00:00 - Isaac Rose-Berman (Guest)
My dad looks back at that story and he's like he was always going to make it. He was always going to beat. Looking back, now I'm 13. Obviously, I had zero edge. I was going on Betfair every morning writing down all of the prices and then picking the players. I had zero edge, pure luck, but like six or seven X my money. Come on, let's go. 

00:17 - Johnny (Co-host)
You think I'm going to come on here and put one of the Aussies in the elite dear. I'd vote for Rob of $25,000. I wouldn't vote for you. 

00:25 - Isaac Rose-Berman (Guest)
I can basically just cheat and get the same bets that they're getting. 

00:29 - Rob Pizzola (Co-host)
It's weird because you can also pay your bills at the same place where you bet. I mean, you're a short guy, what? 

00:39 - Johnny (Co-host)
This guy talks a lot of trash. He's talked a lot of trash about me, rob, a people in the community, but he's refusing to show his face, shouting yourself as a pretty good nfl gambler I I thought you were an idiot say testing, testing. 

00:49 - Rob Pizzola (Co-host)
I'm a cuck. 

00:50 - Johnny (Co-host)
One, two, three, four, the aussies going head to head with the aussies. That's what I drew before and I said get him kirk. And they call me a mean-spirited name. 

00:59 - Rob Pizzola (Co-host)
I don't hang out with them the toronto maple leafs at 14-1 are staring me dead in the face. 

01:05 - Zack Phillips (Announcement)
I'm already getting you know a lot of early this could be the best Circles Off episode that's ever been done. 

01:14 - Rob Pizzola (Co-host)
Welcome to Circles Off, episode number 178. Right here, part of the Hammer Betting Network presented by Pinnacle Sportsbook, I'm Rob Pizzola, joined in studio today by two people Johnny from BetStamp to my right, Isaac Rose-Berman  to my left. I just need to uncircle back this week and talk to them about a lot more stuff today. How are things? 

01:35 - Isaac Rose-Berman (Guest)
boys. I'm a bit of a city snob, new York born and raised, but so far Toronto, living up to the hype. Yeah, is it a mini New York people? People say I've only been here for a day so I can't confirm. But yeah, of all the cities I've been to in canada so far, most similar there's just less steam that comes up from the sewers in toronto than in new york what we got to do actually is you got to try, uh, a street meat hot dog outside vegetarian 

02:00 - Rob Pizzola (Co-host)
vegetarian oh, you're vegetarian, oh I can still get a veggie dog no, we got it. 

02:04 - Johnny (Co-host)
We were supposed to. I would have loved to compare a new york dog, a true new yorker, and see how he likes that toronto street dog. Those are pretty good. 

02:11 - Rob Pizzola (Co-host)
Can't have them too often, though, can't have a corner of uh king and john that vendor there. 

02:17 - Johnny (Co-host)
I've spent at least a thousand dollars there in my life on that one you spent a thousand bucks five dollars in my life when I used to go to blue jays games. I would stop by that one. 

02:22 - Rob Pizzola (Co-host)
You spent $1,000 on $5 in my life when I used to go to Blue Jays games, I would stop by that one on the way to the games. I'd get like two before every single game that I rolled in. Because I don't want to eat and drink at the game, I like to eat beforehand. Pound a couple of sasich, go into the game. You can pound it back afterwards. 

02:40 - Johnny (Co-host)
Very unhealthy for you, obviously Wouldn't recommend them. 

02:44 - Isaac Rose-Berman (Guest)
words very unhealthy for you, obviously wouldn't recommend them but those things are better than anything you can get in the stadium absolutely not even one tenth the price? 

02:49 - Johnny (Co-host)
well, no, actually not even one tenth, like they're five bucks. How much is a stadium hot dog? Nine bucks, whatever. Same, the same shit. 

02:54 - Rob Pizzola (Co-host)
If the closer you get to the stadium, the more expensive the hot dog is. You walk like another 10 yards and the prices go from like five to seven bucks. You walk another 10 yards and the prices go from like five to seven bucks. You walk another 10 yards. You're at like a $10 hot dog at that point. But the key is the diversity in the stand, because I like the spicy Italian ones and some of them don't have that. They just have like hot dog or Polish sausage. I got to find the stand that has the spicy Italian one that King and Johnson. 

03:21 - Johnny (Co-host)
A thousand bucks in $5 increments 100%. 

03:25 - Rob Pizzola (Co-host)
I did. 

03:29
Keeping that guy in business. He's doing quite well. Actually, it's always busy that one. Yes, um isaac. Here is a professional, better specializing, I believe, in tennis. We'll talk soon about that. He's a writer in the betting space as well. You can check out his sub stack at how gambling workscom. You can follow him on twitter. At round robin 42, I had interacted with Isaac via Twitter DMs, oddly enough, about some responsible gaming stuff that he was writing about. We'll talk about that afterwards, but we recently ran into him at Bet Bash and some of the people who've been following Circles Off might have heard some like late night betting stories. You know the night where they sent the vacuum cleaners over to me at the blackjack table. You know you playing some blackjack and craps with me and Isaac was a big part of that. 

04:11 - Johnny (Co-host)
We like to throw down at Bet Bash, this guy. He's a good kid. He's a good kid. He knows how to gamble, that's for sure. 

04:16 - Rob Pizzola (Co-host)
Isaac, let's start with your background in the betting space. I think you told me you started in poker before. 

04:21 - Isaac Rose-Berman (Guest)
Yeah, so my intro I was always a big fan of sports and games and math. I think the first intro I had was fantasy baseball. I was probably in elementary school. I was super into it. I was the kid who was getting up every morning to change my lineups. I was super obsessed with that. Then I remember when I was 13, I was bar mitzvahed it's pretty standard to get cash for your bar mitzvah and I was a huge tennis fan. At that time I switched from baseball and I asked my dad I was like, instead of getting I think it was 500 bucks, could I just get 500 bucks to like paper trade, either the US Open or Wimbledon, I forget what time of year it was Got really lucky that week Did really well and it that week did really well and it was huge from there. My favorite part about that is that my dad looks back at that story and he's like he was always gonna make it. He was always gonna be Looking back. Now I'm 13,. Obviously I had zero edge. I was going on Betfair every morning writing down all of the prices and then picking the players. I had zero edge, pure luck, but like six or seven X my money. So that was sort of the intro. Then didn't really do much sports betting for a while. 

05:26
After that in college started playing poker with some buddies for small stakes, nothing serious. Then COVID hit, was playing online a lot more, ended up just playing a lot more, sort of ratcheted up the stakes a little bit, just the total volume. And then by the time I was graduating college was playing decently high stakes poker, pretty much exclusively live at that point, doing a little bit of sports because it was getting legalized at that time. So a lot of like the bonuses, the sign up stuff. And then after I graduated was working at a startup and playing poker on the side, finished my time at the startup and was like, oh, what am I going to do? And kind of had run hot there in poker and my background is more in sort of politics and policy and so I was looking at jobs in like government and regulation, while I was also playing decently high stakes poker at the time and I remember I was like applying for jobs and I was like I can't take this job you know it's paying me in two months like what I just made last night or what I just lost last night, and so from there. Basically it was like, okay, I also don't want a job, I'm kind of lazy. So I was like, okay, I'm just going to play poker, basically full time, did that for a little bit and then switch from poker to betting fairly quickly, just both kind of a push and a pull. 

06:37
Poker, I think it doesn't. A, it doesn't scale as much B, the hours and the lifestyle were tough. I was playing live. So you know I'm playing like 8 pm to 8 am sort of gets pretty draining. And also I think like mentally, you know you really see the people you're taking the money from, whereas in sports obviously you know you can only win because other people are losing. But it wasn't as mentally taxing because I can sort of think in theory, oh, I'm taking money from the bad guy. So switched over to sports and, yeah, I've been doing that pretty much a full time for about the last year and a half, and then about six months ago I also started doing more writing and content stuff as well. 

07:11 - Rob Pizzola (Co-host)
We'll talk more sports betting for sure. Just on the poker front Um, I started in poker as well. We're more than a decade apart in terms of our age. Moneymaker winning world series of poker was big for me, got me into into the game. But now I try to get back into it and it's evolved so heavily into like gto um, game theory, optimization. I literally have like downloaded apps before where I I'm studying to play poker which hours a day, and then I'm like I'm not gonna do this anymore. I just don't have the time. How much of that gto like were you studying? 

07:44 - Isaac Rose-Berman (Guest)
to play, or yeah, so when I started getting more serious about it during COVID, I was playing a ton and studying a ton. So I was. I was like kind of crazy. Looking back, I bought courses where I was, you know, like studying optimal poker strategy and then switching from online to live. You need a lot less of that, you know, just because online games it's much more all people who are playing pretty close to optimal and so you need to do really well there, whereas live games there's a lot more intangibles, a lot more of kind of the people skills and you don't need to be playing as close to optimal. So I think today I'm not the most studied in that, but I'm pretty familiar with almost all the concepts and basic strategy. I haven't studied or taken a course on it in a couple of years now, but still play, you know, somewhat frequently those courses. 

08:29 - Rob Pizzola (Co-host)
Are they like the equivalent of the sports betting touts, or do you actually learn something from those? 

08:34 - Isaac Rose-Berman (Guest)
I think there's a much higher percentage of the poker courses that are legit, and I think a lot of them are winners Like, yeah, so I think it's much, it's much more legit in general. Maybe I just got lucky in terms of the people that I followed were good, but you get to a point where it's like, yeah, I don't really wanna be just studying this all the time, and especially online, the stakes get as you go up. In the stakes, people are really, really good, and so I think you had Chris Dierkes in the pod talking about this as well where I would say, depending on what site I can these days, I could probably win. It may be up to one, two, maybe two, five online, whereas live I'm happy playing basically any stakes game, just because the skill differential is so different live versus online. And yeah, that's interesting. 

09:19 - Johnny (Co-host)
What's the highest stakes game you've been in? 

09:22 - Isaac Rose-Berman (Guest)
With my own money or with other people's money too oh, it's a good, quite that's a good. Uh, I guess we'll say, we'll say normally either almost almost always played just me, but for for a couple. Like you get an invite to like a particularly big game and then like, maybe, okay, I I didn't have like any specific backers, but I would ask friends like, hey, I'm playing in this big game, do you want a piece of me right? 

09:42 - Johnny (Co-host)
so at that, let's say the highest, with people taking a piece of you. 

09:45 - Isaac Rose-Berman (Guest)
So probably like listed game 50, 100, um. But what do you sit what? How much do you sit behind with that starting? Everybody started that game with 15k, yeah, um. But then the thing is also a lot of these games like it changes right like a couple couple hours in people lose some money. Let's throw on the straddle. The biggest game I've ever played in was it was actually a 2550 game that became 2550, 100, 200. 

