Jack Laskey: How-to Use Poker as Preparation for Life

Brad: Well, hello there. How’s it going, my friend? Welcome to Chasing Poker Greatness. I’m your host, Brad Wilson, founder of poker training site, enhanceyouredge.com, and I am super pumped to have you with me here today. From over the top TV personalities, to the nearly anonymous online grinders, cashing out thousands of dollars a week, to the leaders of poker media, we’re going in search of insights and advice from the world’s best poker players and ambassadors. You’ll hear words of wisdom and words of warning. You’ll look at what keeps them coming back to the table, and what they do in their downtime. You’ll be able to examine how they think and how they deal with the ups, the downs and the almost endless repetition that comes with playing one hand after another for days, weeks, months and years. Some of them have shaped the game. Some of them have grown the game. Some of them have changed the game. All of them have one thing in common. Each of them in their own way has achieved poker greatness. Today, I have the pleasure of sitting down with Jack Laskey. At 25 years old, it’s safe to say he’s likely one of the most experienced young players currently in the game, and speaks with the wisdom well beyond his years. He’s enjoyed success in the online and live poker world since turning 18 in 2012. Although his career and love for the game go back quite a bit before then, like it started when he was 12 years old. Twelve. Jack’s currently a mid-stakes cash game specialist who currently spends most of his table time playing in private games in New York City. You can find him at justhandspoker.com, where he offers pro insights on low stakes games. At the site, you’ll find a weekly podcast, poker strategy blog, and access to coaching services among other things. He’s also signed on as a mid-stakes coach at Solve For Why, a training site created by another Chasing Poker Greatness podcast guest, Matt Berkey, that focuses specifically on live poker strategy. In Jack and I’s conversation, we’ll talk about things such as what poker can teach you about life, the benefits of making negative EV moves, why you should learn to make decisions and act quickly at the table, and why you should be questioning all common poker advice. Jack’s an amazingly deep thinker who asks a lot of philosophical questions. It’s clear that in his mind, the separation between poker and life almost doesn’t exist. He finds a way to use almost everything from one world to sharpen his senses and improve his actions in the other. Many of the answers he gives to my questions weave in and out between poker and life, but somehow, they all make perfect sense and leave you with the feeling that you’ve just been given a new perspective in which to think about things. I love talking to Jack so much that we went way over the normal one hour in what felt like 10 to 15 minutes. And even after we turn the recording off, we still kept going for another 30 minutes. So, settle in and get ready to look at your game, and possibly your life in a whole new way. Ladies and gentlemen, Mr. Jack Laskey. Jack, my man, how we doing today?

Jack: Brad, I’m doing very well. Thank you for inviting me in to your show.

Brad: It’s my pleasure, man. I’m super pumped to have you here. And as you know, the name of the podcast is Chasing Poker Greatness. And greatness to me is one of those abstract terms that can mean a lot of different things to a lot of different people. So, I want to start out by asking you, what does poker greatness mean to you?

Jack: To me, poker greatness is not that different than greatness, independent of poker. And I think being able to think on a high level, and execute on a high level are good goals throughout your life. And poker is a place where I think it’s a good place for people to start approaching their life and approaching disciplines like that since, no, we come from, I guess like school systems and things of that nature that don’t emphasize those kinds of qualities. And poker, is, it’s sort of fun and addictive enough that it can get you over the hump in terms of approaching something in that way. So, to me poker greatness is just like the first step towards greatness.

Brad: Very nice. I like that. Poker 100% teaches you to think critically, if you’re trying to improve that is, regularly. Think critically. Problem solve. Deal with struggles. Mental toughness. A lot of positive attributes.

Jack: It’s such a good teacher that I think this is a really good example of how it’s a great teacher. Something that an anecdote that I got from a friend of mine, Aaron Brown, have you met him?

Brad: I have not.

Jack: He’d be a good guy to have on your show. He’s always been a poker player. I think he was a professional in like the early 70’s, working through some sort of schooling, but he is well known for being the, sort of like an innovator in quantitative finance. I was the, like head of some, or, he had some important title at AQR capital, which is like a big hedge fund in New York. Anyways, he hosts private games here, there, and we had him on our show. Anyways, he talks about an example that I think is really profound, where people who are learning to become investors were studied, in terms of how well did they actually perform under pressure with the things that they were taught in school. So, all these people who went to school to like, learn how to become a finance professional, took a test where they had to wager a certain amount of money out of their bankroll, on weighted coin flips. And they knew that they needed to get to a certain threshold. So maybe they started with $20. And they needed to get up to $40. But they didn’t know exactly how much time they would have. Now, if they had bet, according to the principles that they were taught in school, they would have achieved that goal with like an 85% certainty. But almost all of them, something like over 90%, failed and went broke. And so, even if you learn about these things like risk management, analytical thinking, working under pressure in school, it’s not trivial to implement. And I think we can see a culture of people who, even the ones who you would think would be best trained to, like, thrive under these types of circumstances just aren’t. And Aaron speculates that poker players make much better investors for the simple reason that poker is, it’s very hands on, in terms of learning these things. Like you, you actually expose yourself, you have skin in the game with the types of decisions that you’re making. And so, it reinforces, or it should reinforce good behavior to someone who’s paying attention. And you’ll feel bad behavior in a way that you wouldn’t in a classroom. I think that’s important towards like achieving this goal of greatness.

Brad: And experiential learning is one of the most powerful forms. Do you know why? Why the theoretical people failed, when it came to the test?

Jack: Well, they didn’t implement the theory that they were taught. So, the sort of basic

Brad: What did they do? What was their mistake?

Jack: So, if they had bet, according to their edge in their bankroll, so there’s something called like the Kelly criterion. And it’s basically just a way of calculating your bed size based on your edge and your bankroll. And so, if they had bet Kelly, then they would have almost certainly won, but most of them just made way too large events. And the reason is, I think they would have done better if it hadn’t been this time pressure. But the thing is, time pressure is a, is a constant throughout life, like, you know, we want to make money quickly. Because we can do more. Money is more valuable to us as soon as we get it. And so, it’s very hard to work towards something that pays off down the road. Or it just, it’s natural and economic to try and front load your money to now. But oftentimes, it’s out of your control. And had you just abided by the theory would have been more likely to be successful. So that time preference I think, is the root of a lot of the fallibility.

Brad: Yeah, it, also they don’t know. They’re probably afraid of failing by running out of time. So, they push it. Do you think that’s probable?

Jack: Yeah. The thing is, I wonder what is more embarrassing, like going broke?

Brad: Or running out of time?

Jack: Not getting to the goal? Probably gonna be some. Yeah. It could just be as someone in a gamble as well, you know?

Brad: Yeah.

Jack: I think definitely, most people, like I think there are more people who approach something like poker when they first sit down and play. Have you ever been at the table with someone who’s literally never played before? And they see people folding they asked, like, why are you folding? Like if you fold, you can’t win. Like, it doesn’t it doesn’t it takes them a while to even register why you might not want to just like, put in money until you see the river. And that could just be a feeling of like, you know, math skills and critical thinking from the outset. But I think it’s just a more natural human tendency to like, go for it. And like stick in there until you, so you can hopefully win.

Brad: So, you’re saying humans like action?

Jack: I think humans like action.

Brad: I guess that’s why there’s so many slot machines in Vegas, right?

Jack: Yeah. And it’s like

Brad: Humans like action.

Jack: I think that can sound odd to a poker player who sees a lot of people who clearly don’t like action. But I actually think, that’s why they are poker players, because if you just like action too much, you’re going to be, you’re going to just get slaughtered in poker, and you’re going to naturally gravitate towards these other gambling games. And so, poker, I think it’s actually, it’s a better game. And it sort of attracts in the long run people who don’t like action.

Brad: Sometimes, there are outliers

Jack: For sure.

Brad: That love the action, that are very successful poker players and always in a broken the pits. And I have a few off the top of my head. I won’t get into like, very, like, personal experience with these players. But like, guys that are really, really, really good. That just, they want to gamble. They have some sort of self-sabotage mentality, that that’s in themselves, and they head straight to the pit. But for the most part, you’re right. And in my experience, when I see a slot machine, or will say, a lottery ticket, a scratch off lottery ticket. When I see a scratch off lottery ticket, all I see is I’m giving some dude a dollar. And my expected return is a quarter. And that’s it. Like, I’m giving him a dollar, he’s given me back a quarter, this is not a good transaction, so I stay away from it. And that’s typically how I treat the paid games as well.

Jack: Yeah, I do think that there can be, there can be a time and place to take negative EV to increase your variance. You know, you could imagine like, let’s say, a mobster was after you. And you needed to get this guy a million dollars, you have $500,000. And the only way you can possibly get this guy million dollars and you needed to get them a million dollars, so you were going to die. Like you know, prone it down on black is not necessarily a bad idea in this circumstance. And it’s, I don’t think it’s inconceivable. But there are other instances where taking negative EV to increase your variance makes sense. Like, I even think for myself when I play tournaments. There are instances where probably my EV is higher playing cash. But I’m willing to take a reduction in EV to increase like my overall annual variance. Because just with my living expenses and my volume, it’s hard for me, just purely poker, to move up in stakes, without increasing the variance and a more conscious way, might be short sighted. It also indicates that same sort of preference for money now versus money later.

Brad: And that, it makes sense. I’m pretty sure it was FedEx. They were, I’m pretty sure there’s a story about FedEx where they were running out of money to make payroll. And the founder took like 50k to Vegas and doubled it up, and then came back and made payroll, so that they could keep the company going. It might not be FedEx, but I did read that story. That’s certainly a situation where you’re increasing variants. We’re like, okay, we’re gonna go broke, unless I do something very drastic.

