Seven Things I Learned from Chess

Chess got me a girlfriend, it got me into college, it got me into graduate school, it got me my first job, it helped me raise money, it got my company sold, and it’s opened doors when previously they seemed locked to everyone around me.

People mistakenly think chess = “smart.” This is very wrong. But I took advantage of this myth.

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(Bucket list moment: me with Jim Norton, GZA, Garry Kasparov and Maria Konnikova)

But all of that is superficial. Where it really helped me, where any activity that you devote your heart to for years at a time helps, is the following:


Many people play chess for years and never get better.

I have one friend I see about once every five years. He loves chess but has never once studied the game.

He plays every day. He still plays the same moves. Makes the same mistakes. All of that time spent on something he loves and he is unable to improve.

How come? Hasn’t he put in his 10,000 hours?

It’s not about 10,000 hours. It’s about 10,000 hours where you practice with intent.

You have to get a teacher. You have to study the history (go over games played by all the great players since the 1800s through yesterday).

You have to play and be willing to lose in order to learn more.

Identify the microskills (openings, tactics, etc.) and get better at them.

This is the same as anything.

You get better at sales and management by studying from the best, reading and re-reading thousands of examples, and understanding the subtleties in the history of what you love.

You get better at writing by… writing a lot and getting feedback.


When I first started to play, I improved my skill very quickly but not my psychology.

I wanted to think I was a talented genius. I wasn’t.

Talent is a spark that lights the fire. But the fire needs constant fuel to get bigger.

Maybe I had a tiny bit of talent, like most of us do. But I wasn’t anything special.

I started playing at a late age — 17 is very late for young chess players. But within a year I was the strongest high school player in my state.

But I was a sore loser.

One time I lost and threw all the pieces on the floor and walked out of school. Everyone was laughing. I didn’t come back to school for several days.

A few months later I was playing my father. Here I was, 17 years old, a grown man (almost), and when my father beat me I started crying and yelling at him.

Another time, I was 18 and I was representing New Jersey in the U.S. high school championship. I won my first game but lost my second game.

I trashed my hotel room like I was some kind of rock star and I was so upset my grandparents had to drive down and pick me up. I dropped out of the tournament.

I would have nightmares when I lost. The game being played over and over again in my head. I was at expert level and not quite master.

Finally, I started to care more about getting BETTER than about winning.

Process is always greater than outcome.

I started to study my losses. I would take my losses to my instructor and we would go over them.

And that’s how I went from expert level to master level.

I still don’t like to lose. I hate it. It’s the worst feeling. But I never let a good loss go to waste.

The only way to learn is to study something you never knew before.

Losses are the maps that point you to what you never knew before.


We like to think that life is not a competition. That everything is abundant.

The reality is, to get good at something, you have to be better than others. You have to stand out.

I used to shake before every tournament. I was so nervous I always felt sick.

And if I started to lose a game, I’d feel sick and I’d lose.

Then, I started to switch mindsets.

I would spend more time at the board. I would focus. I would look down every variation.

I became a better player by learning how to be mischievous when I was losing. By learning how to kill when my opponent thought the hunt was already over.

By learning how not to give up when all hope was lost.


Chess is about being paranoid.

When your opponent makes a move, he’s not your friend. He’s your predator. He wants to kill you.

So you look at every possibility. How is he trying to kill you? What is your worst-case scenario?

Much later when I was managing money for people, I was always worried about the worst-case scenarios.

When I was dating women I was also worried about the worst-case scenarios.

I was too paranoid. I was thinking too much that everyone was a predator.

It’s true that everyone is self-interested. This is how people survive.

But I learned to hone it in real life. OK, here’s where I should paranoid. And here’s where I should relax.


For the first time ever, I had friends who were not my age. I had friends of all ages and races and economic backgrounds.

One language united us — the language of chess.

One time I was in Buenos Aires at the world famous chess club where Fischer beat Petrosian, where Alekhine beat Casablanca.

I don’t speak Spanish and the guys running the club didn’t speak English. But my friend told them my chess rating, and they ushered me right in.

I played games against the Argentinian junior champion, who was there, and we got the full tour of such a historical place.

Since I was a kid, I would go to Washington Square Park at the southwest corner, where the chess players have played for 60 years.

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When I was younger it was mostly drug dealers and prostitutes hanging out there.

But there were also chess players and backgammon players and Scrabble players (Scrabble more in the northwest corner).

Ultimately I crossed many barriers that a “civilian” life would not have allowed me to cross.

Perhaps this is the thing I am most grateful for.

It’s not just chess.

When you get good at anything, you learn the language of mastery.


Everyone thinks chess players are smart. It’s a cultural myth.

It’s not really true. There are smart ones and some that are very stupid.

But because of the myth around chess and IQ, I have been able to maneuver.

When I applied to college, my grades were very poor.

But my interviewer was a low-ranking chess player. So I helped him analyze some games for the entire hour of the interview. I then got into college.

When I applied to graduate school, every place rejected me except the one school that was working on the world’s best chess computer. Guess who my office mate became?

When I applied for a job, all of my interviews went bad. I didn’t know the answers to anything. I went outside in my hot, stuffy suit that didn’t fit and called my girlfriend. “Looks like I’m not good enough for New York.”

I then went to play in the park right next door where tables were set up.

I beat the first person I played — a strong master. When I was done, I looked up and my boss’s boss’s boss was watching.

“I never saw anyone beat Ylon before,” he said. And we took an hour-long walk around the park talking chess and internet and TV and everything.

I got the job.

20 years later almost to the day, Ylon Schwartz, the guy I played in the park that day, came on my podcast and we discussed poker, of which he is now a champion.

Chess has meant everything to me. I love it. I’m not the best at it. I’m just good enough to be better than most others.

But you can have these results with anything you love.

When you love something, instant community builds around you to protect you. You become something much bigger than yourself.

We get better in a group. In a “scene.” No matter what your passion.

No matter what I have been interested in life, I quickly find my scene.

AND G) I make sure that scene has PLUS, MINUS, EQUAL

PLUS: people better than me that I can learn from.

EQUAL: people in the trenches with me.

MINUS: people I can teach.

For me, chess, business, writing, investing, comedy, programming, has done that.

I get passionate, I begin to learn, I find my scene. I learn to learn.

I no longer throw pieces at the people who beat me. I no longer even study the game. I’ve chosen to focus more on writing, podcasting, business and other things.

But it’s inside of me and will be forever. Even, unfortunately, the paranoia.

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