10:11
That was the biggest game and that I was shitting myself the entire time yeah, it's tough to play it at stakes and I think also like even now in in betting, losing money at the poker table just feels very, very different, at least for me. Like I can lose 10 times the amount that I would lose playing poker betting and it just doesn't feel as bad. In poker you just like see the money, like the chips just in front of you losing and you're normally at the table other people. I find it so much harder, like I would rather lose. You know I don't want to read numbers here. I'd rather lose a,000 playing poker then, or sorry, $1,000 lost playing poker is a lot more painful than $1,000 lost betting on sports, in my opinion. 

10:50 - Rob Pizzola (Co-host)
Interesting. It's a lot different than Thursday night poker at the bet stamp office $100 buy-in late with Luke, you know, back in the day. 

10:58 - Johnny (Co-host)
Yeah, yeah, no, he's a good player. You should play him. 

11:03 - Rob Pizzola (Co-host)
On the sports betting front. So you've transitioned from poker to sports. Do you have someone that like mentored you along the way? Because, honestly, it seems really challenging nowadays for someone to go from one to another and like fill that knowledge gap. 

11:20 - Isaac Rose-Berman (Guest)
Yeah. So the way I started off was, like I said I I was doing a lot like the promos, like I didn't really know Much about sports betting other than I mean these companies were just giving out lots of free money. Yeah, so a lot of the like. The first I wouldn't even say studying I did, but the work I did I'll give a shout Out to my cousin who's like getting his econ PhD. We basically wrote a paper on the optimal way to use free bets, like that was, and it was okay. 

11:41
You assume the market is efficient, you assume you're losing 2%, what's the optimal strategy to use up the bonus money? So that's sort of how I came into it. And then from there it was just spending so much time basically rolling through deposit matches and bonus money in that and you would stumble across things. Right, you'd be like, oh wait, this site is offering this game at plus 150 minus 170, and the other is offering, you know, plus 175 minus 200, like, okay, I don't even need the bonus here, I can just take both sides, and I was never a big arbor and that. But it was like, okay, there are inefficiencies here. 

12:14
And the main thing for me was that I'm a big tennis fan. Um play used to play a lot more tennis. Not as much anymore. Uh, so I would be like in the in sort of the trenches of tennis markets and looking at all these prop markets, and there was one specific market where the odds on one site were just totally different than on other sites and I was like, ok, this book is obviously wrong. We just keep betting, it kept losing. And you're like, ok, something is wrong off here, do some more work. Ok, actually this site is the one that's pricing it correctly. And then from there I think that's probably sort of how I got into I guess you would call it more the originating side I don't even know if that's necessarily the exact term, but basically to an extent making my own numbers and trying to sort of start from the bottom and say, okay, where can we find inefficiencies in the market? 

13:00 - Rob Pizzola (Co-host)
So when you say that like originating you don't know if that's the correct term. 

13:11 - Isaac Rose-Berman (Guest)
Something leads me to believe you're doing something differently than just standard modeling of tennis events. Yeah, so I think people have a lot of opinions on modeling and stuff. I think tennis is the easiest sport to model, like very, very fundamentally. There's only two players and there's pretty limited factors, and that all you need for a basic tennis model is what percentage of service points each player is going to win first serve, second serve and then you can just simulate the match however many times you want, and so if you have a set, you know one player's percentage of first serve points one is the same as the other player's percentage of first serve return points one, and so it's not that complicated. So I've done a couple of those. Obviously, if you do that and you just put in some basic numbers, you're not going to get a huge edge in the market. So most of what I did starting out, and I think probably the majority of what I still do today, is assuming that the market prices for money lines are correct and then using that to find edges in smaller markets. So, for example, whether it's the game spread, set spread, total, a lot of these varies by book. A lot of books will use sort of a normal distribution and that doesn't always hold for a lot of matches. I think, honestly, a lot of the. 

14:13
I was very lucky in that tennis isn't that popular in the US. So I think, starting out initially, those markets were a lot less efficient, especially the derivative and prop markets, where there weren't that many people betting them. You know it's, it's. The markets are a lot bigger in other countries where people care a lot more about tennis and so I think and you know, in terms of also scaling as well, like later on when I was working with partners and work with people, it's like, oh, no one really bets tennis. So I think it was a lot easier for me to sort of get an entry there as opposed to doing something where, oh, everybody else is already betting this. 

14:38 - Zack Phillips (Announcement)
Oh, hey, producer Zach here just catching up on mysteries of everyday life, and one of those mysteries that I still haven't been able to answer or figure out is why more people don't add Pinnacle to their list of outs. As you guys know, the NHL season is back and I've been leveraging Pinnacle for pretty much all of my Maple Leafs betting whether it's Leafs, money lines, leafs, puck lines, austin Matthews, anytime goal, it doesn't really matter. I've been using Pinnacle for the best odds pretty much on the market, for everything. It's time you guys add Pinnacle to your list of outs. In business for 25 years yes, that's right, 25 years. One of the most trusted sportsbooks in the entire world. Reminder, you must be 19 plus, physically located in Ontario and not available in the US. And if you are looking to sign up, make sure to head on over to Pinnaclecom forward slash hammer. That's Pinnaclecom forward slash hammer today. 

15:41 - Rob Pizzola (Co-host)
All right, we're back in studio. Here you might notice Isaac's in a different spot, johnny's usual spot, and Johnny's not here. Johnny was not feeling well today. He wanted this to be like the michael jordan flu game flu podcast for him, because isaac's in town wanted to see him again. But we just stepped in, told him but go get some rest, it's okay, we'll move on without you. So we're going to continue on here, just me and isaac studio. And what I wanted to ask you in particular with tennis betting is does your knowledge, like you said, you grew up you played a little bit of tennis Does that give you a benefit in betting the tennis market? 

16:14 - Isaac Rose-Berman (Guest)
Yeah, so I think it does. Now, in the past it didn't. So I think when I first started off I was like, oh, you know, I know these players, I know who's going to win. And so I kind of had this arrogance with relation to the market where I was like, okay, I don't care what the prices are, like, this guy's going to win today, this guy's not going to win. And so initially it really hurt me where I was just betting, kind of my thoughts. And then you do that for a while and you're like, okay, this is just not sustainable, I mean particularly for me. Never really had a real job. 

16:41
I always knew, okay, if I wanted this to be my career, I had to win, right, there was no choice. And so I kind of sat down. I said, okay, well, let's try to quantify some of the beliefs that I had about this. So in particular, like I said, a lot of my betting isn't around who's going to win, but rather the more prop and derivative market. So I was like, okay, I have some thoughts about this player and then I can go in and test those thoughts. Right, you know, okay, this guy when he wins, he's likely to blow someone out. It's pretty easy to test, right, you just have a data set with all of the matches and you go in and you can say, okay, relative to this baseline, how often did this guy win in straight set? So that kind of stuff. And so I think when I made the switch to being able to try to quantify my opinions, now it, now it a lot, but when I first started out it really didn't and it probably hurt me. 

17:26 - Rob Pizzola (Co-host)
Yeah, so that kind of speaks to like the psychology of the game a little bit as well. I can't remember which tennis better we had previously talked to here. I mean, we're on episode 178 now. We've. You know, at least half of those have been guest episodes, so someone in particular had brought up like Grand Slams versus just like a regular. I want to say they're like 100 CREs. 

17:45 - Isaac Rose-Berman (Guest)
Yeah, so there's basically there's all different, all different levels of tournaments and, yeah, I mean the markets are very different. So there's four grand slams a year for men and for women. Also, I basically only bet men. I just I never really watched women's tennis, I never really knew that much, and every time I've tried betting it I've lost money, would you? 

18:02 - Rob Pizzola (Co-host)
have like a hypothesis as to why. 

18:06 - Isaac Rose-Berman (Guest)
I think I just never. I mean, frankly, I didn't really watch much women's tennis and so I didn't understand it as much, got it. And then also I would say to your Grand Slam question the majority of my betting is during Grand Slams, not from a sort of total number of bets but from a total amount bet perspective, just because those markets are way bigger, they're a lot more liquid and men's Grand Slams are best three out of five, whereas all other tournaments are best two out of three and women's are all two out of three, even for Grand Slams. And so I think, at least for me in particular, as someone who enjoys sort of the more prop and derivative markets, just the best three out of five format allows for a lot more nuance in terms of different markets offered that I was always able to sort of find bigger edges in. Are there any like cutting? 

18:49 - Rob Pizzola (Co-host)
edge statistics in tennis. That, listen, I'm not. I'm not suggesting that modeling tennis is an easy thing, but it's a pretty data driven sport. There's a lot of stuff out there that you can use. You have different surface stats and anything like that. Do you think that, like most people do get an edge through information you know, like angles? 

19:15 - Isaac Rose-Berman (Guest)
maybe. Yeah, I mean, there's definitely a lot of ways to get an edge. I would actually say information is always like my weakest point, just because I especially and it sort of it varies a lot Grand Slams versus other tournaments as well. But one of the things, like I've said on other podcasts, is I really try to stay away from betting the first round of tournaments, okay, just because there's a lot of information that you might not be privy to, right, whereas after the first round you sort of see you, your most recent data point is a match they played yesterday or two days ago, right, whereas going into a tournament you don't't like I have no idea If something's not public, whether or not someone's sick, how they're feeling, and that might be factored into the market price, and so not only can you, you know, your models or whatever might not work as well, but I just have always found just insane adverse selection in the first round, where I'm going in and I'm seeing all these edges and then I'm betting them and you start watching the match and you're like, oh, you know, this guy's clearly not on it today and that was factored into the market price in a way that I didn't really know. So there's definitely I mean in terms of stats that people use, there's all sorts of things. Frankly, I'm still probably on the more qualitative side, got it? I was happy that you had Costco croissant in a couple of weeks ago so that you know I wasn't just. 

20:19
I like bets based on feel, but yeah, I would say obviously a data-driven approach. 

20:25
But I would say, of the tennis bettors, I know I'm more on the qualitative side, but I think one thing that's been really, really helpful for me in my betting is knowing other bettors who have different approaches. 

20:35
And so I know people who take a much more quantitative, much less feel-based approach to betting on tennis and I try to normally run my bets by them, in particular if I'm betting in more liquid markets, right. So if I a tournament comes out and there's, let's say, 10 first round matchups or second round matchups that I like, I'm going to forward those bets over to a friend of mine who takes a more model driven approach and in my experience, the bets that we align on those are always the ones with the highest ROI, and so it's understanding that. You know, I think that what I do is pretty good, but obviously other people do different things and if they also win, that overlap is going to be the most successful and there's things that you can have different methods of handicapping and arrive at very different conclusions and that could potentially give you an edge in one way or another. 

