Vested Capital
Vested Capital

Episode 9 · 1 year ago

(EP9): Jonathan Little Professional Poker Player With $7+ Million Winnings, Founder PokerCoaching.com

ABOUT THIS EPISODE

Jonathan Little is a professional poker player with over $7 Million in career earnings from tournaments (both online and in person) and is one of the most popular poker coaches/personalities in the industry.

He's also co-founder of PokerCoaching.com, a membership site and training community with over 5500 paying members, making it a multiple seven-figure business.

I met Jonathan via Jason Calacanis and his angel investor syndicate. Jonathan is an active investor in all kinds of different asset classes, from NFTs to Magic: The Gathering cards, although he is of course most focused on poker.

During this interview we go back in time to learn how Jonathan got his start in poker, how he quickly became a professional, earning as much as $30,000 a month playing a specific type of poker online. We also learn how he upped his game to the point where he won over a million dollars from one tournament - twice.

There's a lot of wisdom in this interview, and while much of it seems specific to excelling at Poker, Jonathan's advice can be applied to other aspects of life, from being a startup founder, content marketing and when to invest versus when to spend your money to grow faster.

I enjoyed this one a lot, and I'm sure you will too.

Yaro

Podcast: https://www.yaro.blog/pod/
Blog: https://www.yaro.blog/

Heyy this is yarrow and you're listening to vested capital episode number nine, featuring my guest at Jonathan Little, a professional poker play with over seven million dollars in career winnings and the CO founder of Poker coachingcom and the head coach there, as well a membership site with over five thousand five hundred paying members, so a multi seven figure business. bested capital is a podcast about how people make money, build capital and then put their capital to work. I interview start up founders who've enjoyed big exits, Angel investors, venture capitalist, Crypto Stock Traders, real estate investors and leaders in tech and, of course, now professional poker players as well, as you're about to hear with this interview with Jonathan Little, who has made over seven million dollars in career earnings and is the owner and head coach of Poker coachingcom. In these interview we go back in time and hear about Jonathan's early days, first as a Gamer in magic, the gathering, a different card game that was kind of his gateway to playing poker. It was also a game I used to play as a teenager, so I had to take a little deeper into what type of Magic Jonathan was playing, and also we talked a little bit about the value of magic, the gathering cards, and how much they have increased over time, and Jonathan actually still owns quite a few highly valuable magic cards. We then switch gears into his poker career. He was very quick to ramp up to about thirtyzero dollars a month in earnings as a professional poker player, mostly due to his ability to focus on the math and studying the the game itself. He was able to basically take advantage of something that was available to anyone, but he was willing to put in the work and do the math and also look for certain types of tournaments. I think this was a definitely a trend I noticed in a lot of the advice he kept giving throughout the whole pokus story was just being smart about which tournament you enter, looking at the players and just entering basically a type of tournament where you're slightly better than everyone else playing. It makes a lot of sense to me as well, but I think there's a skill even in doing that, and it's quite a lot of advice that Jonathan explains here. He talks about how he went from. You know, a thirty thousand dollar month poker player, had some some good wins, had some losses, what it takes to maintain a bank roll, how to use your money as professional poker player and then, most importantly, I think, how he went on to actually have a couple of million dollar winnings in tournaments, but very much using the same philosophy. You can certainly see the strategy that Jonathan Talks about a lot in this episode about choosing the Right Tournaments, practicing your craft, getting not just getting good through the act of playing the game, but studying the game. He's a great example of someone who's focused on one thing and gotten really good at it and then he's turned that into a business itself in terms of a coaching practice and a digital teaching empire. He's a an online poker celebrity in terms of how much content he produces. He has a youtube channel now with over a hundred thousand subscribers. So you're going to hear that whole journey in this episode. We talk a little bit towards the end as well about what kind of investments Jonathan has done since he's been in bed an NFT's lately. CRYPTO. He's had some property over the years and in fact I met him through Angel Investing, so you hear about that connection as well. Okay, so if you're new to this podcast, I would recommend you subscribe. There will be a subscription button or a follow button or plus button somewhere in the PODCAST APP you're using to listen to this episode. If you hit that, you will then be subscribed to vested capital and we'll get all the future episode's plus access to the full back catalog of amazing interviews like this one with Jonathan. If you don't get have a podcast APP, though, you can head to my website and you'll find all the subscription links as well. Just go to Yarrow Ya o dot blog blog and you'll find the podcast have there, or you can just go straight to vested capital podcastcom if that's easier. If you to remember, and that will redirect to that page. You can find the show on all the main podcast players as well as online for streaming. Okay, that's enough about subscriptions. Let's start playing the episode. Here's Jonathan Little. All right, Jonathan, thanks for joining me today. It's great to meet you. Thanks for...

...having and happy to be on here. So you are actually the first ever professional poker player to be on my podcast and also a poker coach. I know I've had a poker someone in the past. Left to surface that interview and see if you guys maybe even know each other, but as far as I know, you're definitely the the first person who's ever got the kind of numbers you do in the world of poker in terms of results and also as a coach running a big membership site. That's about all I know about you so far, so I'd love to dive into that history, but also everything else you're doing, and I should say just for the audience like that. We actually connected on a slack room for a syndicate were a part of with adjacent Kannis and his investment groups, so you obviously do angel investing as well. Have I missed anything in summary else that you're kind of involved with or have been involved with? There's a lot going on right no, no, I mean that. Yeah, the main points. I have a poker training site, poker coachingcom I'm part owner of a publishing company that publishes a lot of poker books. All these books up here I had my hands in substantially I don't know, gone head first and NFTS recently. Probably going to work a bunch of money doing that. And that's it. That's it. What kind of NFTS are you looking at? Everything? We have some Crypto punks, we have some me bets, we have some board apes, we have some gift goats, all sorts of stuff. Okay, so my audience probably has no idea what any of those things are, but appreciate the I didn't have any idea what they were until about a month ago and then here we are. We're all in. So, yeah, why not? Just for the sake of the numbers too, I know obviously was with professional poker. A lot of your numbers are reported. You do have like a summary of your kind of results you can share with us from that world? or well, so anytime anyone wants to know about anyone's poker results, they can type into Google the person's name, Jonathan Little, and then GPI. That's global poker index, or Hinden mob. It's kind of the same site, and I will list everyone's cases. Now, cashes don't necessarily mean profits. Cashes mean how much you have cash. Foreign tournaments not counting. You were buyings. Some people who have millions of dollars in winnings are losers. Some people who have hundreds of thousands of dollars in cashes are winners. But I have something like seven million dollars in cashes, give or take. I've been around for a long time. I was player of the year if a bunch of trophies behind me if you're watching the video here, and I've been around for a long time. So reasonally good poker player. Certainly not the best in the world, but I don't know, top hundred tournament player, give or take something like that. Yeah, I don't think the average have one seven million. But can you clarify when you said like some people can win millions but not be profitable? I know there's all kinds of things going on behind the scenes of people being staked and and other things like that. Is that why you might not be profit or was it simply the cost of being a professional poker player? Well, there's all sorts of things, right. I mean, imagine you are a professional poker player and you spend Fiftyzero a year traveling to fancy casinos. Right, so if you win Thirtyzero in the year but you spend K you're down twenty k out the door, right, even though he results I say, look, I'm up Fiftyzero, I'm crushing it, but like not really right. Also, there are a lot of high buying tournaments. If you look at the top, I don't know fifty people on that. The sites I recommend to the global poker and DEX. I would bet some number of them are down despite having, I don't know, fifteen million dollars in cashes because they're buying into twenty Fivezero by in tournaments or million dollar buy in tournaments as often as they can. And if you buy in for twenty five million dollars and you cash for fifteen, you're down to in million dollars. But I think it's generally thought that in the poker world you do not want to actually give clear results for people in terms of this. Players down ten million dollars, because nobody wants it publicly known the you're a big loser at poker, right, because like that's bad for your business to some extent. Right. There a lot of people who just like to gamble and play play some cards. Right. There's always this debate in the poker world of should we have very clear results and their thoughts that like maybe making specific tournament tours where they are going to put out very clear results of WHO's the winner and who's a loser. But at the end of the day, you want to play poker with people who are worse than you at poker because that's how you make money. Make money when people make mistakes that you don't make and that results in you not really wanting the profits and losses of...

