Jonathan Little (@JonathanLittle) got his start by making millions at the poker table, and then found a way to turn his favorite card game into an online coaching empire that brings in millions of dollars per year. His "secret" is a combination of consistency and love: Jonathan has authored countless books, YouTube videos, quizzes, webinars, podcast episodes, and more, and part of why he's able to work so hard is because he genuinely loves poker. In this episode, Jonathan and I talk about intentionally develop skills with a specific future in mind, how to find purpose in your career, and ways to parlay success from one career into another.
PokerCoaching.com – Jonathan's poker coaching business
Jonathan on YouTube – Jonathan's YouTube channel with 60,000 subscribers
@JonathanLittle – follow Jonathan on Twitter
What’s up everybody? This is Courtland from IndieHackers.com, and you’re listening to the Indie Hackers podcast. On this show, I talk to the founders of profitable internet businesses and I try to get a sense of what it’s like to be in their shoes. How did they get to where they are today? How do they make decisions both at their companies and in their personal lives, and what, exactly, makes their businesses tick?
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In today’s episode, I sat down with poker pro Jonathan Little. He has won millions of dollars as a professional poker player, and now he’s making millions of dollars a year with his online business teaching others how to get better at the game as well.
What’s cool about Jonathan is that even though he doesn’t come from a tech background, he’s been able to figure out a lot of the indie hacker challenges on his own. He’s got a web-based subscription business up and running. He is on every channel. He’s crushing it with distribution. He’s figured out his pricing.
Even if you’re not as much of a poker fan as I am, there’s a lot to learn here from Jonathan’s work ethic, his consistency, and about how you can go on to build your won sustainable business doing what you love that supports your lifestyle. Enjoy the episode.
(end of intro) Jonathan Little, welcome to the Indie Hackers podcast.
Hello. Thanks for having me. I’m happy to be here today.
You’ve built a poker media empire. You’ve got online classes, a website, YouTube. How would you describe what you do, and what are all the parts to it?
There are a lot of parts to it. It all started a long time ago, about 15 years ago. I was playing a lot of poker and posting on poker forums. I learned a lot from other people who discussed poker strategy on these forums and eventually I became a good, well-respected player on there.
So I started giving other people advice, and then a few of my friends and I decided, “Why don’t we make a poker training site?” We weren’t necessarily trying to make money from it or anything but wanted to give back to the community and maybe build something.
Well that’s how it started. So we have a poker training site that’s been through many iterations. Now it’s called pokercoaching.com. I also write books. I have all these books back here. I'm in charge of all those.
I work with a publishing company, D&B Poker. I'm in charge of sourcing some of the material that they have, and I do a lot of the editing. We do that. We have a YouTube channel, have about 50,000 followers on there. After this we’ll have 100,000, hopefully.
We’ll see.
And I think a lot of content. I have video blogs. The training site has quizzes, interactive webinars. I do a morning show called A Little Coffee, where Monday, Wednesday, Friday I sit down for about an hour and talk about whatever’s on my mind. Usually it’s somehow related to poker. I try to put out lots of content. I want to be everywhere so people can find me and then inevitably I can help them and then maybe they’ll pay me some money.
Yeah, it’s insane how much content you put out. I talk to a lot of people who put out content for a living, and most of them aren’t anywhere near that prolific. I'm a member of your pokercoaching.com website. I'm getting emails from you constantly.
You’re always popping up on YouTube. You’ve got several podcasts, all those books you've written. How much time and effort does that take? Are you doing nothing but putting out content all day, every day?
It does take a lot of effort. I think what I do that a lot of other people don’t do is I sit down and work. I think a lot of content creators hang out, or they spend a lot of time on things that are not necessarily beneficial when it comes to putting out a product, for example writing a book.
I have a book called Excelling at No-Limit Hold ‘Em that I wrote with roughly 15 other poker players. I was in charge. I assigned them topics, or we came up with topics they’d write about themselves. Each author/poker player was going to write about 20 pages on their chosen topic.
I thought it would be easy. I thought I would be able to give them the assignment, get it back in a month, and the book would be done in a month. I thought it was going to be the easiest thing I ever did.
It ended up taking about a year and a half. Some of the people involved were also authors. Their work got back to me in a month. They said they were going to do it in a month, they got it back to me in a month, no problem.
Some of the poker players, though, were huge procrastinators or huge perfectionists, and I would have to go to their house and help them, which is fine. I get it. A lot of people wanted everything to be 100% perfect.
To be fair, when you're writing a book, you can’t go back and change it. It’s memorialized there, and people will read that indefinitely. So I get the idea that you want it to be perfect. But at the same time, at some point you have to ship the product and get it out there to the world.
I've always been quick to push stuff out. I'm not such a perfectionist I don’t think. I try to do things well the first time. That results in not having to do too many takes. That said, I am trying to slow down a bit. I’m in the process of making this gigantic tournament course. People have asked me to make this for forever. It’s currently something like 40 hours long, so it’s a lot.
I hired someone to teach me how to teach better, and that’s making my process go substantially slower. I would have had this thing done in 50 hours or so. It takes 40 hours to record. I’ll be done in 50 hours. But now it’s taking substantially longer, and I think that’s probably good.
I think when you’re putting out pillar pieces of content that everyone’s going to get directed to, you want them to be as good as they possibly can. So if anything I have to slow myself down a little bit, but that’s okay. I don’t mind.
Yeah. We were talking earlier about this balance between being a perfectionist and quantity. I always err on the side of perfectionism, but I think it’s a flaw. I need to be more prolific.
I need to put things out there instead of sweating it so much, but sometimes that last 5 or 10%, no one notices, no one care about. It’s better to get a ton of stuff out and reach people everywhere they are.
I was going to say, editing audio, for example, for this. You can sit here and edit this thing for forever, or you can push it out.
Exactly.
As long as you know it’s fine, there’s nothing horribly wrong with it, it’s going to be good enough. We both have decent microphones. We both sound fine.
It’s good enough.
So don’t worry about it. Also, I was going to say, something I do very different than a lot of people is, I work. I sit in my office, right here, from about 9:00 a.m. until 6:00 p.m., Monday to Friday, every day. That's when my wife is working, and I sit in here like I have a real job, and I work all day.
