Startup Is Like Playing Chess

Published: 12 Dec 2020 Read time: 5 minute read

Startup is like a Chess game. Think about it.

You have:

  • Opening: Find team, validate idea, raise seed funding
  • Middle game: Build MVP, Get traction, Scale fast
  • End game: Hire employees, Build out the offering, Aquire or get acquired


Similar traits:

  • Each move you make creates series of possibilities
  • Quality moves create more opportunities, but if you spend too much time your risk running down the clock
  • The more moves you make the thicker the plot gets
  • Build up too much complexity and moves become hard to make. game over

The opening:

Rush to eat more pawns might seem like you have a lot of momentum, but might also lead to less flexibility later in the game. Middle game and end game especially. Aim to be bold but make sure you don’t lock your self into positions that leaves you less flexible later. Early interactions with customers will probably reshape your initial hypothesis, so make sure you have the flexibility to pivot accordingly and still have mandate to change.

The middle game:

The middle game is often turbulent, and planing too far ahead is often unnecessary. But having a plan for what to build is still very important. Planing in periods of no more than 3 months seem to be the sweet spot. Have objectives and milestones. Keep innovating but listen to all the customer feedback you can get your hands on.

End game

Dream big, don’t settle for default solutions. Like in chess, if you only follow routine moves defined in chess books, you will find your self quickly outsmarted by a more creative players, who dares to experiment and try new things. Startups are all about finding better ways to solve problems. You won’t find these “leap-frogged” solutions if you simply do what has done before. Experiment and take risks, or risk becoming a garden variety product. But validate fast, or the clock will run down to quickly.

Micro VS Macro

All the “board” players involved in the actual growth of the startup may not be the part of the board (No pun intended :P). Macro level thinkers (Board guys) empowered by Micro level executors (Startup personas) translate into tremendous value creation.


A player who is restricted by small moves. (In chess)
A person who is given less responsibility but wants to learn (In startups)


A player who moves & destroys either horizontally or vertically (In chess)
A person who brings structure, builds processes & gets things in one line (In startups)


A player who takes unusual steps to find spaces to conquer (In chess)
A person who thinks out of the box to get users/revenue/growth (In startups)


A player who locates his targets and moves diagonally to attack (In chess)
A person who is target driven and his responsibility is to achieve goals whatsoever (In startups)


A player who is second in-command and most powerful in attack (In chess)
A person who has the most responsibility for growing the company and command over other people to make things happen (In startups)


Player who is the commander and who’s death means, game over! (In chess)
A person who runs the whole show and who’s death kills the startup (In startups)

How do these players fit-in?

The King is the Founder/CEO. Founder’s vision has to resonate with each player from the start to keep everyone on the same board.

As a Founder, it’s integral to identify which player to bring into at which stage of the startup and how the player’s ability align with the requirements needed.

Game play

Two type of games. Defensive and offensive.

  • Offensive (Technology focused)
  • Defensive (Operations focused)

For the offensive play, you may need more support from the sales focused — Bishop, who will help you get paying customers and achieve required targets.

For the defensive play, you may need more support from the structure bringer — Rook, who will help you streamline processes and figure out solutions for the operational complexities.

While in both plays, you may need your creative and data oriented — Knight, who will hack your growth by finding new avenues to expand.

Player in abundance which is suitable for both Ops & a Tech play — Pawn. The most underrated, bottom of the rung, yet when it reaches the other end, has the ability to shape into anything. I believe, it’s the responsibility of the other players involved to create that cushion to shape this gem.

However, there lies a difference between the two, From interns to the CEO, unlike the actual game of chess, the end goal is not to defeat the opponent, but to defeat thou self, each day, to grow the company and keep creating value.

To all founders out there, have you identified your players yet? And to all those reading, have you identified who is controlling the game?

Good game!