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- An Ode to Poker
I’ve had a handful of true obsessions in my life – electronic music, financial markets, the startup I just left after seven years, poker, and, of course, a few women.
By definition, an obsession is not just something you enjoy doing. I love diving, skiing, wine, cooking, and many other things, but I can’t say I’ve ever been genuinely obsessed with them.
No, no…
An obsession is that terrorist who takes hold of your mind and doesn’t let go. You don’t have a say in the matter.
It’s that black hole that makes you forget to eat, doesn’t let you sleep late at night and is the first thing you think about when you wake up on Saturday morning (even when hungover…).
As Angie Stone’s classic goes: ”I can’t eat, I can’t sleep anymore…”
Last week, I saw someone tweeting praises about Abigail Shrier's book “Bad Therapy: Why Kids Aren’t Growing Up”. I haven’t read it yet, but it reminded me of one of my teenage obsessions, which I credit for a lot of my personal growth throughout the years.
It’s high time I wrote something about poker.
2004 – 2011 was the golden age of online poker.
As internet penetration in the developed world crossed 50% in the early 2000s, online platforms like PokerStars, Full Tilt Poker, SportingBet, and others introduced the game to the masses. Suddenly, you could sit on your couch and play with as little as a few dollars.
Something very similar occurred in the 2010s, when smartphone penetration enabled mobile trading apps, making trading feel like child’s play compared to the ‘90s vibe of some traditional brokers (e.g., Interactive Brokers).
But I digress…back to poker.
The World Series of Poker (WSOP), the annual mega tournament in Vegas, transformed from a bunch of sweaty guys trapped in a windowless casino into Burning Man—a yearly pilgrimage desired by millions.
The TV show High Stakes Poker launched in 2006 and created poker legends like Daniel Negreanu, Phil Ivey, Tom Dwan and many others.
Casino Royale also premiered in the fall of 2006, making poker irresistible. That, and being tied naked to a seat-less chair while an angry man swings a heavy rope under the chair (maybe something to discuss in the future)…
I was 14 at the time, starting 9th grade in high school. At the start of the school year, my classmate said - "I found this thing called No Limit Texas Hold'em poker...we can play it online. Check it out."
Long story short, I spent the next five years playing more than 200,000 hands online and in person. After high school, I also organised and played in tournaments at university in the UK and, more recently, several underground and home games in New York.
A few random moments in my life shifted my entire future trajectory, and this is undoubtedly one of them.
To this day, I still don't know why my mother gave me her debit card to open a poker account at the age of 14. She could have easily refused (and rightly so).
Maybe there is a parenting lesson about giving children and teenagers a certain level of freedom so they can learn to be more independent.
In any case, after some negotiations, I had a funded account and was ready to play.
Now what...?!
I will never forget losing my first $10 shortly after starting. For context, $10 in 2006 in Bulgaria was not insignificant for a 14-year-old from a middle-class family. My face turned red, my pulse exploded, and I started breathing heavily. I had to run to the restroom to calm down. “What is this strange feeling that I’m experiencing?! “
My mate and I were the first to start playing in our high school. The mania was real, though, and in the next 12 months, everyone around us was hooked. We were playing at school – between classes, in classes, skipping classes – organising home games, and joining ones at other schools.
This was the first thing I was utterly obsessed with in my teenage years. I would return from school, play 4-6 tables online for hours nonstop, watch poker videos, argue with my parents about skipping dinner, chat on forums, go to school, play more, talk about wins and bad beats, rinse and repeat...
The money I made was nothing outrageous, but it gave me independence as a teenager. I was personally financing my lifestyle. Money was no longer anything special that I feared - just life tokens you should respect but never fear.
All this gave me tremendous independence and perspective at an early age.
But poker only gives you what you are ready to take out of it. For most people, it’s just entertainment (similar to trading). It's something to give them an adrenaline rush, kill the time, and hopefully make a quick profit.
Immediate gratification trumps patience and discipline.