I'm not watching TV or goofing off or anything like that. I'm working. And I think what happens to a lot of people, especially content creators, is they have freedom to do whatever they want, or they’re doing it as a hobby to some extent.
They’re not doing it as a career. I recognize I'm doing this as a career and that requires me to treat it like a career.
I think when a lot of people become founders, become indie hackers, it’s a tough transition for them. I mean, you’ve been a professional poker player. All of that’s self-discipline. There’s nobody who’s like, “You need to come in at 9:00 a.m. every day and learn poker, Jonathan.” You’ve got to be self-motivated.
But a lot of people who come from more of a traditional career are used to having a boss or colleagues who expect them to stick to a particular schedule. Suddenly, when they're out on their own and they’re at home, it’s hard to stay focused. It’s hard to stay on track without that external motivation. Where do you think your motivation comes from, Jonathan?
I do not have a good answer to that. I'm a pretty good grinder. So whenever I was a young person playing poker, when I was 18, 19, 20, 21 years old, I would literally sit in my room for about 16 hours a day either playing poker or studying poker. It was 10 or so hours of playing and 6 hours of reviewing those hands and studying and trying to get better.
I did that every day for three years, consistently. I didn’t have any problem with that. I had no social life. I had no real friends besides my internet poker friends, and I had a pile of money. So I recognized I was trading these things for something else.
Now, writing a book or making a new class, if I want to be doing it, I can sit down and do it no problem. I like having a lot of things to do because that allows me to pick the thing that I really want to do at that moment. I’m always motivated to do it because perhaps I haven’t done it in a little while or it’s somewhat pressing, and I need to get it done immediately.
Also, my life is compartmentalized to some extent, because I still travel and play poker a decent amount. I would typically play poker somewhere on the live tournament poker circuit. There’s a big tournament somewhere all the time, but usually there’s one big tournament per month.
I would usually spend about a week per month going to do that. During that time, I’m usually recording a video blog but that it is pertaining to work. I have a team that helps me with support emails and whatnot, and I prerecord everything I can ahead of time, or I prewrite articles such that I do not have to do anything besides play poker when I'm going out to play poker.
That’s almost like a vacation to some extent, or like a getaway from the 9 to 5 grind if you want to call it that, and that allows me to come back refreshed. Then after a week of playing poker I'm usually ready to be done with that so I go home and get back on the work grind. Then after three weeks of the work grind, I'm ready to go play some poker, so it works out pretty well.
There’s some hidden wisdom there behind the fact that you don’t need any tricks or hacks to do what you do. You naturally grind against certain things.
Well I like doing what I'm doing. I think a lot of people, especially people in the startup world, start a business because they want to make money or because they perhaps even see a hole in the market that’s very obvious to them, but they don’t care about it.
I mean, I think if you care about something, you’re going to be way more motivated to do it than if you don’t care so much about it. Fortunately I like playing games, I like poker, and I like helping people to get better at poker.
I wake up and I want to get to work. I don't think I've had a day in a very long time where I wake up and I’m like, “Oh, I have to go to work today.” Normally, I'm thrilled. I want to do it, and that makes it easy.
It’s a trap a lot of people fall into, where they’re like, “You know, I don’t see how everyone else is working so hard. I'm grinding. I'm pushing myself. I don’t like this but I'm going to get that gold at the end of the rainbow.”
They don’t realize a lot of people are doing things they like, where they naturally have a lot of energy and they wake up every day and it’s not a grind. Almost everybody has something that’s not a grind for them, that they’ll do all day obsessively if they’re allowed to and they can make money doing it.
If you can find a way to start a business in that area, find a way to make money and create a life for yourself in that area, it’s probably where you have the biggest advantages rather than doing what you were saying, finding a gap in the market and ending up selling wedding cards or something where you don’t care about weddings.
For sure. I always liked playing games. I mean, a good example of this is I played chess as a kid. I played Magic: The Gathering as a kid and I played poker once I turned 17, 18 years old.
I pushed those other games aside to some extent because I realized poker is a game where you can make substantial money. So I have other things that I enjoy doing, perhaps more than specifically playing poker, but poker’s good enough and you can also make a living from it.
So maybe you don’t get to do the exact specific thing that you would like to do, like I could sit and play Magic: The Gathering all day, but you're not going to make any money from it.
So you have to be realistic with the things that you decide to devote your time to, because some things are hobbies. They’re fun. They can be fun, but at the same time they’re not going to give the opportunity to make substantial income, if you care about that.
I knew I wanted to start a family one day and have some money, so I had to play a game that gave me that opportunity, that did not require any athletics because I'm not a particularly athletic person, so poker was the only option. That’s why we played this game. I would definitely tell you to find things that you like and do them and get good at them, but at the same time, make sure they have a future.
Let’s talk about your poker history. I think it’s a cliché, at least in the tech industry, that the founder drops out of college to pursue their passion and start a startup.
I've talked to half a dozen people in this podcast who’ve done that thing. But you dropped out of college to play poker, not to start a startup. What was it like to make that decision?
Well it was easy. I was going to school to get an engineering degree. I had an academic scholarship, so it was free to go to college. But I was also working a job at an airport and a job at a comic book store at the same time.
At this point, I started to make decent money from playing poker. I got to where I was making, I don't know, $200 or $300 per hour playing poker online when I was 18 years old. And I was working a $10 an hour job at the airport.
I would purposely work the graveyard shift, because I would go in. I would do the routine work, and then not a whole lot of planes would come in that you would have to service, give them gas or whatever they need.
Not a lot of planes came in late at night, so I would usually have four or so hours where not a whole lot was going on, and then I would download Party Poker on the computer and play poker during those four hours.
I was good at one particular from of poker that’s a nine-person tournament, and you can’t leave until the tournament’s over. Every once in a while, once a month, a helicopter would fly in late at night and they would require you to give them gas.
It was like an ambulance helicopter, so you really want to go service the ambulance helicopter because they were going to go try to save someone. Two days in a row, I was playing four, $200 buy-in tournaments and the helicopter came in and I had to give away that $800 and go fuel the helicopter.
Oh, man.
That happened twice in a row. It was like, “Okay. This is enough of this. I can’t keep working this $10.00 an hour job and grinding high-stakes poker at the same time.” So that’s when I quit that.
