The game of poker is quite profound when you really think about it. Jerry ‘Imperator’ Monaco is one such deep thinker who has a wealth of insight into the game’s many philosophical underpinnings. He’s a poker polymath who has earned a reputation in the Red Chip Poker forum as having a unique and fascinating spin on strategy and the game as a whole. Get a new perspective on poker in this week’s podcast.

Featuring: Shaw & Monaco

Jerry Monaco, also known as Imperator on the Red Chip Poker forum. Welcome to the Red Chip Poker Podcast.

Jerry: Thank you very much and I’m happy to be here. It’s been a long time since you first asked me.

Zac: Yes, it has been. I’ve seen you here and there in the casinos while I’ve been playing. So I know you have been active in the poker and I’m excited to hear the update and the latest from you. I know that you are a poker philosopher. And for our listeners that don’t know, Jerry is well known in the forums as a philosopher of poker. I wanted to start from that angle. We were just talking, before we rolled about philosophy and poker and the intersections. Tell me about how this love of philosophy started and how you dovetailed it into poker.

Jerry: I started out wanting to be a physicist and I went to school at a very good school and I met a lot of physicists there and found out that they were geniuses and I was not. I still retained my love for physics and for scientific theory in general. I was never good with experiments or anything like that. I was always very theoretical in my own mind. So it seemed to be an actual switch from my undergraduate physics to philosophy and specifically the philosophy in history of science was my graduate school work. Also, since I was a child I was interested in games. Games of various kinds seemed to give me something to think about all the time when I wasn’t thinking about reading Anna Karenina or reading something by Bertrand Russell on relativity theory. It was games that gave me something else to think about.

I learned both chess when I was about six years old and I used to sit around at my family poker games, where they played dealer’s choice, mostly stud and variations on stud and learned poker very early, from seven or eight years old from my grandmother. What I was always interested in, sometimes, was the intersection between how you think about rule based games and how you think about theories and models in science and philosophy. We were talking a little bit before the podcast that you sort of come at the two of them from opposite ends. What you do when you try to think about the rules of an ecosystem, if you’re an ecologist or evolutionary biologist, is that you try to derive the rules of the ecosystem from what you study. You test out various theories and you make the models. The models become part of your theory and you try to derive the rules of any particular kind of ecosystem from your models. In other words, the models and the theory and the study of the ecosystem come first and the derivation of the rules or what you might call in some areas of science the laws of nature come second.

What is interesting about rule-based games, whether it’s poker or backgammon or gin or chess, is that you make the rules first and you don’t know necessarily where the rules go. You try to derive the what you might call the ecosystem or the natural laws of the game from the rules that you made that provide your model in the first place. So for me, playing games seemed to be science and philosophy turned upside down. That is one of the things that has always attracted me to whatever game I’ve played. I’ve always dedicated myself to one game at a time, whether it was chess or for a while backgammon, and also for a while gin, though I was never very good at gin, and now poker. I’ve never dedicated myself to two games at once. I’m kind of monomaniacal about that. I pick one game and that is where I go.

Zac: Monomaniacal is a word that I bet applies to a lot of our listeners, when it comes to poker as well. That’s really fascinating. I’ve never thought about poker that way. For our listeners who might have never really considered deeper philosophies behind poker, one of the things that we talk about a lot on the podcast are the interactions and intersections between poker strategy and life and living life and your philosophy on life. Where do you see those two things interacting and for someone who’s just starting to think about the philosophy of poker, where do you start?

Jerry: Well, I start from the fact that we live in an economy that is an economy of life and limb and I’ve written about this on the forum. It’s one of the first things I ever wrote about on the forum. We live in an economy of life and limb. You have to go out and make money and help to live the life that you want to lead for yourself and your family and your social group. There are people that literally will lose their lives or lose their fingers from the work that they do. I was once a union organizer and I encountered mostly women of color trying to organize a chicken processing plant. They were some of the bravest people I ever met. They risked their jobs. They risked being kicked out of their houses and only to form a union to maybe make a few dollars more. This is the real economy of life and limb. When we create the economy of poker. We are creating a artificial economy with its own rules. And you have to approach it within the subsystem of those rules alone. But it’s not like those two economies aren’t connected in some way.

