Jay Rosenkrantz – The Storyteller of Online Poker

This week no deep tournament runs, bracelet bets or all-time-money-list related discussions. Jay Rosenkrantz is by no means a tournament player, but one of the true online cash game legends. Under his handle “pr1nnyraid” on Full Tilt Poker and “purplEUROS” on PokerStars he won millions, but poker hasn’t been a part of his daily routine for quite some time. The former star and producer of Two Months Two Million, founder of DeucesCracked, producer of From Busto to Robusto and creator of The Micros spent nearly three years working on a huge project which will totally change the outlook the world has on our beloved game, online poker. BET RAISE FOLD: The Story of Online Poker is to be released this summer and Rosenkrantz granted iGaming.org an hour of his time during these extremely busy times.

Frontpage photo: BET RAISE FOLD director/editor Ryan Firpo and Jay Rosenkrantz

Has it been a road filled with bad beats on your way to creating this movie, and maybe even tougher than it has been fun?
I would say it was equal parts very, very difficult and taxing, and at the same time incredibly exhilarating and fun. It’s definitely a fun thing to be making a movie about something that you love and have deep ties to. You really feel a responsibility to do this right, and make a lot of people, who want to see something like this, happy. It’s fun to be a part of the team working on realizing something as ambitious as that. On the other hand that responsibility can sort of seem maddening when things are going wrong. This project has devoured three years out of my life, and at times like when Black Friday happened, or when we applied to film festivals and weren’t getting in, it gave us a feeling of, “Can we really do this?”

Everyone had moments of doubt, and there were always issues coming up. Something would cost more money than we had budgeted, or we made a mistake in the motion graphics that we wanted. So we lost money there, and we had to come up with money from elsewhere. You have to make sacrifices, and it was a mixed bag, but I’m glad we’re here because now we get to look back on all of it and see how worthwhile the time spent was. It took so long, but now those three years of toiling away are just a memory. Now we’re moving into the exciting part. It’s surreal to know that we’re actually here. We have a finished movie and we get to show it to people.

Let’s just make a reference to the show you were previously on, Two Months Two Million. Were there times where a tilt room would’ve been nice during the process of making this movie?
Yeah totally! I had to create my own tilt room metaphor to stay sane and the gym was really good for me. Having a regular gym and writing routine was very important to me, just so I could focus on something completely unrelated to what I was working on. It’s good to be alone in the moment when you’re destroying yourself in the gym so you can forget everything else that’s swirling around outside. Having an actual tilt room would’ve been fun too though.

How expensive is it to make a movie?
Pretty expensive, but I haven’t talked to Taylor (Caby) to know how comfortable we are putting the exact budget out there. It would be cool to eventually release the budget to show where the money went and analyze our wins and mistakes. I’ve told people that the film cost more than $100,000 and less than $1,000,000. That might give you a sense of how expensive it can be, but it’s all relative to what kind of movie you’re trying to make. Documentaries are usually on the low end of movie budgets, especially now since the technology to make a great film has gotten a lot cheaper. Even during BET RAISE FOLD, which started production in 2010, we saw technology becoming so much cheaper and better towards the end. For instance, we wanted to achieve this type of shot where the camera would be sliding back and forth. We had watched a few “netizen” documentaries that were doing cool things with people who spend a lot of time on the Internet. In that genre they would have to figure out how to make scenes of people sitting behind a computer screen look visually interesting.

So the sliding camera was a way we saw to do this that seemed like it would work well for online poker. A few years ago achieving this kind of camera movement would’ve cost a ton of money. But towards the end of shooting, when we were running out of money and had just a few days left with each character, we found that we could buy some new portable tech to do this for just a few hundred dollars. By the next project this stuff will probably get even better and cheaper. So now we have the experience, we’ve learned from our mistakes here and the technology keeps getting cheaper and cheaper. It’s expensive to make movies, but it’s doable for anyone. We started out making short films, From Busto to Robusto, and the budget for those was closer to $10-20k. You can start smaller and build your way up while learning how to do it, kind of like poker.