Jack: Yeah. That, in that case, I think that might be a breach of fiduciary responsibility.

Brad: Maybe. They, I don’t think they were like FedEx back then. You know.

Jack: Yeah.

Brad: But yeah. I definitely get where you’re coming from in a few weeks, whenever the mob is after me. And I need to raise a mill. I’ll be out there. You know.

Jack: Slinging the duet table.

Brad: Slinging it after that they will for sure. So, can you tell the audience, how did you get started playing cards? What’s your story?

Jack: I think my story is pretty similar to a lot of people, except for I think I was just on the young end of the age curve. I started playing with friends, just when we were really young, playing dumb games. And then we kind of realized that

Brad: How old?

Jack: Like, you know, 10.

Brad: Oh, wow.

Jack: And then at some point, probably like, around age 12 or so, we realized that hold’em was kind of like a standard game. And a lot of the games that we played like, there was no sort of like high level version of it. So, we kind of reduced the scope of what we’re doing to really just hold them and then sometimes PLO and we, we ended up going to like a grocery store. So, by the way, the guys I was playing with back then, a few of them are also professionals. We ended up being very successful. And I think the reason was we sort of got exposed to the broader world through just sort of stumbling on into online poker. We created an account together that we would play on as a unit. And we deposited money from like Visa gift cards that they would sell the grocery store.

Brad: And you’re twelve?

Jack: Yeah.

Brad: All right.

Jack: So we’re like playing on the couch together on like full tilt, putting, like sit and goes, and then we would, we would do okay in sit and goes and then kind of blow it on cash, and then have to go buy back or go get another Visa gift card. And then eventually, what we also would play against each other in home games. And I think just our sort of desire to beat each other, caused us to seek out whatever resources we could to improve. And then we would obviously share each other because we were incentivized to keep each other in the loop. Because we were playing as a unit online. And I think there’s there was actually a very good way to learn. We ended up by the time we were 18. We decided to take like a road trip up to Michigan, to a casino where we could play at a place called the Soaring Eagle, in Saginaw, Michigan. And we realized that like, we were a lot better already than the people who were playing live. And so that was pretty motivating to continue to improve, realizing that this was no viable source of income. Like by that point, online poker was basically not an option. For a while there, we were trying to scrape by playing like free rolls, because we no longer had any way to deposit. But then eventually, that kind of died off. Ultimately, I was able to build a bankroll through playing on like carbon poker, in probably like 2012 or so.

Brad: How old were you? When you were, or year was it? When you were 18?

Jack: When I was 18, I guess would have been right then, 2012. Yeah.

Brad: 20, 25 now.

Jack: I’m getting there.

Brad: Getting there.

Jack: Yeah.

Brad: Just a kid. But you’ve been in the game for 13 years?

Jack: Yeah. I’ve been playing, I’ve been playing pretty seriously for I mean, since I was 18. And then playing pretty well, I would say, since I was like 16. Playing pretty poorly from like, ages 10 to 16. That’s okay.

Brad: Yeah, I think I think you can accept that, that you were not a great card player at the age of ten.

Jack: Yeah, we, I mean, we were the classic beneficiaries of early run good. And a little bit of delusional thinking that we were better than were. But I think that kind of motivation is a little necessary. If I have always wanted to pull the field of like tournament players, and just get their like results from like their first five tournaments lifetime. I have to think that like, they’ve done phenomenally well over like that first classroom example.

Brad: For sure. I can tell you, my story is very similar, that I moved to Florida, played on cruise to nowhere, I saved up 3k. I was 20 years old. And won like my first 12 sessions in a row, just went on a tear. Deposited money on party poker. A few months later, I think a tournament for 15k. One of their nightly, and then it was kind of off to the races after that. But had I gone down to Florida with my 3k immediately gotten busted and lost everything. I have no idea what my poker career would have looked like. I have a feeling that I still would have gravitated towards the game because I loved the game. But it didn’t hurt. It didn’t hurt to run really good right in the beginning, right?

Jack: No, it does not. It’s very motivating to win, I think. I’ve always had a much greater desire to play during an upswing advancing, it’s obviously not unusual. But I think maybe some people have more of a propensity to want to chase their losses, where I find the losses like they make me just want not want to play and think that my time might be better spent elsewhere. Whereas when you’re winning, you just want to be at the table all day, for me at least.

Brad: Yeah, most people like protecting their wins, and then chasing their losses. I think that’s just again, going back to human nature. I feel like that’s how people react. And I’m like you. I lose, I get stuck. I’m like, I’m not feeling this. My decision making is not on point. I can go spend my day doing something else, something more productive than, then sitting here. But it’s more like a learned thing through poker, I think. I don’t think people innately just quit when they’re, they’re stuck.

Jack: Yeah. I think I personally, if there’s a type of tilt that I’m prone to at this point, it’s definitely more so like a winner still. I think it’s a similar dynamic at play. I think I’ve solved the problem, mostly. But definitely I’m well known in the games I plan for not playing a lower variance strategy when I’m ahead.

Brad: Yeah.

Jack: And I think people appreciate that also. Because I’m, why play most so I live in Brooklyn. I play mostly in private games at this point. And so, the people who I play with, I think to some degree, understand that I’m winning. And I think they appreciate that I’ll give action, even when, you know, I’m ahead. And we’re nearing the end of the night, like a lot of these games have a set ending time, where the action can kind of wind down a little bit, or at least people who are ahead, tend to wind it down. So, I think it’s a good quality in this circumstance. But definitely the sort of general, or just the general tendency of wanting to play more and more, as I’m winning, is something I’ve noticed.

Brad: Yeah. And like you said, the players appreciate that, too. I, in every home game that I’ve ever been to, we had a little talk before we started recording this episode about being fun to play with, being good for the games that you’re in. And giving action. Gambling with folks is certainly a way to be fun. And whenever my students who come to me that play live, you know, they’re like, how do we work on my image, stuff like that. I’m like, just gamble with them, like play red or black. Like take some, either slightly negative EV, or breakeven sports bets. Just have fun, you know, just give people action. And it goes a long way.

Jack: Yeah, I agree. I think depending on situation, different things are valued, more or less. Definitely I think the ability to have a conversation is important. If there’s the easiest topic to learn about, and be able to cover a large field of this sports. I know a lot of players who don’t know anything about sports, and therefore, like, have a really hard time talking with like, male strangers, it can be worth just like trying to get into something, just to solve that issue. And give yourself more of like common ground with the kind of like, one of the male persons that you’ll end up meeting at the poker table. Yeah, I agree. Sports bets, red or plaque, is a good way of giving action, obviously never been the one to say like, no, I’m not doing a random straddle. Never been the one to say like, no, we’re not going to do a bomb pop right now. It also, I think acting quickly, when possible, is helpful. A lot of people don’t like that, don’t like that suggestion. But I think it’s really good just to keep the game flowing. And working on being able to make decisions more quickly, is worthwhile in terms of getting invited and staying invited to games, if that’s something that’s important. If you’re playing in casinos, there’s not as much of a cost to not acting quickly, which is kind of unfortunate. You know, the fact that it’s a public game, it’s sort of suffers from a lot of the same things that like the public versus private dynamic suffers from in other aspects of life. He does have no incentive to like, try and improve the game, since it’s not your game. Yeah, I definitely would recommend for anyone in a private game situation, just try and act quickly. Don’t worry about your last like one or 2% of EV, it’s not worth it compared to being a good contributing member of the game.

Brad: And I’m just going to say, even if you’re in a public game, act fast. Nothing drives me crazier than somebody that takes forever for each decision, like half your job as a professional when you sit down and play people in a live setting is to be entertaining to make the game fun, so that people want to come back. Like, and I feel like that’s forgotten a lot of the time in a live setting.

Jack: It’s, it was really bad during the main event this year, even to the point where like, and I’m not necessarily the guide that they want coming back. But I almost had to say like, I don’t know if I can play this again, because my tables were so slow. I might do one table draw was not great. I had like the VD could tie a bunch of like, South American pros who played well, but they took so much time, like we were playing maybe, maybe 15 hands an hour, probably more like 10. And it was just excruciating for everybody. And I just, I understand that to mean the man that you want to play your best. But at a certain point, you have to realize that like, you know, it’s just a classic tragedy of the commons like no one’s incentivized to change unless everybody changes and therefore no one changes. So

Brad: Yeah.

Jack: There’s not much to do about it other than just complain about it with jar.

Brad: When I worked for run at once, you know, they built their own poker platform. And I had a call with their developers, and I pitched an idea, and I’m like guys, for tournaments, instead of just having the time structure, why don’t you create a system where you have a pool? And the levels go up based on a certain hand threshold. So, you play whatever, 70 hands per level. And once everybody in that pool finishes the 70 hands, then the level goes up, right? To eliminate the stalling aspect of it, and places are determined by which hand you bust out on, in each level, and in the chip stack for the specific hand to get the places right. I mean, there has to be a better way to incentivize people to act quicker, because I don’t play live tournaments. And I don’t play online tournaments. And that’s why. People act so slow, it drives me crazy. Like we are here to play poker. We’re not here to stall, and act like every decision is the end of the freaking world, because I know it’s not. Like, you know, your decision was made two minutes ago, like, why are you taking time out of everybody’s life by stalling? It just, it drives me absolutely insane.