21:32 - Rob Pizzola (Co-host)
I would think that if you're betting tennis something like fatigue, especially over the course of a tournament you could probably model that out in some way. You could probably also gain some sort of substantial advantages by watching a match and seeing how someone is reacting relative to, like, their baseline performance late in the match. 

21:48 - Isaac Rose-Berman (Guest)
Yeah, I mean, I think live betting and pregame betting they're totally different things, right. 

21:53
So I think, frankly, I've had a lot of success live betting, although and I would say very little of it is model-based, and I think that's where you can sort of get more of a feel based on your knowledge of the sport. And if you watch all these players a lot, then you can get an edge. And I also think, because in tennis the odds are a lot more dynamic in game, just the way the scoring works we don't need to go into the specifics of that you can just often line shop to basically zero vig or like, even like it's not uncommon if you're watching a tennis match for there just to be pure arbs in game just because the odds are shifting so much. Right, if someone has a break point and they save the break point, it's a crucial stage in the match. These things have huge swings and so, like I know people who make a lot of money betting tennis live and they don't know tennis at all. Right, you're just picking off books which are half a second slow to update. 

22:37 - Rob Pizzola (Co-host)
That's not really what I do, but I think, in terms of live mainly, it's almost purely feel but obviously line shopping to the point where if you're betting into a market with almost zero hold, it's not that hard to win. Yeah, so in sports I'm more familiar with, like football and and and hockey. Um, when I'm betting live, I know that certain teams have certain tendencies in situations. The goalie pull is very obvious in hockey, but some teams will pull earlier and some teams just won't pull to later in the games. Football will be your play calling when you are trailing versus leading how quickly you run plays, things of that nature. I would imagine you can gain a similar edge in tennis just by knowing how players play in certain like if someone goes down for love in a set, they might just give up on the set versus somebody who might actually try like. I feel like that's where the edges? 

23:27 - Isaac Rose-Berman (Guest)
no, no, there's. 

23:28
That's definitely true, I think, especially when you talk about things like maybe not the money line, but like the game and set totals and spreads right. 

23:34
So if, for example, just as you said, and this is particularly true in best of five matt and by survive, like if you're playing a best two to three set match, you can't really give up on a set, right, but in the best of five match, let's say you're up two zero and in the first you win the first two sets, then the third set you go down that early break, especially if you're someone whose game style is maybe like more serve dominant and you're probably not going to get it back, like some of these american guys like seven feet tall, right, they're basically just winning on their serve and losing when they're not serving, and so if they go down in that break early, they're probably just going to give it away. 

24:03
And so then, knowing that, in terms of for things like the game spreads and the game totals and that yeah, it's a big thing, and you think there's some funny things where, like a couple of matches where a person will be up to two sets to one and then they'll lose the fourth set, like six zero, and then the final set. Now it's competitive because they're actually sort of coming back in and trying Got it Makes sense. 

24:21 - Rob Pizzola (Co-host)
Would you say you have a better edge on bigger edge on pregame or live tennis. 

24:26 - Isaac Rose-Berman (Guest)
I think pregame, just because there's a lot more props, like in live, I'm almost exclusively betting money line and set winners just because there aren't as many in game in game bets live. 

24:36
But I think the volume live is way higher. Like if I'm for a tournament, I'm probably, let's say, I have an edge on or I'm betting maybe one-tenth or maybe 15% of matches pregame, whereas live, if I'm watching, you can pretty frequently find good bets in almost every match and, like I said, it's not just because I have some giant edge, but the markets are moving so much that if you're getting to zero vigor, if you watch a tennis match and you have at least a few books available to you, you should be able to get some just pure ARBs at some point in the match, and so it's pretty easy. I don't bet as much live these days just because it's a grind and, yeah, it's just so much volume that it can be overwhelming to you. I love tennis, but to watch it like 12 hours a day every single day, like during Grand Slams, that's what I'm doing, but outside of the really biggest tournaments. 

25:25 - Rob Pizzola (Co-host)
On Circleback. On Tuesday we pulled up a tweet from Always Betting podcast which was in related to getting limited. We talked a little bit off air but you had mentioned that you enjoyed the episode with Mr Limited that we did a while back. On that front, when I'm talking to other sharp bettors or people who are doing this for a living in the space, like you are, I'm curious are there any tidbits or things that we haven't talked about? You don't see out there right now? That may help someone avoid detection as a sharp yeah. 

26:00 - Isaac Rose-Berman (Guest)
So I think it depends where you are and what stages you are. So, for example, I mean most obvious thing we talked about this on Circleback when you're starting an account, like, don't fire a lot of sharp stuff right away so just the account priming is obviously crucial. If you're someone who's maybe lost for a little while and now you're transitioning to winning, you don't have to worry about that as much. But yeah, I mean, I think just creating this picture of what a recreational customer would bet and thinking like, OK, maybe you have this one edge in some random prop market and not just going in and firing exclusively that betting major market stuff, I think one reason that I've been able to have more success than others in terms of keeping accounts open is that A I kind of am a gambler and I'm happy to give some money back, and I think this is maybe something that you also get from poker as well, where it's like you sometimes have to take some minus EV spots to be an action player, because if you don't give action, you're not going to get action Right. So if you don't, if you open up an account and you're only betting stuff where you know you're going to win and it's going to steam a lot. The sports looks not going to keep you around. 

27:00
But if you actually are OK to give some back, obviously you don't want to give, you want to minimize the amount that you're giving back. 

27:06
But in poker, you know, the same way, you're going to play a few extra hands pre-flop. You know, when you open an account and even if you're betting other sharp stuff, being able to go in and fire some stuff on NFL Sunday or stuff where you pretty obviously don't have an edge and I think even for pretty large amounts is the key as well. Like a lot of people will say oh, you know, I gave back on this account and you look at their account and it's like, okay, they're betting the max on all these props and then once in a while they're firing like a hundred dollars on an NBA money line and it's like not that mispriced. And you're like, okay, it's not actually that equivalent, Right? And I think if, if you are a sharp better and obviously you know people's bank rolls vary if you're betting, let's say, a thousand dollars on an NBA money line and you're losing what like 30 or 40 bucks, right, You're not actually losing that much and I think, just thinking, in terms of expected value Exactly. 

27:53
Exactly. And obviously you can win that bet or you can lose that bet. But thinking in terms of expected value and, like you know, if you place a lot of chart bettors I know don't want to place like thousand dollar bets that they don't have an edge on and it's like I'm kind of fine doing that if I'm fairly confident I'm going to be able to recoup that later on. And yeah, obviously it sucks when you place 10 bets that you're just kind of doing it for shits and giggles or basically to prime the account and all of those lose and you're like, wow, damn, I'm out. I'm now out 10 grand. I don't even want to bet these things. But you have to think in terms of expected value where like, ok, I'm other strategies as well. I mean, I know we're going to talk about some responsible gambling stuff later. 

28:31
Just one thing that I've experienced a lot and I think it's sort of informed a lot of my thoughts on responsible gambling is just literally and I had a piece on this recently acting like a degenerate and potentially even like an addict. I mean things like chasing losses, work on your accounts. So if I open up an account and I deposit, let's say, $1,000 in it. I'm not betting $50 units, I'm going to be betting at least a few hundred dollars and like, ok, the account looks better if you deposit $1,000 three times than if you deposit $3,000 once. And all of these things like, ok, you lost, now you're going to double your next bet, you're chasing losses and seeing how that rewards accounts definitely informs my betting in terms of keeping accounts open and I think it also, you know, obviously informs some concerns about some sort of predatory aspects of the business. 

29:19 - Rob Pizzola (Co-host)
Out of curiosity, have you ever had a sports book reach out? 

29:20 - Isaac Rose-Berman (Guest)
to you when you exhibit those behaviors. Never I've had them reach out when they exhibit those behaviors to give me VIP. I've never in my life had a sports book reach out to me for responsible gambling considerations Not once. 

29:29 - Rob Pizzola (Co-host)
Yeah, because it's very prevalent in market nowadays. 

29:32 - Isaac Rose-Berman (Guest)
You see all the ads, but they don't. They obviously don't care. These companies don't care it depends on. 

29:36 - Rob Pizzola (Co-host)
I would say that I generally agree. I do think the vast majority don't care. I think that's. I think there's people within responsible gaming setups that do they actually do care. 

29:49 - Isaac Rose-Berman (Guest)
Sorry to clarify. I don't think that the people who are working in responsible gambling at major sports books want people to be on the streets and lose all their money. I just think these are for-profit companies and that's the prevailing. That's what they care about the most is making money, and you want the situation where you have a customer who's losing enough that they can continually lose, yeah, yeah. 

30:12 - Rob Pizzola (Co-host)
I think it's more so, just from my perspective. I think that sports books, especially the casual, recreational sports books, they just want people to bet, literally as a form of entertainment, not looking for an edge, not price shopping site to site. Just use the site because you know, instead of going to the movies for 20 bucks, you lay down some bets for an edge. Not price shopping site to site. Just use the site because you know, instead of going to the movies for 20 bucks, you lay down some bets for 20 bucks. You have the opportunity to win and I think that that behavior is encouraged provided it doesn't go overboard. But I'm not sure that I would agree with you that I'm not sure that they do enough when they do go overboard. 

30:48 - Isaac Rose-Berman (Guest)
Yeah, I mean, I think it's a tough question, which is why, in general, you know, I don't think the sportsbooks should be the ones in charge, Like, obviously they should be in charge of their own responsible gambling campaigns. But I think, you know, you got to have some outside, whether it's, you know, rules or regulations and, I know, hotly debated for all sorts of reasons. But I, yeah, I mean, it's just silly to do this and, to be clear, I think they have a hard job, right? No one goes to no one goes to a bakery and they're like, oh my God, this baker makes the best muffins in the world and we're going to blame him because someone goes in and buys a bunch of his muffins because they're so good. Modern sports books they, they do an incredible job. I mean, the product offerings are amazing. Sports betting is so fun for a lot of people. 

31:30 - Rob Pizzola (Co-host)
I can tell you, I've been betting for 20 years and it's night and day. Yeah, if I had to go back to the sportsbooks I was using when I was 16, 17, even the paperheads have come a long way, even though they've barely moved, but it's night and day now I don't know what I would do. 

31:50 - Isaac Rose-Berman (Guest)
Yeah, and I mean, I think it's hard to tell them you're a for-profit business and we want you to be able to make some money, but we don't want you to be able to make too much money and you can't make too much money off of certain people. It's, objectively, a really, really hard thing, which is why I think you just need to have some sort of regulation or government intervention in some way to basically make some rules about what happens. I don't know exactly what those should be, but it's a tough question. 