When you were a professional poker player there were very many things that influenced your learning curve. Talking to players, reading articles, watching strategy videos and playing are all a part of that process, but how does that work when you decide to switch to making films?

I think it’s a very similar process. I went to film school, but after my pro poker career I had to retrain myself to be a filmmaker. I found myself doing this by applying all the lessons I had learned playing poker. In poker you can study, read all the books, watch all the training videos but if you don’t play poker, and play a ton of it, you’re not going to improve. You’re not really going to know what you’re doing; you’re just not going to get better at the game and make more money. It’s really the same thing I’ve seen with making films.

I produced the short films From Busto to Robusto, the reality show Two Months Two Million and The Micros which is a scripted animation of about six to seven minutes. Even at DeucesCracked, creating and overseeing the production of hour long training videos, provided me with useful experience and lessons. All of those are kind of the hands I put in, and I learned a lot from the people I worked closely with on all those projects. Kind of like the friends in poker and the people on 2p2 I learned a lot from, back when I was getting better at poker. In that sense it has been kind of similar. Through playing poker, coaching poker and training people on DeucesCracked. I learned more than poker in doing that, I learned about how I learn best. Being able to take the lessons from how I improved at poker and apply them to improve at filmmaking and story telling. That has been very useful and accelerated my learning curve. It’s just the way the human mind learns a skill. You need practice, repetition, to analyze and talk about it with other people. You really need to just do, you can’t just sit around and dream about it.

What would’ve been more likely if I told you, back before you even became a poker professional, that you would’ve been a professional poker player and film maker?
Probably poker, because even when I was younger I would be thinking about making something like StarWars, sit down, write, and think, “I would rather be playing poker” after which I managed to do that all night. Poker would just pull me into its grip and take hold of my mind. I just really loved the game and it seemed to make me money, which was something I never had when I was growing up. I wanted more money and a better life and that fantasy was really appealing. It wouldn’t have blown my mind where I am now to my 18-year old self, maybe the extent of it, but I think it would also probably make sense to me. Eighteen-year old me would be proud.

Were you someone with high hopes and aspirations when you were growing up?
I was always really ambitious and I wanted to have some great destiny. Like I said before, I really liked Star Wars. I identified myself with Luke Skywalker. He ended up going from this nobody on the edge of the galaxy, to this hero who learns to trust in something bigger than himself and in doing so blows up the Death Star and saves the galaxy. Those kinds of stories always appealed to me and I always wanted something better for myself, I was always thinking and strategizing. Determined to succeed. AlexeiMartov (Martin Bradstreet, who is a character in the movie) and I have a lot in common in that regard. I think we fancy ourselves a little like the Great Gatsby. In the end of that book the narrator is shown a book Gatsby wrote in when he was young, and inside it is his daily to-do list. It reads something like, “Wake up at six am, do push ups, read the Financial Times for one hour, practice posture,” and that was a checklist of things he wanted to do in order to escape his upbringing and become a better person, improve himself and do more with his life. I feel like I was always like that, I was always making lists, had goals and thought logically about how I would get there. I learned a lot while playing poker when I was young, around 12 or 13, when Rounders came out. I was supporting myself by playing poker through Middle and High School, so I kind of learned to be self-sufficient and think outside the box in regards to what was possible.

At the Superbowl

Was poker as a profession something you anticipated, or did that just happen?
It just kind of happened. At first it was pre poker boom, and I was making small attempts. I read a couple of poker books and that of course automatically made me better than my friends who I was playing with regularly. But I didn’t understand what bankroll management was so I took shots, wrestled with the degenerate side of me, going broke and dealing with the sometimes unbearable emotional pain of losing. When you’re in that mindset you’re still a bit of a donkey, because you don’t really understand a lot of what’s necessary to be a professional.

