I think a lot of the tenets of Buddhist philosophy resonate with me. And so I just think worry about what you can control. If something's out of your control. You know, stoicism's like that as well. Anything out of my control, I tend to not really focus on. I look at my dog and this is not to be funny, but he's got a great life. Is he worried about exactly what's happening next? Like probably not. Look at him, he's sleeping now. He's having a great time.

1:15:16He knows he's going to get his meal at four o 'clock at nine o 'clock in the morning and maybe I'm going to leave and he's going to come with me, maybe not. And it's just like, he's literally has a great life. So I'm not saying I want to be a doodle in the future with AI as my overlord, but I don't really care. Like I really, this is going to sound awful, but like, I mean, humanity, like, yeah, that's not in my wheelhouse. Like I don't, you guys are, you're smarter than me. You can worry about humanity. I'm going to worry about me and mine. Really, honestly, I just want to worry about myself having a good life, treating the people around me with kindness if I can.

1:15:45It's scary, for sure. But it's scarier the more you obsess over it. That's my philosophy. The stuff that you guys worry about, I worry about a bunch of other different things than AI. I worry about just the idea that humans are losing autonomy from different ways. I just worry about the ability to actually earn a living and get up from under. If I was in my 20s or 30s, I would be more terrified about whether I was going to live like an actual chicken but as a human being. In other words, not being able to own a home, being forced to live in these rented places, having some sort of central bank digital currency controlling my every movement, having some totalitarian regime take over.

1:16:28I think I would be more worried about that. Maybe the AI help is what's going to make it easier to control the humans. and that's something that definitely one path yeah that's something that I would worry about more than just like the AI is taking over I think the humans are scarier than the machines do you have any ideas of solutions? no not really I mean I don't mean to like it's just it's just kind of like I feel like I think about young people a lot and I just think like I look at them and I'm like okay what is like they're they've been given these devices to and and endless entertainment as though a draw like So it's two things that happened.

1:17:04The ones who want the actual drug are getting the drug. The fentanyl, the cheap drugs, the whatever. And the ones that want the entertainment drug are getting that. And they want the dopamine hit, they're getting social media. And it's just kind of made them blind to what's happening. Can you imagine if when we were growing up, if someone said the world was just going to shut down and everyone was going to have to stay in their homes for a while, that would have been a completely fantastical. But everyone just accepted it. And the way our information is presented and the way everything is kind of, you know, the way we access information and how it's like highly curated and your feed is curated, your social media feed is, like you no longer see the posts from your friends and the order they send them.

1:17:46It's like, oh, and plus you might also want to see, you want to see this, you may forget about, oh, Igor, but what about this guy? You want to see this guy? This guy might be more interesting. And it's just, there's a lot of that. And I think that to me is, and that's, but again, that's fueled by AI. So it's the same thing, but I would just, but I would have more worries about that and more empathy for young people there than anything else because I feel like that's an inevitability. The AI thing is kind of fantastic. And I think, by the way, the AI thing could be like kind of a thing that's kind of a distraction, like a magician's distraction to what's really happening too.

1:18:15Like, oh, let's worry about the stuff out of our control while we protect you from the AI. Now we're going to put you in these situations to protect you from the AI. And so it's just an odd time to be alive. What advice would you give to your younger self, age 20, if you could now? I think that I certainly sacrificed personal relationships and growth for money and for success primarily financial because I played a game where you kept score with how much money you made that's like my job was how much money you made and I wanted to solve for that all the time so I would probably go back and be like yeah at some point enough is enough you're good spend a little bit more time I think I was more of a I think for me work represented an escape.

1:19:02I never drank, I never did alcohol, I never did drugs, I never had any bad habits, but I was a workaholic. And I think that's very common amongst a lot of people who hadn't identified why they were a workaholic, but they were. And so a lot of people that had some sort of stuff they hadn't worked through yet from their youth will either get into drugs or get into whatever, but the other people will work. And so I think the thing I would probably tell myself would be just to try to figure out exactly what it is you want out of life, like really what you want not like what you think you want and what you think will help you avoid dealing with like some level of pain that might come later or something like that.

1:19:36Is there a method to figuring that out when you don't have the wisdom that you have you know in your mid-40s? Yeah, you can read books from great people who like you could, I mean it's kind of like cliche to talk about Marcus Aurelius meditations but like you could read that book. Here's a guy who has like been through it all and knew he was going to die at an early age, died at an early age and you get this beautiful treasure of him writing his thoughts not for other people but just for himself. He didn't intend it to be consumed but yet it's out there for everybody to read. And I think, yeah, had I discovered that when I was younger, I think it would have had a big impact on me because a lot of it is just like it's just probably like the most it's the best advice you can get, I think especially as a man.

1:20:18I don't know what it's like as a woman but as a man, what I think of as a man what it means to be a man, which is to care for people or to be someone who operates in high integrity, does the right thing reading something like that I think as a young person can't do anything but help you for sure so there we go folks thank you for listening and of course huge thanks to Bob for such a fun conversation and for being such an open book on so many of his like strategies and fun stories do check out the show notes below uh some links to of course cd castellan as well as some sort of betting strategy stuff lingo that sort of thing I do also give him a follow on twitter and And also apologies for the quality of Igor's mic.

1:21:00It seems like we forgot to plug it in. Podcasting is hard. That's all I will say. But yes, thank you so much. And I will see you next time. Until then, keep on win-winning.