...everyone to be very, very clear. Okay, I didn't realize those as high as a twenty five million buy in tournament. Twenty Fivezero buy it. Okay, I was going to say, but there are million dollar buying tournaments. Okay, I think the biggest one ever was a million pound by in So there's there a few very big buying tournaments. Yeah, I don't play in those. The biggest I I plays typically about a hundred thousand dollars and that's on the upper end of what I can handle. It's important to make sure, if you're trying to be a professional, that you do not act like a degenerate gambler and you don't risk too much at any individual point in time. So you have to have some discipline and you want to make sure you're playing in games where there are worse players than you, because if you're the worst player, you're not making any money and then you're the gambler. Fair enough. And in terms of your coaching side of the business, any numbers you're happy to talk about there, because I thought a pretty big business this you've got going right. Yeah, we have about, I don't know, five thousand, five hundred active paying members. It's some membership site where we have all sorts of content. We have interactive quizzes, we have live webinars where the students can interact with a lot of the best players in the world in real time. We have live streams where you can watch some of the best poker players play their high stakes games live and asking questions. We have in depth courses. I have a tournament course there's about forty hours long, which will teach you everything you need to know to be poker tournaments. It's big, it's an in depth, it's advanced, but that's the kind of stuff you need to be studying to actually succeed at a reasonably high level. There's a lot of stuff there. People can check it out at poker coachingcom free and I hired some of the coaches to teach like relatively low level content because I realized a lot of the people who come to me our beginners. But then I also hired some of the players who are like literally the best in the world and I hired them to effectively teach me because I'm always trying to learn from the best players in the world. We have one guy who was recently the number one online tournament player in the world. He's just playing all the big games and crushing it and I want to learn from that player. So there's there's low level stuff, high level stuff, whatever you need to succeed at poker is they're awesome. Okay, so poker coachingcom and slash free. If you want to get start for free. You that. That's awesome. Appreciate the the share. I'd love to know how that business crew but I really would like to start at the very beginning here with you, Jonathan. So can we go back even I don't know, teenage years? Was that when you were interested in poker or what we you focused on at that time? And where were you born as well? Yes, I was born in Pensacola, Florida. There was no casino's, no gambling in Pensacola Florida. The closest place was Bluxey, Mississippi, which is about a two hour drive away, and so I didn't know anything about poker, gambling, etc. But I played a lot of games as a kid. I was decently good at chess and I found a game, magic the gathering, that I was really good at as well, and I would go play magic the gathering tournaments. This is a card game, kind of a mixture between chess and poker. It also has some financial implications with trading, which is neat as well, like baseball cards or whatnot. So anyway, we would play magic tournaments every two or three days and I would play. I was a very good magic player there. In one day, another one of the players said, why don't we play a one dollar buy in poker tournament, tiny stakes, after the magic tournaments. So we all said Shure, we all put up our dollar and it turns out that guy and one other guy won almost every time. And I knew chess was a skill game, I knew magic was a skill game and I thought maybe this pokers is skill game. So I bought a few poker books and I studied them, I read them, and then I put fifty dollars into an online poker site called party poker and started playing tiny stakes games. I played I think twenty five cent, fifty cent limit hold and limit holds kind of a dead game. Now. This was fifteen years ago, seventeen years ago, whatever was two thousand and three eighteen years ago. Goodness, time flies. So I played tiny snakes games and over the next few years I turned the fifty dollars into something like three or fifty thousand by the time I was twenty one. So we grind it up up. I've eventually transitioned to no limit hold him, which became popular back in that time, and I got very good at a particular format called sit and goes, which are essentially nine person tournaments. Everyone buys in for let's say a hundred dollars, and then the winner gets fifty percent...

...of the prize pool, second place gets thirty percent, their place gets twenty percent and that's it. AER rails gets nothing. These were very fast structure tournaments that resulted in you becoming very shallow stacked quickly and as the stacks get shallow, it becomes more of a straight math game because there's no reading people or anything like that online to some extent, so you just follow what the math says. And there were a few programs out there that I had access to that apparently other people did not or they didn't use them properly, and that resulted in me being a big winner in those games. So by the time I was twenty one, I was making, I mean, I don't know, thirty or Fortyzero a month playing this really like easy mathematical game, and that resulted to me dropping out of college because I was making a bunch of money back then. When I turned twenty one, I started playing live poker tournaments because I was watching people on the world poker tour and world series of poker play and I thought I could probably play better than them. So that's sort of giving my launching pad into the live poker space. The fact that I know studied that game a lot. Yeah, that was that. But I mean whenever I was one, nineteen to twenty one, all I really did was play poker and study poker like fourteen hours a day, every day, and that will make you really good at poker or whatever you're doing, but like pretty bad at everything else a life. So I had no friends, no good relationships or anything like that. And it's tough because I don't know if I would recommend that to people because it's not it's probably not good for your mental wellbeing to sit in your room all day studying poker and playing poker and at the same time, if I look at a lot of the best poker players in the world, they've all done that exact same thing. So to get really good at anything, I do think you need to have some period of time where you just go really, really deep on it and learned as much as you possibly can. Okay, now I want to continue the poker story, but I have to go back to the magic years. I was actually image at the gathering player in Australia sort of the mid to late S. is that when you were sort of playing? We playing the pro tour. I did not play the PROTOUR. I qualified for okay, I don't know, fifteen years old or whatever. My parents would let me go to China or wherever they had it. I think was I don't know what it was. Anyway, I was playing like locally at you know, I would travel to Louisiana and South Florida to play tournaments and I was not like the best player in the world or anything. I was I played a lot of vintage. Unfortunately or fortunately bepends on I look at it. where I lived, they played a lot of vintage because they a lot of people just wanted to play with the cards they had. This is a format where you get to play with all the cards and I was, I guess, better than them. And at magic it's in vintage. It's unfair to some extent where you could have just way better cards in your bonus. So I would like never lose me. And when other guy had all the good cards, everybody else did not have good cards, so you just me and the other guy won every tournament. Uh So I got to be number eleven in the world ranked and vintage at one vintage. Well, in vintage, and does that mean you're like? I mean they got rid of the rankings a long time ago. I looked at US still like number fifteen or something. That's fine. While playing in many years. The rankings are clearly silly, though. Yeah, they were fun to look at, but I'm curious and if you played vintage in this really ties into I guess we look at today's world of Magic to gather and you look at like a Black Lotus card or the power nine. Those are investments in themselves. So did you have and still have those cards from back in the day or yeah, so I had a very good magic collection back in the day and I was working a job at an airport. That resulted in me. I played a magic tournament one day. I got home at four am, had to be at work at zero am the next day. Okay, got home, left all my stuff in the car, went to sleep and somebody robbed me. So they took all of my good magic cards, but I went back. I I remember I bought a deck for like twenty dollars out of the the common bin or whatever, grinded it back up and had a good collection. Then, after I got into poker, though, I played like no magic, because if you're making many hundred dollars per hour playing poker, why in the world would you good play Magic to make no money? So I stopped playing magic and then, it must have been about ten years ago, I sold my collection for like Twentyzero bucks or something, which you know, is a good amount of money, but today probably worth a million bucks or something. Yeah, something like I don't know, must be eight years or ago or so. Now I just started like buying up magic cards because I thought I noticed the...