Jack: Yeah, I think, I think drastic changes would be necessary to fix the problem. And it’s not necessarily a bad idea. I think the things you could do. The problem with going hand for hand earlier, or even like, 70 hands for 70 hands is that you solve the problem of stalling by making everyone wait, you know, as long as like the longest table that actually had to play out played out. And so that can be helpful, but it has its own issues. So, I think like in live at least, a shot clock will make a big difference. And I know that it’s like a sort of uphill battle to train dealers and to get people used to it. And it probably would cost money short term. But I think in the long run, it would pay off. If you want to sort out the bubble, I think you’d like to shorten the shot clock on the bubble. It sort of sucks, but it’s fair like it, you know, everyone has 30 seconds to x. And then when you get 100 off the bubble, you know, in a 10,000-person tournament, like 10 seconds shot clock, better know what you’re doing.

Brad: It’s an interesting psychological thing too, because, you know, you mentioned and that’s the problem, right? The 70 hands, you have to wait for the slowest table. However, with the current system, to get to 70 hands, you would likely be waiting much longer to play 70 hands, it’s just the waiting is in between each hand. And not all right at the end, you know. But I’m with you, like shot, do something like, whatever it is that you got to do, do something. Because it’s the worst aspect of tournament poker, like I would play tons of tournament poker, if guys acted faster. But that’s my, that’s my biggest pet peeve. And in cash games, it doesn’t happen so much. Because there’s not, the incentive is to play more hands per hour.

Jack: No, it’s a, it doesn’t happen. Part of it is that there’s, there’s no, there’s really no tolerance for it. Like, the culture is play fast. Whereas in tournaments, the culture is not play fast. The culture is like, it’s informed by the sort of televised version, where, you know, people sort of glorify in sitting there on camera, you know, waiting to fold.

Brad: I just, maybe we just need to hire somebody to walk around the tournament and just slap these guys in the head when they take too long, like consistently, like you’ve had the clock call on you four times, boom. Okay, go.

Jack: Yeah, we were talking about this before we started recording, but you were saying that the culture of seriousness in tournaments is frustrating to you. And I agree with that in this context. I was saying earlier that the vibe of tournaments where people are taking it very seriously, doesn’t bother me compared to like, the vibe in some live cash settings where it’s just sort of a general disinterest. But I will say that the serious swiftness with which people are taking these actions makes it feel very personal to them. When you insinuate that like maybe they shouldn’t be maximizing their edge and instead should be doing something else. And I was faced with that. I actually called the clock on tend to Vt kaitai after it was taking like, nine minutes on like a not so huge river decision and like level three main event.

Brad: Yeah, God.

Jack: And another pro said to me, like, after I called the clock and like the whole thing unfold at the end of the folding. No surprise. It was like, why would you, like why would you do that? Like, no, this is like the main event.

Brad: Because due to taking nine minutes to make a decision, I Lord, I’ve never been involved in. I’ve been playing cards for 15 years. I’ve never been involved in a hand where in the first three minutes of tanking I needed the next six minutes to come up with a decision. Like it’s that sort of thing is just wild to me. And we are, I’m going off on a tangent way away from my questions.

Jack: Yeah, let’s stir back in.

Brad: Yeah, let’s go back in instead of complaining about these idiots taking nine minutes a hand. And yes, I called that guy an idiot. Because

Jack: it’s sad though. Because they’re not idiots. They’re so smart. But

Brad: They’re social idiots or something?

Jack: Well, just I think it’s an important lesson in life, something that I have come very in focus with over the last couple years that like, there’s a lot of very smart people who are just wrong and stupid about specific things. And this is one of those areas.

Brad: You would think that the great tournament players would want to get more hands in to, in each level was

Jack: I think the greats tend to.

Brad: Yeah.

Jack: More so.

Brad: It’s the goods.

Jack: The goods tend to be the problem in life, because the goods, the greats are so great that they understand, they see the big picture, and that’s what makes them great. And the goods don’t, but see themselves on the level of the grapes and therefore think that their decisions and opinions should have the weight of the greats.

Brad: Yeah.

Jack: I disagree with that.

Brad: That makes a lot of sense.

Jack: And it’s not to say that I am a great at it by any means. I just, maybe this sounds wrong, but I guess I think I have some level of intellectual humility to think that, you know, or at least social humility and think that maximizing managing the situation is not necessarily the right thing to do.

Brad: Right. So, what is your biggest poker failure?

Jack: I don’t know. I don’t know that I’ve had one.

Brad: Okay, what’s the time that you felt the worst about playing poker?

Jack: Okay, that’s, I have that. So, when I graduated from college, I went on a road trip with a friend of mine, who was my former co-host on the podcast that I do, Just Hands Poker. He and I wanted to do a road trip where, you saw a lot of country but also played a lot of poker, and played all over the country. So, I’m thinking like, alright, you know, I have, I have X dollars now. I’m moving to New York after this trip, to live with my girlfriend, who’s now my fiancée. She’s the reason I ended up moving to New York. I did not move to New York for the poker, although the poker is very good. Anyway, so we set out on this trip. And I’m thinking that this is like, you know, how I basically spin up my savings into like, an appropriate amount of money to live in Manhattan. And so, it’s like a two-month trip until like six weeks in, we’re in Las Vegas. And, you know, I’m starting to, we start off the trip, I’m on a huge downswing. So, we get to Florida, I’m not waiting

Brad: What does huge mean?

Jack: Huge means like, relative to the amount of dollars that I had to my name, probably like 40%, were gone. Yeah.

Brad: That’s big. That is huge.

Jack: Luckily, at this time, I had access to staking. So, like my ability to play wasn’t necessary, or it wasn’t dependent, me like having that assets. But the idea at the beginning of the trip was to like, spin up my net assets. And so, by that point, I was like, already heavily supplementing my role, through staking, which really was going to limit my potential upside, and sort of broke even up until Vegas, and then we get to Vegas, and we’re playing 5/10. And I just got crushed. Over not a very large sample. But if that moment, it became clear that like, my whole planning around like, my results in a two-month trip, probably putting in like, I don’t know, something like 25 hours a week over a two-month period. It was very naive to think that I could count that was money in the bank for me, and that I should be like planning based on having a very successful two- or two-month period. And so that was a tough lesson to learn. And it put me into a pretty tough spot that luckily, I’m on the other side of years later, very much on the other side of. But it definitely made having to like, pick up on my stuff and move to New York City with a lot less money than I was hoping to have, in my earning potential greatly limited. That was a big

Brad: How did it feel? What were you thinking, when you’re going through that downswing? Did you cut your trip short?

Jack: No, but I was planning on going after the series, and I didn’t do that. So, no, I mean, it was overall was still a really fun trip. But as far as, as far as I had set this goal for myself, which was it wasn’t unrealistic, but it was unrealistic to think that I was going to achieve that goal more than say, like, 50% of the time, and I definitely underestimated the downside. So how did it feel? It felt like, I was kind of fucked, but am I allowed to say that?

Brad: Yeah, go ahead. I don’t care.

Jack: Yeah, I felt like I was kind of fucked. And, you know, I ended up just getting into great games in New York, and like, running really hot, and it all worked out. I don’t know.

Brad: Yeah.

Jack: It could have been bad. I mean, I could have had to like, either, have my now fiancé be basically supporting me, or like move back to Cleveland where it’s a lot cheaper to live. But I didn’t have to, I didn’t end up having to face that decision. But it got very real for a second. And so, my financial planning based on anticipated poker results, has since then started to include a lot more room or a lot of room for deviation.

Brad: Yes, playing poker with expectations like that. Oftentimes, I found in my career, they just smack you in the face. I, currently right now, I’m doing a thing were, called a 30k, in 30 days, for this month of September. Documenting, I’m recording every one of my sessions. And the goal is to make 30k for the month of September, and I’m a weekend and minus 11k. And I’m documenting everything. So, I have a session where I lose 10k. And I’m like, I’m really going to upload this and put it on my website, and people are going watch me lose 10k. It’s very, there’s this high level of vulnerability in doing that. And I’m like, okay, now I got three weeks to win 41k like this is, and typically in my poker career, when you when you have expectations, like oh, I’m going to make, you know, my goal is 2000 a week or 10k this month, or whatever it is. For some reason, those are the times that things spiral out of control, for me, is when I play with no expectation, just making great decisions that things go well.

Jack: Yeah. I think it’s sort of the same thing we were talking about earlier, where when you introduce that time pressure, and then you increase like, your preference for short term results. It’s dangerous from a mental game standpoint. And it’s also, I mean, for me, I think it made me play a lot worse. I think I was by during periods of that trip, I was playing poorly. I think I probably was not winning, just because I wasn’t doing the number one thing to do in live poker, which is like, fold a lot versus aggression from weaker players. And I was just trying to convince myself that like, this was the exception to that. And even if you only do that for like a week of your life like that will, that week will cost you a lot of money. Unless you’ve run very hot.

Brad: For sure. And I had the tape for me, so I can review it. And I do plan on, I do plan on reviewing these sessions where I get crushed, just to see if the social aspect and the time, the time limit is affecting my decision making. But, what do you consider your biggest poker success?