Then when I quit college I went in for some class and they gave us a pop quiz and I got a zero, so I got up and I left. A lot of poker players have an issue telling their parents that they’re going to drop out of college to pursue poker, and I'm sure the same thing with startups.
Yeah, I bet.
I was very fortunate in that I was a definitively clear winner in the games I was playing, and I had very good records. I had this notebook back then. Now there are programs that keep track of this.
But I had a ledger that said how much I won or lost every day. I had something like a year, year and a half worth of data that showed that every month I was making $20,000 or $30,000 like clockwork.
Crazy.
Yeah. It was the prime time to play poker. And if you see a lot of people in the poker world who are the best poker players in the world, they’re roughly my age, somewhere between 32 and 38 years old.
Most of them started in college or perhaps in high school. That is when the game was amazingly popular. That had a big influx of bad players, and we cleaned out the bad players.
We also had a lot of time to devote to it. This is why a lot of the older people did not quite get into it, because they were busy working a job or living their life, whereas a kid in college can do whatever they want.
Then people younger than me, they were in high school all day. They didn’t have time to go play poker. So I was in the right place at the right time, like if you look at a lot of tech founders. They grew up where a computer was located.
Back in the day there weren’t very many computers, and if you grew up near the computer, you are way more likely to become someone in tech. So I was in the right place at the right time to some extent. I totally forgot your question and where we were going, but that’s that.
That’s the luck component, I think, of success where, right place, right time. You can’t control where or when you’re born. But whenever you see somebody who has this outsized success story, there’s always some component that’s luck.
A lot of time it’s timing. You mentioned in the startup world, you have Bill Gates and Steve Jobs who had access to computers at a time where very few other people did. A lot of people in that age cohort built these massively successful and influential tech businesses.
Poker, same thing. You were in the right place at the right time, and you ended up becoming a professional poker player. I think you’ve not cashed something like $7 million in tournament winnings and now you’re teaching.
How do your tournament winnings as a professional poker player compare to the money that you’ve won with your media empire and teaching others how to play poker?
You’re winning it if you get it through a media empire? I'm not sure.
The money that you’ve made.
Well now I definitely rely more on the business because that is what I'm devoting my time to. Turns out there’s a lot of variance in poker, kind of like in startups, if you’re investing in startups. I’ve invested in something like a hundred startups at this point.
Lots of them go broke even if they are doing their absolute best. They’re smart people doing good work. It’s hard to make a successful business. Poker tournaments are like that, where 80-ish% of the time, you’re going to lose even if you go there and you play great.
You have to have a very strong mindset where you fly across the world and put down a bunch of money and realize, “I am going to lose this 80% of the time. I understand this is going to happen. I’m not going to be unhappy if it does happen.”
It’s a little bit different than the startup world though because you get to devote two or three days to your tournament, whereas if you’re starting a startup, you get to devote two or three years to it or more before you figure out if it’s going to work out or not. So that’s fortunate for me.
But you realize that there is going to be a lot of variance in poker, and to be fair, the last few years I have not been particularly great in poker. I think it has to do with running well at the wrong time.
So I think, since I've been focusing on the business, where I'm only traveling one week a month, I think I've won about one tournament per year, which is pretty good. If you play 50 tournaments in a year that have 500 people, you’re supposed to win one in 500 but I've won roughly one in 50, which is good, the problem is that they’re usually the smaller buy-in games.
Whenever you’re playing poker tournaments, you can buy in for all sorts of amounts. I usually buy in for between $1,000.00 and $25,000.00. So if you win the $1000 tournaments but lose the $25,000 tournaments, it’s not going to work out so well for you.
That’s been happening to me the last few years. I've had a bunch of almost deep runs in the big ones but not quite enough. The way poker tournaments are structured, by the way, is the winner of the tournament will get something like, let’s say for simplicity, 25% of the money that was bought in.
So if 100 people put in $10,000.00 each, there’s $1 million in the prize pool, which means the winner will get about $250,000, give or take. Then second place will get maybe $150,000, third will get maybe $100,000, fourth will get $75,000.
But then ninth will get something like, I don't know, let’s say $60,000. So if you get ninth, you get $60,000. If you win, you get $250,000 or $300,000 or something like that.
So there’s a big spread in the difference between first and ninth, but really, the person in ninth place probably lost one or two more hands than the person in first place. If you happen to get a bunch of ninth places in a row, you’re going to have a bad run. You’re not going to win any money.
If you win instead, you’re going to have all the money. There was one year, goodness a long time ago, I won every hand towards the end of the tournament and I won Player of the Year. That’s what the big glass trophy is back there. I ran hot. Every year someone runs hot, kind of like in startups. Every year, someone breaks out.
I’m not going to say it’s random who it happens to, because if you look at the people who are the Player of the Year every year, usually they are a very, very good player. But there are also a whole lot of other very good players who have bad years.
It happens, and you have to know what you sign up for. But anyway, business is very consistent, or at least more consistent than poker. So I found that it’s nice to have steady income.
How lucrative is it to run an online teaching business where you’ve got hundreds, thousands of students paying you like I am, a monthly fee to learn poker?
Yeah, thank you. So a long time ago, when I started the site, we were losing roughly $5,000 a month, just paying coaches to make content. We were making the content ourselves as well. That persisted until maybe 8 or 9 years ago, something like that.
So I had this six or seven or eight-year period where I was losing $5,000 a month. I didn’t view it as losing, I viewed it as helping out all of the other poker players. I was making plenty of money. I didn’t care.
I was doing it almost as a community service because I wanted to help out other people who wanted to get good at poker and succeed, like I did, because I realized I would not be good at poker if I did not get help from the people who came before me, who knew more than I did.
I don't know if I necessarily felt like I committed to it and had to do it or I would lose face or something like that. I don't know why I was doing it, necessarily. I was losing $5,000 a month back then. It probably doesn’t make a whole lot of logical sense, does it?
But I don't know, I enjoyed it. I liked it. It was fun. So about 9 or 10 years ago, I broke up with my fiancé and I was at a casino, drinking and betting on sports like a degenerate. Not a good thing to be doing.
We’ve all been there.
I randomly ran into a guy, his name’s Dan, and he liked my poker products. He had just gotten out of some sort of marketing class and said, “Why don’t you make me a video of you playing online for like eight hours, and I’ll see if I can sell it online. We’ll split the money and we’ll go from there.”
