It's something every entrepreneur, investor, leader, or creator of remarkable things struggles with.  If they don't, they're either lying to you, or to themselves.

Is your judgement right? Or did you miss something in your blind spot?

Your judgement was right, but you didn't persist.

It's a mind-f*ck struggle.

Judgement can become a slippery slope of sunk costs, confirmation bias, and wishful thinking.  Persistence is the ability to compartmentalize and endure.

The future is a complex set of probabilities. Unmercifully, the outcomes are binary. And that, generally and in retrospect, is how success is defined.

Judgement can absolutely be improved.  Judgement is about developing a deep understanding of the variables and probabilities (developing a superior process).  Every piece of data or feedback along the way can help refine your judgement. Look past the data point itself and understand why that data point happened, or didn't, as you expected it would. Why did it, or did it not, turn out the way you thought it would?  What can you learn? How can you refine and improve?

Persistence on the other hand is different.  I'm not sure how to put a finger on it, but it seems more about conviction and commitment in the face of negative feedback.  Lack of persistence results in a bad outcome when the judgement (the process) is sound.

There's a path to improving judgement, but I don't know how, or even if, you can systematically improve persistence.  Maybe it's one of those things that you either have it, or you don't.

"If you don't get what you want, it's a sign either that you did not seriously want it, or that you bargained too much over the price."