Leo Wolpert: $10k Heads Up WSOP Bracelet Winner

Chasing Poker Greatness Podcast Episode 216

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Today’s guest on Chasing Poker Greatness is a practicing attorney who has racked up close to $2 million in career live MTT cashes, Leo Wolpert.

One highlight of Leo’s career that you’re about to hear all about is his WSOP gold bracelet win in the 2009 $10k heads-up event where he bested the likes of John Duthie, Dustin “Neverwin” Woolf, Jamin Stokes, and Michael “The Grinder” Mizrachi.

While the poker world has certainly gone through its fair share of scandals in 2022, I think it’s especially important to shine a bright light on the folks in the community who spend their life force doing noble work and, to me, Leo fits the bill perfectly.

In today’s show with Leo Wolpert you’re going to learn all about his journey through the world of poker, a devastating statistic regarding our beloved canine companions, how poker currently fits into Leo’s life, and much MUCH more!

Now, without any further ado, I bring to you the one and only Leo Wolpert.

Click any of the icons below to find the CPG pod on the platform of your choice. Then sit back, relax, and enjoy my conversation with Leo Wolpert on the Chasing Poker Greatness Podcast.

If this is your first time on the Chasing Poker Greatness website, be sure to check out our groundbreaking poker courses to help sharpen your strategy and profitably implement solid, data-proven solutions to your game today:

Transcription of Chasing Poker Greatness Podcast Episode 216: Leo Wolpert

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Welcome, welcome. Welcome my friend to another episode of the chasing poker greatness podcast. As always, this is your host, the founder of chasing poker greatness.com. Coach Brad Wilson, and today’s guest on CP G is a practicing attorney who has racked up close to $2 million in career live in TT caches, Leo woolpert. One highlight of Leo’s career that you’re about to hear all about is his WSOP gold bracelet when in the 2009 10k heads up event where he bested the likes of John Duffy, Dustin never win Wolf, Jonathan Stokes and Michael the grinder. Ms. Rocky. While the poker world has certainly gone through its fair share of scandals in 2022. I think it’s especially important to shine a bright light on the folks in the community who spend their lifeforce doing the noble work. And to me, Leo fits the bill perfectly. In today’s show with Leo Wolpert, you’re going to learn all about his journey through the world of poker, a devastating statistic regarding our beloved canine companions, how poker currently fits into Leo’s life, and much, much more. Now, without any further ado, I bring to you the one and only Leo. Well.



Brad: Welcome to chasing poker greatness, sir. How you doing? Man?

 

Leo Woolpert: I’m doing well. Thank you for having me on. I appreciate you having me here.

 

Brad: Yeah, it’s my pleasure. My pleasure. And as we do on this show, you can’t really Chase poker greatness without some sort of story, and some sort of beginning. So let’s talk about your origin story. And what did what did your entry into the world of poker look like?

 

Leo Woolpert: I got into poker through just basically being a competitive kid who was always into sports games, and kind of hit my ceiling pretty early. And a lot of the competitive endeavors I got into, especially sports, I feel like my my sports career peaked at somewhere between the ages of 12 and 14, and not very high. So after that, I kind of gotten to quizbowl, which is academic competition trivia. Basically, four,

 

Brad: could we could I ask you about why competition resonated with you so much, especially if you know, the pinnacle of your athletic career peaked at 13? And very high? Right. So what was it about the allure of competition? That yeah, just made you want to want to keep engaging in it?

 

Leo Woolpert: Um, that’s a great question. I think. I’m not sure if really fully examined that. But it’s got to be related to just loving winning.

 

Brad: I love winning so so you can see the rabbit hole.

 

Leo Woolpert: Exactly. I love winning. And then from there, it kind of flows naturally. And also just, my dad got me into watching sports and being a fan. He got me into playing sports. And just also, I feel like I was a pretty sensitive kid and became a fairly sensitive adult. So the highs and lows of winning, I think I felt those somewhat more intensely than then some people and that probably also drew me in.

 

Brad: What is it about winning, then? That makes you enjoy it so much?

 

Leo Woolpert: I’m not sure. It’s a feeling it’s tough to define. Just a sense of accomplishment. It’s just it just makes my brain feel good.

 

Brad: sense of accomplishment. Anything else? And we’ll we’ll move on, like internal if you could describe the feeling of like winning, right, you know, you have a WSOP gold bracelet. That’s a pretty pivotal landmark in a poker player’s career. So what what were those feelings that kind of came with that kind of accomplishment?

 

Leo Woolpert: That was deeply satisfying, I would say, not just because of the financial windfall, but kind of knowing that in that time period, I had played a lot of heads up poker. And I had been somewhat moving away from it. So to know, quote, unquote, that I still quote unquote, had it just spite when tournament not being proof of that was, again, satisfying. And also, I had sold some action. So it was really satisfying to make my friends some money in that tournament. But just overall a lot of pride, a lot of it was validating to my ego. It validated the previous four or five or six years that I had slowly gotten into and become obsessed with poker, and validated that it was worthwhile time and not just a fanciful, wasteful pursuit.

 

Brad: Nice. So, you know, we’ve kind of, I guess, so we’ve kind of set the stage here of like what you know, you’re building to as this 12 year old kid, you mentioned that you entered Quiz Bowl, right? Like so. A new competition? And how did you do in Quiz Bowl? And why quiz bowl?

 

Leo Woolpert: Oh, well, I’ve always liked trivia. I’ve always like the kind of just answering questions, especially questions that are one right or one right answer, just that there’s a TriCity, of that the kind of simplicity of that. And also plausible played in high levels, I think is really engaging, because it tests both breadth and depth of knowledge. And so it’s a good entree to know a little bit about a lot of stuff. So if you find something that does interest you, say, a certain author, or a certain historical period, or a certain some field of science, from this quizbowl knowledge, it’s superficial, you can kind of latch in and you know, enough to learn more. Yeah. And then you can go and take a really deep dive into certain sub topics and get security like, yeah, that’s it combines the confines the competitive element with, with the knowledge element of just burning that kind of learning stuff, and then being able to use it in a competition.

 

Brad: Yeah, it gives you more opportunity to explore your curiosity.

 

Leo Woolpert: Absolutely. So

 

Brad: as as you’ve entered quizbowl, during the competition, and exactly what is quizbowl? I guess we should probably start

 

Leo Woolpert: With that. Yes. So it’s, we’re teams of up to four people each compete in trivia competition with different kinds of questions. There are two kinds of questions. There are toss ups, which are questions that are open to anybody. And anybody can buzz in to answer them. And once somebody buzzes in, everyone’s locked out, and they get to answer it, if they get it wrong, then they get points deducted from the team score. If they get it right, then they get a, what’s called a bonus, which allows you get to a usually in standard formats, three times more points. And these bonus questions are usually three sub questions on one topic. And they have kind of, they’re supposed to have like an easy, medium and hard part to really differentiate the skill and talent levels of the teams. And also the toss UPS going back to those, those are kind of not just testing reflexes, but they’re supposed to tap that the depth of knowledge by kind of going from gradually for more obscure clues to more obvious clues. So think of an example of the top my head because I’m been so far out of the game for so long. I mean, I stopped playing quizbowl probably in 2007 as poker was more taking over my life, and also I was aging out of it. I was already by that by those standards that dinosaur having played in college and grad school. So um, but yeah, so I can’t really think of a question off the top of my head,

 

Brad: but Institute team competition. How do you go about like compiling a team? What does that process look like?