The way I would say they’re connected, the intersection of them, is what we call our poker bankroll. You can analyze the artificial economy of poker and see how it’s connected to the real economy of life and limb, which involved casinos and rake and underground games that I play in where the masters take their own rake. In that case, it also involves the force of law and many other things. That and it’s actually what you call your poker bankroll that is the intersection between the two. That is why I personally come at strategy from two areas. I think you have to come at strategy from two places at once: top down and bottom up. Somewhere in the middle you meet and you get things like game theory and for me, the behavioral economics and how people general think and mis-think about probabilities and you also get what I would like to talk about at some point, portfolio management or how I would note it as the Kelly Bet. There’s a lot of things-

Zac: Let’s explain that a little bit more because that is fascinating. You seem to have an interesting tangent to go on there. Go for it.

Jerry: Well, the last thing about portfolio management, you mean?

Zac: Yeah.

Jerry: Okay. Well, for one thing, we should look … if you’re going to look at things from top down, the game theorists try to do an abstraction backwards, a retro analysis from the river backwards. That is one way to look at tactics and strategy from the top down. You look at the river backwards. But if you’re looking at your whole meta strategy, what you’re looking at is your buy-in. You should … I believe that players should look at each buy-in as a single bet. No matter how many times they buy-in at the game or how many they plan to buy-in at any specific game, each buy-in is one bet. You should look at your own portfolio or your own poker bankroll as how much that bet can counter. Now, if you start off looking at each buy-in as a single bet, something becomes clear in any no limit game. I’m talking about nay no limit game, whether it’s a poker no limit game or some other no limit game that you can imagine. What becomes clear is that you have a ratio between attacking the stacks of others and protecting your own stack.

In some ways, no limit hold’em is that balanced ratio between attacking the stacks of others and defending your own stack. Now, that is not something that … when you talk about it like this, we’re talking abstractly. But when you’re in the midst of trying to construct your strategy, what you have to realize is that somehow by working backwards through the whole session, and I believe the proper area of analysis is a session of any particular poker game that you’re in, you are constantly trying to balance those two. My problem with people that play too tight is that they’re constantly protecting their stacks. My particular kind of argument sometimes with the great players on Red Chip, like Soto and Berkey, that they, underneath they realize that there is some stack protection that you do, but when they talk in the forums and in general, there’re not much talking about the other balanced side of defending your stack.

My point about this right here is that if you look at the whole session from the … and do a retro analysis from the back to forward, you realize that sometimes you’re going to risk your stack in a way that is going to lose it. And you just have to do it because if you don’t do it at times, you are not going to be able to either protect your stack in a way that you want to or attack the stacks of others in the way that you want to. If you look at it in this context, things like stack to pot ratio and when you calculate stack to pot ratio and aggression versus game theory and all of that stuff becomes a lot clearer. You suddenly realize that the kind of analysis that looks at your buy-in, whatever that buy-in is, as a single bet makes everything within the context of all of the arguments, the whole strategic landscape of those arguments a lot clearer.

My argument with people like Doug Polk and stuff like that is that they don’t look at this whole landscape and they don’t … even though they constantly harp on things like balance and such like that and even retro analysis from the river backwards sometimes, they don’t actually go far enough into the meta strategy of the whole session.

I’ve basically come to this strategy through the arguments in the forum, even though I’ve not expressed this very much in the Red Chip Forum myself, but that was the beginning, realizing this was the beginning of developing my own strategy. Where portfolio management comes in is that I’ve always been very fascinated by the mathematicians, like Claude Shannon and a lot of the people that gathered around him including Thorpe, who developed card counting in blackjack, they … unknown, Claude Shannon who developed information theory also contributed to betting theory to a certain extent. One of the people around him was named Kelly, who died young and developed what was known as the Kelly Bet, in which he analyzed through mathematics how much of your bankroll you should risk on any bet or investment. When I started applying both information theory, as opposed to game theory, information theory and this kind of portfolio analysis to poker, is when my own particular strategy began to come together. That’s it.

Zac: Does it recommend a specific percentage of your bankroll to risk at any given time or is it more of an algorithm?