Jack: To me, I think a lot of my successes. So, I’ve been successful playing like, I’ve managed to like support myself in a very expensive city, mostly from playing. And I’ve had a lot of success playing like tournaments in the last couple years, playing live tournaments. And I was successful to have grown like an initial bankroll playing online, you know, on sites like Carbon Poker. But I think that my biggest success has just been from like a learning standpoint, learning about the game to the point where I have a lot of people who really value my opinion, and learning a lot about myself and a lot about the process of learning through doing that, such that I’ve been able to pick up other things in life, that are really important to me now a lot more quickly because of it. I think that’s my biggest success, that for me, that kind of crystallized in like, relatively early in my career being approached by Matt Berkey to join the software y team based on, not that long of a relationship. But one that sort of really featured the way I think about the game, and just my general like professional approach. And knowing that he valued that enough to bring me on as a coach for them was really validating. So, I think in a lot of senses, that’s probably my biggest success. But like I said, I think I’ve been pretty successful throughout. And I feel very lucky to be able to say that.

Brad: Yeah, I’m with you. It’s hard to have a sustainable career, playing cards taken from somebody that seen many, many people just disappear off the face of the earth over the years. And I’m not sure if you’re reading my follow up questions or not. But my very next question is, what is your process for regularly improving your game look like?

Jack: So, when I was younger, definitely it just looked like consuming as much knowledge as I could from other people. Because at that time, there was still so much, sort of more advanced thought out there for me to be exposed to so many concepts to learn about, and just have people kind of guide me through the process of thinking about poker, what I think you can

Brad: What people?

Jack: Yeah, you know, I actually learned a lot early on from like, the Full Tilt Academy, which was kind of like a silly thing, but just learning about all these terms and plays and stuff and trying them out for moving people, just like Gus Hansen. You know, that was an important way to get the ball rolling. And then later on people like, you know, Galfond, and I really love Thinking Poker podcast, which was helpful thinking, hearing sort of maybe, you know, a level of thought in between those two sorts of people. But really, I was pretty, I’ve always been, I tried to be liberal with who I’m willing to, like, entertain your thought process, because I don’t think it’s an, I don’t think it’s good for anybody to just take someone’s word for it. And if you know how to try and verify someone’s conclusion for yourself and think things through on your own, you can learn a lot from a lot of different people. Because you don’t have to just rely on blind truth. You can just take something from someone, take something from somebody else. Like in the last couple of years since working with like networking those guys, I’ve definitely learned the most from them, although I disagree with them on a lot of things. And the ability to do both of those at the same time is really important.

Brad: Yeah.

Jack: I think accountability is a really important thing to have in life. And being accountable for like, your thoughts and opinions, and your process and your strategy is a really good way to improve. And part of that accountability comes just from playing and having to deal with the financial results of the decisions you made. But I think that we can all see that the level of potential self-deception is rather high. So, I think having other forms of accountability is  really important. And so, for me, it was, okay, so to preface this, I am a piano player. So, I went to school, in part to study piano. Brad can see that I have a grand piano, five feet behind me. So that’s, that’s a big part of my life. And so, I have a really wise teachers for piano, who really pushed me early on into teaching, even though I wasn’t, you know, any kind of great player, I knew enough to be able to teach people who know knew less than I did. And my teachers, sort of mantra was like, if you can’t explain it, you don’t understand it. So, for me, it’s always been a very natural and obvious thing to do, to try and put whatever I was thinking at the moment out there in some sort of educational format, to sort of prove to myself that I actually understood what I was trying to do, well enough to communicate it to an audience. And also, to subject myself to the feedback from that audience. People will tell you if they disagree with you. And I found that format of just trying to get my thoughts out in words, in a way to try and communicate an idea to somebody else is the best way of trying to tease out like, what are the things you really feel comfortable with? And know, what are the things you thought you knew, but when you try and explain it, you really don’t know it? And going through that process again and again, you know, I’ve recorded 160 episodes of my show. I have a private slack group for listeners who want to support the show, and they come on, and they can ask questions, they can post hands. I’m giving written responses, like all day, every day, to people who are asking me questions. And I think that that process of trying to make things very explicit, it’s really important for growing in for learning. And so that’s, that’s really my main study now is teaching and I think it’s the best kind because everything that you’re processing in your brain, or our brains are kind of, like hardwired to be language oriented. And so, if you can put things in the language in a useful way, it’s a much better way to like learn and retain, versus just kind of like, let’s say looking at like a solver and I use solvers, obviously. But like, if you just look at a solver output, you can feel like, oh, yeah, I got this. And then when you get to the table, like if you can’t explain in words with the solver was trying to do, it’s going to be very hard to implement. And the truth is, it’s really hard to pull out a solver trying to do in words, because solvers are not wired the way we are to think in terms of language. They think in terms of math

Brad: In the solvers, you have the, you have the Geico issue too, where, you know, garbage in, garbage out.

Jack: Yeah.

Brad: If you’re putting in bad data, and then the solver spits something out, you’re like, okay, this is what I should do. But, you know, however you structure your nodes, however you’ve analyzed the situation is incorrect. Then you take that to the table, and then you get crushed. And you don’t know why. And plus, I think, in a lot of ways, like solvers are pretty impractical too. When you have a mixed strategy to implement, you know, you check 38% of the time. Humans are not wired to be able to check 38% of the time. It’s just not how we are.

Jack: Yeah. Yeah. I think solvers are more of a research tool, than a tool for generating useful strategy. And the way I think about it is like, solvers, by the way, that they actually come to solutions using algorithms like counterfactual regret. They are able to pick up on all the details or the mathematical details that we would describe through concepts, and they are able to discern those in proportion to one another. And so, if you get a result that is different than what you might have expected, I can kind of indicate that your weighting of the various factors that you kind of have in terms of like, linguistic concepts in your head, is probably off in this situation. You can try and tease out why.

Brad: Yeah.

Jack: But in terms of like, trying to play like a solver, like, have you seen this thing that, uh, what’s the, what’s the, like, high roller? There’s a guy or Nietzsche, just came out with like a trainer.

Brad: I’m gonna say no. Because I don’t, I’ve never, I’ve spent some time with Pio. But for the most part, I haven’t spent a ton of time with all the software, like snowy and stuff like that.

Jack: Yeah, I think the point of this, the point of this software is to like, teach you to play like a solver against the solver. So, it’s like turning the sort of solver study into a more interactive thing. Which is, I mean, it’s, it’s kind of cool in a way, and I think it would be fun. But putting that as the goal in the forefront as like, what we want to do is train you to play like a solver play against solvers.

Brad: Yeah.

Jack: This, to me, it’s like moronic.

Brad: It’s stupid. Yeah.

Jack: And it’s not just because of the impracticality. But it’s also like, solvers don’t actually make that much money. Like, if you try this at home, run a solve, and then make one of the players way worse, and see how much more money the solver makes. It’ll disappoint you. Solver. It’s designed not to lose, it’s not designed to win. And not being able to not lose is a good skill, in a sense. But we’re not here to not lose, we’re here to win. Rake will eat you up. If you’re just not losing, you have to be winning. And so, learning via solver with a goal of playing like a solver, is a very poor way of spending time, in my opinion.

Brad: And plus, in a live poker setting, I’ve never once been sitting in a table, heard the floor, say seat open, and a solver come in, sit down and play against me at the poker table. Not once in my 15 years has a solver set down so that I can play optimally against it. Human beings just are not solvers. We don’t think that way. We don’t react that way. That so yeah, that it’s very silly thing.

Jack: Yeah, and I think like you, even in an online sitting where like, you may actually be playing against something like a solver. That is not something to really worry about. I actually think one of the greatest things that’s happened, for me as a poker player. And what I like about sort of my timing in the industry, like obviously, I think I would make more money in this game had I been able to play live earlier. But what’s nice about this moment in live poker is that you have a lot of the stronger players trying to gravitate towards being able to implement these solver type strategies. And the truth is, they don’t make very much money, which means that I can’t lose very much money to these players. So, you essentially just have these sort of bot type people around the table, who are kind of like a wash against me. I don’t even have to think about them. Because, you know, I know what they’re trying to do. And I understand it, maybe better than some of them, I think likely. But it doesn’t even matter because I can’t really win or lose against them. If they’re, the better the implement, the less I can actually win or lose. And so, I just totally focus on like, what are the bad players doing? Or does this person ever tell? Because if you’re trying to implement perfectly polarized ranges, and you have a tell, fuck you’re done,

Brad: Yeah, you’re done.

Jack: Yeah. So yeah, I think it’s really nice to not worry about being exploited. I have to say.

What is up you future star of poker, you. Coach Brad here and I just wanted to take a moment to let you know about PKC poker. If you’re sitting there wondering, why? Why is coach Brad promoting this PKC poker app thing? Allow me a moment to explain my why. Battling in cash games has been my livelihood for the past 15 years. It’s how I survive and put food on the table, which makes it imperative that I either test out or seek qualified opinions on all the poker platforms on the market. One juicy fine can mean the difference between a meh year and an amazing family vacation and why kind of year. With that said I’ve tried almost all the major poker apps on the market to date and despite the hype about amazingly juicy games, I’ve come away from the experience unsatisfied. I was just never able to find amazing success against seemingly weak competition. And in one specific case was getting outright destroyed by passive villains playing more than 50% of their hands. What the heck was going on? After many evenings sitting in the bathtub, wondering if I had lost it, I finally dug into the data and learn something that shouldn’t have been too surprising to you. These dudes were colluding and super using their pants off. So, I swore off those free money, decentralized devil apps and decided to go back to my more familiar streets of ignition. It was then that I was contacted by a good friend of mine who turned out to be the Vice President of Worldwide Operations at PKC. Him and I had a long in-depth conversation about security, the ecosystem and the future direction of PKC, and he managed to convince me to give it a shot. That shot turned into an incredible six months with an hourly rate, that’s about five times what it would have been playing on any other US platform. As it turns out, I didn’t forget how to play, I just needed a level playing field to return to my crushing whites. I have no doubt that you, my community, my audience is going to play poker somewhere. And I want to be damn sure that you don’t go through the pain and frustration I felt by messing around with any poker app besides PKC. This is why promoting PKC is a no brainer. I love my community. And I want to put you in the best position to succeed at this game that we both love so much. So, if you’d like to join me in the streets of PKC, simply head to enhanceyouredge.com/pkc and get your invite code to play. You must have an invite code and you must be 21 years of age or older. One more time, that’s enhanceyouredge.com/pkc. Best of luck, and now on with the show.