 

Leo Woolpert: You people who come to practice? It’s a really self selecting group. Yeah. So when I went to the University of Michigan, there were practices that were going to have dozens of people but okay, maybe two dozen people I miss but or doesn’t. And so you could divide the divide up into teams divided up into separate rooms. So you could just kind of have kind of intramural competitions in just like practice. And from those practices, you learn what subjects people have the most depth knowledge in. And so you can form teams based on specialties. And that’s essentially what we did. And we ended up my senior year we won a championship. I was the fourth best player on the team. But, you know, the winds the wind, baby.

 

Brad: How many teams were in the championship? What does the championship entail?

 

Leo Woolpert: Okay, so a championship involves some qualifying tournaments. And then the national championship tournaments, which were held in April. And there were two main quizbowl organizations back in the day, and I think they both still exist now. And AQ T was one of them and ACF was another. And there were they each held national championships that a different college campus, usually within two weeks of each other in April. And if you qualify for those, you go there and they play, I think they’re usually between 30 Something teams, I want to say like 32 teams maybe. And they play, it’s not just like a straight up single elimination bracket, because people are traveling just, you know, long distances to get here, they want to get their money’s worth. So there’s a round robin aspect, people usually divide into eight or nine divisions, and then have a round robin within those and then make playoff divisions. So overall, you’re getting a lot of matches in a weekend, maybe 1516 games. And I think that’s also in one thing about crystal is like it is pure competition, there is no real money in it. We’re just kind of doing it for the love of the game and kind of knowing that you had that you had won the championship over people who had self selected to be just as equally obsessed with this silly game is, you know, yeah, that probably meant a

 

Brad: Lot. I can imagine. I mean, there’s not many people that are national champions at anything. And so I think that is on, you know, it’s not as if I haven’t ever heard of quizbowl. You know, I’ve heard of it. It’s on like, I assume most college colleges have some sort of team like across the US. So you know, it’s not a not a small group of humans that want to win this thing. What lessons, you know, what, pause in your story for a moment, and what lessons did you take directly from competing at quizbowl. To felt?

 

Leo Woolpert: I think first resiliency, maybe, is there were several matches where we had to come back in quizbowl. Maybe not that good question. I am not sure. Yeah, honestly. Not sure what directly correlated from quizbowl. Other than just kind of having that skill overlap of decent memory,

 

Brad: any sort of training that helped any sort of like memory techniques or learning techniques? Actually,

 

Leo Woolpert: no, no, that’s, that’s good that you asked that, because I think it helped me realize that I learned best through reading and not through visual or audio means. Just because the way we would improve a quiz bowl was kind of dissecting old questions into their constituent parts, the clues, and then write those clues down in a notebook. And then if the board just looked through the notebook, kind of put your hand over one side, so you don’t have the answer readily visible, and you see it, then. Okay. Almost. Also, flashcards. That was another big one, writing questions yourself. Is was a great way to improve and also serve the community because if you’re writing questions, you’re giving more people the opportunity to play. And of course, that could backfire if you wrote really shitty questions to go mock for it. But if you’re doing a write, I think writing questions and quizbowl is one of the best ways to just learn new facts. And you also have to anticipate what other people are going to what other people are going to write about. It’s not exactly the most or is actually a pretty insular community. So there’s kind of, there’s probably some sort of advantage to just kind of knowing the tendencies of writers and knowing people’s pet subjects are.

 

Brad: So we have this element to of understanding people how they think how they operate. That benefit you and obviously in poker, poker is a game of people and understanding. Understanding your opponent’s strategy better than they understand it themselves is like, one of the things that I think separates the higher level players from the lower level players is that like, yeah, you can get, you can get into the mind of a weak player and sort of understand how they’re thinking about poker and how they think about all the things and then create counter strategies to exploit that. Whether or not higher level players sort of verbalize that. I’m not sure. But I know that like, for a long time, this is like, exactly how I play poker, without being able to articulate it. It was like, Oh, I know you’re folding your whole range here. But you don’t actually know that you’re folding your whole range here. And that’s good for me. If I’m bluffing, right. Alright, so now we can go back a little bit to after quizbowl. And it sounds like actually, we can talk about your college career and how kind of poker entered your world. But it seems like there is this like pretty quick transition from leaving quizbowl to poker right?

 

Leo Woolpert: Now, so there’s a lot of overlap between gradually ramping up at poker and gradually phasing out of quizbowl. Because I would say my interested poker really started in college.

 

Brad: And how old are you by the way to sort of set the timeline.

 

Leo Woolpert: So at this point in the story, I’m 18. And this was in 2002.

 

Brad: You and I are the same age. So you’re 30. Right? Yes. Okay. There we go. Are you what you’re asking my current ages? Oh, yeah. So that we can kind of like, you know, do

 

Leo Woolpert: not in the narrative. Yeah, right. Right. Right. Okay, so I can kind of remember the exact road trip I was on, it got me into poker. And it was in 2002, after my freshman year and ended up back from Michigan to the eastern seaboard. And our semester had ended a couple of weeks earlier than most of the East Coast schools had. So a buddy of mine said, you know, why don’t you just hit me up on aim? Like, hey, why don’t you come up to Princeton, and it’s there no classes week, we’re supposed to be studying for exams. Everyone’s just gonna party all week. And I was like, Sure. I don’t have a job. He had my job as a star for two weeks. So I’m up there. And I got there Thursday. And they had a dorm room poker game going. And they got me in there. And I knew the I knew the rules. I knew what hand the what, because I had dabbled in the play money, five card draw on IRC back when I was 12. So yeah, that’s another story about it. I knew the rules, but I didn’t know how to play at all. Like, we were playing stuff like baseball, the seven stud variant with the highest speed and the hole wins. And I was just getting to the river with the king of spades in the hole and like two pair showing on the board and like, I didn’t have better than two pair. And some guy was just like betting and raising it to me, people were begging me to fold like, yes, the AST is the probably the flush to and I was like, No, you’re just trying to trick me into thinking that’s all cool. So So, so I do just call eventually, but I got shown the ace of spades and a flush. So I quickly got got taken for the 50 or $60 I had brought, but it was worth it because I learned a really valuable lesson and that is that poker is a skill game and not just random gambling, because obviously it was really obvious in the moment that they were doing strategies and tactics that were just superior to my just putting the money in there and, and hoping and so when I got back to Michigan, a friend of mine, who is a psychology student emission, he’s also getting into poker. And so from there I just started I bought some Sklansky books I bought the Legions winning no limit or winning low limit Hold’em and just went from there deposited on party and started grinding $57 limit Hold’em back in 2003 2004

 

Brad: Yeah, the old limit Hold’em days.

 

Leo Woolpert: From there from there I went to city goes and they’re sitting goes, I played those 10 some low stakes MTTs I mean, I used to love that 11 rebuy on stars that were there’s no rake on the revise and could just fire off $200 in that and still and be the person who spent the most on that. And there’s five fingers up top and at $11 ribeye that was great. I would play those. And eventually through, I guess, around 2005 when I was graduating and about to go off to graduate school in computer science, I was in the something awful forums, and I met Jason Somerville. And he just helped me get my game to the next level. I mean, he was probably the first person who really taught me through concepts that it wasn’t just reading in a book from some author from some author who just might, I mean, I don’t want to denigrate Sklansky here, but there was a lot of he was exactly a no limit guy. Well, it was right at least for a while. At least he wrote that book with Ed Miller. Yeah,

 

Brad: I mean, advanced Hold’em was a limit book to my

 

Leo Woolpert: Hold’em for Hold’em poker for advanced players, it was EPT fap was the acronym there. I read that I did like when I remember the term of poker for advanced players that’s going to head and I remember this. There’s a passage where he says, he goes on an OSI where he’s like, if you don’t know how I arrived at this figure, you should put this book down, you’re not ready for it. I was like, Okay. And so I went, and I derived it myself, just to prove them wrong. It’s like, okay, I do know how you got this figure. I’m gonna keep reading this book. Think that David Sklansky.