32:09 - Rob Pizzola (Co-host)
Let's dive a little bit more into legislation and policy. Obviously, with your substack, you write about stuff like this a lot. I've chatted with you privately about this. You genuinely have an interest in legislation. What drew you to this area? 

32:25 - Isaac Rose-Berman (Guest)
Yeah, so a bit of background. Both my parents are political scientists. Okay, makes sense. So that's sort of like when I grew up in the house, that's what we're talking about policy and politics and all that sort of stuff. In school I studied politics. I almost went to get a PhD in political science before. I decided to become a professional sports better. 

32:42
Yeah. So it's kind of a ridiculous transition there, but so I've always been very interested in sort of the politics as well. I also think it's just kind of an interesting question. I mean, in the US especially, this just got legalized. It sort of coincided with, you know, when I was able to start betting and you're like, wow, these companies are now here. 

32:59
It's, the landscape of sports has totally changed. You're like, ok, this is just, it is a genuinely interesting policy question. And so a lot of you know, know, the writing and stuff I do is just because I'm like I don't know how these companies like should operate in society. All right, and I think, in particular, one of the things that drew me to this is that a lot of the people who are making the regulations or even talking about the sort of stuff, they don't have any experience betting. They're not better themselves, and so it was like I can provide some perspective, not necessarily even as a sharp, better, but just as someone who uses these products and understands them to think, okay, here's how we can inform policy in a way that's not going to be detrimental to any of the different parties. 

33:37 - Rob Pizzola (Co-host)
Yeah, that makes sense. I was going to kind of ask you about that in particular. Like to me, I see that as the biggest roadblock in the space. Right, I've experienced it firsthand. You know I'm a co-owner of Betstamp. I have the hammer, we work with sportsbooks pretty regularly. But I've had conversations with Ontario regulators and I think there's a significant knowledge gap that exists there. 

34:00 - Isaac Rose-Berman (Guest)
Yeah, I mean I don't want to give any details. I've been in a dispute with a major US regulator for a long time because they basically owe me a lot of money and they won't pay me. And it's just because there's this fundamental misunderstanding of how gambling operates. And when I first started writing, I had this idea of okay, you just give more power to regulators and then they'll do all of the things that are necessary. And I've met a lot of regulators and policymakers. I think they're almost all extremely well-intentioned, but there is a knowledge gap a lot of the time, and so I now don't think that's the case. I don't think you can just sort of blindly give power to regulators and policymakers and expect great things are gonna happen. There has to be whether it's sharp bettors or anybody just kind of informing them so you can craft policy that actually works. 

34:45 - Rob Pizzola (Co-host)
Yeah, I can say 178 episodes in of Circles Off, and we face challenges in doing content because we have to be very, very careful with the words that we use and this is our legal departments that are giving us advice on this stuff. 

35:06
But we could potentially be taken to court for something that is completely misconstrued. And I think back to like the plus ev analytics case against Caesars, where, in my opinion, there is absolutely zero chance in hell that he should not have won that case. Yet he was fighting an uphill battle the whole time, couldn't get anyone anyone to talk to him, and people are always asking questions on our Q&As about taxes, multi-accounting, this and that, and I simply just can't even speak to them, not because I don't want to, but because the words can be taken out of context and used against me down the road to parties that just don't understand. Imagine just a hypothetical where I'm in court for something and I have to explain to a judge who knows nothing about betting or a jury or anything like that, and it almost feels like the same thing in the regulatory space, where it's just it's really hard to regulate industries when the people who are regulating them don't have the foundation to be able to do that. 

36:16 - Isaac Rose-Berman (Guest)
Yeah, and I mean I know there's obviously a lot of debate around regulation when it comes to sharp betters, specifically this idea where, especially for things like limiting right, like oh, we can regulate, we can have mandatory limits and all this stuff. And I think I know we agree on this issue where I don't think more regulation is good for sharp bettors. I think if you are a professional bettor, it is almost certainly in your interest for the industry to be relatively unregulated, and so when I talk about wanting more regulation and policymakers to be more involved in this stuff, it's not because I think it's going to be good for me Honestly. I think it's going to be good for me Honestly. I think it's probably bad for my bottom line as someone who bets on sports for a living. And if you want to criticize me, that's totally fair. 

36:53 - Rob Pizzola (Co-host)
Well, the only thing I'll say is that you clearly have gotten more outs by doing this yes, for sure, yeah, I think so. The positive is just the sheer amount of spots you can bet For a top-down. Better as an example, especially in Ontario. Better as an example, especially in Ontario Ontario's got 30 plus regulated sports books right now. That's a dream for someone who's just price shopping and picking off bad numbers. But I'm curious what you think the biggest downside is. Downside of what? Of regulation? 

37:21 - Isaac Rose-Berman (Guest)
for a pro. Basically, it's just any change to the status quo. 

37:25
If you're a pro and you're making a lot of money, you don't want things to change and regulation not anything in particular, but it necessarily adds new complexities which might be bad for you. And but my point is like I don't think we should have more regulation because I think it's gonna help sharp bettors and I think from a policy standpoint, sharp bettors don't matter. It's like 1% less, it doesn't even matter. The have more regulation is because legal gambling has meant a lot more people gamble and a lot of people. Gambling means a lot more people are going to be harmed by gambling and that is bad for society. 

37:55
I think it's bad for people individually and I think to the extent that we should try to help those people and prevent a society where a lot of people are getting screwed over and losing a lot of money, like obviously we know tons of people are. You know that's the government's job to try to do something about that. So that's sort of where I come from in terms of my interest in policy. Like maybe it's too naive and idealistic, but that's what I care about. 

38:17 - Rob Pizzola (Co-host)
Well, what is the real world solution to that right? Because you have corporations who are providing a lot of tax money and, frankly, I mean you would hope that that tax money is being put to good use. You can have the debate on whether or not your state is using your tax money properly, or your province, or whatever, but the reality is there is some sort of payback to society through the corporations as well. It is viewed as a form of entertainment by many. I'm with you. I'm not putting you in a corner and saying, well, no, this is a ridiculous take. I think the real issue is the lack of education, but I don't know what the solution is to that. 

38:58 - Isaac Rose-Berman (Guest)
No, I totally agree. I remember, like when I first started writing, I was writing things which were more educational, explicitly, and like here's how you can be sharper, like here's how you can line shop, and I was like, oh, I had this idea that, okay, well, there's a small percentage of the population who are problem gamblers, and then there's the vast majority of other people and if we can just help those people be like a little bit sharper and, you know, line shop a little bit, they'll lose less money and they can be an entertainment activity. And I still kind of think that's true. But, like, people don't care and you know it's their prerogative, right, they should be able to do what they want. 

39:30
I think recently I've come around to the view that there's a big difference between sports betting and online casino, and so I think, from a political standpoint, like there should be legal sports betting but not legal iGaming. 

39:44
And I think, when you talk about the regulatory side, a lot of the problem is that the regulator's incentive is to raise tax money and these companies are bringing a lot of tax money, so their incentives are actually aligned there in a way that, you know, sharp bettors think the regulators care about them? No, they don't care. In general, they want tax revenue. Right, so I think. But at the same time, you know there's a percentage of what people are losing, and especially for things like iGaming, where just the numbers are crazy in terms of how much people lose. Whatever you want to say about sports and obviously it can be addictive and obviously there are people who lose a lot of money the numbers for iGaming are so much worse, and so I think, at least for me, sort of the political angle I try to strike it's tricky is, you know, there should be more regulation of sports betting and we should sort of try to put a stop to online casino, at least in the us. 

40:29 - Rob Pizzola (Co-host)
I'm not familiar with the canadian context, where I know it's a little bit more widespread, but in the us it's only kind of a few states that have legalized it yeah, I mean, it's just ontario of legalized uh gaming in in canada right now, soon to be uh alberta and and possibly bc down the road as well, but it's just ontario right now. I think you hit on a really good point there where I think, where regulation has let bettors down especially newbies who are just in the space for the first time is that the regulation seems to be more aligned with making the sportsbooks happy than protecting the consumer. Now, it might seem hypocritical for me to say this, because we've had this topic come up a few times, but we have the American Better's Voice, which was co-founded by Spanky and Richard Schuetz. Thank you for the pronunciation. I don't know who else is involved in that. I met Richard at BetPash this year very nice guy. Shirt at BetPass this year Very nice guy. 

41:35
But I don't want a coalition speaking on my behalf as a better, because I think all betters are different. 

41:37
Maybe I'm contributing to the problem in the sense of saying like don't speak on my behalf type of situation, but as a pro, selfishly, I think that betting is like a dog-eat-dog type of world, right, and everyone can win if they put their mind to it. Anyone can win, I mean if you've watched every episode or listened to every episode of this show, I would guarantee that you have the principles to win at sports betting. It's very easy, but scaling is very different and that's another problem to solve in and of its entirety. So I constantly balance. This is kind of unfair that you can limit a percentage of the population but take huge bets from whoever else with. Well, this is my livelihood and I can get around those limits a lot better than maybe I'm like 98th percentile in being able to do that. That's a big edge for me right now because a lot of my previous edge, which was strictly the modeling of sports, is slowly being eroded because there's so many people who are now involved in the space. 

42:45 - Isaac Rose-Berman (Guest)
Yeah, no, I mean I agree. I think like when I talk to policymakers and regulators it's more sort of on the same question. They don't no one cares about sharp bettors. But you say, oh, you know, if you exhibit signs of addiction or problem gambling and your limits, get 10x right. That's what people actually care about. 

43:00 - Zack Phillips (Announcement)
And so protecting addicts. 

43:03 - Isaac Rose-Berman (Guest)
obviously it's a very important issue, but specifically from like a political standpoint that's, it's so much more salient than anything when it comes to sharp bettors. And so I think, like, especially in the concept on the you know topic of limiting, like that's what actually sort of moves the needle is the realization that the same mechanisms that are sort of restricting winning customers are sort of expanding those limits for losers, and that's obviously people don't like that. 

43:22 - Rob Pizzola (Co-host)
Yeah, and that is. It's definitely a problem. 

43:25 - Isaac Rose-Berman (Guest)
But I mean, even even I'm I know this is true for me like even probably true for you as well Like that is something that helps me Right, Like I I'm not going to go into details, honestly, because I'm giving up edges, yeah but like there are things that I know that I can do to increase the limits on my account, and part of those are, you know, not necessarily acting exactly like an addict, but there are behaviors that you can do that make you look like a real loser and increase my limits, and so obviously, bigger limits mean you can bet more and make more money. So it's like if that were to be changed from a policy standpoint, it would decrease my earn, and so I try not to be like I'm not someone who thinks that regulation is gonna make it easier for me to make money I don't but I think it's just probably not good for society. 