So I sat down. I played that day. Small stakes game, small stakes 180-person tournaments. I think I won three or four of them, which is just insane. You’re supposed to win 1 in 180. I think I played 50 and I ended up winning all of them. So I ran hot.
We got this video and then he did his magic. We made something like $10,000 in sales from that video that month. And then the next month he kept selling it and made something like $6,000 or $8,00 the next month.
So here’s this one video we made that took eight hours of work or whatever, me just sitting down playing poker, and it was very successful. So Dan is in charge of my marketing, and he has been since then. He’s my longest relationship I've ever had.
So that’s how things started to change and look up because I was running a training site that was failing, by myself, and then I found someone who was good at something that I was not good at. Because I did literally no marketing. If you find Jonathan Little, maybe you’ll sign up to the site.
Then he started doing more marketing with affiliates and whatnot. We made an email list. I didn’t know what an email list was besides you sign up for the site and you get an email, giving your information. Things started to take off then.
So what does the revenue look like today?
Oh, there’s no question. How do we do now? I think we’re on track to do something like $1.8 million-ish in sales this year or something like that, give or take.
Crazy.
Maybe more, maybe less. I don't know. I'm always skeptical we’re going to die at some point. I don't know why, because it just continues going up. I don’t get how it continues going up, but what it amounts to is if you help people, they will reward you. So you just have to make sure that you are adding substantial value.
I'm lucky to be in an industry where people are happy to spend money to make more money. And to be fair, if I charge, at the most, $100 a month for my highest-tier membership, if you watch one video a day you’re paying three bucks per video, which is very, very free in terms of high-end education from many of the best players in the world.
I'm not the only coach on there. I have a lot of other coaches, and goodness, I don't know how much we spend each month. It’s like, I don't know, $70,000, $80,000 on content, employees, et cetera. So we have expenses. Don’t get me wrong. We’re just not pocketing all the money.
But anything that you can learn from and make substantially more money, usually people are pretty happy to pay for that. I mean, I've proved it over and over again. I can take losing poker players and turn them into people who can win a hundred bucks an hour playing live poker at their casino. I’ve done it many, many, many times and that’s what I do to people. I help them go from losing money at poker to winning money at poker.
And it’s worth a lot of money if you can help somebody win money. For example, if I pay you $500 or something and yet I win $10,000 at poker, that $500 is free to me. In fact, it was almost like you paid me.
Well you think about it, right? Let’s say you sign up to my site. You study, I don't know, 20 hours a month. Let’s say 30 hours a month, an hour a day. And you stay signed up for a year at the highest tier membership that costs you $1,200 a year, assuming you don’t catch it on sale or anything. So if you’re paying the maximum, you’re going to have to spend $1,200 a year.
But if over that year you learn how to make $100 per hour, you have to play 12 hours and it gets paid back. If you start doing this 40 hours a week, 160 hours a month, you’re making $16,000 a month. So you pay me $1200 for a year, and you can then make $16,000. Now obviously, everyone does not crush it, but the people who are dedicated, the vast majority of them do.
The genius here is that by starting a business where you’re teaching, you’re checking off a lot of these boxes. Number one, you are doing something you love, because generally you're not going to be able to teach something you’re not very good at and if you’re very good at something you took the time to learn it and you probably love it.
So that’s a great hack for figuring out what kind of business you can start that you're actually going to enjoy going to that won’t feel like drudge work or a terrible grind. Start teaching people something that you know.
And also, when you teach people, they’re very grateful for it because you’re helping them to get better at something. And then in your particular niche, it’s lucrative because you’re not just teaching somebody a skill that's completely valueless and they’re just doing for fun.
You’re teaching somebody a skill that’s going to help them make more money. Consistently, the most successful educators that I see are those teaching people how to code, teaching people how to make a lot of money playing poker, teaching people the skills they need to get a promotion at their job or get a better job, et cetera.
So I think you’ve created the perfect alignment in all of these areas where you can do something that you love and charge a lot of money and get paid.
Well to be fair, we don’t even charge a lot of money. That’s the interesting thing, is that the lowest tier on my site is $10 a month, essentially, if you buy three years at a time. If you pay full price I suppose it’s $40 a month.
I also put on a ton of free content. I do that just to make people aware of me, because if I become known to them, they’re now going to look at my content. I have content for players of all skill levels, and you’re going to start giving them wins.
They’re going to go from perhaps a big losing player to a smaller losing player. If you normally play poker and you lose $20 an hour and now you’re only losing $10 an hour, it’s actually a huge gain if you think about it. It’s the same as making $10 essentially.
I put out a lot of content to try to help people get better at poker. I know that I'm improving essentially their quality of life, because you’d rather not lose whenever you’re playing your games. And people are happy to pay you back for that.
And they realize it. It’s expensive to hire other poker coaches to make content, and I've devoted my whole life to this. I could be out there playing poker today and who knows where I would be? Maybe I’d be a better poker player. I don’t even know. And that’s okay. I’m willing to give that up to help lots of other people.
There’s this idea of a talent stack or a skill stack where let’s say you get good at one skill. You’re a fast sprinter. If you want to be one of the best in the world and make any money, you have so much competition.
You’ve got to better than 99.999% of people. But if you can combine that with some other skill, you don’t have to be as good at either one of them. You can combine the two of them and be maybe top 10th percentile in the world and succeed.
When I look at what you’ve done, you’re good at poker. You're a pro. You’ve made millions playing poker. You’re a great teacher. You’re dedicated at producing content. You’re not afraid of tech. You’re comfortable building websites from scratch with technologists.
Exactly. But a lot of people are afraid to hire someone. They think, “I have no idea how to do any of this. I'm not a developer myself so I guess I can’t make a website.”
You’ve seen this with other poker players, too. I think Phil Ivey has a master class or something where he’s worked in collaboration with this company, Masterclass, to put out a video.
But I guarantee he hasn’t made anywhere near as much money with that as you’ve made by combining all these skills and putting them together.
To be fair, he probably didn’t work nearly as hard, either. He just showed up and recorded for a while. I was very fortunate in that I had a head start to a lot of people, because I was already known in the space.
