Lessons I Learned From Poker

Yesterday in the Twitter Q&A that I give every Thursday @GiraffesCanSwim asked, “what did you learn from playing poker?” I gave a 140 character answer. Something like, “you learn quickly that all your friends lie to you all the time in order to steal your money.”

But I’ve been thinking a little more about it.

First off, I spent 365 days straight playing poker in 1998-1999, including the night my first kid was born. Including my birthday and my anniversary.Including Christmas and Easter and whatever Jewish holidays occurred during this time.


I used to play at the Mayfair Club on 24th Street and the Diamond Club on 20th Street, both illegal clubs. The Mayfair would close at 4am and some stragglers would head over to the Diamond, which never seemed to close. Ultimately both were closed down permanently by Giuliani. I had a house in Atlantic City and would play there on the weekends. I’d go via helicopter Fridays at 5pm and fly back on Sunday night.  Occasionally I would go to Las Vegas and play. This was pre-Internet poker, TV poker, and pre the big money that is in poker now.

The only time life had any color in it for me during this period was when I was sitting around a table, chips in front of me, cards getting dealt, and guys with nothing else in their lives making jokes back and forth while everyone tried to take everyone else’s money.

A few weeks ago, my wife and I ran into the guy who had once owned the Diamond Club. Oddly, we were at a party for the Wall St Journal on some rooftop bar all the way west in Manhattan. The Diamond Club guy wouldn’t give us a straight answer for why he was at the party. All he kept doing was talking to my wife, pointing at me, and saying “this guy was the lowest down cheap hustler there was. He’s a born criminal. Watch out for him.”

I told her later he was kidding around. But the way he said it flattered me actually. Poker is a charismatic game. People who are larger than life play poker and make their living from playing  games and hustling. That’s what’s attractive about it. That’s part of what’s attractive about being an entrepreneur, or doing anything where you eat only what you kill and you survive in life only on your instincts.

I played because I was unhappy doing anything else. I played because I loved games. I played because I thought everyone at the table was smart and witty and I liked the repartee that was always darting back and forth. I wanted to be friends with these people.I had just sold my company and  I hadn’t yet lost all my money so it wasn’t the money that brought me to the table. It was the game. The charisma. The excitement. The way people adeptly played with the chips in front of them, or threw their cards into the pot when they were out, the language of motion, the gestures, the beautiful ballet of every movement in the game.

The only time I played after those 365 days was one time I went up to Murder Inc Records about ten years later and all the same guys were playing there as if they had never moved but the table had teleported over. Irv Gotti, therapper who owned Murder Inc, won about $2000 off of me in a big pot and I left after that and didn’t play again. I went to the game with Lenny Barshack who had just sold a poker sofware company.

(Irv Gotti)

On the way there Lenny told me how one month after he sold his company he had a heart attack on a ski slope and had officially died.

Running a company is like being mugged. When you are mugged you get a jolt of adrenaline that SCREAMS to your body: FIGHT! or FLIGHT! But when you run a company its like you are constantly being mugged but you still stare at the computer all day. So the adrenaline builds up with nowhere to go. All the adrenaline does is keep you alive because otherwise you’d probably die from being mugged so much.

Once the stress is over (in Lenny’s case: when he sold his company) the adrenaline hits you full force. So Lenny had a heart attack one month after he sold his company and his heart went to zero for at least two minutes.  Only a smart doctor brought him back to life and less than a month later we were heading over to Murder Inc Records so I could lose that final pot and then never play poker again. Poker sucks. Here’s why:

A) Everyone at the table is your friend but they are all lying to you to steal your money. I wanted to be around these grubby guys more than I wanted to be around my wife and newborn. More than I wanted to be around real friends. More than I wanted to be around my work colleagues or my family.  I don’t know why. Something was wrong with me. All day long I read books about poker, and all night I would play.

I felt for the first time in years like I had a group of “buddies”. Like I was one of the guys.

Here’s the problem. We all were buddies but we spent the entire night lying and trying to take money from each other. You could think, “oh, its just a game”. But I watched some of my friends go broke and cry and borrow and beg and steal. Nobody liked losing all of their money. I watched lawyers get disbarred trying to steal enough money to play poker. I saw guys escape to Israel to avoid extradition when they lost their IRS money to the poker table.

