Teenage Poker Pro

I played online Poker nearly every day from the age of 15 to 18. When I started, I had several years of competitive Magic: the Gathering under my belt, so I understood the systematic process of learning a card game. For a brief period, I played both Poker and Magic competitively. After barely missing the top 8 elimination cutoff of a high-level Magic event, I began focusing all of my energy on poker.

This came at the expense of school, health, and proper socialization. I had zero interest in studying anything that I didn’t think would help me improve at poker. During introductory Physics I read Harrington on Hold’em. I got barely any exercise and ate mostly pizza, oatmeal, and breakfast tacos. I lost the ability to empathize with anybody who was not a gambler.

Poker is exotic. It got me a weird sort of recognition and popularity in school. I went to Westlake, an upper-crusty, white bread, super wealthy public school. Popularity at Westlake is a function of how much you flaunt your wealth, how many AP classes you are taking, and how good-looking you are. By senior year I was playing $3/$6 and $5/$10 no-limit, and had a bankroll of $100,000. I drove a ’98 Camry and wore hand-me-downs, but I found ways to backdoor my self-made wealth into conversations. Eventually it percolated through my class that I was “that poker guy”.

Westlake High

But in terms of the Poker world, I was still a minor leaguer, a leatherass, a set miner. An uncreative player who only won because most players made so many terrible fundamental mistakes. I am a competitive person, so even though some people in school all of a sudden wanted to hang out with me and invite me to $10 buy-ins at their palatial houses, I felt like an absolute fraud. I had a similar complex when I played Magic, being the guy who had lots of success at the state level but always choked in national events.

The above problem actually persists to this day, as I am a late-bloomer programmer. There is so much I don’t know. I am sometimes overwhelmed by the feeling that I will never be a first-rate anything. In Infinite Jest, the main character is the second-best tennis player in an academy that is a preparatory school for tennis players. Most people in the academy revere him. He sees himself as a failure, because he knows he will never make it in the big leagues.

The early 2000s were the boom years of Poker, and one could get away with playing very straightforward and algorithmically. On the 2+2 forums, where I learned most of my strategy, a certain conventional style was celebrated so intensely, most people who posted different ways of thinking were criticized. This drove away many people who actually had something to say. There was a notion of a “standard” play. Leading into the preflop raiser on the flop is not “standard”, you should always check-raise. Buying in for less than the maximum amount is not “standard” because deep-stack play is the only cool form of poker. Calling a reraise with deuces when you are 100 BBs deep is not “standard” because you are no longer getting proper odds to flop a set.

You know that annoying die-hard Gang of Four design patterns programmer at your company? He’s playing “standard”.

There is a trade-off between being hungry for the top and making a consistent living. I know of guys who cruised through 2004–2009 playing $2/$4 and $3/$6 and simply killed it playing ABC poker. These are the guys who celebrated “standard”, and many of them probably have upwards of $2 million. Good for them. But those guys are probably pretty boring and I don’t think I would want to hang out with any of them in real life.

In order to get to the top, you have to “take shots” at the high stakes games, experiment with new styles, and play out of your comfort zone. In the boom years, the hardest jump to make was from $5/$10 to $10/$20 no-limit. People at $10/$20 were just so damn good. Samoleus, Bldswttrs, cts, loloTRICKEDu, durrrr, H@llingol…there were some legends that broke new ground in terms of how the game is played. It’s funny — while everyone on 2+2 championed “standard” play, these guys were just raking it in, exploiting well-documented strategies by thinking outside the box. By the way, to give an indication as to how tough games have gotten, $1/$2 games today compare in difficulty to $10/$20 games back then. Options trading provides a reasonable analogy to how online Poker strategy evolved. At one point, nobody knew how to really trade options effectively. Because of this, the first people to use Black-Scholes made a lot of money off of that huge knowledge gap between them and everyone else. But now everyone understands Black-Scholes and much of vol-arb is a metagame built on top of it. Similarly, the hyperaggressive players from the days of PartyPoker were reraising in position every single hand because nobody else understood how to do this properly. For them, it was like taking candy from a baby. Today, you can’t step out of line nearly as much.

Sophisticated players understand that creativity is necessary to succeed. By this I mean strategic creativity. You can’t call out of the small blind with J3hh without a good reason. But if a play makes sense within your personal, well-architected framework, you don’t owe anyone a justification. This sort of framework, if properly constructed, is an abstraction which integrates human psychology, probability, and heuristics developed through personal experience.

A player’s Poker strategy can be thought of as a Hidden Markov Model. Making a decision in Poker is as easy as traversing an HMM. This is why it is easy for Nanonoko to confidently play 24 tables at once. He has played so many hands, he rarely has to significantly update his HMM and he can traverse it super fast. This definition of a framework also illustrates why it is impossible for one player to copy another’s style. Copying a heuristic is less effective than developing your own*. This requires creativity.