...power of nine did not really increase recently. These are of expensive magic cards and dual land same thing. I thought they were all relatively cheap, at like a hundred dollars per card or whatever it was. So now I have a pretty big collection again. I have a instagram account called daily Magic Muse where I post a magic card whenever I feel like I used to post every day, but whenever I feel like it. Have a pretty big collection. Have a I'm really into signed and altered cards. I also noticed that it's going to sound a little bit more bid, but if the artist of the card dies, that card goes way up in value if it is signed and or there is art on it. So I have like an altered power nine set. All my dual lands are altered in some way by the original artist, and that may pay off, it may not. I think it will, though, and it's good to have fun unique stuff. That's kind of high end. It's almost like our right, there's one Mona, Lisa or whatever, and it's incredibly valuable. Right, there's only one altered Black Lotus like mine, by Christopher Rush and sitting right down there on the floor. So anyway, is it a Beta or unlimited or no? No, no, you do not want to get the Beta ones altered. I was going to say one's are worth a lot more money. You want to get the unlimited beat up ones altered because then, like, you can't really decrease the cards value all that much because from a collectible point of view, of a card is in like pristine mint condition. You don't really want to mess that up. But if the cards already like the lowest grade, it can be within reason. You can't really make it any worse. So it only improves a value to get it altered. At that point makes sense. I can see why you're into NFT's. If we fast stored to the president that the collectible, individual unique aspect of that would tie in right, right, nicely. Oh Gosh, who knows? It's tough, because you know who knows? This is a bit of a gamble, but you know, you find spot. Do you think are good you load in and and pray. Well, who would have thought that magic the gathering still here today, like, you know, thirty plus years ish ago, and these cards are worth so much? I would never have guessed that in you know, when I was playing so so, funny enough, my parents were just in town and my mom brought it was called a memory book from when I was in eighth grade and there was a page on it I'm my three favorite things. They were computers, it's like an apple computer, magic the gathering, and what was the other one? Oh, Nintendo, and I was thinking, if I had invested in those three things back in the day, we would just be filthy rich. Yeah, all of those talks have gone through the roof. And instead I didn't. I just played the Games and now we're not mean, we're doing well off. But you know what I'm saying. Right like and the page was called fantastic fads. I'm like, look, this wasn't bad at all. Three of these things are booming. That's awesome. No, it's funny too, because then we've become adults and we start something else, in your case poker, and you know, that becomes our main focus. But it's not that unusual. I remember when I was playing magic. There's so many people who went for magic. It was like a gateway drug into poker, a professional poker, I feel like. So can we continue your story, switching back to poker land. So you're making like thirtyzero ish a month playing online with your sort of mathematical formula, which is not a guaranteed women it sound like at that time it was certainly an advantage for you. What happened next? Like do you do? You say that money, like, how does a poker player think about this? That you buying property on this side. Are you thinking, I want to graduate to bigger tournament, so I need more money to buy in. Like, what's the the philosophy there? But two questions there. So first things first, all you really have to do to win at Poker is find a game you can beat, play it a ton and keep a proper bank roll. So back then I was playing these two hundred dollar by and sitting go tournaments, nine person tournaments, and my edge was relatively small. I would win five dollars or ten dollars per game, but I would then play three thousand or four thousand of them each month. And it turns out if you're putting in a lot of volume, even with a relatively low edge, you just like can't lose. I think I had like two losing months and they were like marginal losing months over the course of two years doing this, and that's is how it works, right, if, if, at the end of the day, volume cures variance is some extent where you'll have swings, but you just know they don't matter because you are like a clearly proven winner. Now, in Games like multitable tournaments with a lot of people, like a hundred people or tenzero people, there's gonna be way more variance, right, and that's why,...

...you know, volume becomes very important. Want to play a lot of games and that makes it to where you essentially get to the long run at some point and as you are playing games with more and more people, like five hundred person terms or thousand person tournaments, you need a proportionally bigger and bigger bank roll, because you don't win a five hundred person tournament all at often. Where's you win a nine person tournament pretty often, right, even if you're break even, you went at one in nine compared to one in five hundred. So if you only get a good pay out one in five hundred, one and two hundred or whatever it is. If you play one game per day, you're in get one or two good scores per year, which is not very often. Right. I realize that a long time ago and I've always put in a lot of volume purposefully whenever I am playing, and I still do that today. Whenever I play, I try to play as much as I reasonly can in the time I have allotted. Back then, what did I do? So by the time I turned twenty one I had about three hundred fifty thousand, which is a good amount, probably not quite enough to be playing the highest stakes live tournaments back then, which were tenzero buying games. In reality you probably need, I don't know, one and a half million, give or take. So the first year I played I was playing mostly thousand dollar tournaments, fifteen hundred tournaments, which were which are still most of the tournaments that exist, and I did very poorly. For the first year. I lost about two Hundredzero, which is frustrating, but I understand why. It's because I was really good at that short stack mathematical poker game. I was not good at the deeper stacked game because I not studied it at all. Right, I was really good at a particular form of poker, but not the form of poker that was being played in live casinos, where you're playing deeper stacked and the payout structure was very different. Member back to the nine eight to tournaments, thirty three percent of the people get money back. Where's in a multitable tournaments and casinos that you see on TV, something like ten percent of the people are fifteen percent of the people get money back. So the PAL structure is very different. Also, if you win a nine person tournament, you get four or five buyers, right. So if you buy in Foro two hundred bucks, you get nine hundred dollars back, let's say. But if you buy into a two hundred or tournament with a thousand people, you may win back Gosh, I don't know, sixtyzero right. It's like a substantial amount. More so the PAL structure was very different and I did not properly adjusted those things for a while. But it was always talking a good other other good poker players on poker forms and studying from them. I eventually realized the air in my ways and things started going better. When I was twenty two. I had a good score in the Bahamas and that was a fifth place in a world poker to our tournament for three hundred twenty thousand, which it's quite nice, going back to backing I was back then, but I still got to keep a large chunk of it. We kept Weri handing it up. That means like take the winnings. You can't put it into the next tournament. Winnings. Lesser thing or will. So you asked, what do we do with the money? Yeah, thank again, at twenty three to well, I made a few errors with money back in the day. Well, I called a call the mayors. Looking back, it's like fine, but my parents always taught me you're just to go to school, get a degree, by a house and then your set. So I bought a condominium with my money when I was like nineteen years old. So I had that three to twenty K, but then I put like a hundred thousand dollars of it down on this condominium. That was effectively paying it off, but then that kind of locks up that a hundred thousand dollars and for all practical purposes is just gone right. So when I was twenty I went on a bit of a down swing at some point. I forget exactly how this went, but I resolved that I was going to move down to the small stakes games and just went a hundred buyers at every level. So it's we play ten dollar games when a hundred buyers. If I want that, I move up to twenty, than thirty and fifty, one hundred and over the course of a few months I got back to the top. But there's one point where I forget exactly how the numbers work. But like half my money was locked up in this house and I really didn't want to go broke. Some poker player ars think it's exciting or extravagant to feel risk and to feel excited and feel adrenaline when you're playing, but I want none of that. I just want to be printing my money right. I just want to show up, use my skills, print money and not worry about not being able to eat or having a roof over my head. Right. So I've always been a little bit more conservative with my bankroll in general than some poker players, especially the old school poker players, who were often either really rich or really broke. But I think a lot of people who came up in poker like I did, have been relatively...

