Chess and Entrepreneurship


I learned to play the game of chess as a kid, although I’m certainly no Gary Kasparov. I have always been intrigued by its simultaneous complexity and simple elegance. After running several startups, and going through the exit process more than once, I have come to the conclusion that running a company is very akin to playing chess, although running one effectively is probably closer to mastery of the game. Chess is a great game for entrepreneurs – it is a lot like entrepreneurship at its core.

For starters, consider the pieces. Chess is played with a number of pieces, ranging from the pawn (the lowly foot solder) to the queen, the most powerful piece on the board. Although the various pieces are each equipped with their own unique abilities, they are all critical to winning.

The Opening

There are two sides in chess – black and white. Your company is one side, and your competition is the other. Two armies standing toe-to-toe, each trying to topple the other.

Traditionally, the player playing the white pieces moves first. This is the first-mover advantage. As experienced chess players will tell you, many amateur players lose the game on the first move (the opening move). However, it isn’t enough to simply have an “opening move”. A monkey can make a first move. It is knowing what to do after that first move that really counts. How will you execute once your plan has been set in motion? Unless you have a plan, don’t move. When you move, move with a purpose. As Sun Tzu once merrily quipped “Let your plans be dark and as impenetratable as night, and when you move, fall like a thunderbolt.”

The Pawn

The pawn is the most common piece on the board. Each team controls eight (8) pawns. The pawn is a “soldier”, and while they can only move freely in one direction (forward), and can only attack in one direction (diagonally), they are critical to the game.

For starters, the pawn is the only piece that has a different set of movement rules for their first move. They can move up to two (2) squares forward on their opening move. However, after their opening move, a pawn can only move one square at a time. Just like employees in a startup company – everyone is juiced coming out of the gate, but eventually, they normalize, and don’t move with quite the same fervor as before.

From a strategy standpoint, the concept of pawn chains is an important one in chess. A “pawn chain” consists of two or more of a player’s pawns connected (lined up diagonally), where a rear pawn is protecting a vertically forward pawn one rank forward and in the file to the left or right of the rear pawn. In other words, one pawn is covering the ass of another. With a nice arrangement of pawns, you can really block an opponent. Think about your employees – do they cover each other? Is there sufficient cross-pollination and a team-culture in your ranks?

The Specialty Pieces (Knights, Bishops, and Rooks)

While pawns are cool, the real fun can be had in mastering the various specialty pieces: the knights, bishops, rooks, queen, and king. The specialty pieces are analagous to your management team, each excelling in their own field.

Bishops can move any number of squares, but only diagonally. Rooks have the same freedom of movement, but along the vertical/horizontal axes. Knights have a quirky set of movement restrictions. They can move two squares foward, and then once to the left or right.

Okay, so those rules are fairly easy to understand. However, to effectively win in chess, you have to not only master the movement constraints that accompany each piece, but you have to master the various ways in which the pieces can be used together to accomplish your mission. I don’t think I have to point out that the same can be said of running a company. Unless your rooks, bishops, and knights can work together, the king and queen are dead. The same can be said of marketing, sales, engineering, public relations, and IT.

The Royalty (King and Queen)

The king is the most sacred piece on the board. The King can move in any direction, but only one square at a time. You lose the king, and the game is over. I like to think of the King as your “Chairman of the Board” (or “chairperson”, if you prefer). Powerful, but limited in its ability to affect the game.

The queen, on the other hand, is the most powerful piece on the board. She can move any number of squares, in any direction. This is your CEO. She can kick the ass of any piece on the board, but if you lose your queen in battle, you are sunk (unless you are Gary Kasparov). It is incredibly difficult for the remaining pieces to rally together for a victory if your queen falls.

A Random Thought (Does Size Matter?)

In chess, the pieces are often different heights/sizes. The pawns are the shortest, and the king is the tallest. In theory, they can be arranged from shortest to tallest, in the order of their relative importance to the game. While an argument can be made about the sizes of bishops, knights, and rooks, at the end of the day, the king/queen are taller, and the pawns are the smallest. However, in the world of business, this is where the analogy to chess ends. While the CEO is important, he or she alone cannot win the game. Without the minions in play, the game wouldn’t last very long.


A search on google for “chess business” reveals that I am not alone in my thinking. Here are a few selected entries if you’d like to take a look:

Food for thought. Have a great holiday season everyone! I’m gonna settle in for a game of Chess Titans, courtesy of Bill Gates. :)



  1. I love using chess analogies in entrepreneurship discussions. Here are a few of my favorites.

    1. Wilhelm Steinitz, one of the early great chess players of the modern era (generally defined as after 1870) espoused and articulated the principle of winning chess by building a series of small advantages that ultimately put you in a position for the decisive blow. This is consistent with the venture capital model. To position yourself for the exit, you have to do a bunch of “little things” first and do them well.

    2. Alexander Alekhine, the first World Champion of Russian descent (though he was a French citizen when he won) also said, “Nobody ever won a game by resigning.” This is true for entrepreneurship as well — if you don’t persevere through uncertainty and adversity, you’ll succeed more rarely, and often just by hanging in there, you can succeed in spite of your own doubts.

    3. Thinking ahead. Top players think well over a dozen moves ahead. Good amateurs can generally process about 5-8 moves ahead. Good chess players have a plan in place and then constantly re-evaluate the plan as the board changes. So do successful entrepreneurs. You get into your business and find the environment is different than you anticipated. Do you force the issue, possibly dashing your pieces against the rocks of a solid defense, or do you change plans to reflect reality? That choice faces most entrepreneurs as well.

    Great blog Scott

  2. Oh and another interesting parallel with chess.

    The king can never win a game by himself. (if you’re left with King vs. King, it’s an automatic draw). Generally, the same is true with founders.

  3. Interesting post. Never thought about it form this perspective.

    This analogy might be more accurate if there was a version of chess where you got more pieces as you played the game. No startup begins the game with a full set of chesspieces. At the start, your queen has to work as a rook, a knight and a couple of bishops. OK, this is a bit ridiculous, but you get this idea.

  4. Actually, that does happen in real chess. At the start of the game, you actually can’t move most of your pieces. Initially, only your pawns and knights can move. Over time, more pieces become available as you move pawns out of the way. So maybe the analogy holds.

    I’m going to go home and re-install Fritz!

  5. The Enigma of Chess

    Chess, as with human design, presents the mystery of allowing sufficient time and space, or more accurately, comprehending one’s limitations. Much like driving a car, one learns the benefits or consequences of allowing sufficient distance between vehicles as to provide sufficient time for reaction.

    Human design, as does chess, provides symmetry in the form of blessed duality — two hands, two arms, two eyes, two ears, two feet. In likeness, chess provides pairs of knights, rooks and bishops. The key to survival on the chessboard is relative to a player’s ability to synchronize this cushion of duality into spacial probability and operational harmony, versus its more focalized (and more critical) destiny, singular finality. Each player must constantly weigh the proximity of material, time, and space in proportion to one’s degree of aggressiveness as to elasticize the difference between ‘concept’ and ‘reality’, moreover, freedom versus terminal entrapment.
    — Stan Kern

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