There are a lot of poker players who tried to make training sites. I’m presuming they don’t make a whole lot of money because it seems clear to me that they’re not. It’s because they were not as well-known as I was in the poker world.
I'm very fortunate to have an immense amount of authority already purely based on results, which is different than a lot of things in the tech world unless you’ve already founded a successful company.
If you’re a new founder, you’re going to have a difficult time becoming known unless you are already an authority in some space. But I was already an authority in the poker space without even knowing what I was doing, just because I was very, very good at poker.
Also there were very few people doing what I was doing in the poker space. There had been a few poker training sites that have come and gone throughout the years. I might have the one that’s been around longest now that I think about it.
All the other ones have gone broke for whatever reason. It’s going to sound bad, but most people are not very good at teaching who also play poker. Because a lot of people in the poker space who do make content very often are not necessarily doing it to help as many people as they can.
They’re doing it to try to give themselves additional credibility, or to sound smart, or to try to appeal to very, very high-level poker players. If you’re only trying to teach very, very high-level poker players, or trying to impress people by using terms they don’t understand, then you’re going to turn off the vast majority of actual poker players, the people who need a whole lot of help.
If I try to teach a world class player something, I mean, they could probably teach me. I still hire coaches because I know they’re better than I am, and that’s okay. But I am substantially better than every recreational poker player, and that allows me to provide lots of value to them.
And there are a whole lot of recreational poker players, but not a whole lot of very, very high-level poker players. Make sure you’re targeting some sort of a big market, unless you’re going to charge infinite money for your product.
To be fair, there was a book a long time ago in the poker world. I think they sold it for $5,000 for a 300-page pdf by one of the best poker players online. I don't know how many sold, but I'm sure he sold some.
You know, you write a book, sell it for $5,000 and you sell 30 of them and I guess you’re happy. But we sell our books for normal prices and you have to sell a whole bunch of them to make any money, but that’s okay.
What is the most lucrative part of what you’re doing? Your YouTube channel’s free. I guess you might be able to make money through ads.
No, I purposely have no ads. I do not want ads. I do not want to have a bad viewing experience for the people watching. I'm a big fan of not advertising random stuff, toothpaste and deodorant or whatever before you have to watch my content. You don’t need to do that.
I advertise by promoting my products. I’ll say, “Check out my site, pokercoaching.com.” Or I will link back to an article that I wrote about a particular thing. I have a bunch of URLs stuck in my head. You want to know about bankroll management, go to jonathanlittlepoker.com/bankroll.
I have all these in my brain index and when it comes up, I’ll throw it out. Somebody will go to that site. They’ll check it out. They’ll read it. It’ll help them and maybe I get their business. So essentially, I am the product. I want people to see me, not an ad for toothpaste.
So you don’t make a ton of money on books really. If you sell a physical book, you make roughly $3.00 as the author per book. Poker books, if they’re good, may sell 10,000 copies in a year, give or take.
I have the best-selling poker books, and I know I make a little bit more than that, but not a ton more. Back in the day, it was thought that this one book sold 100,00 copes. That was the most successful poker book.
That was in the poker heyday. So you’re not making a ton of money from the books and I realize that. I'm more so making the books to again, try to get in front of people. Amazon is a big search engine, and I want Jonathan Little stuff to come up when people type in poker into Amazon, cause that’s another way for people to find me.
Same reason we have a podcast, right? That’s free. I do that so if people are on iTunes or Stitcher or Overcast or whatever, they type in poker and maybe they’ll find me. Same reason I write articles for physical newspapers and physical magazines and all this stuff, because I want them to open up their newspaper and see an article about poker and think, “Oh, that’s cool. Let me read that,” and they see it’s by me and maybe they follow me.
So a ton of the stuff I do does not make money. What makes the money is the membership site, because that’s the thing where you can charge $100 per month and you get to keep all of it. There are no real expenses, whereas with a physical book, the thing costs $20.00 to print.
With a website, I mean I have employees and they get paid very nicely, but that’s where most of the money comes from because it makes sense. It’s the thing with relatively little overhead and it’s quick to iterate on and quick to put out new content.
Right here, we’re making a video right now. It’s going to take us the hour and a half we’re making it, and then it’s done. I can do this all day every day.
I think it’s a smart model as an educator because like you said, you’re being genuinely helpful. You’re not doing this just to make yourself look good. You’re doing this to figure out what people need help with.
If they see you in all these different channels, they’re like, “Hey, I've seen Jonathan every time I search for poker. I trust him. He’s got good advice. Maybe I should pay for his training.” Because paying for any sort of membership website or education, you want to know that the person you’re going to buy from is reputable, that they're going to be good.
For sure. I've done some things to try to make myself more reputable, and that’s often done by collaborating with other people who are also thought to be very reputable.
I just finished up a book that, kind of like that book I wrote with 15 people, I wrote it with 9 other people this time. They are many of the best online poker players in the world. They’re thought to be some of the best poker players in the world.
Collaborating with people and showing that these people work with me and I work with them, even if people perhaps don’t respect my poker game for whatever reason, probably because I’m my age. I'm not a young kid anymore and I'm not grinding online poker all day every day. Some people may think, “Perhaps he’s not the best poker player anymore.”
But they see you collaborating with people who are the best, which means I am hanging out with these people, talking poker with these people. That gives credibility to what I’m doing. With my poker training site, I've hired people who have equally good or better results than me, purposely, because if I am not a big enough draw to get people to the site, maybe these other people are.
That’s also smart. All these other people have probably spent a lot of time building up their own audiences and now you have access to their audiences. If somebody wants to read one of their books and they find a chapter from you in there, then suddenly you’re reaching a lot of people you wouldn’t have reached otherwise.
For sure. It’s like when you have a startup, if you have a board. If you have a board of five well-known people, that’s going to give you way more credibility even if you have five random people, even if they’re not doing a time. To be fair, I'm sure the boards do a lot in a lot of cases, but being associated with those people makes you look competent.
How did you learn to do all this stuff? I think it’s fascinating that you’ve grinded it out with poker. You did what it took to become a professional poker player.
Then you grinded it out with online business and you figured out how to maximize your uses of all these different distribution channels and become a respected educator. What would you say are some of the similarities and differences in those processes that somebody who hasn’t done anything like either of those would benefit from knowing?