...conservative with their bankroll to the point that they're never really at risk, and locking up a third of my money, it made it to where I did not have the opportunity to play bigger games profitably that I otherwise could have done if I did not do that. That said, the alternaive would be to rent a place, and that's sometimes good, sometimes bad. It depends on your licenary. But as a young kid I did not need to be buying a house because who knows what I'm going to continue living in that exact place for any amount of time. That was probably a mistake, but you know, whatever, it's fine. The money's locked up. It does okay. It's not like it's the end of the world. It's hard to say. Like your risk profile at that age meant you probably would have been happy to put more money into riskier things than a property. At the same time, it's the most common advice we get from most generations is to buy properties soon as you can. It's safe, it's consistent. So, you know, it sounds like you kind of did both. You still managed to, you know, have a start of a poker career right, so yeah, so well, what I did is, after I started winning poker term as eventually want a tournament for a million dollars and another one for a million dollars. I was a player of the year and bunch more trophies up here. For all the people who are watching the video, it was all. I all we died pretty well right, and every time I well. So eventually you don't need any more money in your bankroll because your bankroll is so big to the point that you are probably bankrolled for the Games. So I mentioned we needed a million and a half dollars to play these tournaments. Anything more than a million and a half dollars, in theory, should be invested in something else, because it's just sitting around not really doing anything for you. And back then they did not really have tournaments bigger than tenzero. It's very different today, but back then that was kind of like the biggest that you could play. So once we got above some amount, I would start buying a house every time and then using it either to live in or to rent out, and they ended up with four places over the course of a few years and they were all generating some amount of rental income, and that was good. What a lot of poker players do with their money initially when they went as they go on, they party and they blow it. But I never really had that issue. If anything, my quote unquote leak was locking up money to the point that sometimes I would have liked to be able to access it, but I couldn't. Write. So I would not necessarily recommend and like real estate to poker players, particularly because it's not liquid. You kind of want your money to be in something that ideally returns capital but is also a liquid go like the angel investments, probably not the best investment for most people because that money is super locked up. At least you can sell a house if you need to. You can't really sell a small fraction of a company that is, you know, two years into existence. It is not worth a ton of money. But that said, as you get more and more money, you need to find more and more ways to lock it up, and I diversified way or in ways that you just enjoy that you think will be reasonably profitable, and I mean that's what I do. I've been lucky to the point that I've been able to lock up some money right a lot of poker players find themselves in a spot where, let's say, their bills are FIVEZERO per month and they make Sixzeros per month on average playing, and so they're not really banking a ton of money each month. But I was always like, I try to live relatively cheaply, like I never flew first class or never stayed in Nice sweets or anything, and I was reasonable. Is What it amounts to a lot of poker players. When they get hold of a million dollars, they start being very unreasonable and they start flying first class everywhere and staying at the biggest suite in the place. And I recognize that I had been relatively fortunate to win a few big tournaments and I realize I could easily go on a down swing because I remember back to my first year playing live poker. I like lost everything for six months and I've had multiple bad down swings in live tournaments since then and in between those two scores right and it happens and I understand the variance that is inherent of poker and I plan for it to some extent. I don't just think I'm going to continue winning and definitely because I mean, look, whenever you play you have an edge, but you only really cash out that edge in tournaments when you win one of the big tournaments, which happens when in a hundred times, which isn't that often, and if it's a one in a hundred shot, you may not get it for five hundred tournaments. Which leads me to the question. What does it take to get to the point where you even have that one in one hundred chance to win like a million dollar return in poker? Like what change? Even your own life? Practice, you know, skill set. What how much is practice versus luck, versus just time...

...playing those sorts of things? Well, so a lot of people view poker as a get rich quick scheme to the point that they tried to win that million dollars. They see people like Chris Moneymaker, who turned whatever was twenty five into two and a half million on ESPN. When you won the world series of poker back in two thousand and three and thought, oh, I'd like to do that, it's like yeah, obviously, but it turns out poker's a great way to get rich slowly, but a really bad way to get rich quickly, because then you're just kind of treating it like a parley. Like imagine you had to watch the baseball games today and pick five of them. They all have to win the easier said than done. It's like really, really hard to do that, even if you bet on all the favorites. That's kind of how a lot of people treat poker. I mean every year a lot of people play locally in games they can beat and they play a lot and they win five or Tenzero and then they take all of that money and they go out to the world series of poker, which is a big poker tournament series in Las Vegas, and they play way bigger than they normally do, because at home maybe they play a hundred dollar games, but at the world series they play fifteen hundred games and they give themselves a few shots to try to get rich and when a thousand person tournament and they almost always all go home broke. And then they do it again the next year. They try to win Tenzero, they win ten thousand dollars, take it back out, lose it again. Yeah, you get rich sometimes. A why would you not just grind at home and make tenzero for let's say five years? Now you have fiftyzero. Can go out there play five hundred dollar tournaments with a hundred buy INS and give yourself a real shot to actually grind it up. But instaid, they want to try to get rich and that results in most people failing. So that you have how do you get in a space where you can win a million dollars and a poker tournament? You can go about it in a lot of ways. You can gamble really hard, you can be really knitty and I've been pretty pretty cautious and with my bank roll in those situations, and that's giving me actually a good shot to do it, because I was willing to sit there and grind it out by myself in my room for fourteen hours a day for three years straight to get a hold of some money. Right. And then when I played live tournaments for the first year, I played like every small snakes tournament because I realize that's what I needed to do. I was not properly bankrolled for the big games and if I did hop right into the big games when I turned twenty one, I would have lost all my money. Would have gone broke because I probably lost fifty buy INS, but fifty three hundred dollar buy and it's only fifteen tho bucks. Whatever it is right. Where's fifty tenzero buys is five hundred thousand dollars and I only had three hundred fifty and a hundred of it was locked up. So I would have gone broke if I just hopped right into the biggest game. So I try to be reasonable with it, right. But when you say that those a lot of this is your studs are you're crunching numbers, but how much of this is simply you getting better as a poker player? Yeah, ideally want to get better. Well, so, going back to the things you have to do to succeed, you have to find a game you can beat. Right, finding it can be played a lot. Keep a proper bankroll and you can either find a game you can beat by playing with worse opponents or by improving your skill to the point that people who are equally skilled you become worse opponents. Right, if you look at a lot of the biggest winners in poker, actually they are not actually all that good at poker. They just play in really soft games. There are people who play private games in Los Angeles with celebrities or hedge fund managers in New York who play and they don't let pros play. It's just like a bunch of okay poker players playing, but if they're playing gigantic stakes and someone there is the best player, someone's usually the best player, that players going to be a gigantic winner. This is like Molly's game, that you have to find a game you can beat. Right. So you either do that by selecting your game better or just substantially improving your skills, and I always realize that you want to be as good as you possibly can because, like in chess for example, if you're just worse than your opponent, you lose right and at the end of the day, if you look at poker, the best players like always wins a long in the long run. There is no gamble in it in the long run. You just have to get to the long run. Okay. So in your own personal journey was simply a case of just graduating up each level in terms of both your bank roll or skill set, and then you play enough, eventually you start winning. That the bigger numbers basically right. And the thing is is you make some amount over turn on investments every time you play a poker tournament. It's kind of hard to know exactly what it is, but it is some positive or negative number right, and if you are adequately skilled at assessing...