And nobody really cared about them. A guy would stop showing up and then he would be forgotten. Nobody really cared about me. We were friends. Until we weren’t. And that was that.

B) If you find yourself playing a game all day, even Angry Birds, or Poker, or Chess, ask yourself: what might be wrong in my life? I was happy I had sold my business, but maybe I wasn’t happy working for a boss now. Or maybe I wasn’t happy in marriage. Or maybe I wasn’t happy that all of my friends were work-related and I had lost every other friend. An addiction is a symptom. Find the real genetic roots of what is going on.

By the way, not every game player is an addict. Some people make a good living at these games. You have to judge for yourself whether you are a professional or an addict. The professionals win money from the addicts who win money from the amateurs.

C) As for poker itself, and this goes for all sorts of ways to making money: you want to sit immediately to the left of the dumbest, richest person at the table. He bets, then you raise – no matter what is in your hand.  Then everyone else is out and it’s just you and him. In the long run you get all his money. This applies to every business endeavor.

D) Poker is a skill game pretending to be a chance game. Many things in life are like that: sales, negotiating, entrepreneurship, etc. All of these things have the element of chance in them but the ones who are skillful will take all the money from the ones who aren’t. The problem is: most people think they are good because it’s hard to rank yourself and many people go into denial when they lose money. They tell people, “oh, I broke even” when they lost money most of the night. How do you get better at any skill game:

  • Read as many books as you can written by players  better than you
  • Study hands and the analysis of those hands
  • Study and think about your mistakes. Don’t regret your mistakes. You’ll always make mistakes. The better you are, the less mistakes you make. The only way to get better is to thoroughly analyze your mistakes. So the more mistakes you have, the more opportunities you have to get better. Of course, this applies to everything you do in life.
  • Talk to people smarter than you. Try to learn from them anything you can.

E) Conspiracy theory.  If you have a bad hand and someone raises you and someone then raises him, you’re going to most likely need luck to win. Back out and try again later.

There’s a theory in programming chess computers that applies to other areas of life, including this one. It’s called “conspiracy theory”. If too many things have to happen in order to bring about the situation you want, then back out of it and try again later.

For instance, if you are in love with a girl but she has three kids, is unhappily married, and lives 5000 miles away, then at least three things have to conspire simultaneously for you to ever end up with that girl. In poker, if you are facing two potential hands that are better than yours, plus you have to wait for two more rounds of betting to occur (where you can lose more money), and you are waiting for very specific cards that are unlikely to arrive, then too many things have to conspire to make the hand work. For every situation you want, determine your “conspiracy number” where you back down if that number of items has to conspire together. A conspiracy number of “three” in most things is enough for me to back down.

F) Be the Bank. I was once in Atlantic City and I was playing at a table with one of the best players I knew, Joe. Another guy at the table needed chips and Joe said, “I’ll sell you some of my chips.” So the guy handed over money and Joe sold him some of his chips (an activity that is illegal in Atlantic  City but it was 4 in the morning and nobody cared.) I asked Joe later why he did that. Joe said, “Always be the bank. If you’re the source of everything at the table then it makes it harder for them to bet against you.” This is a weird version of “Give and You Shall Receive” but it works.

In September, 1999, one year to the day after I started playing every day, I stopped. I started another company instead and lost millions at it. Perhaps then I realized that all of life is a game of high stakes poker. And on every hand you risk losing everything you’ve ever worked hard for. Or maybe the final thing I learned is that it’s all just a game. And eventually you can just stop playing. A first kiss is better than winning any hand.

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  • Quietjim

    Awesome! Can’t believe you sat out the poker boom both live and online. Probably helped that you were the only one at the table rolled for the stakes you were playing. Hey, Louis C.K. just made 200k selling his concert dvd directly on the web for 5 bucks a pop. Think he is a fan.

  • Steve

    Someone (you?) needs to make a movie of your life.

  • Anthony

    This blog is total wank, UNSUBSCRIBE!

    Just kidding Altucher.