44:05 - Rob Pizzola (Co-host)
Well, I mean, it's actually sad when you lay it out like that. But yeah, I mean, listen, I'll just clarify what you're saying, but it'll come out of my mouth. I mean, it's a big time goal for me, when I'm betting with a rec book, to try to get into the VIP program of that book, because then you're betting into very soft numbers at high limits and it's sad that that's become part of the game. You would think that, okay, liquidity shouldn't be a problem, but it is. And ultimately there's pretty easy ways to go about doing that, but you do have to exhibit the behaviors of a problem gambler. And then you go back to the top point, which is like, well, aren't all these responsible gaming practices in place? How does it get? 

44:46 - Isaac Rose-Berman (Guest)
And it's just a really yeah, I mean, if anybody's sort of interacted with VIP programs, you kind of know how ridiculous the responsible gambling stuff is. I mean, I've, I've been VIP at, I think, most of the major legal books either me personally or I have a friend who has become a VIP in some capacity and sort of just seeing the inner workings of how that works and yeah, like I've lost you know five $10,000 in a book and then you have a customer service representative I'm not gonna say from any particular sports book, but like start messaging you and soliciting, you know, 20, 30, $50,000 deposits. And I have an article coming out on this at the time which honestly, has been a long time in the making, just because there's a lot of tricky things to talk about. But it's like, yeah, you know, there was no income verification and obviously there's a lot of stuff about affordability checks. Those are iffy for a lot of reasons. 

45:34
But yeah, the fact that I signed up I was 22 at the time signed up, lost like $5,000, got an invite to the VIP program. Two days later I have someone texting me asking me to deposit $50,000 without any sort of income verification no job, I mean, and that. And then you see those that same company has, you know, run running responsible gambling ads. I mean I mean, come on, it's pretty ridiculous. 

45:55 - Rob Pizzola (Co-host)
Yeah, I think at the end of the day, people aren't stupid, especially in the sports book business. You know the vast majority of your income, your revenue, is coming from a very small subset of players. Now I don't think that you have to like sportsbooks should be required to prohibit everyone from betting. I think the onus is on the sportsbook to make sure that that person is actually comfortable with losing the money that they're being afforded to bet. There's just going to be people who don't care Whether they have money or they do it for the thrill of betting. They literally it's not going to affect their well-being. Obviously, they'd rather win than lose, but they're doing it for the rush of betting. They'd rather win than lose, but they're doing it for the rush of betting. 

46:54
I don't think I've, you know, as bad as I was at some point. I don't think I was ever at that level. But there are some people that it's just not, and to me that's not the sign of a problem gamer. That's someone who's very much aware of what they're doing and they're betting with money that they can afford to lose. The problem is that is like the nurturing of bettors, and when you're in the door you deposit a certain amount of money and already you've got the VIP team. That's like, okay, maybe this guy could be a guy. And that's where I think the responsible gaming practices fall short. I agree completely. Yeah, how do you define responsible gaming? 

47:29 - Isaac Rose-Berman (Guest)
It's a tough question. I know the first time we ever talked over DM, I was writing an article and I asked you and you said they were like I sort of asked what is the difference between? You know a's really tricky. A responsible gambler is someone who not only bets within their means but kind of understands what they're doing, and I think far more of it is just emotional, right and just, and yeah, it's, I don't know, I don't have. I don't have a set definition. I wish I did and I go back and forth on it all the time. 

48:11
I know what a problem, I know what a problem gambler is and frankly, I think there's no good definition of what a problem gambler is. So you can look at the DSM-5, which is what psychologists use to identify problem gamblers, and it's like here are nine criteria and if you fulfill three or four of them, you're a serious problem gambler, and if you fulfill one or four of them, you're a serious problem gambler, and if you fulfill one or two of them, you're like a minor problem gambler. Right, and I look at those lists, I feel like five or six out of them and I think most professional sports bettors or most professional gamblers in general, probably do that as well. Yep, and so I don't? Yeah, I don't really know. I remember there's a Joey Knish tweet from once where he was like do all professional gamblers to some degree? Are they all addicts? I remember that tweet and I think it's an interesting conversation. I don't know. 

48:59
I think people think there's this difference like, oh, now you're a professional, you must not be an addict or you must not have sort of gambling problems. I don't know that that's true, and I think most professionals that I know have at least at some point in their lives had flirtations with problem gambling or maybe not gambling addiction. So yeah, I don't know. I mean, I think it's a hard issue and I think a lot of people think, oh, you know, if you just win, that solves it. But no, I mean you can talk about poker. Some of the best poker players in the world go broke just because if you were the best poker player in the world but you sit down at the table with your entire bankroll, obviously bankroll management is more important and I think that's particularly a problem in sports as well. 

49:38 - Rob Pizzola (Co-host)
It's a good question that he posed. The thing is, professional gamblers can very much be addicted to their job, just like anyone else could be addicted to their job. I remember when I was working at the score, I mean I would spend 50, 60 hours a week in office. I really liked what I did. There is a negative doubt. There's a downside associated with that. Your personal life time you can spend with family, and just like there's downside with with you know, responsible gaming issues. But I mean I don't know that I would call it an addiction. It's a means to an end for me and sure, I guess I'm addicted to it because I'm making money, but I don't, like I view an addiction in a negative connotation. 

50:21 - Isaac Rose-Berman (Guest)
Yeah, I agree, I agree, yeah, I mean, I know I'll talk with friends and they're like you know, if you lose a lot of money, you can almost always tell, right, so you wake up the next day I live with roommates and they're like so yesterday was a bad day. I'm like, yeah, and they're like well, you know why don't you just take this week off? And I'm like it's how I pay rent, right, like I can't just take this week off. Is you place bets with a positive expected return? And more bets if they have a positive ROI means that more money for me, right, and so even and handling like the ups and downs, that's obviously, you know, I would say probably the majority of the battle. 

51:01 - Rob Pizzola (Co-host)
Yeah, I'm going back through our old DMs and I gave you these warning signs. Trying to win back money lost by continuing to gamble or betting larger amounts to cover losses that's like the classic one. Neglecting work to gamble is a big one, in my opinion. Hiding or lying about the extent of gambling to friends and family happens all the time. Unfortunately, I've been through that situation before. Using gambling as a mechanism to cope with anxiety or stress. Borrowing money to gamble Sad, but it happens. Denial of gambling problem I mean, a lot of these are the same warning signs. Whether you had alcohol addiction, drug addiction, a lot of it's the same thing. Neglecting personal relationships to gamble, that's another one. So those to me are like the biggest warning signs altogether and it's scary because, like when you lay them out that way. I mean, I've known so many people who've exhibited those patterns. 

51:57 - Isaac Rose-Berman (Guest)
And you can exhibit them, sometimes right and like not all the time. I mean, anybody who's gambled a decent amount has chased their losses, at least I think Like I could be wrong. And so you go like I remember I was talking to a social worker recently and we were trying to like delineate okay what actually signs. And she's like well, if you, if you chase your losses, that means you're a problem gambler. I'm like that literally describes a hundred percent or 90% of gamblers at some point. Um, and obviously they're sort of they're varying degrees, but it's really hard. 

52:23 - Rob Pizzola (Co-host)
I do chase losses in sports betting. Now let me clarify really quickly here I don't chase losses where, okay, I had a losing NFL Sunday, I'm gonna go put a bunch on Sunday night football to win it all back. But sometimes if I'm having let's say I bet a bunch of pregame college football props on a Saturday and the early slate doesn't go well, I don't always bet midday on Saturday but I might find myself betting midday on the late stuff. With that said, I'm not just firing randomly to win my money back, I'm looking for edges. 

53:05 - Isaac Rose-Berman (Guest)
it's basically like I'm gonna work To try to make the money back. 

53:09 - Rob Pizzola (Co-host)
Yeah, so it's not. I don't view it as a chase because I'm still finding positive expected value bets, but ordinarily, yeah, I might have been out on Saturday or out on Saturday night, and if things are not going well, I might be at the desk for the rest of the day. 

53:23 - Isaac Rose-Berman (Guest)
No, I mean, I do the same thing, like for big tennis tournaments. I try to sort of keep a decent schedule because, in terms of both, like prepping, pregame stuff and then also live betting, and it'll be like, okay, I'm going to live bet, sort of maybe the morning slate or whatever, and then there's fewer matches in the afternoon, I'm going to take a break. The morning slate is bad, I'm not leaving Like I'm, I'm, I'm going to, I'm going to keep, I'm going to keep betting. And yeah, most of those try obviously all of them to be good bets. But but yeah, I mean you, chasing losses is natural, I mean it's, and it's part of it's, part of gambling, it's. I think it's probably, you know, impossible as a human to not want to chase losses in our psychology. 

53:58 - Rob Pizzola (Co-host)
Yeah, I will say like, even at the blackjack table, craps table, a different form of gambling, but I'll chase losses. The only the only thing I'll say and some people might call me out and be like oh Rob, this is like. But when I pull that money out of my pocket and I put it on the table to buy in it's gone. I assume it's gone and that's my mentality. I am betting this as a form of entertainment. I'm totally comfortable with losing this. If I lose this, I'm not going to ATM and pulling out more money. This is my betting betting fund for the night. 

54:29
Now I'm lucky in a sense that I can do that, because some people can't. They don't have the luxury of of having a disposable income to bet for entertainment and they're you know they're betting to try to win. But when I know the odds are stacked up against me in a game, I'm not an idiot. If I'm playing roulette, I know that if I play X amount of spids over time, I'm going to lose X amount of money. Bet. It's a mathematical formula and I'm fine with that. I'm just hoping to get lucky. If I'm down a little bit more, yeah, I might press it, but I I know that I came here expecting to lose that and that was kind of like the biggest differential, because Rob from 20 years ago wouldn't do that. Rob from 20 years ago would go to the casino, I could count cards and I'd have an edge in my favor. It didn't go right. I'm going and pulling out more money betting more than I can afford to lose. I don't do that anymore. 

55:25 - Isaac Rose-Berman (Guest)
Thankfully it's Canadian money, so it's fake. 

55:28 - Rob Pizzola (Co-host)
It's not even real. I can take a couple US sportsbooks for a spin and I'm right back to where I need to be. But yeah, I think that's kind of like the perspective, and I do think that that's what RG is trying to ingrain in culture, especially in the sports betting space is that it's fine to lose a little bit for entertainment, but I don't know how that message is ever going to be like. The problem to me is getting that message across to like 21 to 25 year old males, because you can send someone to talk, to give a speech to a college campus. You know who's going to listen to that? None of those kids Zero. How do you make like RG cool in a sense? 

56:15 - Isaac Rose-Berman (Guest)
I have no idea. Yeah, I mean I think I would say it's like the person does that's going to be very rich, but obviously you're not going to be very rich, you're just going to do a good service for the world. Yeah, I have no idea. I mean, I know you guys have talked on the podcast about like different types of content and you've like book it with Trent, right, and there's like, okay, maybe this is glamorizing, um, some problematic behaviors, but it's also funny. I do think the content is pretty good and pretty funny. 

