How Startup CEOs are Like Chess Grandmasters Playing Speed Chess


Ben Horowitz wrote The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers. This is a great book that deals primarily with his struggles and successes as a CEO. In it he described his agonizing struggled and some successes. Many times he focused on the sacrifices he was forced to make and the agonizing decisions he needed to make on a daily basis. He even mentioned that CEOs must act with just 10% of the information in order to act in time which is equivalent to speed chess. He also mentioned the similarities to chess several times, one time even comparing his decisions to an “8 level chess game” because of their complexity. With endorsement from him on this matter is easy to see how CEOs are like Chess Grandmasters who are always faced with a huge number of options but only having one or two best play moves if they are lucky.

Chess Grandmasters are constantly analyzing a board with 32 pieces and hundreds of 1000s of movement options and limited time to make decisions. A startup CEO plays, not regulation chess, but speed chess and not for the common 7 minute setting but for the 1-3 minute setting. He must make many daily split second decisions on many different things and must attend to dozens if not thousands of employees, investors, and customers’ needs in a fair manner while putting the company first. The company being the chess game that must be won. Sure in the book Ben mentioned his priorities are people, investors, and customers but really he did not mention the obvious which is that every action he took, every sacrifice he made, was to make the company win the game—therefore the company came first above all else. In chess all legal moves (and sometimes illegal moves by shifty grandmasters like Matulovic aptly nicknamed “Jadoubovich”) are fair and pieces are just tools that give you the win. Sacrificing them is par for course and a great Grandmaster does not hesitate to sacrifice a queen to achieve a win or a draw. Ben did so when sacrificing his first product. The game dictates that not losing is all important and that the Grandmaster must dispassionately sacrifice everything not to lose. Although lives (and many times friendships) are at stake which makes it an agonizing rather than dispassionate decision, a CEO must make these ruthless decisions all the time and sacrifice pieces (people, products, and more) to achieve a better position and align herself for the ultimate win. A draw being a sales that saves the people and the company if the company is in trouble. An acquisition and/or IPO while in great standing being the win. If already not a startup, maintaining relevance and optimizing the company mission is a win though the game never ends—but despite the game going on for years and years, it does not get easier and the CEO cannot stop playing a Grandmaster level game or she can lose big time.

Chess Grandmasters are known for their prowess in different areas of the game or for having different playing styles. In the book Ben mentioned that he was told he was a great all around CEO because he was able to be a peacetime and wartime CEO. In chess peacetimes CEOs are great at the opening. After all it is structured and unless a new innovative opening or move come along it is rather peaceful, yet opening experts still have an advantage over regular players because they know it so well they can force mistakes early on. Even with prescribed scripted moves there is still much strategy that can happen in the relatively peaceful opening. Wartime CEOs are middle game warriors, strategizing and pushing hard to get to the end game with an advantage or forcing a mate before the terribly difficult end game starts. However, I think there is at least one more type—the endgame CEO. These endgame CEOs are super strategist like Steve Jobs and John Legere who can come in and save a dying company and make it turn around completely because each move they make is as perfect as possible since in the end game a single wrong move can lose a game. No matter what type of chess Grandmaster or CEO a person is, they weave the game (company) through many dangers and come out the other side triumphant or at least without a loss.

Everyday a Startup CEO plays her best moves to get the company (the chess game) up the latter of success and closer to a win. Like chess Grandmasters they use every tool and sacrifice a great deal to make it to exit or to keep the company relevant for the long term. There is much of chess that can assist CEOs learn in decision making and in making the hard decisions that more often than not are needed for a startup to succeed.


Like Chess Grandmasters CEOs must make many grueling difficult decisions each day and must be right most of the time Click to Tweet

The CEOs first priority is the company, by law and practice, which makes her job unbearably difficult when hard decision affect other lives

There are several kinds of CEOs. Peacetime equivalent to chess’ opening, wartime equivalent to middle game, and endgame CEOs that rescue companies Click to Tweet

There are so many moves possible in chess and in a Startup that making the right move is deadly difficult and can have deadly implications for the company Click to Tweet

In chess there are miraculous seeming recoveries and CEOs are often in the miracle business for their company Click to Tweet

Chess mirrors business life and a CEO mirrors a Grandmaster playing in the game of life both using strategies to not lose Click to Tweet

CEOs play must make move at speed chess timing because real life strategy comes down to split second decisions and there are too many decisions to linger on each Click to Tweet

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