...player strengths, you can kind of figure out if you're a win or lose money. And if I don't think a game is good, I just don't play it because I'm not going to play poker in to get my gamble on, I'm going to try to win money. A good example of this one time I flew to Los Angeles to play a tenzero buy in tournament. That is always a good tournament. They have a lot of people in it. There's things called Satellite Poker tournaments where people buy in for like one ten of the buying and in one in ten gets their way to the bigger tournament. They're trying to parlay it and get rich quick. You want to play with those players because they're usually not adequately skilled, right. But the day before this Tenzero by in tournament there was a five thousand dollar tournament with no satellite qualifiers. So the main event was gonna have a thousand people there a lot of bad players. was going to be great. But this five thousand dollar tournament, smaller buy in, had sixty people in it and they were all really, really good. So I flew to Los Angeles looked at this tournament just didn't play right, even though I was probably slightly profitable in the game. My return on investment there maybe, I don't know, five percent or ten percent. So I really want to sit there for two days or a day or however long it took to win two hundred and fifty bucks? And the answers no, I wouldn't. I'd rather sleep. Funny enough, I actually went and played cash games, a different form of poker that I got to play, and there were like no good players in the cash game because they were all having ego battles in this five thousand dollar tournament. So ended up winning like Twentyzero in the cash games over the course of that day because the games were super soft. There were no good pros in it. So that's a good example, like game selection right. Like I flew to the flew across the country to play that tournament. Yet the tournament didn't look good, so I didn't play it. So you have to have good discipline like that. I was actually just in Vegas recently. They had the US poker open, which is a series put on by poker go, which puts on a lot of live tournaments they stream on the Internet. People would check that out of poker gocom and you could reenter the tournaments if you lost. So for like six hours or something like that. If you play the tournament and lose, you could play it again. There was one day where I had the option to re enter and I just didn't because I looked around the field, ever, the people still playing, and they were all very good. The weaker players at all busted to so be me reentering in a game with a bunch of very good players, like there's no edge. Another day I busted and they were a bunch of bad players still in the field, so I happily re entered, right and and that's because I realize I'm going to be in good shape against the weaker players and marginal shape against the best players in the world. Right. So you want to make sure you're finding games that you were profitable in, and this this applies like all forms them investing. Right, like, if you don't know what you're doing and your opponents know better than you, you're probably not going to do so well. Right, which is why we might choose someone like Jason and be part of a Syndeykick, because he's the one putting in the time to select the companies to invest in and so on. Well, that kind of goes to the idea of like poker backing, where you ideally want to be backing good players, where you buy, you give them money to buy a percentage of their action. Do you do do that? Do you ever back other players? Are I have a piece of a backing company called pokercom, Poca arrecom. Essentially, what they do is they take players at the smallest stakes games, like five dollar buying tournaments online, and teach them to the point that they become some of the biggest winners. The number one player in the world I mentioned earlier used to be a back ei there, and you want all the money for them. Right. So, I don't know. They back some number of hundreds of players online and it's like another low risk way to make money because they're putting in a bunch of volume. Right. It's not like so today, imagine there's a hundred players playing for me, I don't know, Twenty Five Cent Dot, twenty five cent poker tournament on average, right, because I've a tiny piece of everybody and that's great, right. I just it just it is collect the money, collect the profit and YEP, it's like a little little army of poker players every day. That's exactly right. Other players do this in a much more gambling way. Like I still sell action and whenever I play Twenty Fivezero by in tournaments or higher, and then I essentially sell people action. It a tiny markup, meaning less. Say It's a hundred thousand dollar tournament. One percent would normally cost let's say a thousand dollars. Right, maybe I charge a thousand twenty dollars. May say, why even charge the extra bit, because in theory I think I have...

...a bigger edge than that two percent vigue I'm charging. Maybe we have an eight percent edge or something. So then what happens as me in the backer split that difference. Some people get agreedos with the markup, though, and they charge like a twenty percent vague. And that's only good if that you are a lot better than your opponents. But if you're a lot better than your opponents, why do you need to get backed? Right? Yeah, there are I'm not going to say they're necessarily scammers, but there are people out there who try to essentially take advantage of people and you want to make sure you are not one of those. You always want to make sure you're if you are selling action, your markup is reasonable, and I gu suppose this happens in investing as well. Right some people send it, gets charge a ton, some charge a little. You have to figure out is there an edge there? Maybe there is, maybe there isn't. It's hard to know. Have a question regarding I mean poker as an ecosystem. There's a lot of things that have sort of come on the size, as they sometimes say, that you know, the pis and shovels that support the poker players or the different ways to monetize poker without actually being the person to play poker, like supporting someone back and you sell one. When did you start looking at that as an option? Because if you had made you get a couple of million dollar results there. You must have been still thinking this is my career, I'm professional poker player, I play this game for a living, but now you're a coach. You just said you're, you know, part owner of a backing company. When did that start in your mindset as something you thought would be smart to do? I don't know if it ever really occurred to me that I was doing it. I used to post on a various poker forms where I would get advice from people and I would give advice to them right, and it turns out a lot of people liked the advice I freely gave to other people, and that makes you a value member of the community, right. I eventually made a training site with two other guys that taught people how to beat sitting those which probably wasn't the smartest idea because it was an easy game. And it turns out sitting goes today are not really all that profitable. No one wins at them. So that's a bummer. That games dead. Right. It's like, why do people may as? Why don't you just keep doing that, because the game's not hard. Everybody learned and now nobody wins. You can't find the game you can beat anymore at the medium or high stakes. So you were kind of partially responsible for killing the game and you started in poker with I was unfortunately very responsible for killary okay, which is a bummer. It's funny today I have people come up to me all the time like, Oh yeah, I I used to watch this. It in no games singo videos you made and I beat them until they died. I'm like yeah, well, so did I. So anyway, that's unfortunate. So you have to be a little bit careful that you don't you don't make the game one beatable. But now how did I get into so I was making videos for a training site called it was a European poker site, doesn't really matter where it was, and another person there was the owner of a publishing company, D and B Poker, which I'm now part of, and they asked me to write a book because they love my videos, they love my posts on the forum and they thought I could make a good poker book. They didn't have a book on Poker tournaments. They asked me to write it and I'd already taken on a few private students and what I would do is, every time they would ask me a question, I would just write an article about it so I could get it to anybody else who asked me the same question right. Essentially scaling. Back then for a new what scaling was, and I would write an article one time and be able to share it we whoever wanted it, whenever it made sense, and I actually had like four hundred pages of articles written on various topics already because you know, you asked me a question about a topic, I'll write a page or two about it. There it is. We're good to go at about four under pages worth and I made an outline for a book and we put it all together. There are a few spots I had to go through and fill out. You know that that had not written about, but I had them five hundred page book in something like two weeks. I like, Oh my God, this guy rid five hundred page book in two weeks, but I already had it done right. I like didn't even know I was doing it, but I mean, like, how did I get into it in the first place? I was helped by a lot of people. I would not be where I am today without the help of people who came before for me and are still crushing the biggest games. And it seems reasonable to get back to other people, right. I mean they help you, you help other people, you help them in whatever ways you can and you all build and grow together. I poker looks like a solitary game, but it's to some extent as kind of a team sport where you're not the best at a lot of things, and I'm not the best at a...

