Start up the boat and idle slowly. Uncurl your rope and throw the end you attach to your tower/pylon into the water. Hang onto the handle and let all of the slack out into the water, trailing behind the boat in a straight line. Then just roll it up. Basically, you are just rolling up the rope with the handle inside of the boat instead of rolling it up from the other end.
Don't know why this works, but whenever my yellowjacket line gets kinked, I just roll it up just like this and it always works.
Hope I helped. For something so easy to do, it was hard for me to explain.