Life is Like a Game. Here's How You Master ANY Game

life is like a game

I swept the chess pieces to the floor and ran out. The pieces were still popping around on the ground like popcorn when I left the room where the match was being played. It was my school versus some other school. I had lost.

I didn’t care at all about the rest of my team. Losers.

The coach of the team, an English teacher, ran out after me but he was sort of laughing. “Stop,” he said. “Wait.”

But I didn’t want to. I had lost. I was worthless. I hated myself. I hated everyone. The rest of my team was laughing. I could hear them. Laughing at me. The other team was in shock.

I am a sore loser. It’s not that I’m so competitive with others. But I’m competitive with myself. I like to do better than I did before. Sometimes that means something very bad: I like to be perfect at the things I’m interested in.

Of course, it’s impossible to be perfect.

I had nightmares that night. My dad opened my door at 3 in the morning and asked if I were ok. “No”, and there was nothing he could do.

I didn’t go to school the next day or the next. I was a loser with acne and now a bad chess player.

A year later I was the highest ranking under 20 year old in my state. And then I basically stopped playing except when my life was in big transition in the 90s and then I played quite a bit.

But I played other games, during other transitions. I always played games to escape the bad things that were happening in my life.

The best games are a metaphor for life. So I would always escape my life (a bad relationship, a bad trade, a bad business, feelings of being useless, etc) by playing games.

I played a lot of the game “Go”, when I was burntout and about to get kicked out of graduate school.

I played a lot of poker (365 nights straight, including the night my daughter was born) when I was, well, becoming a father! I played a lot of Scrabble when I went broke. And then Hearts. And then backgammon.

There is a particular grammar to mastering a game and it’s not different from the grammar of mastering anything. Once you learn how to speak one new language, it’s easy to learn how to speak a third language and even easier to learn how to speak a fourth language.

I’ve seen this across every game player I know. Someone who is good at chess can easily master poker. Or, and I’ve told this story before, there’s Falafel.

Around 1994 I started playing Falafel in Washington Sq Park. He was homeless and often had grass in his dirty hair from wherever it was he had been sleeping the night before.

We’d play for 50 cents a game, sometimes a dollar depending on what he could afford to risk losing. He wasn’t as good as me so I’d give some odds. His name was Falafel because that is all he would eat.

Then he disappeared. It was six months before I saw him at the park again. He was smiling.

In just a few months time he had become one of the best backgammon players in the world. He had started playing Wall Street bankers in a price club on the Upper West Side. He build up to a bankroll of $800,000. Then he lost it all. Then he made it all back. A game player can’t be stopped.

20 years later, I think he is now ranked #1 in the world at backgammon when comparing his moves with the moves a computer would make.

Then there was Ylon. He was a chess master (the first time we ever played, I beat him, but then he solidly has turned the table on me) who switched from chess to backgammon to poker. Now, $6mm in poker winnings later, he runs a bar in Brooklyn.

Mastering a game requires you to do the exact opposite of what everyone else does. Since 99.99% of people won’t master a game you need to do the reverse to conquer them.

I don’t know, maybe that above paragraph is the only rule you need to know. But I love games so much I have ten or eleven other rules.

Here’s what I’ve learned from mastering the various games I’ve played:


This applies to everything: games, business, relationships, everything in life.

I see it happen in reverse too many times. People think of a “what if” and then go way deep down analyzing that “what if” as if there was a 100% chance it would happen rather than an almost 1% chance it would happen.

Like “what if my wife is cheating”. or “what if my idea is bad” or “what if this marketing plan doesn’t work out”.

In the 1950s classic chess book, “Think Like a Grandmaster” Alexander Kotov’s first technique is to: “List all the candidate moves first”.

In other words, list all the options that can happen. Don’t go deeply down ANY OF THEM. Then start to look slightly deeper down each one and see which options you can quickly eliminate.

This saves you mental energy and time. This one technique raises your IQ.

It turns out, some 30 years later, this is how chess computers are programmed. The best chess computers are now solidly better than humans. The first thing a chess program does when looking at position: it lists the candidate moves.


Games are all about taking risks.

But if you take too many risks, you always lose. In Backgammon, if you leave too many “blots” open, you will get hit, sent back to the bar, and eventually get blocked off the board and lose. If you play too conservatively, you’ll also lose.

Trial and error tells you how many risks to take, but err on the side of not taking risks.

This is true for business also. People say to me, “I have a great idea! Should I quit my job and just go for it?”

Answer: NO.

Do both at the same time. I was at my fulltime job for 18 months while pursuing my side business. By the time I left my full time job to be a full time CEO of my side business I had 11 employees.

I took a lot of risks in those 18 months. But I didn’t do anything that would risk losing the game.


Every game, and almost every life situation, has short cuts: ways you can get better without learning the entire literature of the game from beginning to end.

A great example is Scrabble. If you want to be the best Scrabble player in the world then it certainly helps to know all the legal words.

