This is the story of how I started playing online poker, earned enough money to pay for college, world travel, and whatever else I wanted. It’s the story of my first real taste of entrepreneurship in coaching and investing in other poker players. It’s also the story of the hard truths I learned about myself (and life) along the way.
The world of online poker became my obsession.
I’ve always been a dabbler and a tinkerer—always following my curiosity, but never going deep into one domain.
Until online poker.
When I saw Chris Moneymaker win the World Series of Poker, I was drawn to poker like a moth to flame.
(If you don’t know who Chris Moneymaker is, he’s just an average guy—despite his convenient last name—and he won the World Series of Poker’s Main Event. That’s hard enough to do as a pro. What made Chris special is that he got his ticket to the Main Event by qualifying through an online poker tournament.)
Just like Roger Bannister and the 4 minute mile, once Chris showed the world that it was possible to make money playing poker online, the floodgates opened. And I wanted to be one of the first through that gate.
After Moneymaker’s big win, a friend of mine started hosting home games where we’d play no limit texas holdem and buy in for $5 bucks. These were casual games designed more for fun than for profit, but that’s not the way I saw them. Even $5 was a lot of money to me back then—I probably had about $1,200 to my name, mostly scraped up through allowance and saving the tips I made working at a Chinese restaurant.
I had a hard time seeing the game as recreation, because money was involved. Instead, I saw poker as an opportunity to make money doing something that interested me.
Although I didn’t know it at the time, this mindset was the beginning of my future problems in poker. But at the time, my desire to win—or perhaps, to not lose—was what motivated me to get better at the game.
I turned to books and forums, studying them intensely in between home games. It didn’t take long before I was consistently beating my friends—mostly due to their lack of skill, rather than my surplus. This was awkward, because I was the only one that was optimizing my play for money rather than fun. But the game had its hooks in me, so I didn’t care.
It didn’t take long for me to compare my hourly rate playing poker to my rate working at the Chinese restaurant. I was making about the same in both “jobs”, but by playing poker I could avoid cleaning up bathrooms used by people who couldn’t handle their kung pao chicken — a benefit I couldn’t turn down.
Up until this point, I’d only played in live games, because I was 17. I vowed that once I turned 18, I’d put $100 online and see if I could make a go of it. $100 was about 10% of my net worth, so it wasn’t a small decision to me.
When my 18th birthday came, I deposited $100 onto PokerRoom.com and began playing. My first games were 5c-10c limit holdem with 9 people at the table. Even in those early days of poker, these games were easy. So easy that even my limited knowledge of the game was enough to dominate them. I ran my $100 up, moved up to 25c-50c and ran it up again. When I went on small losing streaks, they only motivated me to learn more about the game.
Eventually, I built up enough money and confidence to make the jump into no limit holdem. This was a huge moment for me—in no limit, you can lose 100% of your chips in a single hand, compared to about 10% in a limit game. So my potential losses increased without even moving up in stakes. Of course, the rewards were also greater. I could capitalize on a player’s mistakes far more in no limit, meaning that my winrate would skyrocket if I played well.
I quickly realized that if I wanted to get better at no limit, I would need to look outside of books for knowledge. People like me were gathering in online poker forums to discuss the game, and at the time TwoPlusTwo was the premier forum.
I joined and started to comment on hands here and there. But most of my poker growth came from joining a chatroom that people playing at stakes 10, 20, even 100x higher than myself used to talk about the game.
Lesson 1: It’s okay (even preferable) to be the dumbest person in the room…but you have to be in the right room
In my entire time playing poker, I was never the best player in that chat room. If I’m being honest, I was probably in the bottom 10%. Back then, that fact would give me a lot of anxiety. I constantly asked myself questions like, “How come I can’t play like he does? What am I missing that he sees?”
Now, I realize that the fact I was not the best player in the chat room allowed me to reach the level of success that I did. It caused me to ask “dumb” questions like “Why?” and “Can you explain why you made that play in a different way? I don’t understand.” These dumb questions forced my friends (who were playing at stakes that would make most people physically sick if they lost a hand) to explain the core logic behind their decisions, illuminating the thought processes they used to play the game.
Being the dumbest person in the room is important for growth. But being in the correct room is even more important.
I was already a player trying to get better at the game, which puts me in a small minority of poker players. Not only that, I was on an online poker forum! That’s even more rare in the ecosystem of poker players. But I went a step further, and literally inserted myself into a chat room where some of the absolute best minds in poker would work through the toughest hands that they played.
Put that in any other context and you can see how valuable that is.
Lesson 2: A deep understanding of your emotions and how they affect you is more valuable than raw skill
Even though my skill at the game continue to improve as a result of study, play, and discussion with better players, I kept hitting a wall. I couldn’t seem to win consistently at the stakes that my friends were playing at — 2/4, 3/6, or 5/10 ($400, $600, and $1000 buy-in tables, respectively).
To me, the obvious answer was that I just wasn’t good enough. No matter how hard I tried, I couldn’t be as good as the grinders at those stakes. But sometimes the obvious answer is wrong.
I go into this in more detail in my article on the mental model of tilt, but the basic idea is this:
In games of skill + luck, your ability to understand, plan for, and mitigation your emotional reactions is often more important than being better than your opponent.
My main problem wasn’t my lack of skill (although you can always be more skilled). It was that I didn’t understand how my emotions were affecting my decision making at the table.
I’ve always been a calm and collected person, which led me to believe that I was immune to tilting at the poker tables. But I wasn’t…I just didn’t display it in a typical way.