Brad: I want to circle back to something, and then we’ll get into the lightning round. Because I have more questions. If we don’t get start getting to the questions, we’re going to be here 10 hours, it’ll be the longest podcast episode ever. I was gonna ask you about playing the piano. Do you think performing like in a public setting? Do you think that’s had a positive impact on your poker career, your ability to perform under pressure?

Jack: I think a little bit. But I think it’s more important when you’re playing on like TV. So, I’ve played on like live with the bike a couple times. And I think maybe that’s less of a sort of weird thing for me because I’m used to being on stage. Also, one of the more challenging things I’ve ever had to do, although it’s very fun and like very natural. I think it came out well, is a content. I think that Matt Birkin, those guys do something called Poker Out Loud. where basically, they play a game, and we’re playing for real money. And there’s a we have a whole camera crew set up. And basically, everyone’s wearing headphones, like blasting music. And when it’s your turn, assuming it’s not just like a preflop fold, you pause your headphones, and you speak to the camera, like what you’re thinking in that moment. And that’s hard because like, even it’s an, it’s a step beyond just like sort of pontificating about a hand on like a podcast, for example. Because that you’re out of the emotional moment of that decision. This is your emotional moment of that decision, and you have to explain what you’re doing. That’s a really valuable thing to do. But I think that kind of being in that kind of spotlight is maybe a little bit more natural for me, because of my experience as a performer. Although I will say the piano player in the jazz setting normally has their back to the audience. So, it’s maybe not, if I were like a singer or something, maybe it would be even like an order of magnitude more comfortable. But I would say for the most part, I don’t think it has much of an effect.

Brad: Okay, if Berkey is listening to this podcast, can we get something set up for the dude that tanks for nine minutes? Let’s put some headphones on him. I want to hear his thought process for all nine minutes on what’s going through his head in a tournament setting. But it’s kind of like twitch or I guess twitch or recording like a live play video where you’re giving your thoughts before the actions and everything is live. Just a lot is the live version of it. Right?

Jack: Yeah. I had, I twitched for a bit. I didn’t like it. Because you, the format It’s such that, you’re, you’re given very little time to talk about things that you could talk about for a lot. And then you have a lot of dead time to talk about things where there’s not much to talk about. So, I find that challenging, although I know some people are really successful with it, those people are just funnier than I am.

Brad: It’s more entertainment than instructional content, for sure. You can’t really, you can’t pause the video and go in depth with some analysis and bust out, you know, some kind of software and break things down. It’s very, it’s quick, and then it’s over. Alright, let’s move to lightning round now.

Jack: Alright.

Brad: What’s some common poker advice that you completely disagree with?

Jack: That you should listen, or I think in a way, like, I disagree with all poker advice, because I think you should be contrarian. It’s, it’s a game that rewards the person who’s thinking and playing differently. And so, if anything is like common poker advice, you should disregard it. Although I, obviously, you should come back to it if you think it’s right. But you should immediately see that this common advice is potentially your edge. And so, anything that like is presented as a common poker advice, it should be something that to me was a question.

Brad: That’s a great answer. And I’m 100% on board, you know, when nothing, it drives me crazy when somebody is like, you do this because it’s standard, and it’s mandatory. Well, why? Why is it standard? Why is it mandatory? Let’s dive deep. Like you find your edge against the other players by figuring out what’s not standard and playing above the rim, when everybody else is making the quote, unquote, standard play?

Jack: Yeah, when I went on to like a first coaching with someone, it’s hard for us often to like get beyond the first hand. Because by the time I’ve, or there’s just so many things that it’s clear that like a student has never actually thought about why they do it. Such that like, when you actually get to the thing that they think that they’re trying to like think about and that they’re unsure about, they’ve realized that they’re actually they have no foundation. And they’re just, they are built on like a layer of assumptions that are totally untested.

Brad: And that’s a problem too, when you watch your favorite poker player on TV, and they take an action, they do something, and then you take like the monkey see, monkey do approach. And then you try to implement it into your game. And the conditions just aren’t there to make that a profitable play, but you don’t know what the conditions are in the first place.

Jack: Yeah, not to make this like too universal, but I think it’s important. That’s a process that can be applied anywhere in life. And we should realize that, like, it’s a possible, you have to consider that there’s a possibility that like, you’ve been fed a bunch of garbage throughout your life that you’ve never actually bothered to test and put to rigor. Like you could consider something like, for example, like what’s your knowledge of like American history, if you live in America? Like where did that come from? Probably you learned some stuff in school. And you’ve built your whole like basis of understanding off of like that history. And if you’ve never teased, try to tease out the truth of that and see if like, what you were taught was actually true. Your whole set of foundational assumptions, at least that relate to American history might be wrong.

Brad: Christopher Columbus is a great guy, right? That’s what I learned. He an upstanding citizen, who massacred a whole set of people in committed genocide. He’s a good dude.

Jack: Yeah, I mean, if at this point, that’s, that’s well known.

Brad: That’s true.

Jack: And they actually, I bet ,the schools I think, like, teaching that kind of thing now, but

Brad: Are they?

Jack: The high school was. I came from like a really, like super liberal bubble kind of suburb of Cleveland.

Brad: I have a decade on you and came from ultra conservative place. So

Jack: Yeah. So regardless of like, what bubble you were brought up, in, likely, there’s assumptions littered throughout your life that like, deserve greater examination. And I think poker is a good place to start that process because your money is at stake.

Brad: You got skin in the game, like you said earlier.

Jack: Yeah.

Brad: And just to expand on this one lightning round question more. There aren’t many universal truths in life anyway. Capital T, truths, and questioning everything, it just for life experience sake. To me, it would be so sad to live your life under some false assumption, that is just not true. And if you were to dive deep into it, you would realize the fallacy and realize how you could have acted differently.

Jack: Yeah, well, it’s a difficult process too, because you not only have to question the knowledge, but you have to question the source. And you have to question like, your process of how do I actually go about gaining knowledge, like is that something and it’s actually likely to yield any useful information. And if you find that you have zero foundation, then it can be probably too daunting of a task to even go about it such, you know, given the sort of economic pressures of daily life. And so, it’s not the kind of journey

Brad: It’s a luxury.

Jack: That everyone can, yeah, it’s a luxury. But if you have time to listen to this podcast, and you might, you might just be one of those people.

Brad: That’s a very good point.

Jack: This isn’t worth listening to. But, you know, we’ve already sort of separated a lot of the field, you know, through this filter.

Brad: For sure. What’s something that you feel folks who are chasing their poker dreams don’t spend enough time thinking about? And that’s probably a bad question, because we’ve just answered it.

Jack: But I think, to give us a different answer, I think thinking about what is your edge is really important. Because if you don’t focus on what’s your edge, and you focus on playing well, your version of playing well might not actually give you an edge. And so, if you can focus on like, what’s my edge, and how can I increase it, I think that’s a more direct problem to be solving in terms of like, your ultimate goals in poker, which are probably to make money. And if you have this sort of abstract notion of playing well, that doesn’t sort of fall in line with actually having an edge that you’re trying to increase. You could spend a lot of time trying to improve in ways that are not productive. I think we’ve seen that process manifest a lot in the GTO community, where they might actually be reducing their edge by playing GTO, but they feel like they’re playing better. So, I would just caution against that, and focus on your edge.

Brad: That’s, that’s a great answer. Great answer, just the process of trying to improve your play, to make more money, chasing money to me, is a toxic goal. It’s not very emotional. And it’s not going to drive you to be great at poker. You need emotional goals, like you said, when you’re defining greatness for yourself, you know, making a living playing the game, taking care of the people that you care about, not being a leech, to your girlfriend, being able to live in New York, you know, these are all emotional goals that drive you forward, and they drive you much farther than purely chasing money.

Jack: I agree. And so that actually ties in to my sort of glib response about which people spend less time thinking about, and the answer being poker. I think poker is a great game. And there’s a lot of opportunities to be had. And there’s a lot of lessons to be learned. But when you quantify your goals, it’s like, I want to take care of like, the people in my family, you know, I want to, you know, build wealth, like support the people in my life, and support life causes I believe in. If it’s possible to poker is not the answer. You know, it’s not necessarily a game where potential edges are increasing, like where your max profit is increasing over time as the game develops. And so, I highly recommend, like I have a lot of friends who I recommend, like, oh, you should play poker, because like, I don’t necessarily make this so explicit. But my sort of beneath the hood reasoning is that, you lack a lot of skills that poker will teach you faster than anything else, partially because poker is a great game. And so, I personally plan to always play poker. But for me, when I, when I like, sort of looked in the mirror and tried to quantify, like, what are my goals, it’s clear to me that like poker is not like what I’m going to do for the rest of my life. Because when you put those goals at the forefront, you might sort of discover a different course of action than what you expected.

Brad: The path just isn’t there to reach the goals through poker, is that what you are saying?