But despite its outside sex appeal, poker is a brutal game that grinds you out, and sooner rather than later, you have to face the music.
Poker pushes you out of your illusions, beyond your incorrect comfort zone — if, that is, you want to win. If you want to be a good player, you must acknowledge that you're not "due" — for good cards, good karma, good health, money, love, or whatever else it is.
Lessons
I’d lie if I said that all the lessons poker taught me were learnt in my teenage years.
Many things were internalised at the time, and only later, as I transitioned to financial markets and the real world, was I able to identify the frameworks.
Humans are stupid monkeys, so I don’t think we ever truly master these lessons. We merely get better at them, which makes all the difference.
In any case, here is a curated list of my favourite ones. I’ve kept them short and sweet, but in reality, each can be an individual post.
(If you want to dive deeper and read more stories, I strongly recommend Maria Konnikova’s phenomenal book The Biggest Bluff.)
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Play the Cards You Have, Not the Ones You Wish You Had
Part of what you must learn is how to handle mistakes and new facts that change the odds. Life, in part, is like a poker game, wherein you have to learn to quit sometimes when holding a much-loved hand.
Outside of some fundamental dynamics of the game, this is probably the first thing you get hit with, and yet, it’s one of the most difficult to master.
Simply put, just because you have great starting cards doesn’t mean things will stay that way—and vice versa. Poker is dynamic, and the situation can change in an instant.
Guess what, life is the same. The only constant is change.
Whether it’s your health, love life, friends, or career, what was once great can (and likely will) change, and you need to be able to recognise it, accept it, and adapt to it.
As my ex-boss would often say:
Stop saying, "It should be like this or like that." It makes no difference. IT IS! You have to deal with what is and not what could have been. What could have been is irrelevant. This is happening, so what does it mean?
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Thinking in Bets
You only think you know, as a matter of fact. And most of your actions are based on incomplete knowledge and you really don't know what it is all about, or what the purpose of the world is, or know a great deal of other things.
It is possible to live and not know.
Fundamentally, poker is a game where you never have all the answers and constantly dance with uncertainty.
But that cannot stop you from acting. You must keep making decisions – bet, raise, fold, all in. You have to keep moving.
You look at the situation, assess everything you know, and make calculated choices—hundreds of them per session.
In my opinion, one of the most essential life skills is being comfortable making small and big decisions (i.e., bets) without having all the answers. It is adjacent to ‘negative capability’ – “the willingness to embrace uncertainty, live with mystery, and make peace with ambiguity.”
You will never have all the information to see the whole picture, and continuously overthinking won’t help. Often, making a decision gives you new information, enabling you to understand the situation further.
In that sense, poker, like life, is a long game in which your goal is to continuously improve your decision-making skills using the limited information you have and a blend of intellect and intuition.
Life, like poker, is one long game, and there are going to be a lot of losses, even after making the best possible bets. We are going to do better, and be happier, if we start by recognizing that we'll never be sure of the future. That changes our task from trying to be right every time, an impossible job, to navigating our way through the uncertainty by calibrating our beliefs to move toward, little by little, a more accurate and objective representation of the world. With strategic foresight and perspective, that's manageable work. If we keep learning and calibrating, we might even get good at it.
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Master Your Emotions
It’s not about defeating your neuroses. It’s about becoming a connoisseur of them.
Before enlightenment, I was depressed; after enlightenment, I am still depressed, but the way I relate to the depression is different. And that makes all the difference.
I can’t say it much better than those two quotes.
You never really become a master of your emotions in the sense of eliminating them. It all boils down to self-awareness.
Even professional players, as well as people who have been meditating for 20 years, get emotional and angry.
We all feel the same. It’s what we do with the emotions that counts.
It’s about proactively observing your emotional state and navigating it.
If you are angry, don’t say or do something stupid in the moment. Walk it off. Sleep on it if you have to. See how you feel afterwards.
If you are getting bad beats (in poker or life), don’t complain or frame situations as “happening to you”.