Jerry: Yes, it is a algorithm. If I remember correctly, when he was talking about investment strategy, he was mostly saying that no more than 5% at any given time should be risked in any single investment. That doesn’t mean that you can’t do less or at time, given the calculation that you couldn’t do more, but it’s generally 5%. If you lose that 5% in a single bet, then the next 5% is absolutely less compared in size, though the same amount compared to your bankroll.

Zac: Well, I’m really glad you brought that up. That was a great discussion in our forum about the philosophy behind bankroll management. It’s a tricky subject that requires a little bit of philosophy in order to really understand it fully. I would say the same of mental game in poker, it’s something we talk about on the podcast a lot. I’m sure there are many intersections with philosophy there. How do you approach this game of poker mentally and use you philosophical prowess to gain and edge over the competition?

Jerry: I am sometimes better at that, after the fact that I am over the table and it depends on a lot of things. The first thing that I need is sleep and exercise and if I don’t get that, no matter how much of my own personal stoicism and philosophy that comes into it, it really doesn’t matter. The first thing that I would recommend for anybody is sleep and exercise. Beyond that there is a certain amount of mental fortitude or mental toughness that comes in. The thing is, is that some of this stuff is a matter of life experience. The fact is, I’ve been very poor in my life and I have family responsibilities now to people around me, but I’m not afraid of being poor. I’m not afraid of losing everything, if it comes to that. In truth, I keep my poker bankroll separate from the investments I made in my life, so I don’t have to be too afraid of that. But the fact is, is that I play poker as if the poker bankroll is all that I have. That doesn’t make me risk adverse, it just makes me realize both the privileged situation that I’m in and gives meaning behind every bet that I make.

But is also can cause tilt if I am not rested and in good health. As I say, that’s the base on which everything else is built on. Besides that, like I said, I’m not really afraid of losing money. I’ve never been. Even when I’ve had very little money. I’m not afraid of losing my last $10. It is a little bit easier for me to make the bet that will satisfy the EV than it is for other people. At least that’s what I’ve found. When I lose, there are times when I’m frustrated. And the frustration usually doesn’t come from losing, it comes from whether I’m playing well or not. There are times when I realize I’m not playing well and for some reason I can’t make myself quit because one of the things that you should do when you’re not playing well is take a break or quit for the evening. That is my main form of, I don’t even know if you would call it tilt, but that’s my main problem. I don’t want to quit when I all of the sudden realize I’m not really playing well, I’m not thinking well, I’m not hearing my own brain very well. There is too much noise and not enough information coming through.

But, when I am playing well, I don’t mind losing. It never sends me on tilt. That’s the only thing that I say. I just want to make the best plays. I want to be a very good player at all times. I want to be able to read the cards and read the people around me in a way that I see clearly. That is what concerns me. Having that in mind, I don’t go on tilt for those reason. Now, let me talk about a time I did go on tilt last week.

I was so tired. I’d been playing … I’d been having a goal of playing four sessions a week at 25 hours a week about. But that week I’d played close to 40 hours that week. Plus, I did about 40 hours of my own personal work: writing. So it was an 80 hour week and it was a Friday night and I was just pushing myself. And I was so tired, I didn’t realize what I was doing and I didn’t care. So I had a $1,900 loss in one night, which is fine because I’d been doing so well and it didn’t really hurt me but it was one of those times when I could have quit when I was $700 down. I just didn’t want to make myself quit. I knew I was too tired to play, but I just didn’t want to make myself quit because you have this ideal of yourself that even though you’re older, you still have the stamina of the 25 year old who marched through mountains in El Salvador and got shot at and all of that stuff. You can be my age and still feel as if, in your own brain, you’re 25 years old. That’s a mistake. That’s a mistake in self analysis. That’s a mistake in your own self perception.

I think that tilt comes from those kinds of misperceptions of yourself more than anything else.

Zac: Sure. The thing I get out of that cautionary tale is just the idea that even if you’ve been playing poker as long as you have and studying the game as seriously as you have, that never truly, completely goes away. We are all humans living this human experience and prone to human mistakes. Now, I’m going to ask a tricky question. It’s tricky because it’s not strictly a strategy question, but I’m going to try and make it a strategy question eventually. I want to talk to you about morality in poker. It’s something that we’ve talked about off table. You mentioned the privilege of being able to sit here and bet all this money. You also have talked about charitable ideas in the past. I’m curious to hear your thoughts on, just in general, the morality of playing poker, winning other people’s money, having the skill edge, lock all that stuff, give me your philosopher’s take.