When I went to college I stopped playing as often, though I still played home games and at Foxwoods sometimes. After a couple of years I found out about 2p2 and the people there who put a lot of thought into doing this sustainably. There were some people that played four tables of Limit Hold’em and made $15 per hour plus rakeback. They had a system, and that appealed to me. At that point I realized that I didn’t have to go to a casino and sit at a table full of sweaty people, I could stay home in my chair and earn much more money than at any other job I could get at the time. At that point I just became obsessed with 2p2 and online poker.

Have there been many eye-opening moments early on in your poker career that you might recall helping you a lot?
The one that I always remember is realizing that I could make a huge call on the river with ace-high. Understanding that you could win a pot with ace-high on the river in No Limit Hold’em was a very eye-opening moment for me. I remember winning that pot, there were a bunch of missed draws and I put two and two together. I sort of saw the world in a new way and I felt like I suddenly understood much more about how hands worked at the poker table. I was playing about 100,000 hands per month though, so it was less like having these, ”A-ha,” moments, but more like I was absorbing all the information and my own style of poker was evolving along with that. I would just play fanatically, coach a lot and every day I was posting a ton on 2p2. I posted in the mid and high stakes forums and during those days everyone was sharing and learning a lot. This is when some of the best players in the world were actively posting there. I started winning more and more and moving up. Through coaching I started to understand the game a lot better because I was talking about it constantly and forced to relentlessly explain my thinking.

Isn’t that a really big step, going from catching the poker bug to playing 100,000 hands per month?
I became obsessed! I had graduated college after which I moved to New York City. I was really just playing all the time, and I had built enough of a bankroll to support myself. I remember now, and I haven’t thought about this in a long time, but I was trying to win $100,000 in one month. I really wanted to do that since I had two roommates and I promised to pay everyone’s rent if I did it. I finally did it – but right after the lease ended.

Was moving up more important for you from an accomplishment point of view, or was it all about the money?
I think it was probably a little bit of both. I was trying to define who I was through how well I was doing. At that point you’re thinking, “If I can play $5/$10 I can make X per hour and that will allow me to buy X, Y and Z. If you then can somehow play $25/$50, well holy shit! The sky is the limit.” Things that I never thought I would be doing were within my reach all of a sudden, and I could reach points like that in as little time as a year.  My ego got a boost from being known as a good player and thinker on 2p2, and your ego is everything when you’re playing poker professionally. Every aspect about my life became about being an online poker player, a poker professional. 

Were there some crazy purchases from that first money you won?
I just read the Ship it Holla book, and in there they say that the first thing an online poker player buys with his money is a good set up. A sweet computer coupled with big monitors is a better tool for generating money, so that’s the first one. The second expense is a baller watch and the third one is a really nice car. I was really into watches, and I still have a lot of nice ones. Some of them I look at and think, “What the hell was I thinking?” When I was 22 my taste was disgusting, but I still have a lot of nice watches and some of them are so extravagant.

All in all think I spent more on experiences like traveling. For instance, we stayed in a five star hotel in Copenhagen and went to a three star Michelin restaurant during the EPT. I also really liked throwing parties, like one in New York City with an open bar where everyone wore felt animal masks. I really liked taking care of my friends, because I grew up with a lot of amazing people around me. It just felt like I was in the middle of this incredible roller coast ride that I wanted other people to be around for, to appreciate the absurdity of it.

What was the most absurd thing you spent money on during those days?
I bought a $15,000 watch a long time ago that might have been the most absurd. I don’t really wear watches anymore, and to spend that much on a watch seemed crazy. It’s hard for me to remember, because it feels like it was another life of mine. I’m trying to think back to all the summers because in Las Vegas we all did the craziest things, especially during the Two Months Two Million shooting.

I do remember one night in New York City when Whitelime (Emil Patel) and I went to a club. At a table across from us we saw Michael Strahan, the former New York Giants player, and we got into a bottle buying war with him. He was ordering bottles with sparklers and waitresses were bringing them out dancing and drawing a lot of attention. We started ordering them, and it ended up going back and forth. Eventually he just put us out of commission though. He probably asked somebody, “Who are those guys?” and no one of course has any idea. He then probably went, “Well I’m Michael Strahan and I’m just going to order more than they can ever think to compete with.” That was that, and there were some five-figure club tabs that seem kind of stupid after the fact.