56:40
Yeah, I have like this ridiculous dream where, like somewhere down the road, you have a book it with Trent type figure who's somehow advocating for problem gambling, and I don't know if that's even feasible or possible at all, but I think it just has to be good content, right. I mean, the only way people are going to engage with something is if it's high quality, if it's entertaining. Not even high quality if it's entertaining, I think, is the main thing. And yeah, I have no idea how to make entertaining responsible gambling content. If anybody does, please send me a DM. 

57:10 - Rob Pizzola (Co-host)
I'd be very curious so a secondary goal of creating Circleback was to do just that. So for me, picking on bad tweets that are out there that are sending bad messages to sports bettors about bet the farm on this, do whatever you know by the farm on this, do whatever you know by using those as examples and then having kind of making fun of them in a way, I actually do think that that could cater to the masses still in our infancy of doing that show. But the demographic skews much younger than this show in particular and that's the only so responsible gaming is very important to me and it always has been, because of the amount that I lost when I was younger and I went through serious depression lost relationships, didn't talk to, literally avoided people for months, years. I've lived through that and, um, you know, I don't want other people to have to go through that. Once you go through that experience you're like fuck, this is rock bottom, like people shouldn't have to go through that. 

58:19
I'm very aware that I own a business, co-own a business in the betting space that sends people to sports books. We produce content here that is sponsored by sports books. We're in the betting space. I try to do this as responsibly as I can and be as open with the audience as possible. But circle back to me as much as we wanted to create like a TMZ type of you know the view fucking round table, it's just as much about like education in the space that I think people might actually watch versus a 10 minute YouTube video of here's how to manage your bankroll. Not to say that that doesn't have value, because it does. I think that it's good that all that stuff is out there, but it's gonna take a specific type of person to sit down and watch a half an hour video of like Captain Jack. Yeah, and he does a really good job of it good thumbnails, good content, and the one thing that I will truly respect about Jack is the amount of effort that goes into creating those videos. Like. 

59:26
I don't want to overstep boundaries here, but when we first launched the hammer, I reached out to Jack and said I'd like you to be part of this in some way, and he was very candid. He said Rob, you don't understand how much of a perfectionist I am when it comes to this content. I like to own my own content, control it. These videos I put out that are 10 minutes, those will take me a week, two weeks sometimes, because I'm so much of a perfectionist. I respect the hell out of that and there's a place for all of those perfectionist. I respect the hell out of that and there's a place for all of those. He's carved out a very good thing for himself and YouTube and people will watch those videos. 

01:00:00
I will still produce those videos honestly, whether they're sponsored by Pinnacle or not. I'll I will put out educational videos because, listen, if even a few hundred people find it, it's a few hundred people that have found it. But how do you reach the masses? And, like, you have sports books that are putting out commercials, you set responsible gaming limits and this and that and whatever. I don't think that has an impact at all. You have people talking at college campuses that lost a lot of money. I mean, most people are going to it's. How do you reach, like that TikTok Instagram demographic? And that was truly one of the point, one of the reasons that I wanted to do Circle Back, Obviously we're trying to grow our content. 

01:00:47
I'm not an idiot Like I run a content network. We got to get views, but that's an easy way to promote RG principles that I think maybe might resonate with people, and there's nothing hypocritical about it. 

01:00:58
Yeah, no, I agree, agree 100% Because you could get Book it Trent to do an RG video at some point or another and be part of an RG campaign. That would be great. But how can you do that when you're part of a brand that's putting out like a sharp report every day with frankly stuff that's putting out like a sharp report every day with you know, frankly stuff that's not sharp Betting. You know steam after it's already steamed, reverse line movement, all the stuff right, you can't. That's the problem with the influencer type of stuff. 

01:01:30 - Isaac Rose-Berman (Guest)
Yeah, no, I mean there's no easy way to make money off of helping people save money. That's kind of the problem. 

01:01:36 - Rob Pizzola (Co-host)
Yeah, in your opinion, what's the role of a pro bettor and the industry in general in promoting responsible gaming? Do you think that there's an onus on? 

01:01:50 - Isaac Rose-Berman (Guest)
bettors to promote it? I don't think so. I don't think anybody has an obligation to do anything that they don't want to do or that's not, you know, in their own interest, like I don't. If you want to just be a pro bettor and make your money and ride away into the sunset, totally fine, I don't think you have any obligation. I know for me, I do feel an obligation. 

01:02:09
I think part of it is, you know, I know a lot of people who maybe aren't problem gamblers but who exhibit some of those signs. You just you be around the space enough and you've met, you meet enough people who have been negatively impacted by gambling. I think it's really easy, especially if you're pretty sharp better, you spend most of your time around sharp betters just to not realize how many people not only obviously lose but do it in an irresponsible way. And I think maybe, coming from poker, I sort of got more of that, where you're just spending time maybe in casinos or around people. It's like 3 am and you're like fuck, this guy probably should not be here, and so I maybe just experienced a lot more of that firsthand. And I mean even myself. 

01:02:51
I think I'm very fortunate to have found my way into sort of betting profitably. But so much of what guides me is the fact that I have all of the sort of tendencies of a problem gambler, like anybody who's been to the casino with me knows. Like I'm a DJ and like I go crazy and fortunately I'm I. You know I can afford that and I sort of set that aside as an expense and it doesn't impact my livelihood. But yeah, you know, in in another universe where I didn't stumble onto some edge and then go down that path or whatever, or maybe had you know, 5% less impulse control, like I would be a problem gambler. Right, and so it really. It just hits home to me. So, yeah, I mean I care, but I don't think anybody else, anybody else has to care. 

01:03:31 - Rob Pizzola (Co-host)
Yeah, makes sense. Looking ahead, where do you see the future of sports betting? Are there any big trends or changes that you anticipate in the industry? 

01:03:41 - Isaac Rose-Berman (Guest)
I think you're going to see probably fewer ads. I think is a big thing, not as much, you know, maybe on the industry side, but in terms of, like the viewership angle, people are just tired of them in the US. I don't know how it is in Canada, I'm sure it's the same thing, it's not quite as bad, I would say. 

01:03:58 - Rob Pizzola (Co-host)
I was in the US three weeks ago and I could say that I mean, listen, we do have gambling ads in Canada, but they're more centered around brand or product than they are. Deposit this, get that type of thing. It's actually illegal in Ontario to advertise that way, so it's not quite as bad, but I would tend to agree that? 

01:04:17 - Isaac Rose-Berman (Guest)
Yeah, I mean, I don't even think it's. I don't even think it's the content of the ads. I mean there's people who were like, oh you know, this is a predatory ad to run risk-free thousand dollar bet when it's not actually risk-free, whatever. All that sort of stuff that's. It just annoys me. I hate it. I hate how many ads there are, and I know people hate it a lot more than me. If you don't bet, you're like why is this being thrown in my face? Why are my kids watching? Your kids want to watch sports and they can't watch it without being inundated with betting ads. So I think that's probably the main thing. 

01:04:51
Other than that, yeah, I don't know, I think you're going to see more consolidation into a couple or a few books. I think you're probably going to see some degree of federal regulation. I don't know exactly what that's going to look like. There's a bill in congress right now that a lot of people don't like, called the SAFE Act. But yeah, I don't know, I think it's just going to be a what's the SAFE Act? 

01:05:14
So the SAFE Act is basically it's a lot of restrictions, both on ads and in terms of what people can, in terms of mandating deposit limits and affordability checks, all this sort of stuff. There's even some weird stuff in there about banning live betting. People got really upset about that. But yeah, that's not going to pass. But there's a lot of interest just because this stuff is. This stuff is everywhere, and so I think, yeah, I mean also just with the. You're probably talked about how I don't like iGaming, but you're probably going to see the expansion of iGaming, especially as, uh, you know, states realize this is just a cash cow. You can make so much money doing it. Um, and yeah, eventually there's going. But whether how that goes against sports books and states making money, I don't know. 

01:06:03 - Rob Pizzola (Co-host)
What do you think technology and, like AI, the role of technology and AI. 

01:06:05 - Isaac Rose-Berman (Guest)
What will they play in the next era of sports betting? Well, first of all, I don't know what AI means, but technology more generally. I think you're just going to see you don't use any AI at all. I use ChatGPT. 

01:06:13 - Rob Pizzola (Co-host)
Okay, so you do know what it is. Yeah, um you know what? 

01:06:15 - Isaac Rose-Berman (Guest)
yeah, I'm I, I know what, I know what ai is. But like people say ai, it's like what is that actually? It's true, it's very loose. Yeah, it's very loose. I think, um, greater personalization is the big thing. Yep, um, you know, when you log on to a sports betting app right now, they just show you whatever's live, or maybe the nba money lines for tonight, yeah, but, but you know you're going to be crazy yeah. 

01:06:36
Yeah, but you know, presumably in a few years you're going to log on and they know exactly what you want. They're going to spoon feed it to you and it's going to be to be clear. It's going to be a way better user experience, yep. And that's the thing where you have the incentives of the industry to make a good product, which obviously they should be allowed to do. They should be able to try to make money. But them trying to make money means more people losing more money, which is generally bad for society and those people. And you can say, oh, you know, these people would have spent $100 going out to dinner. Now they're spending $100 at the sports book. It's just, it's not the same thing and I wish Johnny was here because I know he has opinions this as well it's just not the same thing, because you can't go bankrupt going out to dinner. I guess you can, but like, it's just, it is. 

01:07:18
Gambling is an addictive product and more legalization means more people will gamble, more people. Gambling means more people are gonna lose a lot of money and it's gonna have really bad effect and you're already seeing that and you know the data. There's data out there. It's to get in a few years, when it sort of comes to fruition. The negatives of gambling, I think, far outweigh the positives and, to be clear, I think I don't think that means that gambling should be illegal. But yeah, I think it's not good for society. 

01:07:46 - Rob Pizzola (Co-host)
Yeah, so what you talked about with, like the, the products themselves, right is is one of the pet peeves of mine. This is why I'm I'm certain we will see consolidation in the betting space. Right is one of the pet peeves of mine. This is why I'm certain we will see consolidation in the betting space, because there are so many books in market right now that don't have a USP, a unique selling proposition. So you know, there's the rec sports books that are way ahead of the curve. 

