Hi Matt
An old Coot in California showed me how to do that. What you do is put a 3/8" piece of leather through the hole. Punch a hole in one side and the offset another hole on the other side about 1/4”, punch three or four holes on both sides, then weave the leather threw each side. Make points on the leather to get threw hole. When done cut the points off. Hope this helps, a key point is getting the right leather…I want to call it Latigo, but I am not sure about that.