I do a whole lot of studying as I go, to some extent. I don't know a whole lot, but whatever I need to know I make a point to sit down and learn it. So there’s a book by Tim Ferriss, The 4 Hour Workweek, that got me into the idea of maybe I should try to be more serious about my own business.
It’s worth mentioning that a lot of people who aren’t poker players, their goal was to become sponsored by a poker site where you play poker. The problem with that is these sites don’t operate within America, and the ones that do are usually unlicensed, unregulated, and they could go bankrupt at any point in time, so I don’t want to represent them.
So I understood a long time ago that no one is going to give me a deal because I'm an American poker player. That means if I want to make money from poker besides if I'm going to the tournaments and grinding it out and playing, I need to figure out a way to do that, right?
So I already have the training site for fun, and I decided to ramp it up a little bit. I like the 4 Hour Workweek. There’s a podcast called The Smart Passive Income Podcast with Pat Flynn. I've listened to all of those. Those are very good, and those were the two main things.
I made my website jonathanlittlepoker.com myself because I wanted to see if I could do it. Pat Flynn inspired me to do that and I had a blog there, a written blog every week for about five years. I've let that go in exchange for focusing on YouTube. Now I put out three or four YouTube videos a week, which is easier, more fun, et cetera.
I try to find people who I can model myself after who are crushing it and I try to learn everything I can from them. I listen to a ton of podcasts, even today, basically all the time when I'm not working. I used to get to listen more because I’d be traveling to play poker tournaments and I would listen all the time.
You can grind through a bunch of them. You listen. You try to learn. Today, I listened to a podcast, This Week in Startups with Jason Calacanis. I like his podcasts a lot. Some people hate him. Some people love him. I love him.
He’s a polarizing figure.
He is a polarizing figure. He told me to read this book, The Lean Startup. Here it is, right here.
Yeah, by Eric Ries.
I was going on a trip. I sent him a message, “Hey what book do I need to get?” He said, “Read this book, The Lean Startup.” He has a book called Angel. You should read his book, Angel, if you want to invest in companies.
Yeah. As he’s fond of saying, he’s the world’s leading angel investor.
Yeah. I worry he may be like Phil Hellmuth in that he just thinks he is, so I'm not entirely sure. There’s a poker player, Phil Hellmuth, who has the most World Series of Poker bracelets, kind of like Jason has some of the most unicorn angel investments or whatnot.
You don't know if they’re good or just lucky. But I played with Phil Hellmuth and he does some absurd things, then they always seem to work out. So maybe he actually is a genius figure. I love Phil. I worked with Phil. I helped publish his biography and he collaborated with me a few times. I like Jason, too. They’re fun.
But I learn as I go. I definitely do not know how to do a lot of things, and the things I don't know how to do I’ve been very comfortable with outsourcing or hiring someone to do it who knows better than I do.
Let’s say you dove deep into this tech world. The fact that you’re listening to these tech podcasts, you’re reading these tech books. You're not sitting on the outskirts. You’re learning from other people.
But I think also, what you’re doing, you don’t have that many role models to follow in their footsteps. There aren’t that many other big poker coaching websites and people who are succeeding the way that you are.
So who do you look up to? Who are you inspired by, and what playbook are you following? And what’s the end goal of all of this? What is pokercoaching.com at its highest potential? What does that look like?
These are the things I don’t think a whole lot about. I just sit down and do the work. I'm definitely not good at chilling and relaxing and thinking about, necessarily, what is the end goal. Because at the moment, I have no desire to quit.
A lot of people in the tech world want to build something and then sell it, and then do something else. I don’t want to sell my company. I do not want investors in my company, unless I absolutely love them. I have zero investors currently. I own a hundred percent of the business. I'm not trying to quit.
I think a lot of people who think in that way want to get out and retire. I don’t want to retire. I'm happy with doing what I'm doing. That’s said, the goal is to continue growing. I know some numbers from the biggest training site in the past that is now defunct.
They have roughly 20, 25% as many people as they had the peak of the poker boom. We’re charging more money than they did. They were charging $20 a month. We’re charging $100 sometimes. We’re charging more money so we’re maybe we’re making as much money. I’m not sure.
But the goal is to be at least as big as they were, and perhaps bigger. In the ideal world, everyone who plays poker is aware of me, right? And that’s not the case. There are only three or four household names in the poker world among people who know poker.
I’ll still go, and I’ll sit down at a random $1,000 buy-in tournament, and only half the players will know me, which shows that there’s still room to grow. Those are people who are buying in for $1,000. These are not people playing at the kitchen table with their friends.
The people who got famous, at least household name famous from poker, like Phil Hellmuth or Dale Negron or Doyle Brunson, they did very well around 2003 to 2010 and they got a bunch of coverage on ESPN.
I did not have the benefit of that, so I have to try to figure out a way to replicate that in some different manner. But in the ideal world I will be big names like those that will allow me to reach the entire poker market, and then we’ll clean up.
I think, when I talk to Indie Hackers who are building profitable businesses, there’s much less of a desire to sell out. There’s much less of a desire to take on investors and eventually get bought, and there’s more of a desire to build a business that is cohesive with their lifestyle, where they get to do what they like doing and grow their revenue and be happy doing exactly what you’re doing.
Yeah. I mean, I realize I have a solid lifestyle business. I’m never going to make a hundred million dollars in revenue from this business, because the market is definitely not that big. I recognize that, and that’s okay. I don’t have a problem with that.
So I think I’m fully aware of the situation I'm in and I realize that poker is still popular. For all I know, in five or ten years the game could be dead and then the business is dead, we have to figure out something else.
That's one of the reasons I started looking into angel investing, because I think I have a good temperament for it because it’s like playing poker tournaments, where you fire a lot of bullets and in good situations it can hopefully work out. Maybe they do, maybe they don’t.
Try to be helpful as best you can, giving advice whenever the founders need it. And it’s something that I could realistically do. You want to consider things that you can do after what you’re doing in case it dies or fails or whatever.
Some people don’t like having a backup plan. I’d rather have a backup plan than not, especially if it has the opportunity to somewhat passively-ish make money. Like now, I invest with Jason Calacanis a ton. So you find people who are crushing it, learn from them, and with any luck you’ll figure out how to replicate it if you need to.
