Everyone wants to win. Everyone wants to be a winner.

Winning is great, its fun, its epic. Losing seems less attractive.

Winning is elusive, so by design its less common. For every startup that wins, there are nine that fail.

My experience tells me that winning, is the headstone of the sum of your ambition. Not the sum of your efforts. Many make great efforts, and many confuse activity with progress.

What does that mean?

Imagine an NBA championship game, between two teams who fought hard to get to the finals. One will win and one will lose. The winning team may just play better, and that is why they will win. The losing team may be troubled by something on their minds, which caused them to be just a bit less on their A game.

The mindset of the team when they take the court is key. Some teams play to win, and some teams play “not to lose”. That is not the same thing.

The sum of the ambition of the team that wins is the reason for winning. All of the forces at play, and not a single this reason or that.

When a team aims to win, when they make that their collective goal – they play the game differently. Same with startup teams. When they decide to do something and focus on that, the rest are “issues to be resolved” and not problems. The minute you stare at the obstacles, you lose.

For example, imagine you are skiing down a slope. There are many trees in front of you. You know that you can pass between the trees, there is plenty of space. Yet… the moment your mind shifts from finding the spaces BETWEEN the trees, and its focused ON the trees… you will hit them.


There is a difference between skiing down to the finish line, and always looking for what you need to do to overcome the next obstacle (tree), and between skiing down hoping not to fall on you ass. When you ski in hope that you don’t fall down, you are playing “not to lose”. You are not playing to win.

There is one more thing about winning, which is not fun to talk about. So let’s do it.

To win, you don’t only need to do everything right. You also need to undo everything that is wrong.

If you hired an executive that is holding you and the team back, only after the pain of relieving them of their duty – you will win. Avoiding the hard stuff is not the way to greatness.

Let me repeat.

Say that you made a mistake, and it is clear to you, and the team that it is a mistake. It happens. The easy path, is to ignore it. It is to avoid confrontation. It is to think that it will get better with time. It is easy to focus on the “good” stuff that is happening, because it feels like it is getting you close to winning.

But winning is the sum of your ambitions. It is not enough only to do good things. It is ALSO about undoing the bad. Releasing the dead weight. Confronting the ugliness of admitting mistakes, and the dread of having to deal with the consequences.


Yes. That is part and parcel with “winning”.

Back to the basketball example. Say that of the five players on the court, “only” one is not a fit. Only one player is not gelling with the team, or playing with the same level of confidence, professionalism, care for winning, gusto and so on. What if only one player is playing “not to lose” and the others are playing to win?

What happens to the team dynamics? to winning?

Without going to great details, you can see that instead of being a fluid team, that trusts each other to beat the competitors – this team is fighting itself.

In the back of their minds they are thinking “should I pass the ball to the guy who is one degree less hungry to win, or should I pass it to someone else who is not in a great position to score, but cares more?”

There. THAT is the slight difference that can bring a score to 98:96 on a final game. That.

When you analyze the game, or the journey of a startup – you can see the little things that made a big difference. What if the team had full trust with the one another? What if they only thought about who should have the ball based on their position at the moment only? What if they eliminated all the extra algorithmic work that factors the seeded doubts about the team player who was not up to snuff?

The coach should recognize that underneath all that is seen, there is an unseen layer. That layer is part of what needs to be handled, to win.

It is not only important to do the good things. To practice shooting baskets, to train heart and lungs to take on the stress of a game. It is also important to undo the mistakes. To deal with a player that is a misfit for this team. The player may be amazing for another team, that is often the case. But if you want to win, you will need to also deal with the unpleasant business of fixing mistakes.

In startups, the same team dynamics occurs. If the team observes unethical behavior by the leader, or other team members – they now spend time thinking about that instead of the competition. The team is busy with the rumor mill instead of obsessing over customers’ success. You have to deal with this if you want to win.

Only then, when you are exhausted from all the work, all the good things you did. Only then, when you dealt with the not so fun things to undo the bad. Only then, the win arrives, it is well deserved, it is just.

References and Quotes:

Hanlon’s razor

Top 40 Winning Quotes (2021 Update) - Quotefancy