How come you seemed like the more normal person of the group at the time when Two Months Two Million was on TV, because listening to these stories makes you sound a lot more like a crazy degenerate?
In some ways, but those guys would surely call me the craziest one of the group by far. They call me “Crazy Krantz.” They’re actually all pretty reasonable, and I think that as a group we were as well. We were not Ship-it-Holla level with our money. We liked to have a good time and we were really young. We just thought of fun things to do and I think that’s probably why Two Months Two Million ended up getting made. The people who ended up getting involved in the show saw that we were coming up with creative fun ways to spend our money and we were just having a good time. We were really enjoying this really fortunate, lucky position that we ended up being in.

Jay Rosenkrantz during the shooting of Two Months Two Million playing golf with his buddies

You reached out to some high stakes poker players to get funding for the movie, what was the actual pitch you made to them in order to convince them and who are involved?
The players involved in backing this project are; Tom Dwan, David Benefield, Taylor Caby, Andrew Wiggins, Cole South, Ben Sulsky, Aaron Jones, Andrew Lichtenberger, Peter Jetten, Derek Scallon, James Bord, Ariel Schneller, Brian Hastings, Dan Morris, Martin Bradstreet, Andrew Robl and myself. I think that’s everyone. The pitch was basically a comprehensive business plan and story that Ryan Firpo wrote. It opens up with this quote from Gerolamo Cardano, a gambler and mathematician from the Italian Renaissance:

“Even if gambling were altogether an evil, still, on account of the very large number of people who play, it would seem a natural evil. That’s why it’s not absurd for me to discuss gambling, not in order to practice it but in order to point out the advantages in it, and of course the disadvantages, so they may be reduced to a minimum.”

There was also a quote from James McManus’ book Cowboys Full about the history of poker. The business plan goes on to talk about how poker has changed since the Internet came along, and how Internet and television created the poker boom. We were looking for funding for a feature documentary about the online poker boom and in the pitch it laid out the story of the documentary. We explained the different pieces of the story, like the Moneymaker effect, the birth of the professional online player, the evolution of poker strategy, the UIGEA, the Ultimate Bet scandal and more. We pitched a bunch of different people who we thought make good characters, the investment opportunity, how we might recoup the money and how the money would be used. We sent that around to a few people and most thought it was a good idea.

Now that the movie is done, we’ve set up a Kickstarter campaign for anyone to get involved in pre-ordering the movie, getting a Special Thanks in the credits, and some other cool stuff like a DVD, t-shirt, or tickets to the June 12 theatrical premiere in Las Vegas. This new money we’re taking in from the public is going straight back into final finishing costs on the movie, and our distribution efforts. We want to get this documentary, which we believe contains a powerful emotional argument for poker players worldwide, in front of as many people as humanly possible. And we want all poker players to buy into the message now and team up to help do this together. Kickstarter is a really amazing platform that’s going to help us do that, and so far we’re doing great. We hit our first $20,000 goal, with over 200 backers, in only a little over one day!

Out of the three players the documentary follows Tony Dunst is the most known in the poker world. Why did you not pick one of the three to be a real poker super star, maybe even one of the people who invested in the movie?
We just felt that Tony would be a more interesting personality, but we did look at all the other guys. Some would’ve not been interested to be on camera, because you need someone who’s okay with their lives being intruded on. I think some of the investors wanted to put up money, but not themselves out there. We also felt that Tony was the perfect guy. I mean, why does he wear those suits all the time? Even before he came on the World Poker Tour he wore suits everywhere. He also knew a lot about some very obscure subjects. He had trained himself to be a pick up artist and he was very opinionated about everything, not just poker but also many other areas of life. He was charismatic, interesting and his back-story would be more interesting than that of many standard very good online players. Also, he was just getting the job with the World Poker Tour. That was very interesting given the fact that he started playing poker because he saw people playing on the WPT, and now he would be seeing himself on TV. That put us over the top, because it directly connected to the overarching story of the poker boom.