You start getting into a defeatist mindset, which is the real poison. You begin missing opportunities, stop attempting new pursuits, become less valuable at work, and are less attractive to speak to.
Not to mention, there is nothing less sexy and seductive than a complainer who is not excited about anything in their life.
Subordinate your ego and get your head out of your ass.
Go for a workout, take a cold shower, journal, surround yourself with positive people, and do anything else that might take you out of the downward spiral.
If you face more formidable and persistent challenges, you might need to take more significant actions — choose a different game, move to a different city, change jobs, or choose a different romantic partner.
Mood follows action, not the other way around.
All this is part of what you can control, which is the next big lesson.
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Focus on What You Can Control
Chance is just chance: it is neither good nor bad nor personal. Without us to supply meaning, it's simple noise. The most we can do is learn to control what we can — our thinking, our decision processes, our reactions.
Despite popular belief and depiction in the media, poker is not sexy. It is an absolute grind—hours and hours of monotony punctuated by a few big hands (if you are lucky).
You can’t really force the cards. They don’t care. They have zero emotion. It’s all dumb chance, and it’s your job to adapt as best you can.
All you can do is:
Sit tight and stay patient.
Focus on your process and making good decisions.
Wait for the right moments.
Pick a few small wins here and there.
Don’t be reckless.
Stay mentally sharp and humble.
Be ready for the next opportunity.
Play the long game.
Investing is the same.
Julian Robertson has told me that the vast majority of his money was made on a handful of ideas, and the rest was just surviving.
And guess what? Life is no different, either. While many things can be achieved through sheer will and determination, sometimes you just have to grind it out. It’s not pretty, but it has to get done.
Sometimes, it’s just not the right time for that promotion, new business partnership, or that relationship with the person you like. Pushing it will not achieve your goal.
And then there are worse times when you are in a black hole of sorrow, self-pity, and despair—when everything feels stacked against you, and you are lost in the darkness.
When it’s darkest, there is only one cure—keep walking. Take the first step, then the next. Crawl if you have to, but keep moving forward.
You might be on the ground getting kicked by life, but you are not defeated until you give up mentally and physically. This is in your control.
And what do we say to defeat – Not today!
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Second (And Third) Order Thinking
No, no, chess is not a game. Chess is a well-defined form of computation. You may not be able to work out the answers, but in theory, there must be a solution, a right procedure in any position.
Now, real games, are not like that at all. Real life is not like that. Real life consists of bluffing, of little tactics of deception, of asking yourself what is the other man going to think I mean to do. And that is what games are about in my theory.
When you start playing poker, usually you only think about your cards.
“Do I have good cards or bad ones?”
As time passes, you start thinking about the cards your opponents might have.
Then, as you get better, you also start considering what cards your opponents might think you have based on your table image and how you’ve played the hand so far.
This second and third-order thinking is crucial in poker, business, and life in general.
What feels excellent on the surface might have detrimental consequences down the line. And vice versa, the painful step back you need to take might propel you to a much higher playing field.
That impulsive and passive-aggressive email you send to your colleague (or text to your partner) might feel very ego-satisfying in the moment, but the second and third-order effects are not fun.
(Oh, the emails and texts I’ve sent…my my…)
That said, there is something about spur-of-the-moment, quick, and impulsive action at the right time that I can’t really quantify. Sometimes, the speed of decision-making is more important than the quality.
Also, we can’t suck all the emotion and excitement out of life and calculate every action we take. Sometimes, we just have to live in the moment!
I guess it all depends on the context.
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Context Matters
This has quickly become one of my favourite mental models and one that drives most people mad.
We all want simple and clean answers to everything. If only there could be Ozempic for all matters of life (but without the side effects).
The painful truth is that the answer to almost anything in life is – “It depends”.
The more you play poker (even at an average level), the more you realise that while your cards are important, the context around them is even more important—your position, stack sizes, bet sizes, opponents’ style, history against certain opponents, tells, etc.
You should be adapting the way you play based on the context around the table.