But if you want to be a better Scrabble player than 95% of the other Scrabble players it helps to know just two things:

  1. all the two letter words
  2. all the Q words without U: qat qopf qi qanat etc

and if you want to go one step further and be the coolest guy at the table, learn the six letters S A T I N E

Almost every letter you can add to those six will make a legal seven letter world. Example “E”. Etesian. “X” Antisex.

If you are home for Thanksgiving and someone breaks out the board (and has the latest official Scrabble dictionary so “ZA” and “QI” are legal) then you’ll almost certainly win if you just know those two things.

What if your cousins want to play Monopoly instead? Ok, do everything you would normally do but with one difference. Buy, borrow,beg, steal, to get the Orange properties.

Trust me.


You’re the average of the five people you spend your time with.

When I was playing a lot, many of my friends didn’t want to play me. They didn’t want to lose.

I specifically wanted to play people I would lose to. Over and over again. You learn more from losing than winning. Losing is not failure. Losing gives you a treasure trove of insights into how you, personally, can get better.

When I was first starting out, I would always find people better than me. When I first moved to NY I even moved in with a player much stronger than me at chess.

We’d play all night. I got better until finally I was at least as good as him if not better (we played a match once and when he was two games down he quit the match).

If you’re starting out in business, work first for a good company that has a high profit margin. This is a business run by good businessmen. Learn from them.

If you can’t directly learn from them, read from them. Study what they do. Break it down. Don’t wast time with the people who will bring you down.


I was in a poker hand with Irv Gotti, the CEO of rap label Murder, Inc. He was laughing and everyone time I’d raise he wouldn’t even hesitate before raising me again.

We were in his offices and there were two tables in a private game. The guy next to me had just produced the move “300”. David Schwimmer was a regular in the game. Another guy had just sold his poker software company for $50 million. And Irv Gotti was the host. There was a lot of money around the table.

I had a great hand, Irv kept raising me. And then on the final card dealt, he got the card he needed and won the hand, and I had no money left at the game so I left.

He just got lucky, I thought. And that card was certainly lucky. But he had been in worse hands that night. He had people intimidated with his non-stop talk.

He would aggressively raise so people would be afraid to play against him because he was too unpredictable. Just those things, let him build up a bankroll where he could take more risks even in situations where the odds were against him.

I don’t know how much money he made that night but I know what I left with: $0. I also found out that he took lessons from very good poker players and at that point, I hadn’t played or studied in yeas.

He was more prepared than me.

Whenever you feel like saying, “I was just unlucky” trust me when I say, “you’re probably an idiot.” Analyze the reality. Don’t just try to make yourself feel better.

Blaming is draining.

In chess there’s a saying, “Only the good players get lucky.” This applies to every area of life.

As Scott Adams (creator of Dilbert) said to me, “if you know you’re only going to succeed at 10% of the things you try, make sure you try 100 things.”


Every game, every industry, has its history. A history of successful business models, of successful people, of styles in which the game was played. Of colorful personalities.

If you don’t love the history of what want to master, then you will never master it.

Simon Rich, one of the funniest writers I have ever read, the youngest writer of SNL ever, and now working on two movies and a sitcom, said to me, “if you don’t wake up and want to write first thing, you probably shouldn’t be writing.”

In the course of our discussion he must’ve referred to 50 different books and comedians and movies, etc.

It’s like the movie Groundhog Day. Bill Murray relives every day over and over. He becomes a better person for it.

You can’t do that. You can’t relive the same day. But you can relive the thousands of days before you in the area you are most interested in by studying the history of the field you love.

Writers should of course constantly read. You can’t write a good book if you haven’t read 500 other good books. You can’t write a good screenplay if you haven’t watched 100s of movies and appreciate the beauty of specific shows from the 60s, the 70s and the various eras of movies that came after that.

I don’t think I know a single chess master who hasn’t read through Bronstein’s “1953 Zurich International” tournament book at least a dozen times. Or Mikhail Tal’s “Best games”.

Poker players have read Doyle Brunson’s classic a dozen times. And entrepreneurs have all now read Walter Isaacson’s book on Steve Jobs and dozens of other biographies of successful businessmen.

The history of a game or life is your virtual mentor if you don’t have a direct mentor.


I was a very bad sore loser. If I even lost one game in a tournament I would drop out.

As mentioned above, I lost one game and swept the pieces to the floor, creating a scene, and making someone else clean up after my mess. Not to mention making a fool of myself.

“Failure” is the hip new word. People say, “you have to fail to succeed.” This is not true. Failure is the fastest way to becoming a failure.

Instead, view everything as an experiment. Every experiment has problems. As Peter Thiel says, “Get good at solving hard problems”.

When something doesn’t work out, see how you can make it 5% better the next time. There’s always a next time.

If there wasn’t a next time. Warren Buffett would’ve quit investing in 1956. Or 1957. Or 1958. Instead, almost 60 years later, he’s still learning from the things he tries (and he’s made many multi-billion dollar mistakes even in the past decade) and then he tries to make the next situation 5% better so he doesn’t make the same mistakes.

If you love someone or something, you will have many many opportunities to kiss. If one kiss isn’t perfect, then be 5% better in how you treat that person, in how you surprise, in how you learn, in how you study, and the next kiss will be love.