    2012 is going to be rough for a lot of people. The level of social unrest, in “first world countries”, will be unprecedented in our lifetime. Loads of new material for you coming soon.

    2012 is going to be a great time to make money when everyone else is playing at sheep.

  • Most excellent a post. I was a video game addict earlier this year; I was depressed and would spend 12-18 hour days playing a particular video game. Meanwhile, my life fell to pieces around me. I didn’t make any money either, I just lost what I had. It served me well though, taught me that no matter how bad things got, you can get right back to the top just as easily as you fell to the bottom. Many times the things in life we lose aren’t lost in a single hand of poker, but consistently every day, bit by bit.

  • Horses and stocks. The anti-social person’s way to be a player and have equal opportunity for addiction and action.

    I tried roulette, but too many other people and way too much cigarette smoke.

    Poker, though is fascinating and is based on same thing spurring recent stock market activity.

    It’s all about rumors, except in poker the rumors stay confined in the player’s mind based on verbal and non-verbal cues. Other players, besides dealing with the rumors running through their mind try to discover what rumors are going on in the minds of everyone else at the table.

  • question: in the example of the married woman, what are the 3 things? I only see 2. Divorce and moving.

    • Parvaze

      The third is that the kids have to like you, or at least put up with you

    • Anonymous

      Forget the number. The point is a good one and it is clear. If a number of things have to happen in order for you to win a particular hand, just give up and fold. If you keep betting based on hope, you will lose big. Kapish?

  • You don’t have to feel bad about missing the birth of your first baby, kids never remember that part.  :)
    If you are alive you can’t stop playing.  There is no off ramp. No exit. No opting out. Not even a decent time-out spot. 

    All you can do is try to pick the game you want to play – even that can prove to be difficult.

    • Jerry_Lucke

      kids don’t remember, but wifes become ex-wifes and they never forget!

      • I don’t think it has much to do with kids or exes but more with you.

      • lol – you’ve got that right, but at least if it’s an “ex” – eventually their scorn means nothing.

        ( I would have divorced him the next day – that is if he wasn’t so damn rich.)

  • Jerry_Lucke

    Greatest thrill in the world is playing and winning; second greatest is playing and losing! anything wrong with me?

  • Great last sentence.

    The rest weren’t bad either.


    edit: however, now that I think about it, your first kiss only comes once. after that, is each poker hand superior?

    • Anonymous

      I think that every time I kissed a new person it was a first kiss. That led up to the magnificent first kiss of my soul mate. Once I had that memorized, I preserve that slow motion memory that always makes me smile as my first kiss.

  • P Jaunne


    ““you learn quickly that all your friends lie to you all the time in
    order to steal your money.”  sometimes it feels that way in business too. 
    People try to steal your best idea, your customers, your best employee, your inventory, on and on…


    “Running a company is like being mugged.” 

    never thought of it that way before but geeez that is so true!

  • By now I’m convinced that you are not only an idea machine but also a story machine! Unique, crisp, captivating stories, I’m sure your kids enjoy your stories too. Brilliant post!

  • Maggie

    “For instance, if you are in love with a girl but she has three kids, is
    unhappily married, and lives 5000 miles away, then at least three things
    have to conspire simultaneously for you to ever end up with that girl.”

    Three things have already conspired for you not to end up with this girl. How did you manage to fall in love with a girl with such unsuitable connections and circumstance?

    Specifically, what are the three things that would have to happen for you to get together with this woman? Is infanticide one of them or just abandonment? And why do they have to happen simultaneously?

    How far would you go, just to get laid, in your fantasies? What does this have to do with obsessively playing a card game?

    Love is it? Unbelievable, I just had this same exact conversation with my ex-husband this morning. Why do I take his calls?

    • From your last paragraph sounds like you’re reading your own stuff into just a basic example I was providing.

      I agree: sounds like you shouldn’t take your ex-husband’s calls. Life much easier that way.

      • Maggie

        I did read my own stuff into it. I think it’s polite to do so to a certain extent. Now, I’m curious as to why you created this particular basic example. Your basic example is far more interesting than poker. That one little, basic example is Greek tragedy.

        • Haha, yes. Perhaps I projected my own past experiences into it as well.