There are so many details about each hand that you can’t just say, “This is how you play these cards”.
It doesn’t work in poker, it doesn’t work in business, it doesn’t work in relationships, and it doesn’t work in life in general (with some exceptions).
Of course, poker (and life) is about making decisions, not about endless pontification and mental masturbation.
Look around, assess the context, and make a decision.
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Pick the Right Games
Poker has taught me the pitfalls of the gamble, the necessity of selecting games so that you have an edge so that you have a statistical advantage so that your skill can win.
It has taught me to avoid situations where skill falls by the wayside, where you have to rely on variance alone to break your way because you simply can't measure up otherwise.
A friend introduced me to an underground game in New York last year. I started playing semi-regularly.
Weeks later, after the initial excitement disappeared, I realised this was not the right game for me. The stakes were too high, and there were too many regulars.
Poker is not just about playing the right cards but also picking the right games.
It’s not that I didn’t have the money to play at these stakes, but I needed some time to build the right muscles to play at these levels. I was not making the right decisions because I was not used to playing at these stakes. I had to go down a step or two so I could build up my game and come back up.
When Andre Agassi’s tennis career crumbled in 1997, he went from playing Grand Slam finals to entry-level tournaments with players looking to break into the top tier. He had to start small and rebuild his mental and physical game.
The same applies to many other pursuits. If you want to start doing X, don’t compare yourself to the person who’s been doing it weekly for the last ten years. It will only bring you misery.
Start small, build a habit, stay consistent, and only measure against your past self.
Play your own game.
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Get Used to Competition and Assholes
This one is rather simple.
Life is one long string of small and large competitive pursuits – getting into the right schools, excelling at your career, finding the right love partner, etc.
The sooner you get used to competing—against other opponents and your imposter syndrome—the better.
That is why playing a sport is so crucial for kids at a young age (and why participation trophies are BS). You have to learn to compete, and yes, sometimes lose, and deal with that loss.
What is just as inevitable (if not more) as competition is having to deal with assholes. Life is full of them.
Often, the right approach is to do it with a smile instead of listening to the little angry voice inside your head. Indeed, that is the case at the poker table, where you only win if you take the opponent’s money.
We must learn to mingle with people we don’t like and are competing against.
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There are many other lessons from poker—some more nuanced, some more technical—that I’ve excluded from this post.
Who wants to read about math and risk management anyway?!
Whether you are a poker player or a competitor in the game of life, bonne chance!
And if Lady Fortuna, that cruel mistress, turns against you - keep walking and tell her, “Not today!”
G.
Vibes
I am behind on my book count for the year, but I’ve definitely compensated with quality.
Given the topic of this post, it only makes sense to highlight this masterpiece.
 | The MANIAC is a fictionalised biography (written as a novel) of John von Neumann, the polymath behind some of the most important breakthroughs in math, physics and computer science, written by a Chilean author I had never heard of. It grabbed my attention immediately. |
It’s really hard to describe this book, but I think it's some of the best writing I’ve experienced in a while.
Each chapter is written from the point of view of a different person in von Neumann’s life and masterfully blends facts with great storytelling.
Some chapters are long-form text, others read like a short poem. There is enough technical jargon for the geeks, and yet it is very approachable for simpletons like me.
The whole book is a mini-puzzle that keeps you engaged throughout. Even the title is somewhat deceptive and contains multiple meanings.
After telling von Neumann’s life story, the book fast-forwards to more recent decades and tells the story of how his breakthroughs drove the current AI revolution and what it all might mean for humanity.
The book is yet another reminder that some people are just made differently. They are maniacs from the moment they are born, and competing against them is likely the wrong thing to do. Pick a different game.
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I’m currently in Sofia for month 1 of my sabbatical, and I’m brushing up on my tennis and enjoying my time with friends and family.
Here is a mix I recorded b2b with a friend to celebrate the end of winter.
There is a bit of everything in there — an eclectic mix of disco, house classics, house, and some trance vibes for good measure.
Enjoy!
