My first contact with poker was a handheld five-card-draw video game that my dad gave me when we lived in Nevada. I think he bought it with comp points from some casino. He also got a handheld blackjack video game, but I think I spent more time with the poker one. It was a pretty standard video poker game where you played five card draw and got paid a certain amount if you had a pair of jacks or better. I don't remember the payouts so I couldn't say whether or not the game was +ev, but I do remember going busto countless times employing a strategy of just holding onto any pair or high card higher than a J and drawing trying to pair my high card or improve to two pair or trips or a boat. Six-year-old me had no concept of drawing to straights or flushes.
My parents eventually took that game away from me and I forgot about poker until college. One day I walked into the common area of my dorm and saw a bunch of my housemates playing poker. I basically sneered at them because I initially thought of it as simple gambling and thought they were just shuffling money amongst themselves randomly. But over the course of the year, I became more and more curious about the game and eventually I was convinced to sit at this $0.10/$0.20 no-limit texas hold 'em game with maximum buy-in of $10. Having basically no idea what I was doing, I broke even over my first several sessions. As I played, I began to realize that there was room for skill in this game and that application of skill could potentially be profitable.
My first poker teacher was a housemate of mine from San Diego who started the house game and claimed to have experience playing in casinos in California. He introduced me to the basic fundamental concepts of starting hand strength and being selective about which hands to play and playing aggressively with strong hands. I know that he also played online. This was during the golden age of PartyPoker and the post-Moneymaker poker boom. In retrospect, I'm skeptical of his tales of casino glory given that he spent hours and hours playing microstakes home games with us clowns, but I guess it's not unthinkable.
Playing what I thought was solid TAG poker but what I now realize was weak-tight meganit poker, I eked out wins in that game against my housemates who were playing recreationally.
In addition to the regular house game, I discovered a weekly tournament that was organized by some better players from across campus that usually had a $10 or $20 buyin and paid the top 4 or 5 out of 15-20 entrants. I was incredibly nervous the first time I ever played in this tournament, but I somehow binked first and thought I was rich with my $90 win. With my adrenaline pumping from the win, I promptly sat at a side game for unthinkable $0.25/$0.50 stakes and spewed it all away.
Over the course of college I continued to play in these home games. I often wonder how objectively hard these games were. I definitely frequently felt like I was in over my head against some of the other players, and I know that many of them ended up going pro or semi-pro and making five and six figures online and in Vegas. I sometimes suspect that those college games were some of the toughest I've ever played.
During this period, I investigated online poker and deposited a few times on some Party skins, but my basic pattern was to sign up for an account and deposit $50 and sit with my entire deposit at one table of NL50 and go busto within a few days, and then try to grind freerolls until I scraped up enough money to redeposit. I repeated this cycle maybe 3 or 4 times before giving up on online poker for the time being.
As most of the regulars from the home games I was playing graduated or dropped out to go to Vegas, the games became less and less frequent and by the time I finished college and started law school, I had more or less forgotten about poker.
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