    • Guest

      It’s tough to imagine a person with romantic options would end up with a woman who already had a child. The guy in this example must be a real catch. Maybe his blog would be a good read.

  • Love this article James.

    The last sentence is pure awesomeness.

    Someday when I buy a yacht to sail around the world, I plan to name her “The Pursuit of Happiness” and thanks to this article, I’m going to name the tender dingy “First Kiss”.

  • Parvaze

    I’ve never heard of conspiracy theory, however, as a serial entrepreneur I can tell you that tip right there is gold. 

  • Anonymous

    @TheAcsMan:disqus …….WOW…Тhis is сrаzу…Мy friеnd`s sistеr mакеs 78/hr оn thе intеrnеt. Shе hаs bееn unеmрlоуеd fоr 11 mоnths but lаst mоnth hеr incоmе wаs 7985$ јust wоrкing оn thе РС fоr а fеw hоurs. Read about it here ,………http://alturl.com/jf5wz

  • Dowdog1


    How did the dumb guy get so rich?  Maybe there’s hope for me

  • Life is most certainly NOT a game of high stakes poker. 

    Playing poker programs a skewed version of reality into the mind of the player.  It causes players to believe that they are either winners or losers.  There is no in-between. 

    The fact is, this is not the way the world works.  When I sell a product I make money.  The buyer gets value from the product.  Ideally the buyer gets more benefit than what they paid and I get more income than the cost to produce/deliver.

    We both win and nobody loses. 

    Unfortunately, players take their winner/loser mindset from the poker table to their home and apply it to other areas of life.  It kills relationships by producing a loser when there is no need for one to exist.  It kills business by encouraging cut-throat, win-at-all-cost practices and denies the reality that happy customers expand the size of the pot. 

    • This is a valid point. However, overcoming a “losing” mindset could prove beneficial in the long run. Obstacles do breed opportunities as James mentioned.

      • Absolutely, overcoming a “losing” mindset would indeed prove beneficial. 

        Overcoming the dualistic win/lose mindset would prove even more beneficial. 

        And choosing the nondual mindset where winning and losing are not even on the table… now that’s a sure-fire winner.

        • Hey, I’m into Buddhism so you don’t have to sell me on the advantages of non-duality. Can be a challenge to remember that when you’re living in samsara though.

    • Oz

      No argument about life not being a high stakes poker game: it is only a game after all. But playing poker at a high level certainly teaches important things that apply to life, like 1) don’t be results oriented, make good decisions and the results will follow, 2) stressful situations bring out people’s true character, and 3) an opportunity exists when there are a lot of “experts” that hold a unified position. The reality of the situation is almost always deeper that we give credit for.

      • No doubt there are many valuable lessons to be learned from poker.  There is some awfully heavy baggage that goes along with it too.  It’s important to acknowledge that the baggage exists as well as the lessons. 

      • Anonymous

        What??? “Don’t be results oriented…”. Sorry but you have just reversed what every successful businessman has ever said or written. How do you know if you are making “good decisions” if you don’t know what results you are shooting for?

        • KyfhoMyoba

          Rather than being results oriented, be process oriented.

          • Gumnaam

            What the hell does it mean?

        • Mikeosborne

          You need some other way to measure decisions other than the immediate results, especially when the results are based on events outside of your control. In poker, we analyze whether the decision was correct depending on a number of factors that boil down to the math of the situation. Just because you won the pot doesn’t mean your decisions were good and vise versa.

          This lesson applies to life (and business) in lots of ways. Just because you didn’t make the sale doesn’t necessarily mean you have a problem with your sales skills. Just because you happened to sell a stock at it’s peak doesn’t necessarily mean you have market timing figured out. Etc, etc.

    • Sense Schooler

      Sure the game is rigged, but if you don’t play, you can’t win – R. Heinlen

  • I’ve played in a few high stakes poker games (relatively speaking I’m sure) and more commonly games amongst friends. It’s a competitive game and egos almost always clash. 

    If you know how to maintain a healthy perspective on what’s going on Poker is a really fun game. Plus, whenever I won I was usually pretty generous to those around me since I got all this “free” money.

