I had fear of heights from when I have memory, couldn't even stand near the edge of a 5 meter fall without having a deep fear falling to death.
But for reasons hard to explain I made my first AFF jump and got even more scared, but as it seems I enjoy suffering, I kept jumping and got my A license, and "cured" my fear of heights by repetition.
It took me 50 jumps to get my head out of the plane door without thinking "why I do this to me?", but eventually the fear comes slowly again on long non-jumping seasons
Anyway, I make my living building industrial plants and I have to remember myself that if I fall from a non-railed platform I will die, so being fearless isn't that healthy either...
Edit: My first jump was also the first time on a plane