 

Brad: Take that author. Yeah, that’s I don’t know, if that’s a great thing to put in a book. I haven’t written my book yet. But it probably won’t have something like that.

 

Leo Woolpert: It’d be fair, it did get the message across. And it did get me to do the work. Yeah. Figure it out for myself. So inspirational woman,

 

Brad: you’re probably a rare breed, you know, I would. I would assume most people just read that and kind of rolled their eyes with contempt and moved along to the next paragraph, you know,

 

Leo Woolpert: there was there was a content, but then I realized he was kind of right that if I really didn’t understand some of these fundamentals that I wasn’t going to get the concepts that were in the rest of the book.

 

Brad: Yeah. So what led you to sit and goes, I guess from the limit Hold’em games, just trying out a different format.

 

Leo Woolpert: Exactly. Trying out a different format. And I think one thing, even though I’ve played a lot of cash in my life, I didn’t make this realization till probably way too late, is that I just prefer tournaments and certain goes to cash games, in general, just from just my pure enjoyment aspects. And I think it’s because in a cash game, the meta decisions weigh on me a little too much and kind of ruined the enjoyment of just the pure poker, the meta decisions being, am I good enough to sit in this game? Am I too tilted to sit in this game is am I sitting to the right of the lag when I should be sitting to his left, just all those things added up, were in tournaments, sitting goes those decisions, they’re all just made for you from the outset. You, you play against you, you’re there, you accept who you’re playing against. And if you have a tough table, that’s, that’s gambling, if you have a great table, that’s gambling, like, you don’t, I don’t, I don’t have to use up my mental bandwidth on making those decisions. Also, those those decisions aren’t just poker decisions, they’re really self evaluative decisions that aren’t always the most fun. It’s never it’s never fun telling yourself and admitting to yourself, this game is too tough for me. It’s, it’s never fun. You think to yourself, I’m counting my stack down over and over again, maybe I’m thinking too much about this money and what it means instead of just thinking about it as chips that can be used to win pots.

 

Brad: You know, the, the other route to go is just to you know, be delusional and sit in never have that thought, right. I think definitely

 

Leo Woolpert: Battled through the thoughts to sit in games that were probably too tough for me, but fortunately, I’ve never done anything ridiculously, I don’t know. Take out huge loans to play in games that were way above my, above my station.

 

Brad: Right. I think that’s like quite a different thing. You know, like as long as you’re somewhat rolled for the game. And even if it’s a tough game, like to me, it’s very hard for one reg Have a massive win rate over another reg. And so as long as there’s a couple of amateur players in the game, then the game still should be profitable. Now, it’s not going to be as profitable as if it were full of those players, but it’s still likely profitable. And I think that sort of thought has given me solace of like, yeah, you know, I guess I’ve always been the type of person to like table start on most platforms that I play on, like, I will just sit there and wait for somebody to play with. And if it is a reg, then so be it, they’re probably not going to have a massive edge over me. And if you build it, they will come like what it ended up happening for the most part, when I would start tables, like back in the ultimate bets, ultimate bet days is because they had like poker table ratings. And you could like, Look people up to see their win rate, people, people would look me up and just not sit against me, like, the regs wouldn’t. And then all of a sudden, so basically, like, if we’ve eliminated that player profile, the other player profile is the fish who would sit against me, and then another one would sit against me. And oftentimes, I would find myself at these really great games, just because I sat down and started it myself. And then those type of players kind of surrounded me. And then the guys that were just kind of waiting to swoop in, would be stuck on the waitlist, trying to get in the game. And so like, that’s just, I guess, a part of my who I am or whatever, I just let’s start a game, let’s play. If the game is tough, then I tend to play in it. And if it’s hopelessly tough, then maybe I go grab dinner or something like that.

 

Leo Woolpert: Do you think that’s an essential element of poker greatness is being able to hold your own and even get a get a good win rate in against great competition? Well, it forces you

 

Brad: To evolve. It forces you to think more deeply about poker. And I think that challenge element is necessary to progression.

 

Leo Woolpert: But also it is your strategy of starting the games in the age of poker table ratings, actually, probably really was really ahead of the game, because it’s self selects for people who are ignorant of poker table ratings. So the people who are doing that don’t know that you’re like a 97. Or, you know, it was already up to 100 Right? poker table readings.

 

Brad: I can’t remember. I just thought they had BBs 400. So you could see like, even more important, yeah, did this guy’s a crusher? You know, I don’t want to play against them.

 

Leo Woolpert: Right. But only regs really were looking at that. So you’re only using it to fate the worst action,

 

Brad: right. And I would also do things like always start turbo tables. And always start do seven tables on ultimate bet because like that was a thing. Everybody had two big blinds over their heads and you went apart with like seven deuce. It just adds in this extra element or variable into the game that made the game more fun for me. Honestly, I like those little twists to the game because they the strategies change. And I think that like as strategies change regs edge kind of goes down if they’re not able to adapt or not willing to investigate and learn how to play. But the turbo tables started those because like, nobody who’s playing like 12 tables is going to sit down because they don’t have enough time to act. And the other regs typically hated them. So they just wouldn’t sit down and play. I remember somebody on two plus two, wrote like this long, scathing post about me starting turbo tables, which is like hilarious in hindsight, because they were like, What the fuck is wrong with this guy? Why is he always taking these tables? Like, I’m always typing out and like, you know, it’s just, it’s awful. And I’m like, yeah, like, I’m only playing six. So I’m fine. You know, I can and I tend to act quickly anyway. So like, yeah, it was strategic and beneficial to me. And like, I think that just in general, thinking about poker in that way or? Yeah, just not being kind of afraid to put yourself out there to battle has a lot of rewards over the long run. And yeah, so anyway, I’m talking a lot about my my poker origin.

 

Leo Woolpert: Story, certainly, kind of battling people, especially heads up is what led to essentially the heater that sustained me for the rest of my years through law school. And then also, I suppose, kept me from having to abandon being a poker pro for several years after graduating instead of fully practicing law. Just from I would say teeth I was in? Well, in 2007. First of all, I’d already been kind of going up the stakes, it said and goes that, I guess one to cash on party, stuff like that. And I was fortunate enough to buy 10% of Jimmy Frankie, in the Aussie millions. He was just a second. And yeah, I mean, he’s a, he’s a great, he’s a great guy. And I was lucky enough to have one of it one of the first times I bought action, and I mean, I can’t believe how fortunate I was to buy by accident, somebody who’s not only crushing, crushing that field, but also someone who’s so honest and had had someone I had absolutely no reservations about trusting with the money, you’re trusting they get paid out. And so he begged it just took my role to a spot where I could take a few more shots. And I guess through 2000 2007 and 2008, I just went out to Vegas for the World Series poker 2008, I ended up chopping a bracelet event, a 5k shoot out. And so that just is like okay, well, now I can pay for law school, which I’m enrolling for in which I’m rolling in in a few months. And also that same summer, I was doing a lot of battling heads up. I went on a just a absurd heater against one specific reg at 2550. And it’s funny because when I got to law school, probably not less than eight months later, I played one of his friends heads up. Fortunately, lower stakes and his friends just absolutely crushed me and just talked cute shit in the chat about how lucky I was to beat his friends. Like, you’re probably right. I was running insanely odd. It’s not like not every day you get in a four bed pot with ace queen against ace king and get the ace queen Deuce flop and just get it in like it’s, it’s, yeah, I was certainly running above my skill level. But from there, it made it really easy to feel relaxed in law school and have a real good time.