  • Anonymous

    The nurses and doctors wigged out when my parents told them my father was going to be in the delivery room. This was Miami in the late 70’s/early 80’s. And no drugs. Mom’s choice.

    After the last, Dad ushers me at 4 and my brother at 2 into the hospital room. Mom yelps out that I have chicken pox! Dad now understands my sluggishness during morning roll-down-the- grassy-hill-happy-fun-time. At least I got a peek at little sister through the glass in baby storage on the way out.

    Now, too much internet use is reducing my life stories. Working part-time at home is new, lonely, and scary. Like many here, I am struggling to create a blackout period from personal use. I know I can do so many things, but I just sit and read about it. Seriously though, don’t be jealous… cause I’m livin’ in the red, welllll I’m livin’ in the USA, and I ain’t gotttt a dime to pay, hey yaaaaaa (fades out). Ah, I love a good soundtrack.

    My husband has terrible luck, so our adventures often deal with ridiculous obstacles. We just laugh and enjoy telling the stories. As for my new found alone time, I resolve to do something positive every day. Every ballerina tip toe and fuzzy bunny hop forward counts.

  • Brad

    I have been a professional poker player for 7 years (I’m 27) and I agree with most of what you said. The thing is, people go to poker games for multiple reasons. Before black Friday, the only reason I went to home games was for the camaraderie. Being at home staring at 2 huge monitors while playing 8 tables at a time can be a lonely endeavor.

    After I lost the ability to play online poker, playing at home games (as well as leaving my family for weeks at a time) has become a necessity and I’ve realized how much I loathe the game. It’s become boring and monotonous and winning/losing thousands of dollars no longer has any affect on me.

    I have a website being built (I don’t know the first thing about coding or business … However one partner is building and the other is a product manager, so I think of myself as the ideas guy) and the aspect I love and completely forgot about all these years is how fun it can be to learn. That feeling before a new endeavor when the possibilities seem to be limitless (although I always realize there are, of course, limits).

    James, just wanted you to know I love your blog and can relate to it in many ways. This year has been one of those years for me where I’m laying on the floor bleeding with a very small amount of hope. I’m hoping I can pick myself up, do the daily practice, and start something completely new … Leaving poker in the dust. Take care,


  • I like Robert Ringer’s take on the game; that one day it will be over, and you won’t get to play anymore…so you might as well enjoy playing!  But the business game is brutal, and it does feel like getting mugged every day, and making peace with who you really are, and loving that person cannot be priced in chips or cash.  It’s a different game, and, for me, one that’s played entirely in my head.  One of my goals is to play all of life’s games the same way: with integrity, dignity and consistency.  Thanks for another great post, James!

  • Penny

    I loved what you said about the ballet of gestures and the charisma of the game.  That’s the part that attracts me – not the sterile, anonymous staring at a screen type of playing.

    And then there’s the joy of focus, the swimming through hours without any sense of time.  Bliss.

    You seem more negative about poker than I expected and maybe that has more to do with what was going on in your life at the time (the marriage problem, the kids, the business stress).

    What about all the good things poker can teach such as the ability to make correct decisions under the gun, to read people, to control your emotions and to manage risk  – all skills that any business person needs to develop?

    I also think there’s something very creative about players who play a high level game.  Maybe that’s why artists are drawn to the game.  Did you know Norman Mailer took up the game in the last years or his life?

    As for its therapeutic benefits, I credit poker with pulling Doyle through a life threatening bout of cancer (had to get back into the game – (though maybe his wife would tell you it was the prayer circles that pulled him through).

    One famous player whose name escapes me right now said that poker cured his lifelong depression where 10 years of psychoanalysis had failed.

    Here’s to passion and obsession – wherever you may find it. 

  • Anonymous

    “The professionals win money from the addicts who win money from the amateurs.”

    Exactly. Awesome post.

  • BarrieAbalard

    “If you find yourself playing a game all day, even Angry Birds, or Poker, or Chess, ask yourself: what might be wrong in my life?”

    My husband needs to read this post.

    • JP Morgenthal

      You may not like the outcome, but perhaps it will be more honest than the current situation. One thing that James left out about poker is that it’s a great training ground for learning confrontation. If you can reach professional levels in poker, you’ve mastered confrontation. People who sit in front of a screen playing games for hours are trying to quiet the mind because they are typically avoiding a difficult confrontation.