...lot of things, but somebody else maybe, and you can help them with that. Like I was not really good at playing deep stack poker, so I had to learn a lot from other people, but I was really good and playing the shallow stacked form a poker, so I helped a lot of people with that when they were not so good at it right. And you know, you take your weaknesses and try to improve using other people's strengths and I was just like naturally doing this and some people took notice and wanted me to work with them. We wrote books. The book sold really well. We had the training side. That killed the sit and goes, but eventually moved to multitable tournaments, which is like the most popular form poker that you see on TV, and we started making content for that. Eventually there are two guys in the business. Got Out. I took it over. It went through a few iterations, but eventually we are we are where we are today. The training site was interesting because I had this coaching. This was the work. It was called Poker coachingcom. Okay, it's been to a few other iterations and names don't matter because there are no longer here. But I would basically had a site that was losing money. We had, I don't know, a hundred members instead of five thousand, and I was paying coaches five hundred per hour to make content, which is kind of expensive, but that's they're hourly rate. Roughly. That's what they wanted to whatever you pay. And I was just like losing three or four Tho per month for like two or three years and I didn't really care because I'd made plenty of money from hooker. I viewed as almost like a community service to some extent, because, you know, if I, if I, if I can spend a little bit of money to get good, high quality content from good players, share with other people, lose, lose little bit of money. Who Cares? Right? One day and actually just broken up with my fiance, who's not my fiance today. I'm have a different wife, different wife. I have a wife now who's a different woman, who's very great. Anyway, I just broken up with my fiance. This must have been fifteen years ago or something, and I was at a local casino and I just like randomly played small buying tournament to pass the time while I was drinking sobb wine, and so I met a guy there who had just gotten out of a few marketing classes, and he said look, I know you have your training site. Yes, how I was doing? I said not great. He said, why don't you make me a video of you playing multitable tournaments online and I'll try to sell it through affiliates on this site called Click Bank, which still exists. It's affiliates that where people can just sell your stuff if they like it. So I made an Eighthour long video of me just playing online tournaments all day and I want a ton of buy and I don't know what it was, but it's some mash them. So it looked really good and he sold it, or started selling it through affiliates, and we made like tenzero in the first month. I'm like, Oh, this is good, because I was losing money and now I'm get paid tenzero a month for this one eighthour video. So He's been with me since then. His names Dan. He's great and he does all of her email marketing and it was me and him for a long time and eventually hired on more people to help with all sorts of other stuff, but it's kind of how I got into the content spase. I had my own training site that was failing and I probably would have gave up on that at some point and met up with Dan and Dan Dan made it successful. Okay, do you might talk a little bit about that, because the difference between a hundred members and five thousand, five hundred members in a members of site is huge. That's, you know, like you said, losing money to making a lot of money. My audience being very much in the information marketing space, they're always interested in how you scale something like this and what's the nuts and bolts. So I could guess. I could think it's paid ads. I mean Click Bank obviously is a marketplace. That can get you some customers, but I don't think it scales you to five thousand, five hundred, or maybe it does. But what's work for you guys? Really? Well, we don't do any of that stuff anymore. That was good to get off the ground and it proved and knew what he was doing to some extent. So we had the failing training site. We immediately cut some of the more expensive content creators to make that basically break even to where it became more of a Jonathan little site instead of a me and other people site. Because, like I was not the biggest named person on the site back then. So we got rid of some of the people and we made that immediate profitable immediately, right, so they were not losing fortyzero or whatever. It is good. And we have this individual products called it Jonathan little secrets we so we're selling and making tenzero per month, which is good. We kind of chugged along just making more and more new products. Right. I did not do any email marketing back...

...in the day, but Dan was very good at that, so he was in charge of the email list. I was not good at Web designed and could do that well enough. So, like he did basically everything that I could not do. I was in charge of the content. They was in charge of everything else. Do you know how he grew the emailst just that a curiosity. Well, Click Bank to some extent got a lot of people on the email list, but also I would just start promoting it. I was already writing articles for various poker related publications, like Card Player magazine. They put that out in every local casino and at the end we'd say check out this website to learn more. Than people get on the email list. They had lead magnet's right. I had a lot of free stuff we would give away. It's good. I have like a lot of free articles and I can make videos relatively easily. Right. So content marketing. Yeah, I mean that's basically it will. I have books, right, my books. Anybody who buys one of my books, there's a lead magnet in there to say to get this bonus, go here, get on the email list, and you get people on the email list. We continue selling individual products for like a hundred dollars each for quite a while, but then, something like three or four years ago, actually, I'm sure I'm getting the timeline wrong. I don't call it five years ago, I knew I kind of wanted to slow down, have a family and be able to stay at home if I felt inclined. And tenzero per month is good. You're not. I live in Manhattan. It's expensive here. Need to figure out a way to either well, play poker from home and make a ton of money, which is kind of hard in today's environment from America, or make this training site good. So I started spending a ton of time on it. Instead of making one for six hour video per month, I was now just making a lot of content and I also realized we needed to like revamp the training site to make it very different than all the other training sites on the market. And pretty much all the training sites back then were just me either presenting over a power point or me playing poker and letting you watch and that was it. There three or four other slits on the market. That's that's still all they do today, for the most part. We started doing a lot of interactive stuff, like live streams where you can ask your questions or you have let the students call in and we answer their questions in real time. Basically started doing a lot of live things. Also have one hundred interactive quizzes where it's kind of like you can go through and play hands and then get immediate feedback from me or one of the other coaches. Right, I also going to sound bad. I realized people like me, so I started to try to interact more of the fans. Right. This was kind of before twitter to some extent, and maybe it wasn't before twitter, before twitter super popular, and I got on twitter and started interacting with people, right and like replying and a lot of like Oh my God, I can't believe you replied, but I replied everyone. I read every single email that comes in today and I reply as it makes sense. Right. So basically, I got in there and I did the work and I made friends with a lot of people, right, and I tried to add value. Where's a lot of other people want to show up, do four hours or work per month and be done. I decided turning this into a fifty hour work week job and make loads and loads and loads of content, and that's resulted in other people wanting to work with me and other people wanting to promote the site. Right. Switch we made three or two years ago. Three years ago was to stop selling individual products and just put it all, everything we had in the past and everything we're going to make in the future into the poker coaching premium membership, which cast something like a hundred dollars per month. We run sales for it. I'm not sure if I'm a huge fan of sales or not, but they seem to work. Dance good at the sales. I'd rather never put anything on sale, but I think that maybe a big portion of our success and stuff to know right is one way better or not. I don't know. It's probably better, I'm sure it's, but instead it's well, instead of having to sell a product every single month. Now people just get in the membership and know they're can get a whole lot of stuff included right, and that makes email promotion way easier, because now we just have to get really good at promoting one thing, which is this gigantic membership that has infinite content, like more than the vast majority other training sites out there. That's also interactive and it's kind of like an easy cell because it's just jampacked with value. The other sides are trying to sell an eight hour course for a thousand dollars. We're trying to sell fivezero hours of content for...