 

Brad: I wonder what it is about the space that like humans feel the need to like talk trash and try to bring someone down for some reason. That’s just quite silly. I don’t know what it is about, like poker in the ego. Maybe its heads up to because it’s very intimate and personal. But yeah, it’s just kind of wild to me. I’ve heard a lot of these, like heads up stories about people just talking trash nonstop, and all those things. And it’s like, I just don’t understand exactly why this happens.

 

Leo Woolpert:  33:03  

I mean, it ultimately hurt the guy because I’m not the most sensitive, I’m fairly sensitive, and you start talking about shit. I’m like, Okay, I’m not gonna play you anymore. Right? Well, we could have won a lot more for me if he had just kept his fingers off the keyboard.

 

Brad: For sure. Like I said, it just doesn’t really serve anybody. I just don’t understand why. Like we’re playing a game against each other, right? There’s no reason to, like try to make people feel worthless or feel dumb or feel bad about themselves. Like, we’re playing a game of cards and like, is just always mystifying to me how someone will, someone has their eye who has their identity fully rooted in poker, feels the need to talk trash, that they’re somehow better than this other person because they’re better at some like silly card game that’s played for money

 

Leo Woolpert: is always true. It’s sure I mean, it’s the same for a lot of games. closable is not that much different. There’s a lot of there’s a saying that spite fuels the quizbowl engine and taking ELS to teams where you thought you were that you thought you’re better than that induces a lot of spiteful feelings. And you can fortunately, on our team, we turned that into studying and working harder to get better, but they generally just be turned into surely talking shit. And I’m not gonna lie. We’re all young. We were probably talking shit too. But we also fortunately put in the work to pack up our shit talking.

 

Brad: Yeah, I mean, some people it breaks down and some people it builds resolve, I think, you know, there are some people that like, you talk trash to them, and they seemingly just get stronger and more intense and more focused and you that wakes them up. So anyway,

 

Leo Woolpert: I definitely think also, it was early age The Internet. I guess, kind of the early ages, the Middle Ages, I don’t know,

 

Brad: where the Dark Ages

 

Leo Woolpert: were people were just, I feel like had really leaning into that freedom of not having to confront somebody face to face and using it to say stuff that that they wouldn’t ordinarily say or, I mean,

 

Brad: I don’t I’ve never met anybody in the real world that I would expect him to say the things that people said in those days at poker tables like it. It is obscene. I mean, like, if you can imagine the worst thing that anybody could say to another human, those are the types of things that are routinely said, or were routinely said in online poker chat boxes for whatever reason.

 

Leo Woolpert: Oh, yeah. I mean, they even have, you know, acronyms that people made up to

 

Brad: just bypass filters and

 

Leo Woolpert: should have shorthand for insults. Maybe I need to insult these people more efficiently.

 

Brad Wilson: Right? Or like bypass the filter. Like, it’s like, this is how you spend your time I understand. Okay. Yeah. So you had some success at WSOP? You paid your way through law school. That’s got to be quite gratifying. I assume. were you living in Nevada, because you went to school in Nevada, right?

 

Leo Woolpert: No, I went to the school, the University of Virginia, ah, I’d also gone there for graduate school. But I dropped out as I kind of hit my ceiling in computer science and was coming up in poker and just the frustrations of, of just not cutting it, it turns out that the skills that may be good at it, being an undergraduate, did not translate well to advancing the field of computer science as a graduate student and doing research and just, it did not translate. I was struggling. Yeah, at the same time, I was also coming up in poker. And it was so much easier to just take that path of doing something that I was really enjoying instead of failing. It’s something that I was, it was driving me nuts. And so

 

Brad: easy decision there.

 

Leo Woolpert: Yeah. And so, but I also started, as part of my, I guess, coping with my inadequacies in computer science, I had done a lot of procrastinating. And some of that procrastination turned out to be reading articles about things in the law that outraged me. civil asset forfeiture, no knock raids, violations of civil liberties, violations of freedom of speech, those kinds of things that just maybe it brought up the kind of fight to me, it’s like, I definitely think that this should be changed. And I figured, after I dropped out, and after I’d just been kind of being a quote unquote, poker pro for a little while. I figured, if I wanted to try and get in that fight, law school would be the way to go. So it was at the University of Virginia was the first school I got into doing the best school I got into. So it would that was another easy decision. And it was also in state tuition. So it saved extra, like five grand a semester or something. And so yeah, the summer before I like I said, I chopped that tournament, the five K’s shoot out. And so I was just coming into law school with all sorts of confidence just. And I would say reality hit and a little bit reality set in a few ways. One of which is that I was toward the middle of the pack academically, in law school, probably is just slightly above the median. Whereas in everything up until dropping out of grad school, I just always had outstanding grades. And it was just kind of a shock to be around people who were not only naturally more intelligent and more gifted writers than me, but who are trying a lot harder than I was do. And having had a lot of success in poker, I admit that I was not trying as hard as I could have. But c’est la vie. And also, I guess for the kind of work I ended up doing now, it’s not like by law school grades mattered. So first year, I mean, it goes great, make good friends. And then for the summer, after the first year of law school people usually try and find some sort of, it’s really tough to land a super high paying job, unless you have connections or unless you’re just out Standing legal superstar. So I applied to jobs that align with my beliefs and happened to land one at the ACLU of Nevada. And I also did apply to jobs in in Las Vegas. So I would have an opportunity to maybe fire some tournaments while I was out there. So here’s

 

Brad: my my confusion, I saw that you’re a member of the Nevada bar. And I think that was why I assumed you went to school in Nevada.

 

Leo Woolpert: I feel like I’m a I’m almost a local by now, but I’m not an eight. I grew up my parents were the Airforce and we moved around and settle ultimately settled in Northern Virginia, DC area. But going back to this, I had an internship at the ACLU Nevada, one of five people and there were a lot of really impressive people. Because I think with an organization like the ACLU, it kind of has that prestige that makes people who have these kinds of beliefs and civil liberties and beliefs in checking government abuses and halting government abuses of power gravitate toward, but fortunately, I had time to fire three tournaments that summer. And one of them was the TennCare heads up. And it was it was just one of those perfect timing, things perfect timing, because it started I think on a Friday. So Friday afternoon, Tuesday, I didn’t have to miss up this much work. And then Saturday and Sunday, didn’t have to miss any work then and then it was supposed to end Sunday, but went through Monday. But of course, people were understanding about playing heads up for a bracelet instead of working a day in non paying job. So yeah, just I mean, that was magical. i It’s weird, because I remember a lot of the hands but I’m not sure I remember a lot of the specific thought processes that go into it because that was felt like I was really just in the zone. The match, not like a fugue state. I can try and remember if I do them all. I think the first round was Mike was rocky showed up late and

 