I lacked creativity for most of my Poker career and made money as a copycat forums-reader. The first time I made the jump to $10/$20, I ran good for a couple days, and then got overconfident. I played Straate six tables of heads-up and lost something like $20,000 in a session. I was playing at Austin Java, a delicious restaurant/coffee shop, on my $300 shitty computer that turned off whenever it got unplugged. Straate was so merciless, he just kept reraising me every single pot preflop and reading me perfectly whenever I tried to play back. He was very good at identifying and exploiting timing tells.

For about a year, I moved between $5/$10 and $25/$50. This would be my freshman year of college. I had to attend UTSA because my grades weren’t good enough to get directly into UT Austin. The classes there were so easy, I maintained a 3.8 despite playing Poker constantly both in and out of class. I made no friends in real life. Online, I became friends or acquaintances with some cool people who have crushed the world of poker. I played Words With Friends against Vanessa Selbst, talked about movies with Jay Rosenkrantz, and told samh133 how much of a nit he was — I’m namedropping, but these people are my heroes. I am remorseful that I never hopped on a plane to go to the PCA.

Every day after class, I would go to Einstein’s Bagels to get coffee and a bagel sandwich. I was so determined to get value out of my dollar that I would spend minutes every day scrutinizing the price-to-volume ratios on the cups of coffee vis a vis the amount of caffeine I needed.Around this time I hired riverboattking as a coach, through DeucesCracked. It was something like $500 an hour. RBK is awesome. Every player that was successful around 2006/2007 can probably remember the epiphanic moment when they realized that you have to reraise preflop very often to be successful. RBK taught me this, as well as when to triple-barrel, river check-raise, float, etc. Tons of cool, tricky stuff that wasn’t really online or in books at the time. He would also sing songs to me when I was running super bad. Pretty hilarious. One time he coached me while I was playing Straate, and Straate was still outplaying our collective wisdom. But I ran super good so I reclaimed some of my profit.

Early 2000’s online Poker culture was extremely superficial in a weird way, sort of like a mutation of mainstream rap culture. In mainstream rap, a certain theme is “I was born an underprivileged, prejudiced minority, and now I’m rich so F the haters”. When the 16–22 year old Poker millionaires started cropping up, a certain theme became “I was born rich and educated, and now I am even more rich and educated, so F the poor.” Many poker players (including myself) loved to sigh about how rich they were, how everything was “ez”. I see this in some Silicon Valley kids today and it makes me sick. First world problems, dining on sushi and ennui at your standing desk. I kind of want the other shoe to drop and all of the VC money to instantly dry up and everyone to lose their job, except that would coincidentally be really bad for me.

Growing up in Westlake made me revile ostentatious rich people. So many kids from my school have done next to nothing with all the resources they had at hand. It makes me grateful that I found something to try very hard to succeed at. I didn’t get along with many Westlake people in high school and I doubt I would today, because I’m just unimpressed. I see a lot of drinking and laziness and a lack of understanding for how competitive and complex the near future is going to be. What a waste.

A fact that is easy to recognize as true, but difficult to internalize: money is a means to an end, not an end in itself. I wish that Poker could have aligned better with this. During the Summer of 2007, the game was losing its luster, and I started to wonder if maybe there were other things worth exploring in life. I started looking for ways to translate money I had earned into happiness. I went to Nordstrom’s with Zuhair Khan and bought Obey t-shirts, and $100 jeans that didn’t fit me. I took my friends out to Uchi. I played higher stakes, and kept squeezing pleasure out of Poker alone. I was still better than enough of the opposition, but had stopped loving the game enough to do postmortems after my 2,000 hand sessions.

I had successfully transferred to UT and moved back to Austin. At the time, I was playing mostly $10/$20 no-limit. I enrolled as a Philosophy major, because I figured it would help me rationalize continuing to play Poker despite the fact that I was miserable. A key question for a Poker player is, “how can I use the money I make from Poker to improve my life outside of Poker?” This is so important, because on a certain plane, leveling up in Poker is about life management more than technical play.

As it turns out, academic Philosophy is super boring to me. Luckily, I also took introductory Chemistry and Biology, and fell in love with them. I began to understand why other people in high school actually did well in their classes — because if you enjoy what you are learning, school isn’t as hard.

The first semester of UT was tough, but engaging. I started socializing in real life, and it was a breath of fresh air. But I had too much on my plate. All of a sudden I cared about academics, but had no idea how to properly balance the workload with Poker.

But my Poker activities were becoming more of a potpourri, which did benefit my play skill. I started coaching, and was getting better at the game through that. I regularly had strategic discussions with Haseeb Qureshi, Ken Kao, and samh133. I was becoming a respected member of 2+2. But holistically, I was becoming increasingly depressed and unhinged. If I didn’t have a winning day, I became a total mess. As an emotional salve, I started spending more and more money on stupid stuff. I bought an electronic drum set and an expensive guitar. I frequently went to Half-Price Books to go on shopping sprees, buying tons of books I never read.

