More insightful is how you judge whether or not you could win. And when to have audacity to go against what others beleive your chances are for success.
Also, “win” as a concept is deceptive. Unlike a finite game (like chess or go or poker), the game of business is infinite - there’s no “end of game” that declares a winner. Winning is more about staying in the game as long as possible.
I also read that statement as being functionally equivalent to "if you aren't already successfully in the space, then there's no point in bothering". That's the exact opposite of what we need for a healthy economy.