Brad: easy first round the grinder. You know,

 

Leo Woolpert: and before I played it and lost his brother Robert the first round. Yeah, so and yeah, it’s funny, he thought. It’s fitting because he wrote in the 2001 problem is rocky five instead of six is against by ace, king. And then when I got down to the final match, I thought instead of sixes against a hedge against John Doe thesis game to tie it at one one. Anyway, it was the first round was like was rocky shows up late. I give him some time. I said, like one of his representative shows up. And he says he was running late. We give him something Sure. I’ll give him time. But one of the four allow before it’s like well, we’ll give him 20 minutes, 20 minutes pass and you guys are for like five minutes. So I probably started with like a 5545 edge or something. And chips there. And I think it was also probably somewhat steamed to distract him from having shown up late showing up late in general. I think even somebody of his caliber can get distracted by that. And so the second match was John jawanda. And I think that probably one of the toughest ones there’s just really no way to get a read on him. And he was playing from what I could tell pretty theoretically sound not that I was playing theoretically sound or even really had a strong idea of what your medically sound meant compared to what it means today but by 2009 standards, I guess it felt like he was playing really theoretically sound. And it just happened to get the chips in with with nines and he snapped it off so quick. I thought it was dead but yet he’s Jack and held up. Then play David Pham next for on the bubble. And of course I just managed to to cooler him which was fortunate because I felt like he in a few times. I had played tournaments and cash with them in Vegas. I felt like he held over me a little bit. So I was really pleased that I fought through the kind of intimidation but kind of low expectations against him. Or a little personal expectations.

 

Brad: So, what I’m sensing is not a lot of weak spots in this tournament. Not Not a ton of gimmies

 

Leo Woolpert: Definitely not. There might have been but I didn’t. Yeah, that’s the thing about a heads up tournaments. I guess you’re only gonna play seven or eight different people and you know, the field could be 200 weak players, but you could still end up playing the seventh and eighth tough 730 Toughest

 

Brad: grinder jawanda Dragon.

 

Leo Woolpert: Cool. I think then next was a because Matt Woodward who’s a he’s like an OG, like, limit Hold’em Crusher. I think he was history and was turn the car off on up and he used to just there’s this famous famous by Ferris by poker nerd standard blog post where it’s just him and Matt hora, Lego Haas TVF playing Phil Hellmuth and Phil Hamid just going absolutely apeshit in the chat. And just playing awful and getting crushed by these two, two wizards. But so I want to flip against him. I think it was HK against threes, if I’m not mistaken, something like that. And so that made it fairly easy. I guess when you Windows flips, coolers and flips This is the term poker in a nutshell right? Heads up full ring six Max, it’s all it’s all coolers and flips and tournaments. And I played I think a French Canadian guy by the name of clavate. Matthew are Matthew club a I’ve never got it straight as to which was his first name or his surname. And he ran actually, I remember he ran a super sick bluff on me. And he got me to fold like, top pair Borba, I think I would normally call top hair but just stuff in the river and then just victory with the bluff right in my face. And fortunately, I just got over that by coloring them. It was I think it was over parents or something like that. Which it’s worked out pretty well for me. And for that I think we’re getting down to like that quarterfinals now, and I played Dustin wolf never win. And I felt like I ran pretty good against him. And just this is one of those where wasn’t didn’t just all come down to coolers and flips it’s more just probably me just having a lot of hands and him not having a lot of hands and just being very card dead. And eventually just getting in there as a as a big favorite pre sevens versus sixes. And then for the semifinals, I play Jamin Stokes of Detroit, where this is where it wasn’t very true. Um, I thought it’d be mixing them up with somebody else. But he he was playing great. And this is this is a match where I probably ran one of the bigger bluffs in my life, at least in terms of felt huge. So to set the stage, I guess I open the 10 Deuce suited. And he defends in the big blind. The flop comes Jack 9x No, no, I’m sorry. I’m Mrs. King. 9x. Thank goodness. But anyway, I checked back and forth for some reason, even though was probably a theoretically, I mean I think of silver probably tell you to bet the flop like all the time these days. The turns a jack. So Queen 10 gets there. I think he check calls, I bet. And then the river is a deuce at the turn of the Deuce and the river is the jack. And he checks I bet he check raises and I end up free betting for like two thirds of my stack. Just because and this is like God such a field play. I never really thought of myself as a field player. But this was in the moment. Just such a field play whereas like, I don’t think he has it. And even it was even inspired by I Caxton was commentating on this. Yeah, he might have. He might not have even been commenting on my match because Johnny Chan was playing the other one which of course is going to draw more eyeballs. I was like wow, if I exceed this remember that handy played the PCA gets rained out. I didn’t just do just be like just like that so I turned my bottom pair into a bluff tanked for ages and folded and that was one I had to show just I don’t know as much as I would like to think I have suppressed and a kind of shaved off the the ugly edges of my ego over the years. I definitely still have it in me to put in the needle into to not have the best etiquette or, I mean, it’s not like it’s terrible etiquette show bluff. But I didn’t do it for any strategic purpose. It wasn’t because I was like this is gonna tilt him or this is gonna give me an edge it’s just like I just did something cool. I want to show off somebody needs to see this exactly. Nobody’s gonna believe me if I just said I had at the bottom here that was turning into a bluff.

 

Brad: Right so that that’s an interesting like psychological sidebar we could go down of like needing the validation of somebody knowing because you yourself knowing is for some reason not not good enough.

 

Leo Woolpert: Exactly. So eventually, I won that match. Got it in fluster overflow straw and held, it’s always nice, and ended up playing John Duffy in the finals. And fortunately, for me, it was best of three, because I instantly, instantly there’s a long drawn out, first match, but I lost that one. And that one, I will say ran bad. I flopped a lot of big hands and sets, he would make his drawers in Wuhan. Then the second match to like I said earlier, I got a set of six isn’t like the fifth hand against his top pair top kicker. And we got it in the turn. So just lock that up right there. And the third match was was pretty epic. And it’s a back and forth. Key. John Doe thought one thing he did a lot better than I expected him to do was preflop was preflop aggression on these kind of 20 ish to 30 ish big blinds decks. I wasn’t expecting him to three bet me as often as he did. And I mean, maybe he was getting better than better than average distribution, or maybe he was picking up on the opening too wide or picking up on something. But eventually, I started switching to a limping strategy, which I almost never use online, in heads up sitting goes or it heads up cash at all. And eventually, I left the five free suited got the 10 five free flop against 10 Deuce and got the money in one. And pretty proud of myself in the moment for implementing this living strategy and adjusting to do something that I like I said almost literally never did online. Just because it felt like the right adjustment in the moment to counter his his preflop aggression that I hadn’t previously anticipated.

 

Brad: Right? It’s like, it’s also something that he’s probably not anticipating either is the switch to the Olympic strategy. So he didn’t have some sort of built in plan to deal with it, which is just kind of like a wrinkle or a curveball. And I mean, that’s kind of a thing in poker is like when you do something that’s unexpected, that the other player doesn’t really have a map that helps them navigate. Oftentimes, they do quite poorly. And like you may do quite poorly limping since you didn’t implement it, you didn’t think about it, it was kind of a spur of the moment thing. But at that point, you know, it’s who could do better in the absence of a prebuilt plan. And I think that like just by virtue of you, like being in position, that’s probably fairly helpful when you’re living in heads up. So yeah, I think that’s that’s like a really cool, just a really cool in the moment change that probably helped you when you know, the bracelet.

