My Poker Career (Chapter One)

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”.

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…

(IN THE NEXT EPISODE—HOW BEN STRAATE CHANGED MY LIFE)

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