Jack: That being said, like, I mean, I’ve been in the game for almost 15 years. And some of that was when I was a 10-year-old. But the sort of things that I feel are available to me now, for sure would not be where I not overplay. And so, I might be in a position to say this, where others who are like the beginning of the poker journey, you absolutely should continue. And you absolutely should be, I think, very all in focused on trying to get as much out of this game as you can. But keep those sort of broader long term goals at the forefront as well. Because those might inform the types of things that you prioritize, even in your effort to become a better poker player.

Brad: I’m with you, 100%. And it might just be the natural transition of living the poker life. That inevitably, we learned that to get to where we genuinely want to be. Poker doesn’t always lead us to that path and we have to do other things. But it sets a great foundation, and sets us up.

Jack: Yeah, like I do a lot of teaching. I do a lot of trying to help people who I think maybe are feeling lost or vulnerable or don’t know how to like, get where they want to go. But I would be a lot happier to see those people take the game as a springboard to do something like, create a great reason of business, rather than actually, like become fit or mean, ultimate should be creating great business, or at least I think it’s trying to. So maybe he wasn’t the perfect example. But I think a lot of the sort of lessons I’m trying to impart on the people that I work with and talk to, not necessarily like a paternalistic way, but just in the types of things that I think that maybe I have an edge on, over them at the current moment. I think those can be extrapolated to all types of situations. And poker just happens to be the sort of meeting ground where we begin.

Brad: And there’s a lot of fulfillment in helping and giving back to, helping people on their journey that maybe you don’t get as a professional cash game poker player.

Jack: No. I mean, I think that you’re, you provide a service as a cash game poker player, like, I believe that, I don’t think that you’re like a net negative on society or anything like that. I actually think it’s a really awesome thing, that there’s this place called a casino, where you can go and like play a game with other people and be in a social environment any time of day. Like, I think people don’t necessarily see that as a valuable service. But you can think of probably a lot of these people who are playing poker all the time, like being at home is not a very pleasant experience for them, and there might not be any sort of way out of it for them. And so, having this place where you can go anytime, you know, maybe like your husband, your abusive husband is like on that sort of, you know, trunk and terror. And you go over to the casino, because you know that the public place where you can be that safe, where you’re entertained, and you can be social. Now, that’s a valuable thing to have. So, I think offering that service of taking on variants for a fee, you’re adding to the world, but only to a point. So, I agree that like, from a broader like do good standpoint, there’s other things you could do that probably have a greater impact than play cash games, at the casino.

Brad: And there’s some irony too. You mentioned Fedor Holtz, and him building his business. And when I was playing at commerce, play with a lot of rich businessmen who spend their lives building businesses and all they want to do is play cards. And then I spent tons of time with card players who spend their whole lives playing cards, and all they want to do is build a business. It’s this funny, funny sort of grass is greener irony.

Jack: Yeah, I think part of it is like, something I’ve noticed for myself is that when you identify yourself with a certain thing, your enjoyment and like, your enjoyment of that thing is less, because the results have so much more to do with how you view yourself. So, like, I think for me, improving and enjoying poker has always been relatively easy, because for a long time, I saw myself as a musician, like, I’m a musician, what really stresses me out. And where my performance really like gets to me, is playing the piano. Poker is just like a joyful thing where like, I can just enjoy the process. And what I found is that I sort of struck a balance where I’m involved in a lot of things. I don’t spend so much my time on any one thing. And therefore, like, I can see myself more is just like a person who does things. And my value as a person is not tied into my success at one thing or another. And therefore, I enjoy all these activities, much more so than I would I think if I were fully focused and totally saw myself through the lens of this one aspect of my life.

Brad: And that is a very wise thought, and way to live your life identifying that, you know, your identity is not always what you think it is. Question your identity. If you’re a poker player that wants to be a businessman, just questioned your identity. Think like, you know, will being a business person make me happy? Is that really what I what I need to gain fulfillment in my existence?

Jack: Yeah, I think like, just to put it in the sort of context, like the kind of thing that I would find myself doing would be like, you know, I might walk into a jazz club for like a jam session. And I feel like, are the people here, they don’t really know what I can do. They don’t know what I’m all about. Like, they’re going to underestimate me. And part of the way you might compensate for that is to say, like, well, I have this whole other thing in my life, like this poker thing that I do. I have, you know, these other things I’m involved with and I’ve gained like a certain level of excellence and they don’t have that. And therefore, that makes me superior. And I think that, those sorts of thoughts are really toxic and the kinds of things to be avoided. And the people who I’ve seen who are really, really successful and constantly just put themselves out there, and are willing to fail, and therefore get ahead, are people who just inherently don’t have those kinds of thoughts. And they just see everything as like an opportunity to learn and to grow. And they don’t worry about how they’re perceived by others. They don’t worry about being seen as the best, or anything like that. I think that that’s the kind of mindset I’m trying to develop. I don’t think I’m fully there by any means. But I see that as the goal, is to be able to approach things and sort of like an eternal student with no ego. And let the opportunities and failures and successes just flow as they will.

Brad: And that is a greatness goal, sir. That is a great goal to strive towards the, you know, there’s a lot of documentation about Olympic champions and Olympic athletes too, that they get gold, they leave their sport, and then all of a sudden, they crumble. And they lay on the couch, and they eat all day. And because their whole identity was wrapped up in being an Olympian, and being an Olympic gold medalist. And then once they get there, it’s like, oh, shit, what do I do with my life now? Right? They have that identity taken away from them. So, question that in your day to day life.

Jack: I think that’s also, it gets to what’s empowering about tearing down the sort of assumptions that like build up your life early and proactively, is that when your thoughts and values and understanding is your own, and rooted and has depth in some degree of accuracy to it, it’s a lot easier to sort of weather the ups and downs of the sorts of things you’re pursuing. Since if you have no foundation, and you get knocked back a step, and like your professional setting, then you’re you have a lot farther to fall potentially. I think it’s the kind of thing, like I’m a big Jordan Peterson fan. I don’t know if you, yes, I recommend Jordan Peterson. He’s a, he’s sort of is one of the things he’s associated with is the idea that you should clean your room, which by the way, I don’t do. But the sort of, the idea is that the process of cleaning your room forces you to consider like the various things that you have, and where they might go, and like how you want to sort things so that your room is actually going to work well for you. And that process, and that foundation of having a room that is ordered, in a room that has meaning and function, is the kind of thing that can spring you towards doing the same sorts of things, analogous to cleaning your room in other areas of life, which gives you a foundation of like home family values, which can set you up for the sort of success you’re looking for. In other areas.

Brad: Yes. It spills over to other aspects of your life. If you could go back in time, give your 20-year-old self some poker wisdom, have a conversation with him? What would that talk be like? What would you tell him? And I know this is only four years ago for you. So, you might need to go back to like your 13-year-old self. But just whenever you’re starting out playing poker, what some wisdom you would you would give yourself?

Jack: Sometimes the best thing you can do is fold. And that’s okay. I don’t like to fold.

Brad: Who does?

Jack: Yeah, folding. Folding as a way of winning is a really important skill to develop. And something to understand. And it took me a while to realize that like, sometimes there’s not a better thing to do than fold. And you can get creative. And the trying to get creative again and again, was definitely helpful to me in terms of like, figuring out where some things were possible that maybe I wouldn’t have stumbled on if I had been so comfortable folding at that point. But yeah, I think like I would have saved a lot of money for sure. If I had said, it’s okay to fold. Sometimes the best thing to do is to fold.

Brad: And that’s absolutely true. Like you don’t have to win every single pot that you’re a part of, sometimes you can just fold and that experiential, the testing nature of poker I think is vastly underrated. Where you may see a positive EV play hypothetically, but you don’t know. And then the creativity comes into play, where you test it out and say you do, it five or 10 times, and you realize, oh, I’m getting my ass handed to me, okay. Then maybe your idea just didn’t work out. But if you find that it’s exploiting people the way that you’re intending, then you’ve developed something, you’ve increased your edge over the field and you can implement it far into the future. So sometimes making, quote unquote, lower expectation plays when you’re testing things, can increase your win rate. If you’re insightful enough to implement it moving forward and gain the wisdom that you’re learning,

Jack: I think the one other thing I would recommend to myself on that, I recommend this to anybody, is remember the world from one, or like from one minute ago. And keep that world present in your mind as things change, in your most things change. If you opened 9-7 off suit from the hijack, because you know that like the imposition players and the small blind, like almost never three-bet. And then they three-bet, but you understand that they didn’t just pick up on like the fact that you’re opening way wider.

Brad: You’re right.

Jack: it was what it was, was what you thought a minute ago. And that’s a, that’s obviously a very easy and obvious example. But I think there’s a, there’s a strong tendency to, like, change the whole nature of the world, as the situation changes to fit, like your sort of broader desire.

Brad: Right.

Jack: Which is often to win pots.

Brad: Keep the big picture in mind. You can make a good play, the right play, that doesn’t work out, you can make bad plays that do work out. And so just being self-assured that you’re choosing the correct strategy and moving forward. That in and of itself is extremely valuable.

Jack: Yeah, I think just generally planning throughout a hand is helpful. It is

Brad: Sure.

Jack: Think not to have an A-plan. But just to think about things that can happen, and what you might do. It can help refine the nature of the situation in your head before you’re actually confronted with something to react to. I think that’s a useful process.

Brad: Yeah, if you say this is a bet-fold type situation before you bet, it’s way better than betting, getting raised, and then trying to figure out what you should do afterwards.