 

Leo Woolpert: Oh, definitely. I think, you know, if I raised that fyhrie The by, you know, he’s probably folding nitrogen at time, or maybe he’s just saying, This guy has nothing he’s stuffing in my face and just making that just winning a big party otherwise shouldn’t be entitled to

 

Brad: Yeah, and to be fair, like, dudes made it to the heads up. Oh, you’re watching this event, right. So like he’s probably well studied and fairly well prepared to face a bajillion D different button opens since this is obviously the highest frequency The defense strategy that you’re going to have to deploy is like, facing you know, the to bet preflop.

 

Leo Woolpert: So those days it was more like the the 2.5x, I guess calling radius to bet. Okay. Yeah. Well, I think when I heard that, I was like, Oh, I just My mind went exactly to memories. Some reason? Yeah, I tried to. I just inferred that x after the two. Yeah.

 

Brad: I don’t know why in poker, I’m trying to like, as I mentioned to you before, you know, building out my coaching for profit operation, and just trying to inject language that makes sense that everybody sort of understands, I find it interesting that like, we say open, we say raise first in, but then we say three bet, which is like, why don’t we just say to bet, right? Like, you know, you can also say rays and reraise, right? But like, to me, it’s so such a sequential thing of like, the first bet is the blinds, and then you to bet. And then after the two bet is the three bet. And like that just eliminates the confusion of people saying like, you know, oh, so I three bet and you’re like, wait, no, somebody Lent, and then you just place it’s not.

 

Leo Woolpert: I mean, there’s a lot of wiggle room, if you like poker terminology, and that the more you play, I guess, the more you kind of learn to, or at least the more you talk about poker, the more you kind of learn to interpret what people are saying, even if it’s not technically correct, like, oh, somebody limps under the gun. And then I open for 3x? Well, you didn’t open somebody’s you know, somebody’s lips. So you’re not opening the action, dude. Right. But okay, but you know, what they mean?

 

Brad: You know what they mean? For me, like, and, you know, we can talk about your adventures in coaching as well, because this is another note that I have. But for me, like, just communication as it relates to the coaching student relationship is so key, that I need to understand exactly what you mean. And I need you to understand exactly what I mean for this relationship to be as efficient and optimal as possible. And so from there, you know, the first thing that when people join, my CFP is like, they have a, you know, a flashcard deck that’s like the language of the wolves. And it’s like, this is the language we use to describe flops, preflop situations, postflop situations, action sequences, like, we all use the same language, and like you have to learn and integrate it, so that you know, what we’re talking about and can interpret, you know, the maps that we’ve built and that you’re learning.

 

Leo Woolpert: You got to have that, that lexicon, that shared language, to really get the most out of these ideas or explore them deeply.

 

Brad: Absolutely. So anyway, back to your, you take that take down your brain, even go down that tangent, I don’t even remember what’s not worth exploring what got us there, but you when your bracelet. And as you sell back to

 

Leo Woolpert: go back to the internship, the next day, just keep working, finish it out. Play the main event. I mean, it is a lot easier to do to do work when you believe in the cause. That’s even even when you’re not getting paid for it. So then I played the main event. And I mean, I think I live misclicked like three times somehow plus the day one, but I did find the guy who told me that winning hand and the 10k Did did find that dealer and did to him personally. So that was good. Because that was one of the things I’ve been meaning to do. Just fortunately, personally, so I’m there. Usually I would have been a normal summer I would have had a lot of opportunities, but only playing free tournaments, summer. But anyway, I go back to law school for the second year. And I mean, I’m just I wouldn’t say I’m an egomaniac, but I’m definitely feeling myself definitely feeling very confident about my future and poker, my ability to just cruise through poker play online crush online. And while also being an adequate law student, I wasn’t gunning for the accolades I wasn’t, I was I was pretty much out of the running for the very the various prestigious things that a law student can achieve like Order of the Coif for highest GPA or being on a law review or winning them the moot court competition or any of those. So my goal was just enjoy it. Learn some stuff, get the degree and continue to be decent at poker. Unfortunately, the latter those did not really work out because I started Definitely take around late 2009 to up until Black Friday, probably April 2011. The competition was rapidly outpacing, and I was losing and not just that, not me, guess, I don’t know, I don’t remember if I won or lost in the year or whatever, but I wasn’t winning at a high enough rate to, to make it worthwhile. I mean, it was still worthwhile. But it was in a way, because I was still enjoying the game and learning. But I certainly wasn’t supporting myself and I was starting to get somewhat concerned about, well, if I’m never, if I’m not going to be good enough and half the time to make myself good enough. That’s a very worrying prospect. Because if I don’t have a job lined up and not winning a poker, what am I going to do? It’s a very worrying prospect. So I did do a job interviews for for summer jobs after the second year. And those jobs are, those interviews actually usually take place, early portions of that semester, so I took it, got those interviews in August, or September. And it was, you know, three months after winning that bracelet, I was probably just absolutely projecting. I’m too good for this job. You know, I’m great at poker and too good to be a lawyer, you can make me work the insane hours that big law would make because I can always just bail out and go grind poker if I want to. And so obviously, having, I guess, said those things without saying them, just through my body language and demeanor, I obviously did not get those jobs. So I went back to the ACLU of Nevada for another internship in the summer of 2010. Because again, if not, you might as well play poker. I have a few opportunities today, because of course, I’m gonna win. And I did not win, bricked. And then after I graduated law school 2011, I went out to play the World Series again and bricked a huge series yet again. So just those combined really kind of had me doubting myself quite a bit. And really looking kind of toward the ocean, I might actually have to take the bar and put this to use. So I did take the bar exam and Nevada, and it passed fortunately, and but even after I took that just kept grinding, live cash kept playing the tournament tournaments in Vegas traveled through few and like Florida and stuff like that. And I had certainly approved at that point to where I was back winning again, back making, okay, hourly.

 

And I wanted a couple heaters between 2012 2015. But it turned out that the hourly that I was sustaining was not high enough to beat out the hourly from potentially practicing law. And so eventually, I had to make that tough choice to devote most of my time to practicing law as a vocation. And just become a fun player and play without a lot of expectations of winning or winning huge. But also not playing with the expectation of losing, like playing, lowering my expectations to just having a nice winning year, every year after rakeback I mean, I’m not even donating. I’m not even beating myself for not winning before rakeback it back in the day, if I wasn’t winning before rakeback I would probably be a very self doubting. But now it’s it feels like an accomplishment because of how little time I get to devote to improve your poker. And especially because the contrast between law and poker in terms of one the former just feels like work. And it’s paced really, really slowly especially compared to online poker, online poker, it’s like playing four or five, six tables, you have a decision every couple of seconds. And oftentimes it’s a really good mix of, of trivial decisions and legitimately tough decisions. So you get I get that feeling of okay, no, I know I got this easy one right and then okay, well, here’s a hardware has really challenged me and maybe I’ll get it right maybe this guy will own me maybe, you know, maybe it’ll just be interesting. An interesting hand and but you’re getting a lot of Those every single minute. By contrast in the law, it’s like you draft a long document. Wait for the courts to review it. Wait for your opponent to draft another long document. It’s like, it’s like poker if you got delta card every two weeks, you had to like work 20 hours to get each car. Like, it’s just the paces is glacial. And that can certainly, if that’s really means that when I’m done working the law job, I want to get into action. I want to get in that game thing just fire and make those decisions. And so