...a hundred right. It's just the kind of a no brainer. So that was very beneficial. Also, I started making a lot of youtube content. I hired a youtube betitor who was actually an editor at one of the big poker new sites, got laid off because of covid recently, and started making a ton of Youtube content. We almost have a hundred thousand youtube subscribers now and that had like none two years ago. So that's just making free content, getting people on the email lists. Going Poker coachingcom slash free right, doing stuff like this, and that gets people on the list and then you know, Dan's in charge from their Dan as all the content you could possibly need to make good email promotions and like added value emails too. It's like we're just sending an email saying, by this thing. Good example of this. Today I'm doing a Webinar where I'm going to go through, for like really high level hands that I played on Youtube live, completely free, and then that's going to take forty five minutes, and then for fifteen minutes after that I'm going to promote our next sale that we're doing for Independence Day right, and I don't know, Tenzero, twenty thousand people will watch that and some of those people will like the content, they'll find added value and then they'll go look at it and maybe they buy right, and we do that on a regular basis. Have a sale every month, or two every month, give or take. We do a lot of stuff. Do a lot of stuff. Yeah, it sounds like, dude, it's a lot of content, but really just try to add a lot of value. There's this trophy back here, and that's for me being poker personality of the year in two thousand and nineteen, which is a award voted on by poker fans. They didn't have a two thousand and twenty one because of covid there wasn't. There were no award ceremonies. But if you do good work and that a lot of value and try to be reasonably accessible, people take notice and they like it. What an amount to if people like you, then they will inevitably take a look at what else you have to offer. I think a lot of people, especially a lot of like training site brands, make the air to some extent of not highlighting the person. Right. There's like here's some content with a bunch of basically random people who don't interact with anyone. Take a look. They'll make you better poker probably, but nobody cares. Right, you have to make people care for some reason. People care because they like you. I mean like there are people who stream magic the gathering who I love. Right, not even play magic really anymore, but I still watch their stream sometimes because I like them. There personabal, I like the way they operate and if they had a training side I probably subscribe to it. Right, maybe that's what's happening here as well. It's a great example of the power of being a really helpful I mean that's simply put. You're just helping a lot of people and you're being very approachable and personal about it. So if you do that for long enough, using as many different content distribution channels as you can, you're going to get attention, you're going to get email subscribers and then you're going to be able to get customers as a result. So I can understand the the big picture of the membership site with Dan as as your kind of operational cofounder, I guess in that business. Is that what you would consider your like your main gig now, like you're really coach memberships at owner, or do you still play pokerl as much and continue self a professional player? Plus, I know you said you starting a family, so you probably have a family by now. So things of you know. You don't have a much time to do all of those things. Is that accurate? So I have two boys now. They're two years old and four years old. So for the last five years or so I have been working on the training site a ton before covid happened, and I guess since Co has happened, since it's almost over, it is over. Whatever it is. I used to be exactly. I used to play about one week per month of live over and I would like try to play a lot in that week. So I would go play very high value tournaments or tournament series like a long time, go just play like all the time. I'm just travel all the time and play whatever was available. And there's some tournament series where they have a main event and that's like thirty five hundred right, and then a few small events that before that that are thousand dollar buying tournaments. If you go and play that, you may make on average, I don't know, Sevenzero in the week, which is fine. But there are other tournament series where the main event is tenzero and they have a bunch of other good side events where you may make fortyzero on average. There's gonna a ton of swings, like a ton of swings, but you can do just like simple return on investment math and figure out well, if I have...

...to pick between one or the other, I'm going to pick the one that I can make more money out right. So I'm very selective with the tournament series I go to to some extent. Now mean a good example. I just went to go play at the US poker opened in Las Vegas and every other day there was a ten thousand or twenty five thousand or Fiftyzero poken to poker tournament for a week or two weeks, wherever it was, and that's like a good high value tournament series where I know I'm going to go out there make fiftyzero hundred thousand dollars on average and that's going to be good. So instead of playing everything, I'm playing the highest value games. I also still try to play online poker, usually one day per week, Sunday afternoons. That's usually the best day to play online poker, just because that's how it is. I still try to play some and stay very relevant, but I also work on the training site, like Monday to Friday, nine am till six pm every day. I sit in this office and I work all day and had something a lot of people don't do right. A lot of people want a side job that makes some money, but I'm not looking for real job to make a lot of money. You talked about sponsorships before and it's going to sound a little bit bad, but like White American men cannot get sponsorship deals because there are no major poker sites that operate legally within America, right, and there's a lot of white American men who are good at poker. So it's like we're not very different, right. So a lot of people who get sponsored are not from America from these poker sites. Or if you can't get sponsorship deal, like I've been offered a few very good sponsored deals from sites it operating in America. You're now representing a company that's operating illegally and you don't really want to be the represented for an illegal gambling site. Seems unwise, especially if you have a family. Just to clarify, what? Why is it illegal in America? Legislation, the government? I don't know. I mean, look, there's there's this thing called the UIGEA unlawful Internet. I don't know what it's called. Some, some there was a law passed a while back that was tacked on to a bill pertaining to nine hundred and eleven, like the Freedom Act or something, that essentially made gambling online illegal in America. Now that has changed state by state to some extent now, so states are allowed to do whatever they want. So we see online poker now and Nevada and New Jersey, Delaware a few other places, but you're playing with only people from those states. So infinitely they're just aren't a lot of people compared to a worldwide gambling site. Right. And it turns out that money kind of trickles to the top from the bottom. People went at the small stakes, they lose it to the medium stakes. People win at the medium stakes, they lose it to the high stakes. People went at the high stakes, they lose it to the super high stakes. Right, people is superiy stakes. Cash it out. And the problem is that if there are not all that many small sakes players, are ant very many middle states players and not very many high stakes players, and you can't really make a ton of money. You can make some good money, like I have a few students who live in these places and I've seen their graphs. Are just like amazing and straight up because the Games are soft, because there aren't a lot of good players on the site and they're winning. They probably went a hundred thousand dollars per year, which is perfectly fine, but it's like get rich money, right, it's fine finding good that get rich money. So why is it illegal? Because there's a law that says it's illegal. And that said, some companies still operate in America. One of them band be recently because I said that they are not as safe as a US regulated bank. You should not keep all your money in the unlicensed, unregulated, illegal gambling site. But they have representative saying keep all your money on there's perfectly safe. US gets just not right and I kind of have a I'm kind of a stickler for not inducing people to make detrimental airs. Right back whenever it was called Black Friday, when all a few of the poker sites were shut down by the US government, a lot of people's money was locked up for years and some of the sites and never paid people back, or if they did pay people back, it was like five cents on the dollar, and I don't want that to happen to my students. Right. So, you know, protect yourself to be smart. It's like holding money in a cryptocurrency exchange. You just don't know what could happened. So, yeah, don't leave it all on and exchange. You might get hat seems obvious, right. But you say that publicly, the site will band you because they don't want anyone talk bad about them. Fine, that's a that's a project right. Should probably tell you how they operate in...