Jack: Yeah, when you’re thinking about betting, like asking yourself, like, what would I do if I face calling this card game? You know, and a lot of times, you’re afforded the luxury of letting other people, while other people act, and you get to think about these things. And so, use that time productively.

Brad: If you were to gift, the Chasing Poker Greatness audience one book, what book would it be? And why? Hmm,

Jack: I’ll take a cop out answer because I don’t necessarily have like, a book that I can throw my way behind off of my head for poker.

Brad: Okay.

Jack: But I think a really, really good book that I would recommend anyone read is, Anatomy of the State, by Murray Rothbard. It’s only about 60 pages. I think that’s a good read. It would be helpful.

Brad: What is it about? What’s the, what’s the major takeaway, the overall concept? You got to sell this book, so the audience reads it.

Jack: What is the nature of the state? How has it evolved over millennia? How does? What is it? What are its goals? These are the kinds of questions that are being asked. And I think it’s just, it’s useful, I think, as a first way to gain perspective on a system of control that will affect how you play poker. Because most of us have gone through public schooling. And by virtue of having gone through public school, and we have certain deficiencies, and I won’t speculate here as to whether those deficiencies are accidental or intentional. But I think being aware that like there are systems, whether they’re emergent, or whether they’re very deliberate, that might be giving you deficiencies that are hurting you in poker, is something that’s worth considering. I think that in your contemplation of that notion, you may find an Enemy of the State by Murray Rothbard, to be helpful.

Brad: That’s awesome. And it ties into what we were talking about earlier. And I found that a good question when presented with facts, facts, quote unquote, is, you know, ask yourself, is it true? Is this true? Do I know this is true? How can I prove that this is true? And when you start questioning things on that level, you can uncover some of those deficiencies. Like you said, you can realize, Oh, I thought that was true, but it’s actually not really true.

Jack: Yeah, so basically, the question I think is very relevant to almost everyone in this country is, the following; where is the goal of the school I went to, to teach me how to succeed in life? And if the answer is not yes, then it begs what was the answer, and how will I succeed in life if what I thought was preparing me to succeed in life didn’t prepare me to succeed in life.

Brad: What’s your answer to the question?

Jack: No. 

Brad: What are they? What’s your opinion on what school was preparing you, for?

Jack: My opinion was that school is meant to cause confusion, great curiosity, and limit the ability of school attendees to compete with people who are operating at a higher set of understanding or a higher level of understanding. And now I don’t think that like your school teacher was in on it, or that there’s nothing good that you learn from school, or that there aren’t great teachers, and that nothing, everything that you learned was like, designed to control you in this way. But I think if we take a hard look at like the results we’ve seen from schooling, like everyone knows that, like, Americans do terribly on like all kinds of tests, math test, literacy tests, like literacy has been declining since the beginning of the 20th century. So, we understand that it’s not working. And so, the question becomes like, why is not working? Is it not working because we’re bad at it? Or is it not working, or is or is it working, nd what it’s working for isn’t what we thought? So, a good book, on that question, would be the Underground History of American Education by John Taylor Gatto. And I think anything by John Taylor Gatto, is well worth reading. His some other books like Dumbing Us Down. He’s a guy who, he was a teacher in New York City, he was a New York City Teacher of the Year 89, 90, 91, New York State Teacher of the Year in 1991. And he had a very sort of unorthodox method of teaching in public schools, such that when that attention was brought to him from him being so successful in winning these awards, he was no longer able to actually teach in the way he wanted. He dedicated the rest of, he dedicated the rest of his life to trying to research and understand why the education system was the way it was. And his results are interesting, or his findings and worth looking into.

Brad: I believe that and that, that sounds, it’s piqued my interest. One thing I’ve learned in life is that, there’s not bad people, there’s bad processes. And the people are going through this educational process. And it’s pretty clear that money’s not the answer.

Jack: Yeah.

Brad: Money, money’s not going to solve the problems. It’s a process problem. So how do we, how do we start improving the systems and processes that the underlying systems and processes of the school system to better prepare folks for the world?

Jack: Yeah, and I agree that like, I definitely agree that there’s not necessarily bad people. There’s bad processes. But what I will say also is that there are bad ideologies. And sometimes I think we underestimate what kind of all ideologies could be rampant in the sort of class of people who makes a lot of these decisions. And so, if you trace that sort of ideological history, and the sorts of things that are really kind of hidden in plain sight, because a lot of the sort of foundational texts of Western civilization that are mostly reserved for like elite education, kind of spell this out pretty blatantly, it’s just that no one expects that, like, people like you and I are actually going to read those. And at this point, the conversation has continued in, I think, more discrete settings. Yeah, I would not underestimate the ability of like, bad ideology to form people implementing processes, which we would consider bad.

Brad: We’re going down a dark path. I don’t know. 

Jack: I’m up to this event in the future anyway. Like, I think that’s this is to me, like, the biggest benefit of technology and the kinds of platforms like you and I are doing right now. It’s like, we can, you can get on and say we think you know. And it’s so much easier to get opinions and information from various sources that at this point, it’s on us to just, like, really focus on educating ourselves and building up that intellectual self-defense that’s necessary to traverse a world where there might be people who are acting not in your best interests. We understand. This is why poker helps us because like, you know, there’s no villain. Like you are a hero, that’s villain.

Brad: Right?

Jack: You need to figure out how to be a villain. But does, is there this kind of thing going on in other parts of your life? Like, are you hero and villain. You don’t even realize you’re playing. So, this is not to say that like unnecessary about this kind of thing, but I think it’s worth it.

Brad: I agree. And there are villains, and you have to question, you know who these villains are. And you know why? Why don’t people educate themselves? What’s  the barrier? Where’s the friction coming in? Where were you spending your time? I think in a lot of ways, software companies are a big contributor to distraction to, you know, human beings, we’re not super-duper complex, right? Amazon prime, Netflix, Google, they can figure out the buttons to push to get us to consume their stuff and get us to be distracted. So, having an awareness of those distractions is super important too.

Jack: Yeah, I think that’s a really great example, because it appears on the surface like, these companies are offering us a product, like something like Facebook. Like the idea of the product is that we can connect with our friends, we can, you know, share things and exchange information. Connect with people. But really, the optimization that’s going on is like maximizing ad revenue, which is, in some ways, just a limitation of the way that we can monetize internet activity at this point. So, I’m not saying that it’s necessarily a nefarious thing, but it just happens to be, and we’ve all experienced this that, like, the product is not necessarily what we want it to be, because you’re not the product, the product is your attention. And so, we can think of, if you think of this sort of cosmic situation we’re in is like a much larger optimization question that is very ambiguous. And it’s hard to say like, what should we be optimizing for in life. Realize that like, your welfare might not actually be part of the optimization problem being solved by the people that you think are working in your best interest? And if you don’t realize that that’s a possibility, then you’ll never guess investigate to whether or not that’s true. It might be that like, the people you think are optimistic for your welfare are doing so. And the more likely it will be that some people who you think are optimizing for your welfare are and others are not. And then it just becomes a question of like, to what degree do these systems work on your behalf?

Brad: And it’s a process issue, too. Because, I love what you said, and I agree 100%, that the biggest source of value in the world that everybody’s competing for is attention. That’s it, right? How do you increase ad revenues with Facebook? How do you increase ad revenues for whatever platform you’re consuming? You get people to spend more time there. That’s how you increase it. And a good friend of mine, he’s a software engineer in the Bay Area, and him, and his buddy, they spent, they paid somebody $500 an hour to choose the color of their app. The color! It took them 12 hours to pick the perfect color, for that demographic, to want to open the app and look through the things. And that’s just, you know, a small example of the amount of money that these businesses pour into capturing our attention. Like, the deck is 100% stacked against us, when it comes to controlling our attention. So, having the awareness that look, this is what these guys are after, this is why your phone looks the way that it does. Because it is optimized to, so that you spend more time using it, because that’s how these companies make money. That’s why you know, Facebook’s worth God knows how much now.

Jack: Yeah, I think, so we understand that like there, there are technologies and industries that exist to optimize, you know, our attention, you know, how much attention are we going to spend on this app? I think it’s, it’s less obvious to people that there are similar technologies designed to maybe divert your attention away from something, or to mold your opinion in a certain way. What is public relations? What is marketing? You know, marketing is designed to like break down the resistance to buying something.

Brad: Great to know.

Jack: But the relations are designed to, you know, make you feel a certain way about something. And so, with these technologies are actually being used much more widely than you had considered, you could be much more subjected to advertising and public relations manipulation than you had considered. I think, so another good author is a guy named Edward Bernays. And this is sort of what I’m talking about with things being written in plain sight. It’s kind of the founder of like, the PR thing, which is like a newer, the sort of modern forms of like public relations are new because mass media was not always available, or at least not the same formats. And so, this is basically just a guy talking about what is PR and what do we do? What are our goals? Like, what are methods, you know. And you can learn a lot by seeing what someone who is basically employed by, you know, there’s pictures of this guy with the various leaders of the 20th century, you know, picture with like, Kennedy’s issued with a, you know, LBJ, all the presidents, all the major business people. And so, understanding like, those kinds of tactics is important. In the same way that like, once you realized that, like a phone company was optimizing, to like, get your eyes on the iPhone as much as possible, once you realize that you probably got better putting down your phone. Because you, you understand that like, you don’t want to be manipulated, that you need to make your own decisions about where is this benefiting the worst, or not benefiting. And so in the same way, like when you become aware of like the other various technologies optimizations being used for and against you, you can kind of liberate your attention a little bit so that you can focus on the things that you care about.