 

Brad: Live Live Poker must feel like you’re on the front lines. Like oh my god, this is so great. So Oh, are 30 Hands an hour? This is amazing. Oh, compared to

 

Leo Woolpert: law? Yes. It’s, it’s like, wow, I guess? You know, I gotta see cards every two minutes. It’s it’s fantastic. Oh, wow. Only they only took this guy’s only taking three minutes? Well, yeah. I think we’re taking three months. So with with all that, that desire to play, I think working a normal job really, really sparks up that desire to play when I’m done. And to be honest, I think playing poker being successful at poker, has probably spoiled me for a lot of real jobs and kind of made me maybe not on hireable. But even if I were to get hired, I feel like I would burn out very quickly from a lot of conventional jobs. Even my own law job right now is highly unconventional. In that I work with my wife, we work on, we do stuff we believe in. So it’s so I don’t have some sort of asshole boss who thinks I’m replaceable, and who doesn’t have anything invested at all in my own improvement. And, you know, since I’ve been working with the woman I love, it’s like, you can actually she’s invested in my profession. We’re invested in each other and not just having each other be strangers in office who have to get along because we have to get this work done.

 

Brad: Yeah, it’s, I mean, going back to what you said, I’m pretty sure anything outside the world of poker, I’m pretty unhireable. As somebody that like has a business, I can’t imagine hiring me for any reason, outside of like the poker space. I think just one of the reasons why humans get into poker, and maybe I’m projecting, but I’ve had enough folks who have gotten into poker and had a lot of success on the podcast. And also I have my own journey to kind of lean on. But like you want freedom and autonomy, to just do whatever it is you want to do. I mean, that’s like, I didn’t want a taskmaster, you know, that was the last thing in the world that I wanted. I wanted to, you know, follow my bliss, and poker. For a long time, I’m not gonna say that it’s always been a bliss, and has never felt like work because it of course does eventually feel like work. And there’s a lot of non blissful times and periods to go through. But I do value that freedom and that autonomy and really working towards something that is meaningful with purpose. Having a vision, trying to solve giant problems, these are things that really resonate with me, trying to create things that are impactful in the poker space for my community, my people, trying to have interesting conversations where the listener learn something, these are all things that have a great deal of meaning to me. And maybe there is some job that can fulfill all of those things. But yeah, I don’t know what that job might be. And I also have a suspicion that they probably wouldn’t pay me what I want to get paid after doing all of these things on my own, as well, so yeah, I mean, I think that entrepreneurship resonates with me quite well, as it relates to freedom and autonomy to be creative. I think that’s another thing that I highly value is like being creative, and solving problems on my own. So yeah, I’m just eternally grateful for the world of poker. In that sense. Let’s so as you entered into your law career, what lessons did you take from poker that helped you in your,

 

Leo Woolpert: your new career path? I think one of the big ones is just not being as results oriented as most people are who don’t have a decades of poker variants under their belts. I think it detaches me a bit from some of the kind of losing emotional arguments that some that other lawyers might just be attached to, or other strategies that through my experience in poker, I can, I guess, better estimate probabilities and the payoffs, and use that to guide my decision making. Whereas a lot of lawyers just kind of fly by the seat of their pants and go with their gut. And don’t think about the probabilities, and the payoffs, that their actions, and they can definitely get them in trouble. Yeah, and

 

Brad: there’s also this iterative process of learning to and kind of going back and analyzing what happened, and seeing the lessons you can learn and maybe what went wrong, what you could have done better. I think a lot of people in the world sort of have this assumption that like, they do something one time, and they did like the optimal thing. They just kind of they know 100%, I did everything that I could have done, there is nothing else. And like to me, I’m always just big on doubting myself after the fact, that’s just like a big trait of mine. And just like questioning every little thing and asking myself, could I upgrade this, could I upgrade that I’m trying to really learn from my experiences, I think that poker does teach you that over time. Because if you’re not learning from your experiences, you’re not going to be able to make it as a professional for very long. You just kind of flame out of this world. So it’s like a necessary survival trait really, that I can imagine serving you quite well. Just in really, in any field that you enter into after being in poker.

 

Leo Woolpert: No, absolutely. I think it’s Poker is also maybe more patient in certain respects. Because especially tournament poker, where sometimes you do have to pass up on something that you think might be a tiny edge. Because you anticipate a greater edge coming along. And you don’t want to, you know, ruin your one tournament life. And I think that applies to certain legal strategies as well in just now, I’m not sure how far into it I want to get here. But But now I’ve lost my train of thought.

 

Brad: Well, not very far.

 

Leo Woolpert: It’s, it’s purely careened off the tracks.

 

Brad: Not very far. Oh, cool. So I think that’s, yeah, it’s good enough. And as it relates to your day, your life day to day now, you know, we’re rapidly running out of time. And I would love to have you back for round two to kind of ask you some of the, you know, lightning round questions that I have in my template. But for now, you know, what is your life look like these days? What role does poker play in your day to day? I assume you live in Nevada?

 

Leo Woolpert: Yes, Las Vegas? Yes. Cool. So I would say, pleased a listicle fairly large role in my life, because first of all, I think I’ll always be a fan of the game. So when it comes to keeping abreast of say, Twitter drama, or via live streams or tournament results, sometimes I’ll find myself browsing those. And when it could also feel like poker is my a bit of an escape for me, in that when I get home for doing legal work, it’s nice to just fire up sitting goes and I’m still planted goes mostly in tournaments these days. On w wsop.com, and then sometimes ACR. But the sitting goes, especially hyper turbos, like I said before, it provides a nice mix of easy and tough decisions that I enjoy making. And so it’s just a nice release. And the fun thing to do after work and it’s unfortunately after rakeback I turned a profit. So these days, I kind of view it as doing puzzles for entertainment with it’s like, it’s like if I got if somebody asked me do you want to get paid minimum wage to do Sudoku is a crossword puzzles. I tried to be like, Yeah, okay. Sure. So, so I think I would do for free. Exactly. I do do it for free. So I mean, I’m not sure I would play poker for free because money is such an integral element to it. But I certainly have no complaints about playing poker and riding the swings and ultimately if it comes down to you know, making a few dollars an hour overall that says So in addition to the money making from a job, what would

 

Brad: you say, has been the most unexpected thing that’s come from your poker journey?

 

Leo Woolpert: unexpected thing, probably meeting my wife. I mean, because I met her while we were both at the ACLU of Nevada, that she was she was my boss then and every she’s still kind of a boss now and lawyering. And without poker, I would never have thought to apply to an internship in Nevada, or Las Vegas to say that I would have the opportunity to play poker wall ball was doing that internship. And we’ve never met her. So it’s, it’s probably the most unexpected thing. And also, I guess, we’ve also got three dogs, and I wasn’t a dog person growing up. So that was pretty unexpected. And I’ve really come to love dogs pimples in particular, just a breed that melts my heart. No, no, it’s stuff because I go on Facebook, and it automatically sends me these videos of pitbulls getting rescued. And it’s like, if I watch this, I’m going to be in tears at work. How can I how can i That’s another thing also, my wife and I bought it over is there’s our show pitbulls and Pearl pit bulls and parolees. And we watched an episode and by the end, we just heard each other both sobbing, because we’re just so emotionally wound up over the show. That’s one of the moments so it’s like, Alright, I know, I know, we’re good together.