I think a buddy of mine, I play in a cash game with him regularly, almost every night since the covid-19 quarantine started, but he’s got a cool business. I've got to get him on the podcast. But one of his investors is Jason Calacanis, and I think you’re also invested.
It’s Underground Seller. He does wine delivery. But his story’s fascinating right now because the lockdowns have blown up his business. He’s getting a ton more sales because everybody wants to get wine and you can’t go out and drink anymore.
How is it going with poker? Have you seen more people signing up to play poker, to learn how to play poker, since quarantine started, or has it been relatively unaffected?
It’s up a little bit. I did not know how it would go, because I did not know if poker was going to die. I didn’t know if everyone was going to online poker. That was the big question.
If people stopped playing poker all together the business would have done poorly, but fortunately most people have moved their play to online poker. The online poker sites are currently booming like never before. The games are so soft right now.
I used to not play online whatever I was at home, because whenever I'm home it’s my work on business time and hang out with my family time. I have a wife and one year old and a three-year-old son. That’s what I want to do when I'm at home, not sit down and play poker.
But eventually, I got convinced by one of my coaches on my site. It’s like, “Look, you have to play on Sundays.” Sundays are the big online poker day where everyone plays, so I've been playing Sundays and it’s been going well enough. So sometimes the games are too good and right now the games are too good.
Let’s talk about some of the specific tactics for the different parts of your business and then I’ll let you get out of here.
A lot of people are trying to start a business in one of the many areas that you have your business running in, email or YouTube or courses. Let’s talk about YouTube first. What is the biggest thing you’ve learned about growing a YouTube channel that’s successful?
I don't know. Show up and make content. I think the answer to a lot of these things is show up, do good work, and figure out ways to get in front of people. Some of my content does great. Some of it does not do so well.
It’s not what I would like, but it turns out discussing current events that are very popular at this point in time seem to get a lot more traction than perhaps discussing straight strategy. I would prefer to discuss straight strategy, because I don’t care about gossip or drama.
But I don't know, six months or so ago someone folded four of a kind. They posted about it on the internet and it’s probably a good fold. I made a video about it and I got tons of views. But in reality, every time you got four of a kind you folded it, it would cost you almost no money because you never get four of a kind. So this was an instance that essentially never occurs.
You may, perhaps should, fold four of a kind one time in your entire life, maybe one time in ten lives. Even if you make the call and you lose, it doesn’t matter. There was a straight flush available, for those who don’t know the poker rules. There was one hand that would beat you.
Usually when you lose to exactly one hand you should not fold, but the way this hand played out, more like bet, raise, re-raise, re-raise, re-raise, all in on the river, it’s like, “Okay, guys. It’s a straight flush, right?”
Anyway, that video was incredibly popular, but in my mind as an educator it added no value because you don’t get four of a kind. Who cares? Don’t fold your four of a kind and you’ll be fine. It doesn’t matter, right? The problem is it doesn’t matter, yet the general public likes it.
There was a cheating scandal a while back. I'm not going to go into it. It’s a little bit too intricate to discuss here. There was a guy, Mike Postle, who was somehow cheating. I had the lawyer who was the lawyer for the plaintiffs who were trying to get their money back. I interviewed him two or three times. He’s my lawyer as well so it’s convenient. Those were very popular as well.
But it’s all drama to some extent, right? I don’t care about drama. But there are a few popular poker YouTube channels that are very heavily current events based and they do well. So that’s something I should probably do more but I don’t want to so I don’t.
I’m always on the lookout for things. Folding four of a kind, I guess I can take that from an educational spin. Hey, it doesn’t matter. Anyway, you want to do things that people are talking about, that people care about. If anything, try to piggyback off of other things that are popular.
This is going to sound bad. There’s this poker YouTube personality. I guess he’s out of it now, but one of his marketing tactics was to find people who were successful and then try to drag them down, try to berate them, try to belittle them.
People would latch on to that because maybe they don’t like that person as well. You find someone bashing someone you also don’t like. Maybe you become popular. No one’s going to like you who’s in the know, but you know, random haters will.
Maybe that’s the way to build an audience. I would never do that. But there are all sorts of marketing tactics. But in general, find the content people want to consume and then give it to them with your unique spin.
So YouTube, consistency, giving the YouTube audience a little bit of drama and current events. But what about a podcast? What's helped you grow your podcast?
The podcast has gone through many iterations. For a long time there was just a show called Weekly Poker Hand, where every week I would sit down. I’d talk about a poker hand until I was done talking about it, usually 10 or 15 minutes.
That was fine and good. Usually I’d sit down and record 10 of them in a day or 15 of them in a day and be done for two months or three months. I would not say that’s immensely popular, but now that’s also YouTube content.
When I'm making it, I’m mindful that this is going to go into audio as well. So I’ll read out, put the cards on the board and the cards in my hand. I don’t assume that the person listening can hear. Like this. This could easily be on YouTube. This could easily be on iTunes. It can be on both.
So now, most of the stuff that goes to the podcast is YouTube content that also makes sense for audio. I don’t even know how that does. I don’t even check it. It does get some download. I’m not highly focusing on that.
Again, the goal is to be in that search engine on iTunes search engine or other podcast search engines. I'm not going hard on that but it’s fine enough. YouTube is where we’ve been going hard in terms of making good, dedicated content for that platform, cause that’s where a lot of people are. Turns out that that’s where I had the most followers.
YouTube is huge. It’s massive.
It really is, so you might as well go where all the people are.
Even if you Google for advice on a particular poker hand, the chances that you’re going to get a YouTube video in the search results are pretty high. The chances that it’s going to be one of your videos is also high.
For my poker training sites, every two weeks I have a group of students who will get on. They’ll ask me questions. But before that, I’ll present 30 minutes on a topic.
They request the topics, a topic that has never been requested before, and I record all these videos. I have classes on the site. We have, I don't know, a hundred or two hundred of these things where all the common questions about poker, I've sat down, and I've discussed it with good-thinking poker players for 30 minutes.
So we have the answer to every reasonable poker question you’re going to ask, on the site. It’s almost like an encyclopedia where, “What do I do in this scenario?” or, “How do I play this hand?” or, “How do I play this hand?” or, “How do I manage my bankroll?” or whatever.