Brad: And a good question to ask yourself is, what is the incentive? How is this come? What is the incentive for this company to present something in this way? Because if you understand the incentive, then you can understand the goal. So consistently asking yourself, what’s the incentive? For instance, this is something I didn’t know. I didn’t know, I learned this just the other day, that when you take your car, to the shop, to get an oil change, or to for whatever reason, the people that work there, work on commission. This is why you’re constantly up sold, that you need X, Y, and Z service done while you’re there. When I realized, oh, these guys make money by upselling me, this now, now I see the picture. Now I can get, it empowers me to say, okay, no, I don’t want that. Because now, you’re making money off of the more things that you sell to me. So therefore, I can say no. And before it’s coming from a place of like, oh, this guy is looking out for my best interest. He thinks that I should have my brakes changed, because he doesn’t want me to be driving down the freeway and my brakes give out and I flip and die in a horrible crash.

Jack: Yeah. And that’s, so bring this back to Poker, like,

Brad: Please, God bring it back to Poker, I don’t know where

Jack: I don’t know if this connects well to what we were talking about with, are you optimizing for EV, or you optimizing for like I played well? So this, this kind of traces back to like, your ideology will influence the way you sort of optimize. And so, in the same way that like, it maybe doesn’t make sense what a GTO player is doing, because they’re trying to optimize the play the most GTO and they’re not trying to optimize to like maximize their expected value. The types of things that can be done, maybe don’t make sense on the surface until you understand the ideology that lies underneath that decision making. And since a lot of people both, you know, in the sort of like upper echelons of decision making, and also just everyday people have not put that much reflection into their own, like sets of ideologies and beliefs that they’ve held. They’re very liable to act irrationally, against what their interest really is. Because they have this ideology that’s present that they don’t understand.

Brad: Yeah, that makes a lot of sense. What’s the current big goal you’re working on in your poker career?

Jack: I have, I’m actually, I’m working on something that I can’t really talk about. I don’t have, to be honest, I don’t have any really big financial goals in poker. My goals are really, at this point, just to like, learn more, become a better teacher. But ultimately, I’m in a stage where I’m transitioning out of the game, like I’m working with my former co-host. He and his cousin started a cryptocurrency venture hedge fund, which I’ve been working with them for a couple of years now. And that’s becoming a bit of a bigger part of my life. And so ultimately, like, my days playing a lot of poker, and playing for like a large percentage of my income, I think are hoping coming to the end. And I can just focus on like, continuing to help the community that I’ve developed like through my podcast and through teaching with software Y. Because those are things that I really value and enjoy. So poker-wise, I wouldn’t say that there’s many, although I am working on like, I’m considering building a specific business that I don’t want to talk about. If I decide I’ll do it, I’ll talk about it.

Brad: Eventually you’ll have to talk about it right, though? Because people need to know. Nobody can find it if you don’t talk about it,

Jack: I’ll get, I’ll tease it.

Brad: Alright, open the curiosity gap. And we’ll circle back to it, if it launches, or if it doesn’t launch.

Jack: Yeah. The tease is, I want to build a product. It’s kind of like a game that will be challenging, and help you improve in ways that are actually helpful to winning.

Brad: At what? Poker, specifically?

Jack: So, playing against other human like, ways of practicing playing against other humans in a way that’s constructive. And whether it’s fun.

Brad: Right, instead of playing against Mr. GTO bot.

Jack: Exactly. Yeah,

Brad: That makes a lot of sense. And my next question is, what’s a project you’re working on that’s near and dear to your heart? And it doesn’t have to be exactly poker centric, just any project?

Jack: Yeah, I mean, I’ve been spending a lot of time working on the sort of marketing aspect of our fund. And that often looks like trying to explain why cryptocurrencies why Bitcoin is an important thing. And I think that a lot of the answers that have been given by other people in the industry, are not very good answers. And because they’re not very good answers, the investments they’ve gravitated towards, are not very good investments. And I think I can provide a lot in the short term for people by providing better answers to those questions. And so that’s how I’m spending a lot of my time.

Brad: That is a tough project.

Jack: It is tough. Because there’s a lot of, you’re trying to distill the right segments of your background knowledge into something that’s compelling and educational, look kind of necessarily needs to result in people like investigating things on their own. So it’s a, it’s a hard balance to strike.

Brad: For sure, because cryptos are very technical. And if you start talking about it, people’s eyes just start glazing over. It’s really hard to tell a compelling story that gets people on board.

Jack: Yeah, and the real, the best versions of the story, assume a certain level of like, not just technical competence, but economic competence. And sort of like enough historical understanding and perspective to even see like, why this would be a reasonable thing to watch in the first place. I actually think that the type of pitch I’m trying to make de-emphasizes that. Because I’ve realized, that aspect of things is just too big of an uphill battle. But if you were looking for an idea of what I’m talking about, like, another Rothbard book I’d recommend is what’s called. It’s called, The Case Against the Fed. So like, regardless of whether like the Federal Reserve is an entity that’s like benefiting you or not, most people haven’t considered at one way or the other, and aren’t aware of like, the history of how it was built, or what it actually does. And so, if you if you’re totally unaware of that kind of thing, it’s gonna be hard for you to understand what’s the whole point of Bitcoin.

Brad: Right.

Jack: And so, you know, it’s hard to get someone to say pick up like, a 200 page book just to get the background knowledge necessary to even begin like understanding the significance. So, my challenge has been like, how can I just lay out something that’s simple, compelling, anyone can get from point A to point B, such that like you see things enough the way I see them so that we can I continue the conversation.

Brad: Have you tried holding people at gunpoint? I think that might be the only way you can get them to read a 200-page book on the Fed.

Jack: I can promise that it’s an interesting book. Also, I’m very much not a fan of using course violence to get him to do what I want them to do. I live by the principles that I preach and not shoot anybody for not reading.

Brad: You don’t shoot them, it’s the threat. You don’t shoot people. That’s how you get into trouble. You just threaten them and make them read the book. It’s for their own good at the end of the day, right? Where this is authoritarian fascist 101.

Jack: My favorite types of government.

Brad: Clearly. You love Bitcoin so fascism is right up your alley I’m sure. And personally, I’m a big fan of Bitcoin too. But we don’t have to get into that because

Jack: You’re promoting like a Bitcoin.

Brad: Yeah, Bitcoin poker app which PKC and I know the players involved which is a big thing for me, and I’ve had good success on the app myself. So, it’s a no brainer for my audience. I love Bitcoin and getting more people involved in Bitcoin is an is something that I’m passionate about anyway, and steering my community towards an app. That is fair, that is good. That’s powered by Bitcoin. It’s been a real easy thing to promote for me.

Jack: Yeah.

Brad: Particularly.

Jack: Just to alienate, like, all the big win enthusiasts who are listening to this right now. My big Bitcoin SV supporter, I think. That’s where the action is. So, if you, you can just hit me up, if you want to know more about that. Yeah, I’m a big fan of all kinds of Bitcoin, but I just think that the one that’s most likely to work in the way that we want it to work is Bitcoin SV.

Brad: Which is a spin-off of Bitcoin cash, right? It’s a fork of the fork.

Jack: Yeah. You know, it’s ambiguous, like, who forked off from who? But yeah, definitely. It’s widely known as like the fork of Bitcoin cash.

Brad: Yeah. Right. At the end of the day, what would you like your poker legacy to be? How would you like your podcast audience, your students to remember you?

Jack: I just want them to miss me when I’m gone. I think that would mean that did a good job.

Brad: I’m sure they will, sir. I’m sure they will. So where can the Chasing Poker Greatness audience find you on the inter webs?

Jack: You can hear me talk about poker, very specifically about strategy. Our podcast doesn’t get that much into things that aren’t strategy. It just ends poker. You can find that on any of the sort of podcast players. I teach at Software Y, so if you ever engage with their content, or go to like the software Academy, they’ll see me there. I’m on Twitter its justinspoker, that’s a better way to like, message me than I say, to get my voice, you know, on the feed very often, it’s more sort of promotional stuff. So, if you want to follow like what’s happening with the podcast, it’s obviously a great follow. But I think if you just want to talk to me, then hit me up through justinspoker on Twitter is probably the way to go.

Brad: Awesome. And we’ll get all those links in the show notes. And we’ll also get all of your books in the show notes as well. Sir, it has been a great conversation. I’ve loved it. I hope that there are people out there that actually listened to the whole, the whole two-hour show. It went it went a little long, but I think it was worth it. Like I really love the conversation. Either way, if nobody listens to this show, I loved it personally. So that’s a win.

Jack: Thank you very much for having me on the show. I’m glad you enjoyed it. I also enjoyed it a lot. Hope to have you on Just Hands very soon. I wish you the best of luck with this project you are working on. I think you’re asking a lot of awesome questions. And yeah, I really appreciate you reaching out to me and I’m not the biggest thing on Poker, but hopefully I have some good things to say. And I can help some people.

Brad: You had some great things to say sir.

Thank you so much for listening to this episode of chasing poker greatness. If you haven’t yet subscribed to the show, please take a moment to do so on Apple podcasts or wherever your favorite place listen to podcasts might be. And once again,I also wanted to let you know about PKC poker. If you’re on the lookout for a new platform where the games are safe and secure and the action is amazing, head to enhanceyouredge.com/PKC to get your code and jump into the games. You must have a code to play as well as be 21 years of age or older. One final time that’s enhanceyouredge.com/PKC. Thank you so much and I’ll see you next time on Chasing Poker Greatness.