01:08:08
We all know what those are, with just like really good products, good apps in store, great offerings. You know, pretty fair to people. You have sites like Pinnacle, which are low margins, lower VIG and posted limits, so different. Then you have this cluster of sites that a lot of them are originally originated in the UK and they come to, in this instance, the Ontario market and they just run things exactly like. You know. It's like turn on the product and it's you know you go to bet an NFL game and your main option is Moneyline instead of spread and you got to. You got to make three clicks to get a spread. You go log into a site and you're getting served fucking live Bulgarian soccer like that I've never bet in my life and I'm never going to bet in my life before. And some of these sites it's almost like they're not even trying to make money, I think. 

01:09:05 - Isaac Rose-Berman (Guest)
I think the UI is another one where so many of these apps have garbage. User interfaces, like the apps themselves are bad, Like how can you be a company making that much money and you know DraftKings and FanDuel, other big ones, like they generally do a very good job, but outside of those I don't know? I guess maybe it's just DraftKings and maybe there are a couple others as well, but like so many of them are just bad. Like the search bar is bad. 

01:09:26 - Rob Pizzola (Co-host)
The login is bad. 

01:09:27 - Isaac Rose-Berman (Guest)
Sometimes yeah, and you're like what are we doing here? Like make, and I think it's funny, because I love sports betting, like I, outside of being able to make money and, you know, pay for my lifestyle, like that's amazing. But I actually do love it as a recreational activity too and I have like a significant interest in like oh, I want to make cool products. Like I want to make stuff and it's crazy to see these companies which are, you know, listed on the stock exchange and you have like billions of dollars invested and your app is still garbage and your product offering is so bad. And I'm like what are we doing here? 

01:09:57 - Rob Pizzola (Co-host)
Come on, I don't get it really, especially if you're gonna market that product You're gonna spend, because you're spending all your money on advertising. 

01:10:03 - Isaac Rose-Berman (Guest)
You're gonna hire I'm not gonna say people you're gonna hire, spend millions and millions of dollars on advertising, but you're not going to spend a few hundred thousand dollars to pay better developers. Come on. 

01:10:13 - Rob Pizzola (Co-host)
Well, I mean, the thing is, when you look at the best recreational books in the space, it's fair to assume that a large percentage of the population that has bet on sports has tried one of those books. So if you're going to try to lure one of those players over and you can't compete on product, you're dead in the water. Sure, you can try to compete on bonus, but over time people are just not going to like the experience. If I go to LiveBet and I have a quarter of the options and it's janky, like it lags on my mobile device, it's not going to work. And I think you're right. So much money was just thrown at marketing. It's like, well, you got to compete, we got to get our name out there. Well, the product is not there. And over time you know, you see, the bigger books are really investing in product and with that a lot of the smaller ones are defunct. 

01:11:03 - Isaac Rose-Berman (Guest)
I guess I'll shout out some prior episodes. Like you know, you had Trench on the podcast. What number was that? 

01:11:08 - Rob Pizzola (Co-host)
Oh, I wouldn't be I don't know the numbers off the top of my head Maybe like producer, like 81, or matt matthew training me with uh, with what number? Well, you want me to plug it? No, no, I was, I was gonna plug it. 

01:11:18 - Isaac Rose-Berman (Guest)
I was gonna say like I think we'll put it down in the description yeah, like I don't think people like the, the, how hard it is to make these products is insane. I mean in-game same game parlays like live player props on every single player, every single thing. It's insane. Yeah, um and yeah. You have that moat right where you have. If you don't spend a ton of money on this stuff, you're not going to be able to compete, so that's why you're just going to have that consolidation. Is the stuff just gets better and better? 

01:11:46 - Rob Pizzola (Co-host)
Yeah, yeah, trench is a smart guy, and listen, I again different space. I was hoping that it wouldn't have to come up today, but I do have some experience working on the other side of the counter in the offshore space and it's tough to get stuff done Like product is a real challenge to solve, especially when you're working within a book. Product has its own ideas of what they should be building out. Then you have, like, your sports book team and your traders who are like no, no, no, no it's. It's hard to get everyone on the same page sometimes, but it does seem some of these books have it figured out more than others. You said you enjoy betting. Yeah, where do you see yourself in in five years? Are you still betting on sports as your primary source of income? 

01:12:30 - Isaac Rose-Berman (Guest)
Definitely still betting, not as my primary source of income. Okay, source of income, definitely still betting, not as my primary source of income. Okay, I think. Probably more on the. I hate the word content, but I guess on the more writing side I'll say Writing is just a form of content. I know, I know you don't want to be a content guy. 

01:12:45 - Rob Pizzola (Co-host)
I don't want to be a content guy, I want to be a writer. I tell people I'm a content guy now all the time too, and it's where's your TikTok? Yeah, it's not even that. 

01:12:51 - Isaac Rose-Berman (Guest)
It's just like I personally a lot of great journalists out there doing great work, but you'd read a piece in a major publication. You're like this guy has no idea what he's talking about and that just really frustrated me and I think for me media Is that a motivating? 

01:13:30 - Rob Pizzola (Co-host)
factor for you. 

01:13:30 - Isaac Rose-Berman (Guest)
No, it really is. And I think I am not the sharpest better, like you know, I'm. I'm pretty good at what I do. I'm not the best. I'm also not the best writer at all. Um, but I think like that, that intersection is where I can, you know, do pretty well and, and for me it's like I, I want not only to care about what I do, but I want to be, if not the best, really good at what I do. Like I want to get up in the morning and say there's no one who's doing this better than me, and I'm never going to be that in sports betting. I don't think I'm ever going to be that in journalism either, but I think in that intersection I can be. 

01:14:11
My dad was an editor for a while and what he would always tell me is there were, there would get like three types of writers. There would be people who or there's, there's three types of things, that attributes that a writer should have, okay, there would be people who would be good writers. Then there would be people who know how the world works, and then there are people who could think and it was incredibly rare that you would get anybody with more than one of those. And so, like the journalists would fall into that. They can write really well but they don't really know how the world works and they can't think. You'd have academics who can think but they can't really write or know how the world works. And then you'd have, like policymakers who can you know how the world works but they can't really think or write Obviously an oversimplification. I don't think anybody'm the best at any one of those, but I think you know my background is in politics and policy. I know a lot about that. 

01:14:58
I bet on sports for a living. You know I'm not the best but I'm pretty good at that and I try really hard to be a better writer. It's, you know, a process. You just get better over time and so and he would always tell me like, oh, you know, if you are the, the Holy grail is like two. If you can be two of those, that's amazing and you know, if you can do all three, like that's, that's the best. And that, for me, was always my motivation when it came to writing, which was if I can do this and be sort of at the intersection of all these things and and provide perspectives and have the stuff actually be engaging, like. 

01:15:29
If people read what I think and they disagree with me, that's fine, but at least you know I'm not saying anything that's false. I understand what I'm writing about and it's at least pretty well written. That's what I want to be, and so, yeah, in five years I'll still be betting, for sure, but probably not as my primary source of income. I think it's also just. It's so stressful. I know in a former episode you talked about how you used to have great hair and you lost all of it. I love my hair. I really don't want to lose it. 

01:15:55 - Rob Pizzola (Co-host)
I actually did really have good hair when I was younger. I had long hair, it was flowing. And then I mean it's not only sports betting that attributed to that. There's definitely a lot of stress and anxiety in life over certain things. 

01:16:09 - Isaac Rose-Berman (Guest)
But yeah, I mean betting is. It's so stressful? Yeah, and I remember this last US Open in particular was just so so stressful for me. I mean both on the sort of the money side, but just the swings like every day. I mean over the course of a week I think I slept like maybe 10 hours in total and we had like crazy ups and downs. I remember there was one day I sent Zach a slate of bets. We had 12 bets over 12. And you just feel like you know, you see those videos, zach's fault though. Yeah, no, no, we made it back though. We made it back. We had some great futures. Chase those losses At the beginning of the tournament. 

01:16:46
This is actually very tilting. Taylor Fritz to make the final. Zach hit that. It was like 45 to one. I sent it to Zach somehow forgot to bet it. So Zach tells me he's like I'm like oh, I'm so sorry bro. He's like no, we had this ticket. It was very tilting. But it's like those videos you see, where it's like the Shaolin monk just sitting there and it's just a guy kicking him in the balls over and over again and you're like that's how betting feels sometimes it does All the time. 

01:17:11
And you're like I'm just logging in and I just know I'm going to lose money. It doesn't matter. It doesn't matter if the bets are plus EV. You just know you're going to lose money. 

01:17:17 - Rob Pizzola (Co-host)
It's a mindset, though I think me and you share that one as well. I've done very well betting in my life, even after a horrible, horrible start to that career, and I still have a very negative mindset, like, god bless, johnny, he's the complete opposite, right? He's very confident, um, yeah, it's gonna win over time and this, and that I, I we're different types of bettors, for sure, but, um, I think it's more to like the our persona, me and you in particular where, yeah, I've just find winning bets, but I always expect the worst yeah, and I can't. 

01:17:48 - Isaac Rose-Berman (Guest)
I mean it's, it's so painful. I my worst qualities of betters I can't not check the score, I can't not sweat my bets and I know it's so painful. My worst qualities of bettors I can't not check the score, I can't not sweat my bets and I know it's so bad. I've grown out of that, which is nice and I wish I could do it. I just can't do it and it's just. I don't want to spend my life just being so stressful, being so stressed all the time. 

01:18:09
And I think being a professional gambler is inherently and obviously, like you know, you can get to a point where you're not betting that much or sorry, you're not risking so much where it matters to you, and that number presumably goes up over time. I mean, I remember the first time I won like a thousand dollar bet. I remember it was like on top of the world. I'm right, Literally. I stopped. I went for like a walk. I used to live near a park. I literally walked around the park. I was like this is the greatest day ever, and now obviously the numbers are bigger. But I think another thing as well when I talk to people who have bet for a long time and they've done it and they're like, oh well, that means you're overbetting, that means you're betting too much. If you care about the money, that means you're betting too much and I really don't think that's the case and you know longer odd stuff or you have limits, so you have to be able to magnify those with parlays. 

01:18:59
Like I was talking to a bunch of editors recently, I asked, like people who are young and betting full time, I asked how many times in the last month did you have at least a 50 50 shot of increasing your bankroll by 40 or 50 percent on a bet? You guess it was like I asked 10 people and like, what was the average number of times they said in the last month? So, like what I mean is, let's say, your bankroll is $100,000. At any time in the last month did you have a bet that was even money on making at least $50,000? Like how many times in the last month do you think was the average? These were pro bettors. Pro bettors, people who bet, and I know that they make money. This is their primary source of income. I don't even. I don't even. 

01:19:37 - Rob Pizzola (Co-host)
I actually don't even want to guess, because it's you're putting me in a tough situation where I'm going to look like an asshole. 