Jerry: I think that this is within the circle of the game. All of those things are pre-game considerations and we should talk about them seriously before you sit down at the table. You should think about them seriously before you sit down at the table. But once you decide to sit down at the table, all you’re interested in is playing the best that you can and as far as you’re concerned, those chips, I think I said this once on the forum, those chips could be potato chips and you’re just trying to get the most of them as possible. Now, whatever considerations of charity and love for your immediate family or immediate neighborhood and human beings in general that you have, have to be factored into yourself as a person. I know that we are in a game of probabilities and variance and gambling. I myself started playing this game because I found myself in the position of wanting to save more of the money that I make from work, which is writing, and still give as much as I could away as I’ve been doing ever since I’ve been young.

One way or another you contribute, you contribute with your work and your body or you contribute by giving away part of your capital. It is better to contribute with work and your own associates with other people, but I have not been actively involved in the kind of political organizations that I love for a long time now. I’ve found that I needed … I give a lot of money to immigrant’s rights organizations for instance. When I was a union organizer, I used to organize immigrants into unions. The difference between giving money and organizing immigrants into unions is a huge difference, but giving money is something that you can do instead. It doesn’t make up for active organizing though. I … part of my poker bankroll, over a certain amount, and right now goes to, especially immigrant’s rights organizations and to a village in El Salvador that I was in, in the 1980’s, which is building a water project.

That’s where I calculate at the end of the month how much I made and if I’ve made a certain amount and it’s still above my basic bankroll, then I give away a certain percentage of that money. I don’t feel bad about what some people call a higher level of bum hunting, which we as poker players do when we hunt for the best tables to sit down at and stuff like that because most of the people will sit down at this table … these are first world problems that we’re dealing with as poker players sitting down at these tables. There are some people that are probably in bad shape because they’re addicted to gambling or they’re addicted to alcohol, which makes them throw away their money. The thing is, is that we don’t know who those people are that we encounter.

We don’t know what that is about. You can’t … there are ways to solve those problems in the world, but they’re not over the poker table. Basically, the artificial economy that we create over the poker table is something that we choose. You can’t choose or not to choose to live in a village where you don’t have water or to leave a country where you’re persecuted and come to another country where you shouldn’t be persecuted. Those are life choices that are the force of circumstance. Whereas, we’re not forced by any circumstances to sit down at the poker table. That’s voluntary.

Zac: Brilliant. Well, I think could we have our own spin-off podcast on poker philosophy at this point. Just amazing stuff-

Jerry: I’m actually trying to write a book. It’s more about the philosophy of strategy and how it fits into the real world. I have about 100 pages so far. I don’t know how I’m going to organize it. But partially, you get brief views of it when I write on forums or when I write on Slack and stuff like that.

Zac: What’s the best way for our listeners to reach out if they want to discuss some poker philosophy with you? Should they stop by the forum?

Jerry: Yes, you should, if you’re at the forum, I used to have a political blog. I don’t suggest that you contact me there. I also have a political newsletter that I used to do every week, but since I’ve been playing 20 to 25 hours a week at poker, I’ve been doing every other week. This is all besides my poker playing life. The best way is to just do @imperator at the forum and start a thread that I’m interested in. And I’ll certainly hop onto the forum and write back when there’s a thread that I’m really interested in. The thing is that I’ve been playing so much poker lately that I’ve only had time for my own business writing, my own personal writing, and my own … and my poker playing, so I haven’t been participating in the forums as much as I used to when I was only playing on weekends. Every other weekend or so.

Zac: I certainly appreciate you taking the time to drop by the podcast and I do look forward to continuing the conversation in the forum. It’s always very fascinating. Jerry Monaco, thank you so much for being on the podcast today.

Jerry: It was my pleasure.

Showing 2 comments
  • Alan

    Thank You

  • Satria D

    Beautiful!, Thank you for sharing!