Do skateboards lose pop over time?

no and yes. when you first get it you have to break it in and once you use it a lot it will gain pop, but when it gets really old and the tail chips off then it loses pop. the less tail thats on it the less pop it has. if the tail isnt chipped off of it then i think that you just got worse at ollieing and you need to practice dont worry about it you cant really hurt yourself with ollies unless you are going off huge ramps. good luck