Looking back on Two Months Two Million, do you think it was a success, and would you have done a lot of things different looking back on it now?
We all felt like that if we had a Season 2 it would’ve been a lot better. We went into that show not knowing what it was going to be like and not knowing how to make a television show about what we were doing. Along the way there was a lot of push and pull between us, the production team and the television network trying to find what the show was. That’s why I feel like the second set of episodes is better than the first half.  That’s because we got more used to our roles and that’s why I think the second season would’ve been a lot better.

We were all disappointed it was not picked up for another season. I’m going to watch it all again before the release of Bet Raise Fold and do live commentary on Twitter, because I’m curious to see what I think about it now. So many people are finding it now because it’s on Netflix, probably even more people than back when it was first on TV. It seems like a lot of people really love it, because so many people tell me they watched it like four or five times. They just have it on during their grind, and that tells me that it was a huge success. I felt like, towards the end, that it was going to be something special. One good story: after the last night of shooting, a bunch of us ate mushrooms and were just wandering around that giant mansion doing silly things. So in our drug-addled states I gave a speech to my fellows, before the show aired, about how poker players might really love this show. I was listing off all the great things we did throughout that summer and giving toasts to all the people who were a part of it, and it turned into this really emotional moment for us. Then we got paranoid and adventurous and tried to break into the production house next door to see what kind of notes they were keeping on us. L-O-L mushrooms. There was also another very cool moment for us, sober this time, where they weren’t filming and we were all just sitting in the living room talking. G4 was on in the background and suddenly they played the first television commercial for the show. Everyone was super excited and that was a very surreal moment, to see yourself on television for the first time.

Did Two Months Two Million become a main stream hit in your opinion, and did you get recognized after that show?
I don’t know about outside the poker world, but we do get recognized. We still do and in Vegas obviously it’s the most. I’ve been in the airport in Seattle and on a plane next to a girl from India who saw the show on the Indian VH1. In Austin, Texas now I’ve also been recognized in poker games quite a few times. The poker world is truly huge, it’s a lot bigger than the poker community on 2p2 for instance. There are so many people that just enjoy a game of poker, play in the casino or just home games with their friends. The audience for poker is humongous, everyone who plays or who has played poker. I feel like it has reached that level of saturation where a lot of people have seen it. Especially since it’s on Netflix now, and there it gets recommended a lot when poker entertainment or gambling entertainment comes up. It’s a very unique show and if you’re a poker nerd you’re probably going to want to check it out.

In what sense do you think that this movie, Bet Raise Fold, will be different?
I think BET RAISE FOLD is different because this story is bigger than poker. It’s about more than just poker. The poker boom story is a big American story, firstly because of how it happened. This average guy Chris Moneymaker winning the way he did and how the gambling industry was sort of disrupted by this entrance of the Internet into the way things worked. You’ve also got the way the UIGEA was passed and the political conflict between Congress, the Department of Justice and the poker sites. Whenever you bring in a multi billion-dollar industry like the online gaming industry, which is such a hot topic now, everyone is going to be interested. Now I think more than ever because of companies like Zynga, everyone is playing games online or on his or her phone, Rafael Nadal is a spokesperson for PokerStars and plays poker during big tennis tournaments.

You’ve got those aspects, but also in terms of the way our movie allows people to experience the story, that it could’ve been about you, and with you I mean anyone. Anyone who happened to love poker at that point could’ve gotten absorbed into it, and been a part of this crazy story. The three characters in the movie are relatable, each in their own way. It’s a like fantasy story, because what would you do if you were just following your passion, and by being at the right place at the right time you were able to make a lot of money and be set up for life? What would you do with that, and what would your life be like if that happened to you? How would you respond if that got taken away from you all of a sudden in a situation you had no control over? The story of online poker is an incredible, universally relatable story about everyday people who took risks to follow their dreams, and how they responded when those dreams were suddenly ripped away.