01:19:43 - Isaac Rose-Berman (Guest)
No, just guess Five. Yeah, that was about the average. It was, it was four, it was four, was six, but it was. And maybe these are like we're all vastly over betting our bankrolls. I actually don't think that's the case, but that means literally four times in the last month you've had a coin flip, at least on increasing your bankroll by 50% and like how is that? You can't, how can that not be stressful? I mean, it's an incredibly, incredibly stressful thing. And yeah, I don't. I feel like I haven't done this for that long. Obviously, I'm very young, but in the last few years I feel like I've aged 15, 20 years and so much of that is betting. And I just Fast forward to this hair man. 

01:20:27 - Rob Pizzola (Co-host)
Yeah, no, I need to keep my hair. Stop checking scores. I'll tell you right now that was the biggest thing. I would be completely bald by now if I had continued to check scores. I would guarantee you that Appreciate you joining in studio today, isaac. Obviously, we do plus EV, minus EV every single week. I'll start with you One thing that you think is plus EV in life. One thing you think is minus EV. 

01:20:48 - Isaac Rose-Berman (Guest)
Okay, so can I cheat? I got one for gambling and one for life, sure, okay. So my plus EV for gambling is about hedging, yeah, but it's a lot of debate around hedging. I was actually talking about this with someone recently and apparently there's no expected bankroll growth. There's a lot of math here, but for me it's. You hedge when two criteria are fulfilled A the amount of money you stand to win is a very significant sum to you, and B you're a heavy favorite in the game. And so what I mean by that is, let's say, you have a six leg parlay, all minus one tens. First five hit. You don't hedge that last leg pregame. But if that leg goes up a lot, and now you're a heavy favorite, then you hedge, because not only you hedge with a plus four or five hundred, so you actually risk less and you're paying less VIG, but the emotional the mental thing of being so close to winning so much. 

01:21:44
And I remember I have a good friend of mine, professional poker player, and I texted him once. I was like I have this really big bet. Should I hedge? He's like never hedge, don't place minus EV bets. 

01:21:59
And the way I think about it is you're paying whatever the VIG is to just not care and not have this ruin Like it'll ruin my day and other people stronger than me. But you set a like, an amount that you care about and then a minimum odds that when you're a favorite, and then you hedge, you know you have the, you have the jets plus seven. They go into the half, they're up by 10. For a large amount of money, hedge that bet Right, don't hedge it. You know you have this eight leg anytime. You know all home run parlay and your last leg is plus 400. If you're going to hedge that at the last one, why are you doing that in the first place? Yeah, don't even put it in. But I'm a big fan, okay, I like that. 

01:22:32
And then my life plussy V1 is individually packaged snacks, so like. So I think like. If you think like in your house to have, so imagine you go to the store. Instead of, like buying a big bag of chips, you buy the individually serviced packs. Do you guys have Costco in Canada? 

01:22:50
I don't know Okay so I live right near Costco. It's incredible. Buy these snacks in bulk multiple benefits. So, first off, they don't get stale. Right, the snacks don't get stale. Also, way more variety because you have all these different things. You can be healthier because you can plan in advance. The utility you get is from an individually packaged snack. There's no utensils, there's no napkins or anything. My fridge it's stocked with cans of Arizona and Diet Coke. I don't have to pour a cup. There's no glasses, no dirty glasses, none of that. And then the most important thing is, if you're someone who lacks impulse, like me, you can't overeat, or you can, but you're self-regulated. If I open a bag of chips, I'm eating the whole bag. 

01:23:33 - Rob Pizzola (Co-host)
Yeah, I'm with you. I have a real problem like that, like you've sold me on this. At first I was very skeptical of where we've gone here. Then I'm reliving my life and being like this could really help me. 

01:23:43 - Isaac Rose-Berman (Guest)
No, you just have. If you look at my kitchen and my fridge, it looks like almost like a tech office, a fancy tech office where you just have all of the snacks and drinks in the fridge. And, honestly, the pleasure that I get from opening up my fridge and having like 10 different drinks all individually served, or opening up my cabinet, all sorts of snacks, take them out, eat it, throw it in the garbage no mess, I still. You know, look, sometimes you have two or three bags of chips. It is what it is, but if I get a big bag of chips I'm eating the whole thing. This has helped me tremendously and it's a little worse for the environment. If you care about that, offset it with a little donation. It does matter. 

01:24:21 - Rob Pizzola (Co-host)
a little bit to me. But yeah, you offset it with a small donation you're totally fine. 

01:24:27 - Isaac Rose-Berman (Guest)
I'm all about buying indulgences. So there we go. 

01:24:30 - Rob Pizzola (Co-host)
I like it. I think you've sold me on that one. I think you've sold me on that one. All right, we'll end it here. 

01:24:35 - Isaac Rose-Berman (Guest)
Oh, I got mine. 

01:24:36 - Rob Pizzola (Co-host)
Oh, you got mine, you're not going to give mine is very specific. Ok, and it's it's. It's very specific and better suited for Johnny because he will be very fired up. 

01:24:49 - Isaac Rose-Berman (Guest)
Ok, so now I'm. So now I'm giving off two plus these and two minus. 

01:24:52 - Rob Pizzola (Co-host)
It's all right. 

01:24:55 - Isaac Rose-Berman (Guest)
There you go, you're doing the, you're doing the show today for all of us. So my minus EV gambling for all the Blackjack players out there and I know you agree with me on this is, in Blackjack, not getting your double down card face down. This actually upsets me more than anything else and for people who don't know what I'm talking about, if you have like an 11 versus a dealer six and you get the double down card, they normally give it to you face up. It obviously doesn't change the odds, but you get it face down because if it's face down you get the sweat to see if the dealer busts and then, if they don't bust, you get the second sweat. 

01:25:24
Two sweats for the price of one, two sweats for the price of one. 

01:25:26 - Rob Pizzola (Co-host)
I love that. I will always ask for double down cards face down and for those of you who count, they still flip over the card anyways afterwards. 

01:25:34 - Isaac Rose-Berman (Guest)
So you get to see what the count was and people always ask oh, do you care if someone's at the table playing bad blackjack strategy? I actually don't care, it doesn't matter, but it actually really tilts me if someone is at the table and they don't get their double down cards face down. It really upsets me because we're here. Unless you're counting, you know you're basically paying money for the right to gamble. Yeah, why would you not want to double the amount that you can gamble? I agree, I'm with you on that one. 

01:25:59 - Rob Pizzola (Co-host)
You always feel like you have a second chance. Dealer hits to something You're like all right. 

01:26:03 - Isaac Rose-Berman (Guest)
I got another chance Exactly, I love that. And then I also got my minus CV life, one which is sad Johnny's here because he was exhibiting it earlier on the show was exhibiting it earlier on the show. 

01:26:16
He was in rough shape, bad toilet paper and bad tissue paper. To spend a few extra bucks, get the triple ply, don't it's. It's so terrible. I was at, I was at a nice restaurant recently having a great meal, went there, went to the bathroom Horrible toilet paper, I just wanted to blow my nose. It actually ruined. It ruined the entire meal. And I'm not someone who like writes reviews a lot. I don't, I don't like care that much. I actually messaged the owner of the restaurant and I was like you have a nice restaurant, switch up, switch up the toilet paper. 

01:26:42 - Rob Pizzola (Co-host)
I have. That's a little bit too far, I would say. No, I agree with you. You had me right until there. That messaging of the of the manager of the restaurant, I don't know, I'm going that far. It's a big thing. 

01:26:51 - Isaac Rose-Berman (Guest)
I'm trying to help out their business. I live, I have a bunch of roommates and we live near Costco and once one of my roommates he went. They got like a big thing and I got the bad toilet paper and he was like, oh, let's just run through it. I was like no, we can't do that. He's like, okay, what if I only use it in my bathroom? Comes into my house to affiliate me with having bad toilet paper because it's an embarrassment. 

01:27:19
Listen, I'm with you man, I always spend up on toilet paper For those who aren't watching. At the beginning of the episode, johnny was blowing his nose with some Burger King napkins. I don't know what the Wendy's napkins or whatever the hell he was using. 

01:27:28 - Rob Pizzola (Co-host)
Yeah, I would never do that. Never do that. I like those. That was actually a really good round of plus EV, minus EV. I don't want to ruin it. If you could go back five years and talk to a previous version of yourself, what advice would you give to your former self? 

01:27:41 - Isaac Rose-Berman (Guest)
So, first of all, I'm pretty young, so it's tricky yeah that's true, this is more meaningful for you? 

01:27:46
this question? There's no way in hell. Five years ago, me was listening to anything that I said. So can I keep the same thing one gambling and one life? Sure, so for gambling you guys talked about this in the last episode. 

01:28:00
I think when you have a big edge, plow it. You've got to bet more on those big edges and I think, in particular, if it's something that actually is scalable, reach out to other people. And I think I was pretty lucky early on in my sports betting career when I had an edge that I knew was pretty scalable and I reached out to someone who put me in contact with someone else and I was able to get on a free roll and get a lot more down. Yeah, and you know, even if you're someone with a pretty small bankroll, you know 10% of a very big bet on a free roll is gonna be more than whatever a couple hundred bucks that you're able to bet yourself. So know, when you have a big edge, in particular a big edge that's scalable, and either bet a lot of it yourself or obviously be careful. You don't want to just give out your edges to anybody random and have them steal them, but the opportunity is potentially very, very high. And then my life one. I guess it's just to be more comfortable with uncertainty and chance. 

01:28:58
I think in the past I was a pretty big worrier and honestly I think I got a lot of shit on other podcasts for saying this. I think gambling has made me a more peaceful person, just because you internalize that chance and you don't care when you get unlucky. In other parts of life and I think earlier in life I was so stressed oh, am I gonna do this, is it gonna work out? And just not caring. The cards fall as they do. 

01:29:24
For me five years ago it's like oh, should I ask out this girl? What's she gonna say? Is it gonna be worth it? Who cares? It doesn't matter. Just you know, if someone asks you a question you don't know the answer, you don't have to know the answer. Saying I don't know way better. Honestly, people respect you more. I agree, if you're more comfortable as opposed to just you know going on about things you have no idea about, just being more comfortable with uncertainty and not knowing what you don't know. And then you know not caring when you get unlucky and just leaving the cards fall as they do. 

01:29:59 - Rob Pizzola (Co-host)
Love that advice. Appreciate you joining in studio today. It's been a pleasure. This has been great. We're going to drop Isaac's Substack link down in the description below. You can also follow him on Twitter at roundrobin42. If you enjoyed the episode, smash that like button. Don't do it for me, do it for isaac. Do it for him. It's gonna be really disappointed if he checks the likes of this episode and it's slow. You gotta smash the like button. Subscribe here to circles off. Appreciate everyone who tuned in. We're back next week. It's another guest episode myself. Hopefully johnny's better next week back in the chair. We'll see you next week. Thanks for tuning in to Circles Off.