My issues with tilting became most obvious the higher stakes I played. The higher the stakes, the worse players I targeted. After all, if I was going to play a bit outside of my bankroll, I had to have a good reason. And the only good reason was to play against a player that was SO bad that my risk of losing was reduced.
The one downside to playing against really bad players is that they can be extremely frustrating. Some players are bad in a way that makes them very volatile to play against. If you can play them for an extended period of time, you’re all but guaranteed to come away with a huge amount of money. But in a short period of time, they can decimate you due to dumb luck.
My worst moment of tilt came while playing against a French player on an obscure poker network (for some reason, French players tended to be awful). I was playing him heads up, or one on one, at a $1,000 buyin table. My regular stakes were $2-4 or a $400 buyin, so I was out of my comfort zone monetarily.
This Frenchman was bad — no one would deny that. But he was the kind of bad I mentioned above; the kind that can destroy you because they take every hand to the river. These players are volatile to play against, but are so profitable in the long run it’s dumb to avoid them.
On this particular day, he was running hot and was destroying me. I lost hand after hand, often in statistically unlikely ways. First $1,000 gone. Then, $5,000. After I hit -$13,000, I slammed my fists into my desk so hard I thought I fractured my hand. Not content with that burst of outrage, I took my orange LG Env phone and threw it into the wall, shattering it to pieces:
After that, I destroyed a bottle of Jack Daniels in the kitchen and karate-chopped an unopened bag of pistachios with enough force to rupture the bag and cause them to rain their nutty hell fire down on my entire apartment floor:
This completely unexpected outburst was enough of an emotional release to get me to sit back down and keep playing the French fish. But I was still shaken up and it was showing in my play. I wasn’t worse than him at this point, but I may have been at his skill level simply due to emotions clouding my ability to make good decisions.
Thankfully, I was able to claw my way back to only being down $3,000 before he left the table, with a friendly “GG! Was fun!”
It wasn’t fun for me. Not in the slightest. And it was after this experience I realized I had a big problem, not only with controlling my emotions, but understanding them in the first place. It’s far more important to understand your emotions and how they affect your thinking than it is to have raw skill at the game. You can be “better” than someone—that is, accomplish the goal of winning more money—simply by being less affected by your emotions when playing.
This has obvious applications outside of poker.
Lesson 3: You might be making a lot of money, but if your butt needs to be in the chair, all you have is a high-paying job
After realizing my problem with emotional control, I decided to stick to lower stakes until I could manage my emotions. I began playing more tables and “grinding out” a very solid monthly income, especially for a kid in college. I was dwarfing what I would make if I came out of school.
Then, like every other basic bitch wannabe entrepreneur, I read The 4-Hour Workweek by Tim Ferriss, and came to the realization that all of the work I’d done to become a good poker player just bought me a high-paying job.
If I got up out of my chair and went out with friends, my income per hour dropped to $0. If I read about poker instead of playing poker, my income was $0.
By this time I had built up a name for myself as someone who could beat lower-stakes games well, so I decided to start coaching lower-stakes players. I charged anywhere from $50-$100/hr. It was a good way to monetize extra time I had when my mind wasn’t quite sharp enough to play poker, but more than sharp enough to coach others at stakes lower than my own.
This didn’t solve the issue of generating income while I wasn’t directly working, though. I read about people who “staked” other poker players, giving them capital in exchange for a cut of their winnings (and full exposure to their losses).
I decided to give this a try, using the first two lessons I learned. I would look for players who:
- Had a really good reason for needing a stake (financial hardship outside of poker being the most common)
- Were growth-minded players always trying to learn more about the game
- Were not prone to tilting
All in all, I invested $xx,xxx in five different players and returned around 125% of my money over the course of the stakes.
My experience staking opened me up to the plain and simple truth: if I ever wanted to have complete freedom, I needed to either invest or create a business.
Lesson 4: The worst type of laziness is outsourcing your thinking.
My time in poker was filled with some incredible highs and some absolutely soul-crushing lows.
The game was infinitely deep, which consumed my curious mind. The ability to earn money by satisfying that curiosity made me stick to the game. Through my ascent in the poker world, I learned much about myself, both intellectually and emotionally.
But there was one lesson I didn’t learn until after I quit.
I quit poker after randomly winning a tournament (which I never usually played). It was a nice payday, and I saw the writing on the wall as far as the legal climate in the USA.
So I pulled my money out, and not six months later the FBI shut down the main two sites that I played on, and froze funds in player’s accounts.
I dodged a bullet, and let poker go. But I kept being nagged by the questions:
Why wasn’t I ever as good as the people I learned from? What was stopping me from being one of the most skilled players in the game, earning huge amounts of money?
These questions don’t have a single answer. There are plenty of reasons I could point to:
- I was never fully able to “lose respect” for the real value of money, meaning I was emotionally attached to the amount I would win or lose
- I spent too much time reading hand histories and watching training videos without doing the hard work behind them (the math, the logic, etc.)
- My personality wasn’t suited for many of the traits that were markers of highly successful poker players
But by far, the biggest reason that I didn’t reach the highest levels in the poker world is because I was all too happy to outsource my thinking.
In watching training videos, discussing hand histories with my skilled friends, or reading about the game, I was simultaneously training my brain to not think for itself.
During my poker years, every time I ran into a situation that I didn’t know how to handle, I would seek out the advice of others, or watch a video as a first reaction. What I wouldn’t do was sit down and think through the situation from first principles…which is the only way to really learn something.