What’s really great about this story is how our movie shows why poker is something enduring. Why it’s so important, and how it’s an always been entwined with the American spirit. Or what America likes to think is its spirit. Poker players in particular are intriguing characters because of how they look at life after having learned the lessons that the game teaches them. How they respond to something as devastating as Black Friday.

Maybe there’s something to learn there if you’re not a poker player. I think the way professional poker players deal with a bad beat was always something I was very interested in. When we were making the movie we were thinking about what the important themes were. We always went back to this idea of freedom and how it relates to poker. It is always the goal for poker players to win money but why is that? It’s all to maintain the freedom of being their own boss and to be tested by their own good or bad decisions. I feel like those elements all came together and were hung around this great, huge story. We would frequently say, “It’s our story to mess up: The story is there, we just had to capture it. If you tell anybody who doesn’t really know about the poker boom a little bit about the history, and some anecdotes about what happened and the crazy things you’ve seen, everyone is immediately interested. So we are pretty optimistic about the potential of this. 

You said earlier you weren’t accepted into film festival, do you think that after the release of the movie you can still get some of that fame and recognition?
I think we will, I’m pretty optimistic about it. The reason we didn’t get in was because we weren’t finished in time. A lot of the festivals say that they’ll take a rough cut of the movie, but we didn’t feel good about any of our submissions. We were trying to get as far along as possible with the deadlines approaching, but I would’ve felt a lot better if we could’ve submitted what we have now. I feel like we could’ve gotten in and done well. I’ve been to some of these festivals and watched a lot of documentaries. It will be interesting to see what happens. Our goal is to really hit the core poker audience. We really hope they respond in a big way to it, that they take ownership in it with us and see it as their own story, a coming-of-age story. This is our story as an online poker community, so let’s use it together and hope it does some good for poker. Let’s show it to other people, to our friends and family who might know we are a part of this game but don’t really understand us. Now we have a 100-minute movie that can teach and entertain and dispel many misconceptions. When you put someone in front of it who doesn’t know poker they will come to understand a lot more about you by the end of it.


Jay Rosenkrantz playing a rare poker tournament at the WSOP

If you could, would you trade back the three years you spent working on the movie for those years as a professional poker player making a ton of money?
No, I wouldn’t. One thing I learned about myself through winning a lot of money is that money, or pursuing money as an end, is very unsatisfying. Making this movie is much more personally satisfying for me and I learned a lot of lessons that will help me continue to grow. Hopefully I can combine all the skills that I’ve acquired over the years as a filmmaker and poker player and make up for the years of income I missed moving away from playing poker professionally.

Do you still consider yourself a poker player?
I still consider myself a poker player, but not a pro poker player. I consider myself a poker player in a sense that I view the world like a poker player views the world. Growing up playing this game, playing as an online pro, teaching it and being so involved in it has made me a poker player for life. It’s a core part of my identity now. Movies that I will make and stories that I will tell will always reflect my unique view on the world because I am a poker player. In terms of doing this professionally to generate the majority of my income, who knows. It could be a good idea again if it seems like I need to make some money and the games are still beatable.

Right now I’m content following my dream, the dream that I had when I was younger, to make something like Star Wars. I think that storytelling can teach people in a way that hits them deeper than anything else can hit them. It can hit you in the heart, in the gut, and in the mind all at once. If you watch a great movie or television show you feel something when you learn, it makes you feel and think in different ways than you did previously. In manipulating your feelings the storyteller shows you how to solve a problem or a new way of looking at the world. That’s where I want to be, in figuring out how to keep doing that better and to reach more and more people doing it.  Being able to teach what I’ve learned in different kind of ways that are emotionally meaningful to people. 

Remko Rinkema

Remko Rinkema has covered the biggest poker tournaments in the world since 2008, including many WSOP, EPT, Aussie Millions, APPT, MCOP and Unibet Open events. As an in-depth interview and story enthusiast he tries to do things a little differently. Besides the usual writings Rinkema grabs every chance to appear on podcasts, live streams and in the occasional video.

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