Here's my first go at it. Conceptually, it's working but a few things to change
The problem is that the wheel is rotating. I don't want to use the chain sprocket because I have to perform the same task on the front wheel as well and want to verify i can do it this way.
I have to get a bigger ratchet strap to grab more tire. Also, going to put a little air in the tires. Also, I'm going to move the location of the strap connection so that it's pulling more in perpendicular to the board.