Also, the game was starting to get tough. Due to legislation, there were fewer and fewer bad players. Creativity and innovation became necessary to even stay afloat at high stakes. Studying, database analysis, and use of a heads-up display became crucial. Other players were getting more savvy, and I was being lazy and stubborn, trying to play the same game I had been playing before the metagame shift. Despite my unwillingness to pivot, I still had enough wins to have a profitable semester.

I have some great memories from that semester. I tutored my friend Sam to a level where he could start killing the game. I flipped coins with tcorbin16 for $1000 a flip. I hung out with Haseeb, who was the first fellow high stakes player that I met in real life. It’s kind of weird — I don’t think either of us knew how to properly communicate, because we spent so much time online, but we undoubtedly understood where each other was coming from and I got a lot of solidarity out of that.

But I was not prepared for the rigors of UT. I couldn’t balance school and Poker. Between my first and second semester, I had a sudden existential crisis, when I realized I didn’t want to spend the rest of my life playing Poker. This was extremely frightening. My entire identity, everything I had to brag about, was wrapped up in this game. Outside of Poker, I knew very little about anything meaningful. Seriously. That’s not an exaggeration. Please don’t ever ask me anything about the metric system, or World Geography, or Avogadro’s constant. I wasn’t listening in that class, I was thinking through the hands I had played the night before.

Because of how scary the implications of this crisis were, I suppressed it, inertially barreling on.

At the beginning of my second semester, I had a breakdown. I lost $50,000 in a day, and $250,000 over the course of a month. This was most of my bankroll. There was a negative feedback loop — as I lost money, I became unhappy. As I became unhappy, I played more Poker to try to recover happiness, and lost more money because I wasn’t optimistic. I was playing scared.

This breakdown was the inflection point of my life. David Foster Wallace argues that there is a “rock bottom” that everyone must hit in order to recover from a sharp downswing in life. I hit that point when I was 18, and I don’t really want to elaborate in gross detail. I would rather just gloss over it, and say that on one side of the breakdown, I lost a ton of money, and on the other, I dropped school for the semester and started to consider how the hell I was going to rebuild my life.Around this time, Haseeb invited me to live with him. I tentatively accepted, figuring the only way to recover my former state of grace was to recover my money. But then my old friend Owen, who I met on the first day of kindergarten, told me he was transferring from WashU to UT, and was looking for a room mate. I decided to live with him, and the course of my life changed dramatically. It was the start of being able to disassociate myself from my identity as a Poker player.

Over the next few years, the online Poker world slowly crumbled, and eventually imploded on Black Friday. This was kind of scary to watch, even though I was trying to leave Poker behind. I had been considering it a fallback if school didn’t work out, but at the time, legalization of online Poker was looking increasingly bleak. From 2008 to 2010, I played on and off, with varying degrees of success. My best Poker memory from this span of time is playing $5/$10 heads-up on a bunch of tables against Scott Seiver. I remember thinking, “who is this asshole, and why does he keep shoving when I don’t want him to?” Sometime later, I saw a forum post where he mentioned that his match with me was really tough and interesting, and that’s validating.

Within a year of quitting Poker, I took my first Computer Science course on a whim. I have my brother Joel to thank for that suggestion. Shortly after discovering CS, I quit Poker altogether, and have only played live on an occasional basis since 2010.

From my low point in 2008, I have jumped many hurdles to recover from the psychological damage. I have had to find new hobbies and make new friends. So many times during this recovery, I fell hard and questioned why I ever even left Poker, where I had been comfortable. As Brian Wilson asks “Each time things start to happen again; I think I got something good going for myself, and what goes wrong?”

The fundament of what it’s like to have been a professional online poker player is that I am terrified that my livelihood will suddenly become boring or otherwise unsustainable. This was an awful experience to undergo when I was 18, but I would really hate to deal with it if I were too old to change course swiftly.

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*Prahlad Friedman, Patrik Antonius, Phil Ivey, Viktor Blom: for the most part these guys don’t really care what other people have to say about Poker, and never have. They don’t read books. They don’t ask others for help or criticism. They play their game, within their framework, and crush. They are CEO of their own company. People try to emulate them, and they fail. However, there is an entirely separate model to crushing Poker, involving joining a team. Some examples are:

  • Doyle Brunson, Sailor Roberts, and Amarillo Slim, who teamed up for protection from thugs, and were the first to really take odds into account in any formal mathematical fashion
  • The Crew, a group of tournament players that have since almost all faded into irrelevance
  • Team DeucesCracked, who are responsible for the show Two Months Two Million, and who I was loosely associated with
  • CardRunners, who were super successful but pushed the boundaries of team ethics by multi accounting and sharing hand histories
  • The Ship it Holla Ballas, a squad that includes Durrrr, David Benefield, Andrew Robl, and Phil Galfond; they had a book written about them awhile back

Originally published at www.quora.com.