My uncle taught us many poker games with play money chips as kids, but I started playing No Limit Texas Hold'em for real in 2014 as a freshman in Baker dorm. A group of mostly Sloan business students would come once or twice a week to play in the empty cafeteria after dinner was cleared.
Everyone would buy in for $60 - $300. Blinds were $1-$2. They made an exception for me the first few games as I was just learning, more of a timid spectator than a competitor, and I didn't realize how buying in for $20 or $40 was to my immense disadvantage. But it was fun and cool to learn a new thing.
Poker players usually do a great job welcoming beginners, with lots of friendly smiles, and I soon learnt why... Every time I sat down, I ended up donating all my money!
Years later, I put in a bit more effort to consider how the game actually works. I got good enough to expect to break even, so I'd feel comfortable sitting down at a table in Vegas and sipping free drinks to pass the time. Even so, I've probably lost 3-4 digit sums each year on poker...until now with this 5-digit win.
The turning point came a year and a half earlier, in 2023 while living in Quito. I bought into a big annual underground tournament for $225, lost, and then foolishly tried again 5 more times. Of those, I made it to the final table once, but got unlucky with AA against AJs, and my opponent hit his flush to knock me out 1 spot away from qualifying to the next round.
Each entry to that tournament came with a raffle ticket. I bought in so many times that I ended up winning a moped in the lottery at the end!
Riding the moped home eased the pain of losing, but to say "I won a motorcycle at a poker tournament" felt like a total bluff. Having made it to the final table in one of those qualifying rounds, and having played in smaller home games with some of the other competitors, I knew I was close enough in skill that with a bit of serious study, I could do much better in the future.
I looked up some coaches, had consultation calls, and ultimately bought a package of 5 lessons from Thiago. He's a Brazilian who has won over $100k online. With his help, I managed to turn my own steady profit to the tune of a couple hundred bucks in a fairly competitive environment. It was a great investment.
Each green dot in the above chart represents a tournament I played online from 2023-2024, mostly at the $1 - $3 entry fee level. After completing a few, I would find my best performance to download and send Thiago the hand history play-by-play. We'd hop on Discord for an hour and he'd zip through the whole thing, stopping at critical moments or mistakes to analyze what could have been done better.
As you can see in the chart, big jumps represent times I made the final table and got a relatively large top-10 prize. Variance and the power law are clearly at play.
Thiago's coaching was incredibly information dense, and after our first couple sessions, it gave me the boost I needed. Honestly, I don't think my skill level changed much over the course of the graph. I probably absorbed most of Thiago's insights during the first ten tournaments above.
I'd consider my level of play fairly consistent in a win versus a loss, so downswing patterns—such as from tournaments 25 to 50—didn't correlate that strongly with mistakes for me. It goes without saying that there are always areas to improve upon. But most of "the secret" is that good results simply take time, consistent effort, and patience with a lot of bad results.
I've only played a very small number of live tournaments, but I have to imagine a hypothetical winnings chart would look similar to my online results. Therefore I consider this recent big prize very lucky. It just happened that I placed in a tournament with a high $500 entry fee and a lot of local participants creating a large total prize pool.
For the most part, I stick to in-person cash games and have fun socializing while playing. From the Scale AI office to $0.10-$0.20 in Vilcabamba, from Nagaworld in Cambodia to $5-$10 at The Commerce in LA (Ks cracked by Qs for $2k on my first hand)... I've never played a single game of poker where my objective was to walk away richer.
With both of my latest companies, the team has regularly enjoyed poker as one of our favorite activities during our weekly online social hour. I recommend it to all my friends and family as the only thing I'll play in a casino. You are actively engaged in decision-making while competing against other players, as opposed to sadly pressing a gamble button with 49% - 51% probabilities the house has set against you.
Compared to chess, my other game of passion, poker does a much better job mapping to reality. Others have spoken at length about various benefits and life lessons, so I'll just point to this awesome surprise talk by Jenny Just on "the female market correction and Poker Power" which I saw live and loved at the All-In Summit in 2023. I also remember this blog post, "Your Life Is Tetris. Stop Playing It Like Chess." which applies to poker too.
For any interested players out there, I'll end with a few rules of thumb that you can try out for yourself when you play. Exceptions may be applied as you get more advanced.
Only play hands with a value of 10 or higher, for both of your cards. Be patient, it's OK to play "Texas Fold'em".
Pre-flop, always open with a raise or fold. Never call, unless someone has raised before you and even then, only call if you're confident in what you're doing. Always open raise the same amount above the big blind, for example 2.2 BB, no matter what your hand.
Ideally with a strong hand, you want to bet in order to isolate your opponent and make everyone else fold, so you only play against one other person.
If you have raised, and your opponent calls, then the flop comes and one of the cards is a face-card like a K, you can continue betting. You have a stronger range, since if they didn't re-raise you then it's more likely you have AK, not them. They don't have KK or AA since then they would have re-raised pre-flop. In these situations, it's often more about your position and the story of your hand, rather than your actual two cards.
With the blinds, especially if your cards are suited, you can call a min-raise once 2 or more other players are also in the pot and you'll see the flop. Similarly with two consecutive cards or even an 8-10, since you could flop a straight and you'll get a decent price to see it. Of course, don't do this if your stack is less than 20 BB.
You have to go all-in with decent hands like KJs when the stacks are getting short, as in you have 15BB or less. You block AK, KK, and other strong potential calling hands, and you're going to make 10% when everyone else folds.
When nearing the final table, each pay jump means busting out costs you relatively more money. So be more conservative, and even consider folding pocket pairs like JJ. I made this mistake to get knocked out against the 2nd place finisher at 2am, stupidly calling an all-in with pocket 2s against snowmen. Be a cockroach, you just want to survive.
Read the room and mind the gaps. If 2 people in front of you have confidently raised each other, and another goes all-in over the top, you should probably fold. It's likely one of them has QQ, KK, or AA.
In general, try to play as close to optimal as possible. Deviate only when you have good reason, e.g. you see a specific opponent making a specific kind of mistake. Don't bluff unless you know your opponent is a decent player capable of folding, or just very nitty.
