Capture the Flag -- Jay Rosenkrantz

Jay Rosenkrantz is a 25-year-old high-stakes cash-game pro who resides in New York City. He began playing online at the age of 19 while attending Boston University, where he graduated with a film degree in 2006. In 2007, he was named the biggest winner online in no-limit hold’em cash games. He plays under the screen names “pr1nnyraid” on Full Tilt and “purplEUROS” on PokerStars.

Kristy Arnett: What stakes were you playing when you first got into cash games?

Jay Rosenkrantz: Pretty much anything from 50¢-$1 to $3-$6 no-limit [hold’em], and also $3-$6 limit hold’em. I first played limit hold’em, and was sort of a break-even player. I won a little at first and made rake-back money. I’d take the rake-back money to no-limit to try to get the hang of it. I’d get crushed there and move back to limit. I went back and forth until I found my groove.

KA: What kind of player were you in the beginning, and how did you finally learn to start winning at no-limit hold’em?

JR: Well, I had no fear, for whatever reason. Maybe it’s something that’s just built into me. I don’t know, but I was willing to try a lot of creative things. I played a ton, which was really helpful, and the poker forums helped. I was discussing strategy with people who are now some of the best players in the world. “Good2cu” [Andrew Robl], “Raptor” [David Benefield], “CTS” [Cole South], and I all played in the same mid-stakes games back then, and came up playing high-stakes games together. Back then, there was definitely more of a culture of mutual learning.

KA: Was there ever a huge turning point in your learning process?

JR: In 2007, when I was already playing for really high stakes, I went to Vegas for the World Series of Poker for the first time. I moved in with “Whitelime” [Emil Patel], “foxwoodsfiend” [Ariel Schneller], and “Flawless Victory” [Brian Roberts]. They got me thinking about things I hadn’t thought about before. Flawless pointed out that I had severe timing tells. I was instantly making every decision, and he helped me iron out why I was doing that and told me how other players might interpret it and also how to interpret other players’ timing tells. That really helped my game.

Also, I started thinking about bet-sizing. At the time, almost no one was thinking about bet-sizing, and just talking to someone who had already been thinking about it was really helpful. I mean, before that summer, no one had ever overbet-bluffed, even the players who were playing $40,000 no-limit. Now, it’s kind of standard. People have learned what that means, on the river, especially. No one was playing with reckless abandon to exploit a lot of really good players.

KA: Can you explain exactly why overbet-bluffing is a profitable play?

JR: Let’s say the pot is $10, and you have $100 behind and the other guy also has $100. Instead of betting $10 and giving him 2-to-1 on a call, you bet $100, knowing that based on prior streets, he never has the nuts. He just can’t call you because he has to pay so much in relation to the pot, and you rarely bluff. It’s taking that idea and applying it to every situation on the river when you know that your opponent is not being really heroic and making thin calls with clearly marginal hands, and the river could have made you the nuts or you already told a believable story that you might have had the nuts before the river. You can capitalize on the fact that people don’t want to put that much money in without a nut hand. You can’t really do this anymore in the high-stakes games, but you used to be able to do it, and it was a really valuable secret weapon to have.

KA: What stakes are you playing these days?

JR: Pretty much anything. I play $25-$50 and $50-$100 most of the time now, but higher depending on my opponent. I’ll usually sell off action to Team Israel, as we’re called [laughing], which is the guys I lived with that summer at the World Series. I don’t usually take big shots with my own money, but it depends on the game. If there is a really good $500-$1,000 game, I’ll play it, but I won’t have all of myself.

KA: So, are you an advocate of taking shots?

JR: Yeah, as long as you are willing to move down if it doesn’t go well. Sometimes there might be a drunk fish playing in a much higher game and you want to be able to play. Someone on the forums made a post a while ago that really hit home; it said to play a range of stakes, not just one. It’s OK to take some shots if you are comfortable with bumping down your range of stakes if it doesn’t go well, because you don’t want to go broke.

KA: Have you had taking a shot not go well?

JR: Well, I had a really, really big downswing at $500-$1,000 at the end of last year, and I was taking really big pieces. I just ran really bad. If I continued to keep taking the same pieces, I would risk my lifestyle, which at this point, after four or five years of playing, I’m just not going to do. I have no problem with moving down in stakes. It might bruise the ego a little, but that’s OK.

KA: What advice would you give to those who have difficultly stepping down?

JR: Don’t ever take shots, it’s not for you. Just play and get over-bankrolled for your limit, and then move up slowly. It’s not a race. The only person you are accountable to in poker is yourself. As long as you are happy, who cares about the people posting graphs in the forums or bragging about winning huge amounts? Work on your own game, and work on how OK you are in your head about where you are in poker. If you’re not OK with where you are, work harder.

KA: When can limping in a cash game be profitable? Or, is it always a bad idea?

JR: It depends. I think that in live poker, it’s a lot better strategy. You should be limping with lots of different hands in live play rather than in shorthanded ring games or even full ring games online, because people play tighter preflop online. You don’t have eight people limping in preflop like you do in live poker. So, online, in a six-max game in the cutoff or on the button, I would definitely advocate raising with a hand like 6-5 suited and narrowing the field to get it heads up, in order to make profitable bluffs or profitable value-bets. In a live game, however, I might advocate limping in, just because raising doesn’t do much but build a pot with a hand with which you want to keep the implied odds high.

KA: Who do you think is the best cash-game player, and why?

JR: I’d say Tom Dwan, because he probably has made more money than any other online poker player. He plays a style that no other high-stakes player can emulate successfully. That is really impressive to me. He’s even transcended the online poker stereotype, because he also has gotten a lot of media exposure playing live games without winning a tournament. That’s really cool.

KA: To be a successful high-stakes cash-game player, do you have to have a certain gambling mentality?

JR: You have to have a certain stomach for it. You have to be able to say, “I lost a house today,” or, “I could have bought a Ferrari instead of losing it to that guy,” and be OK with it. It can be really stressful. Sometimes you wish you had never started playing that high, and had just been content to grind $5-$10 and make a decent living. For high-stakes players, that’s just not how the world works. Even though the variance is really high, the money is really good, also.