System Founder

Essays and notes on building a scalable, systems‑driven business.

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The Winners Game

Many habits and mental models of an entrepreneur must be built intentionally. Here’s one that stuck with me. I used to take tennis lessons as a kid, so it hit me personally.

Amateurs play the "loser’s game", while professionals play the "winner’s game". At least that’s how Simon Ramo described it in his book about tennis. He was a well-known American engineer and entrepreneur who also happened to be a passionate tennis player.

Amateurs play the loser’s game because they lose about 80% of points due to their own unforced errors. The winner is usually the one who makes fewer mistakes.

Professionals, on the other hand, play the winner’s game because 80% of their points come from amazing shots. The one who can hit more of those shots wins.

The catch is—you can’t play both games at once. So when you start your company, you need to decide early: which game are you playing? Do you want to make fewer mistakes or to make more winning moves?

Judging by how many founders run around asking “how do I avoid mistakes?”, it feels like they’ve already chosen the loser’s game ☹️. And they’re playing it against professionals—established market players. Which obviously doesn’t work.

So forget about all the mistakes you might make. Focus only on the incredible moves you can make. That’s when you start playing the winner’s game. And that’s when you finally have a chance to beat the pros.

Lately, I’ve been reminding myself of this and learning to play the winner’s game more consciously. I wasn’t born doing it, but I can feel the shift. Every bold move makes it a bit more natural.

Artem Grishanov