...business anyway. Anyway, what are I going to hear? Oh yeah, I do not want to be sponsored by an legal gambling site. Even then they don't pay like a ton of money. Back in the poker hey day of two thousand three, two thousand and two thousand and five, you can get a deal that paid you hundreds of thousand dollars per year, or more like. If I was in the spot I am in poker back then, I'm sure I would have gotten a very, very good sponsorship deal. But that's not where we live anymore. We live in this era where not a lot of site sponsor players. If they do sponsor players, it's for a small amount of money, like three thousand bucks per month, and they want you streaming live all the time on their online poker site, which I'm not going to do because I just have the time for it and you don't need to and I don't need to it. So it's not it's not worth the effort, is what it amounts to. But I realized a long time ago if I ever wanted to make money at poker by not playing poker, are either needed to get heavily in on the backing side or heavily and on the content creation side. So I did both right and, to be fair, most people in the content creation space in general don't make any money or make a minimum amount of money. But you just have to get it get to scale. As what amounts you have to help a lot of people get better or enjoy what they do more, right and I work hard to do that. But the idea a lot of people still have today is that I want to become a poker player and get a sponsorship deal. But this problem is is that's not really worth any money and it takes a ton of effort. Jonathan. So we kind of getting over an hour ish, or just about an hour. I do have a few more questions. So this show is called vest of capital and we've ready covered you were in property early on. Then it sounds like poker became your main source of capital and cash flow. Then it starts branch out to a few little like teaching businesses. Than it became poker coaching, which is obviously a big source of your cash flow. Now you mentioned your part owner of the backing staking company that's got lots of hundreds of poker players that you own a little share how well they do. You mentioned to me, we talked before we record this, that you were Phil Helmets Book Launch Party and your part owner of a publishing company that was to do with his book. So there's a lot of things going on. You have magic card investments, you have nft investments. I'm assuming you probably have some crypto if we've been talked about that. If we look back on everything you've done so far and where you're at now, what has been the most successful source of you building capital and cash flow in your life? If you're if you're willing to share? Well so, yeah, so poker is really good to take a small amount of money and turn into a pretty good amount of money. Right, like you can get a hold of a million dollars playing poker, but you're not going to get hold of a hundred million dollars playing poker, so it's not going to happen. So poker definitely. It was like all of my income for many years. But eventually you transition over and you know, crypto has been fine. Haven't got rich off CRYPTO. They got me on the icos back in the day. So that was great. Should I got into N FT's instead of ICOS, but that's fine, we're not. I'm still up right COOD. Call it what it is, that's that it could drop fifty percent today and I'd be down right. The substantial sources of income of my life have been poker and that is slowly decreased as I've stayed at home work, because if you don't play you don't want any money. And I've been staying home, having a family, staying home because of Covid, etcetera. And now the training sites become the vast major to my income. And and that's just because that's the thing that has done the best. And it turns out I do pretty well when I do things in poker. I do not do especially well when I do things not in Boker, because I'm not an expert at it. Right. Very, very important to invest most of your time and effort in things you're an expert out. How do you get good at something, though? If you don't try? Is always the consideration. But you should try things, especially when you're young, but as you get older and older, I think you should probably try fewer things and focus on what you're very good at. I have a bunch of students. Some of them are like really good at investing their hetchelime managers or whatnot, and I they're effectively my mentors. Right to help them a poker, they help me a life. And I always ask like should I be doing something else? They say, until this poker training site somehow doesn't work, just keep doing this because you have. It's by far your best opportunity. You like it and you're good at it, so don't screw it up. A lot of people either get burnt out or get tired,...

...to get annoyed and they just want to change. Right, but I've done things such as like higher other people to manage the business, to manage the coaches, etc. I thinks I don't really like necessarily doing such as. I can just make good content and I like that. That's what I'm good at and it makes it to wear. I can't really get burnt out from the Poker coaching business and it continues to grow. So whatever, I'm going to do this until there's a reason not to. But I don't. I always can't imagine it's going to continue growing because, like, how many more people could actually sign up? But it keeps growing, so whatever, and keep doing this indefinitely. Everything else, Tho's a hobby to some extent that could take off. And, to be fair, making training content was a hobby. They could have taken off right. Like I said before, I was losing thousands of dollars for a month on this training side hobby. So I was just okay with right. I mean like it was fine and it took off. Who Know? I mean maybe if I stopped a month before and met Dan, maybe would have just been dead and I would have been that. I mean, who knows what's going to happen. Like, for all I know, I seeos could have taken off. They wouldn't and they didn't win. They could have, right, I could have gotten into the one that actually did well, but I didn't. And you never really know what's going to happen in the future and for that reason you want to always keep your eyes open for things that you could get into. That said, pretty much everyone out there is really good at something and you should probably be looking at that space more than others, even if that space is not especially, I don't know, popular, viable whatever. Like poker has been on a slow but steady decline since two thousand and five or so to some extent due to all sorts of things, right, like the bad players go broken, they quit. New players try to get in but the game is tough, so they don't get into it. You, as government, makes it illegal to play online. Like all these things are kind of negative towards it. And if, like, if you look at Google searches for poker and poke a related terms are all just like kind of down, that mean you just have to do a better job of helping people improve. Right. Look, I mean find what you're good at and focus on that to some extent, because that's where you have an area of expertise. I'm not an expert at cryptocurrency or property or gold or n FT's or any of this. So I dabble right, maybe the hobby takes off, maybe it doesn't. Yep, now will. We talked about angel investing right the very start, and that that's another thing that, who knows who could be talking about in five years as a fairly big win fall or not, you don't really know. Yeah, so I've made a few angel investments by myself before I met Jason Callicannis, and they all failed. Okay, and looking at how he goes about Angel Invest and he tries to find companies that already have pretty good product market, product market fit, products that or companies that have a lot of customers, things that are somewhat differentiated, in relatively popular spaces, or relatively I like, good spaces right. Like you'd probably not want invest in a poker training site because, like I said, slowly declining space, right, especially a start up, because then you're competing with the other good companies like mine and a few others out there. I like the way he goes about investing in things that make logical sense instead of things that you just like, right. And it's not like I've invested in a few sites to play poker on and they've all failed, but maybe they could have worked right, it's hard to know. This is his fail all the time for reasons outside of the founders control. And you know I dabble, right, I'm not all in on it. I Dabble and I realized with Angel Investing I don't know what I'm doing here. So you find experts and you follow them and fortunately, with things like syndicates, you can sign up get updates from various company is and learn what they're doing, for example, to Jason, I've invested in fit Bot, which is a APP that teaches you how to work out. Basically it's like a a workout training APP. Membership site sounds kind of like mine. I teach people to get good at poker. They teach people to get in shape and I've learned a lot of stuff about like marketing through looking at what they do and hearing their founders talk. Town twister. Wouldn't think that was a Tong twister about what? So you know, I'm always trying to learn about business and investing through other people who I've invested in. So I'm always trying to learn right. Awesome. I really appreciate the the breakdown you're inna. You're doing a lot of different things, but I love the message there that it's really one thing you got good at and your biggest cash flow and capital sources that power all the other investments really came from...

...poker and then teaching and supporting other poker players. So the obvious connection is there. Jonathan. Let's wrap it up. Is there anything else you want to sort of share with the audience? Obviously, for websites, we've mentioned poker coachingcom forwards. Last free if you want to get started with that? Is there anything else you want to send people to or talk about? People can follow me on twitter at Jonathan Little. My posts all sorts of poker related content there. They can also check out my Youtube Channel, youtubecom Poker coaching. That's it. You know, show up, do good work, add value and good things will come great. Well, I thank you for sharing the time and it's been great to hear your story. Thanks for having me there. You haven't I hope you enjoyed that episode with Jonathan Little and you are now excited to begin. You're a professional poker career or if not, at least you walked away with some insights into what it takes to become a seven figure earner in the world of poker and also some amazing inside into growing a multi seven figure membership side and just general advice on how to get good at something, and also on a great example of someone who's really prolific with content online and how much that's benefited him over the years. So I was certainly inspired by that. Before I go, I just want to mention that this episode of vested capital is brought to you by Inbox Donecom, which is a company that takes over managing your email for you. So if you're drowning in messages, whether it's email in your inbox, it's custom support, helped us tickets, it's even direct messages in your social media profiles, Instagram, Linkedin, facebook, twitter and so on, you need an inbox manager to step in and not just manage and organize your email and your messages, but actually reply to them for you. That's what inbox done offers. It's a company now. It's from running for over four years. They have a team of over twenty five people managing inboxes for all kinds of different companies, from doctors and lawyers, online coaches, venture capitalist Angel Investors, car retail as restaurant owners. It really doesn't matter. We're all struggling with too much email, and if that's you, then you need help. Just head to INBOX DONECOM and book a Discovery Call to talk about getting some inbox managers to help with your email. Okay, that's it for me. My name is yarrow and I will talk to you on the very next episode of vested capital by by.

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