  • Leti Watson

    What does any of this have to do with James’s new comic book now being available for sale on Amazon and B&N? Seriously, your missing the internet poker boom is like imagining Edison reading by candlelight.

    • Well, I was doing other things. But poker is poker. The lessons are timeless.

  • Brad

    Great post as usual.

    One thing — you want to sit to the *right* of the “fish” (dumbest, richest person) at the table. That’s the only way you can raise after he bets!

  • Michael Bartley

    “A first kiss is better than winning any hand”…..I like it, I will think about it.

  • Leti Watson

    But a cool six screen display with ten tables open all tricked out with the HEM stats for ten different variables had your name all over it. J/k. At least you also got to miss the eternal internet poker is rigged debate!

  • Poker Pro

    I’m a professional poker player, and this article is written as if the guy never played before.  He di get it right that everyone is always lying and stealing to get everyone else’s money.  I cant understand what the hell he was saying besides that statement.

  • Thanks for the “conspiracy theory” idea. I developed a corollary “Half the Money in Twice the Time” response to would-be small business people who get carried away with “if this happens, and then I can do that, and then this other thing happens…” and so forth with the result being that they can make good money. I always tell them that if they can afford to make half what they expected in twice the time, go for it. I’ve usually been pretty close to right on.

  • Chazmuze

    According to philosopher/Theologian R.J. Rushdoony, the desire to play poker and other games where the odds are against you in the long haul is a subconscious desire to lose.  According to the Christian Theistic worldview, this is due to being guilty before God without Christ’s substitutionary work on one’s behalf.  Losing is a form of guilt atonement, yet it is only temporary to the mind and conscious. 

    • Michael M.

      Sounds like Rushdoony was a lousy poker player.

  • Poker is a people game pretending to be a skill game. Once you have mastered the statistics… the only thing left is the interaction between the people at the table. 

    Poker is a game people play. Life is about people. Poker is about people.

  • Mildred Love48

    Learning from other people’s mistakes works better

  • My grandfather was a bridge hustler.  He and his law partner played at the city Republican Club against rich businessmen.  Rich businessmen who thought they played bridge better than two good ol’ boys named Fred and Clyde; they didn’t.  The secret of hustling is “You can shear a sheep many times but skin him only once.”  If you don’t play bridge you probably don’t know that bridge players are ranked; they are supposed to tell opponents their rank. Fred never let anyone know his true ability.  Hustling took over Fred’s life. It was an addiction; fortunately he made enough money from the rich amateurs to survive the Depression.  

  • Conspiracy theory of 3— absolute brilliance. Thanks for sharing that, James!

  • Sense Schooler

    okay, so LOTTO – 6 things need to happen, POWERBALL – i’m not sure how to calculate that one, but >6. therefore, if you do want to play the lottery, play the PICK 3!!!!!

  • Bobster86

    The players are those rotten TV poker shows are ugly and obnoxious. It appears you didn’t bring up the average. ;-)

    • Bobster86

      The players on those rotten TV poker shows are ugly and obnoxious. It appears you didn’t bring up the average. ;-)

  • I thought E was the best Lesson. Thanks James.

  • Hugh Lancaster

    “– read as many books as you can written by players  better than you– study hands and the analysis of those hands – study and think about your mistakes. Don’t
    regret your mistakes. You’ll always make mistakes. The better you are,
    the less mistakes you make. The only way to get better is to thoroughly
    analyze your mistakes. So the more mistakes you have, the more
    opportunities you have to get better. Of course, this applies to
    everything you do in life.– talk to people smarter than you. Try to learn from them anything you can.”

    Sounds like trading stocks.

  • Statspotting

    Poker is skill or chance? Some analysis here :


  • Its all about the darwin principle of survival of the fittest james. Nice post! Reminds me of the movie limitless.
    See: http://bit.ly/s12GGw

  • I learnt a lot of lessons from blackjack and Roulette.Never again. 


  • Jesse

    I couldnt find to much other information on this article, so it was nice to discover this one. I will be back to look at some other posts that you have another time.