 

Brad: Yeah, I see this person, I see their spirit. So knowing that you’re someone who, you know, pursues, your bliss chases your bliss, and also pursues things that are quite meaningful to you. What’s a project right now that you’re working on that’s near and dear to your heart?

 

Leo Woolpert: Um, I would say some of a lot of the legal cases we have are very near and dear to my heart, especially when it comes to civil rights litigation. I think that when it comes to suing the police, we have cases right now where police shoot people’s dogs. And obviously we sue over that as because our contention is that it violates their Fourth Amendment Right? To be free from unreasonable seizures, and shooting somebody’s dog, it doesn’t get much more of a seizure than that, because you’re ending the dog’s life. And we’ve had, how did

 

Brad: these cases go down? I mean, is it like, just shoot on site? Like, I don’t know.

 

Leo Woolpert: They go down in all sorts of ways. And it’s, it’s kind of horrifying, in a way, just how many how many dogs are shot every day in America by police. But all sorts of ways. I don’t, but I’m sure one could Google it.

 

Brad: It’s a it’s more than you would think

 

Leo Woolpert: it’s way more than you would hope for. But it happens during the day the execution of warrants where police have an opportunity to plan out a no knock warrant say, and they plan it out. And the dog they haven’t they know there’s a Beware of Dog sign. But they don’t take any measures or preparations to prepare for a dog being on that property when they serve this ward execute this warrant. And that’s the case that we ended up settling a couple years ago where they did exactly that it was they went in just to execute this word, despite knowing the dog was on the property, or dogs plural were on the property and just did shoot first ask questions later. And that, you know, that when we survived what’s called summary judgment. And instead of taking it to trial, we ended up settling. And there’s another case that we’re in right now that I’m currently working on. It’s an appeal, because we ended up losing a district court when our client had his sign that alarm get activated. And a cop came and entered his yard shot his dog, which normally in normal circumstances that might not you might not be liable, because there’s the doctrine of qualified immunity, which shields officers if they’re, they’re reasonable, but in this instance, the officer in question lied about taking mandatory dog encounter training. It’s a Nevada law that all police officers after police officers who interact with the public have to take mandatory dog training classes. And this guy, instead of taking the class, he just logged in, printed the certificate logged out and then represented that he taken the class. And despite that, the district court found that this officer shooting over our clients dog was was reasonable under the circumstances, even though he, like I said, lied about, and admitted to lying about taking this mandatory training, which argument is would have taught him techniques to control a dog he might have been surprised by without resorting to deadly force. And so we’re currently appealing now on and hopefully, hopefully, we get a good ruling. And we were drafting the briefs. Now, it’ll be ages before it really comes out. But in this area, it’s certainly tough because the way the law is being shaped right now by the federal courts, is divergent from what I think it should be. I think the courts are going in the wrong direction and being too lenient in not holding government police specifically to higher standards. And not an extending this doctrine of qualified immunity, which was originally intended to protect reasonable efforts and not protect people who were engaging in law breaking or cleanly incompetent. Which somebody who lies about taking the taking their mandatory training, I think that’s, it’s clearly both incompetent and breaking the law.

 

Brad: Well, it also says something about just not caring about the training and not caring about some someone else’s animals not caring about animals in general. The number that I have here, as I Google, this is 500 dogs a day, something like 182,000 a year shot by the police officers. And I mean, you don’t actually consider that having an alarm, a silent alarm that can get tripped for a variety of reasons. leads to your dog getting killed. I mean, that’s just horrifying. You know, it’s just horrifying, terrible, terrible, terrible thing. And

 

Leo Woolpert: these are the kinds of cases that really, that inspired me to go to law school to begin with just somebody who’s really been trying to get justice for somebody who’s been subjected to abuse of government power. That’s just, that’s just why I’m in the

 

Brad: game, so to speak. Yeah. And that makes you do what you do. We do other work as well. But yeah,

 

Leo Woolpert: I think when it comes to really inspiring passion, that’s, that’s the area where I feel the strongest.

 

Brad: Yeah, I mean, I’m steamed up just thinking about it. This this story in this situation that like, on some level as humans, I mean, there is, there must be some level of empathy, or, you know, in this world, like, how do we not have more research? And how are we not prepared for something that ought to be so common? I mean, how many people own dogs? If you go to these places, you’re going to encounter a dog quite often, and to just kind of blow off training? Because you’re lazy, because you don’t care? I mean, it’s just, I don’t understand how that person could have a badge, why wouldn’t they just be instantly? out of there? Right, like, I mean, because if they’re cutting corners, they’re where else are they cutting corners? Because the answer is many places.

 

Leo Woolpert: Oh, yeah. And I mean, it’s, that’s, uh, you know, I think gonna be one of our main arguments on appeal is that if you’re going to allow, if you’re going to protect officers from liability when they get caught this mandatory training, what mandatory training is next? Like, is it gonna be firearms training is going to be next where they skip that, and then they don’t know what a safety is, and they keep the safety off and shoot somebody isn’t going to be driving training where they don’t know their capabilities of their vehicle, and they try to do some some crazy maneuver and kill somebody on the road like, it’s I don’t want it is a part it is kind of like a slippery slope argument. But I want to the argument is that we got to cut it off here before it slides any further.

 

Brad: My argument is that if you’re there to uphold the law, and you’re breaking the law, there’s this obvious dissonance there like you’re an instrument of the law, and yet you don’t care about it, and you call other people bad guys. And yet, the same rule the rules don’t apply to you. Like there’s hypocrisy and dissonance and like, it’s something that yeah, again, like I said, I’m not We’re in this podcast on a high note. But it’s something that that that really matters to me as well. Because like, yeah, these are just very important things. And like, if you’re going to arrest people for breaking the rules, it feels like you should probably be pretty good at following the rules.

 

Leo Woolpert: Absolutely. And that’s, that’s another thing about poker. And one thing that I’m really grateful about having had success in poker, is that I think it’s allowed me to seek out work that I believe in, and I don’t have to sell my soul. And I just do, like completely anodyne business work, or I mean, we do represent businesses. And you know, we’re, I do enjoy the business clients. But we also I basically don’t have to sell my soul to work as a lawyer, right, and you get to choose your shots. And I have essentially poker to thank for that. Without poker. I could just be working at some some firm where I have absolutely no control over what I do or who I argue for or what cases that I end up pursuing. And I think that would be pretty devastating for me, emotionally. And

 

Brad: Yeah. So we’re going to wrap up. And you know, the final question here, I know you’ve got to take your puppy to the vet, speaking of the puppies. So where can the Jason poker greatness audience find? Or learn more about you on the worldwide? Oh, man, this is a tough question. I’ve only asked it 1000 times. If somebody wants to learn more about where the hell do they go? Where do they go?

 

Leo Woolpert: You can just go to my Twitter page, I guess. Do Walpert on Twitter, I do have a website that I’ve made a lot of attempts of blogging over the years that were very short lived, because I get a lot I do already do a lot of writing and as in my day job. So by the time I am done putting all those legal words on the page, I don’t really have a lot of desire to put anything else on the

 

Brad: page. Make sense?

 

Leo Woolpert: Unless it should post on Twitter that I love those.

 

Brad: Man, it’s been great having you on and like I said, we’ll revisit around two in the near future. And yeah, great learning more about you. And it’s

 

Leo Woolpert: Great talking to you, brother. I really appreciate you taking the time and yeah, it’s fun.

 

Brad: Thanks, man. You too. Talk to you. Talk to you in the near future. Take care.

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