I would like someone to break down the psychology and logic of the following.

Via gambling,
I can & have turned $1 into $2 over and over again.
But I can not & have not ever been able to turn $100 into $200 using the same methods and logic scaled on a Percentage base. 

This conundrum boggles my mind.

(If any common logic is missing from this short comment, assume it was included.)