Better to love than to be bitter, than to think you’re unlucky, than to not be prepared, then to not delight the people around you.


This is a trick in a game called, “Go”. Which happens to be the most popular board game in the world but many in the US don’t know about it because it’s popular in Japan, Korea, and China.

No computer can play Go. It’s too difficult. Much more difficult than chess. And when I play through a game played by two professionals it’s almost like they are not playing a game but mutually creating a new work of art that takes my breath away.

I used to take lessons from a guy who had been the Chinese Amateur Champion a year or so earlier.

I would make a move and he would shake his head. He knew one English word. “No.”

Then he would show me why. He would take off the last few moves made and then recreate the position but put the pieces down as if we had made the moves in a different order.

Then a light would shine, “Ahh!” Because if I had made the move I was planning, in the exact same position but as if the moves leading up to that position were in a different order, then it suddenly was clear why my move was bad.

Example: someone wrote to me the other day that they had made $50 million dollars when they were very young. Then very quickly, the person had lost $30 million and was feeling horrible.

Tewari analysis would say: “Well, what if you had simply gone from $0 to $20 million, rather than from $0 to $50 million and then down to $20 million?”

You would be in the exact same situation, but you probably wouldn’t feel horrible.

Our minds give great weight to the perception of motion. The way to get around this is to rewire the mind to show that forward motion was still there, it just doesn’t seem that way because of how you were perceiving it.

Change your perception of motion and you change your potential for happiness.


One time I was playing poker at a club and Norm McDonald, the comedian, came in and started playing. He was a funny guy so there was a lot of chatter at the table.

Norm would play every hand. Normally in poker you’re probably dealt two hands an hour that are worth playing, and chances are you’ll lose at last 50% of those hands.

But Norm played and raised and played and raised. He had a beautiful girl with him and it was no fun for him if he wasn’t in the hand.

So he lost all his money and then got more money out and then lost that and eventually left.

Someone said afterwards, “when Norm comes here it’s like a vacuum cleaner on his wallet.”

Too many people don’t have the right preparation. They haven’t tested their product. They haven’t studied the game they are in. But they play as if they are already on top. It’s not such a bad strategy to “fake it til you make it”. But make sure nobody knows you are doing that.

The short cut in poker: don’t bluff. If you have a good hand, play it. Count on the fact that someone else will bluff and you will make a lot of money.

If you have pieces in chess that aren’t at their full potential (for example, there is a saying, “a knight on the rim is dim”) then “play your cards” by figuring out how to make that knight stronger in the next few moves.

Don’t go for a full out attack on the other person’s king when your pieces are not really in place for it. Too many people do that.

Just play what is in front of you. Improve incrementally and be PATIENT. You will have your chance to win many times. But you will lose ALL of your chances if you waste them.


Peter Thiel told me that on our podcast. He was referring to business. Guess what? Peter Thiel is also a very strong chess master and the saying “A bad plan is better than no plan” is a saying in chess.

Having a bad plan gives you several things:

  1. realization that you need a plan
  2. opportunities to see if that plan is not working
  3. ways to analyze when the plan goes awry
  4. a chance to change the plan if it’s not working.

Having no plan gives you none of these opportunities to get better.


I remember studying a match in, I think, 1984, between the British chess champion, Nigel Short, and the US Champion, Lev Alburt.

The British Champion wiped him out. I’m not going to google it but I think the final score was 9-1.

When I studied the games I noticed that the British champion was constantly “bothering” the US champion. He would make non-stop, but frivolous threats, against Lev Alburt’s queen.

Alburt wasn’t going to lose his queen but he had to waste a move getting his queen safe. Eventually Nigel Short would have the better position because he had gained so much time by threatening non-stop.

Microsoft always announces software years before it’s done. This is called “vaporware” but nobody really knows whether or not there vaporware will become real or not so this often dissuades competitors.

H. Ross Perot used to buy up shares of a big company (for instance, GM) and start shouting how poorly the company was run and that he could do a better job. He wasn’t really going to take over the company but many people thought he was because of his “threats” and they would start buying up shares.

Then he would sell his shares after they had run up significantly (or a company like GM would pay him off in a process called “greenmail”) and he would make a lot of money.

I love games. Any game. And, for me, studying the subtleties of games are like studying a bible. The metaphors to life are so real that I’ve learned to live my life by the above rules.

Recently, my wife and I have been playing an Argentinian card game called Truco. We can play for hours. Half of the time she is screaming (she will deny this but I have a positive score against her).

I can see there is a lot of strategy in the game. But the game is VERY Argentinian. For instance, if I google strategy for Truco, it doesn’t give me the strategic tips I expect. It just says to joke and talk louder than your opponent so they get distracted.

This strikes me as typical Argentina, a country settled hundreds of years ago by pirates escaping the law rather than by Puritans escaping religious persecution.

Truco is actually a beautiful game and I love it’s subtleties.

But when we are done playing, ultimately I love the person I am playing with.

This is how you master the game of life.

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