Anything you want answered, I have that at my site purposely so that you don’t need to go anywhere else to try to find information. Yeah, so YouTube’s big.
Last one of these. What’s the biggest thing you’ve learned about building your own website where you’re teaching people and selling courses and selling memberships?
Show up and do the work, again. I know it’s the same answer. But you do have to show up and do the work. A lot of people want to work some and then just forget about it and be done. They want to make a course, which is fine and good.
There are people out there who have made six hours of content and they call it a course, and they sell it for $1,500. There’s nothing wrong with that. You’re allowed to make whatever you want. It can be high level, low level, any price.
But that’s almost a side hobby, where you’re going to sit down. You’re going to make this thing. You’re going to sell it. The poker players who do this, they put a substantial amount of money behind marketing. I see them advertising all the time so I know they’re spending money, or at least I’m exactly the person they would try to advertise to, high level poker players. I’m not sure.
But that’s the way a lot of people do a lot of things. They sit down. They make this project. They finish the project, and they’re done. There are courses on poker that cost $1500 or $2000 online. They’re made three or four years ago. They’re out of date. I'm sure some people are still buying it because of the marketing efforts.
But it’s not even high-level, cutting edge material, which, again, is fine. You can sell whatever you want. I have no problem with that. It’s still good content. If they put substantially more effort into it, I think they would have a substantially better product.
But at the same time, that’s probably not what they want to be doing. They want to be playing poker. They like playing poker. They just wanted to do something on the side to bring in some side income and now they’re done.
But the way I do it is definitely a fulltime job, more than a fulltime job. It’s hard work, but I don’t mind the work. I like the work. Try to like the work. That’s the answer. If you like the work, you can do it indefinitely.
It’s obvious you like what you're doing. It’s obvious from watching your videos and listening to your lessons on your website that you like what you’re doing. It’s made me a lot of money and made, I'm sure, a lot of other people a lot of money.
Good. Yeah, go take all of Jeff’s money in a poker game.
I have been. Thanks a lot for coming on the show. Most of the people listening to this are fledgling or aspiring indie hackers. They don’t necessarily have an idea they want to work on, or if they have, they’ve just gotten started and they haven’t put in the work and grinded it out.
What would you leave them with? What’s a word of advice to help them get started and build up some confidence?
If you don't know what you want to do yet, try a lot of things. In terms of games, if I wanted to play games, I should try a lot of games. We’re not considering money at this point, but poker would not be the game that I would play, because I've tried a lot of games.
There are a lot of games that are, in my mind, better than poker, but they’re not played for money. They’re not as popular for whatever reason. Maybe I like the game a lot, but other people don’t and that’s okay.
So you want to ask, what are you trying to accomplish here? If your goal is to make money, then you must get in a big market, to some extent, or at least you have to be able to design something that adds immense value, that is irreplaceable for corporations, cause they’re the ones who can pay a ton of money for things.
So you want to figure out what you’re trying to accomplish. I think a lot of people piddle around and they inevitably don’t focus on figuring out what they want out of life and what they want out of business and what they want out of everything they’re spending their time on.
Also, don’t waste time. A lot of people waste their time by watching nonsense on TV or by playing games or perhaps even studying a lot, learning a lot. I listen to a ton of podcasts. I'm sure I could have been doing other things during those periods of time that would maybe even be more useful. I'm not sure.
Those things have certainly helped me, but maybe I should have been reading more books or maybe I should have been actively talking to people more. I'm not sure. But try to use your time wisely.
A lot of people squander a lot of their time. Spend your time actively working toward whatever it is you're trying to accomplish but sit down and figure out what you're trying to accomplish.
It’s tough to know exactly who I'm even talking to here though, because if you have nothing going on right now, and you want to have a company that’s doing, I don't know, a hundred million dollars in revenue, I don't know where to tell you to start.
I have no other ideas besides exactly a poker training site. If my poker training site died today, I would be in a mess, so hopefully that doesn't happen. And if you have any good ideas, let me know.
All right. Be deliberate about your goals and then be deliberate about how you spend your time trying to reach those goals.
That’s right. Do it. Do the work.
Jonathan Little, thank you so much for coming on the show.
Thanks for having me.
Can you let listeners know where they can go to find you online, find what you're selling and find your advice?
My training site is pokercoaching.com. If you’re new to poker go to pokercoaching.com/fundamentals. There we have a fundamentals course. You can get the first few parts completely for free.
You can sign up to the site and get access to a trial of the site completely for free. I have a Twitter. @jonathanlittle, just my name. YouTube is youtube.com/pokercoaching. Those are the main channels.
All right, Jonathan. Thanks again.
Thanks for having me.
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I really enjoyed this one.
I know not everybody is into poker / online poker but I really was.
I loved watching High Stakes Poker at its peak on YouTube and never had the self-discipline to get past micros online, but really enjoyed playing at casinos occasionally.
I still have a quarterly homegame with my high-school buddies that we honour first Sunday every 3 months.
Courtland, you mentioned you still love poker - I highly recommend this lesser known book referenced from 2+2 back in the day - https://www.amazon.com/Mental-Game-Poker-Strategies-Confidence-ebook/dp/B005RZRHDG/r
^^ it's framed as a book about poker mindset, but is really meta and applicable in other areas of life too
There are many bookmakers on the Internet, but be careful; many of them are scammers. For me, betting is a source of income. Sometimes, I can earn in 1 day what I used to make a whole month. In particular, I like to bet on cricket, here https://www.bollybet.com/sports My father taught me cricket since childhood. I know all the teams and what they can do. Unfortunately, cricket is played only in our part of the world. It would be interesting to see the world cricket championship. I hope that one day cricket will become popular in Europe.
What do you think is the best bookmaker company?
I played poker for a living during the 'boom'. Was easy money lol. Nowadays I'd rather casino it up though but still play some 25 bucks short-handed (8 tables at once) for some fun if bored. I always disliked full tilt for some reason so never had any money on it. My main struggle was to find a place where I could play easily and I know that the game is fair. My friend recommended me https://www.slotsandgames.com and I liked it. It is easy to use and there are a lot of casinos. There is a big variety of gambling games but I like the only poker. Now when I am bored I play some short games on that site to see if I am lucky that day.
Danke für die Auskunft.
Danke für die Auskunft.
This comment was deleted 3 years ago.