A system and method for a skateboard and for propelling the skateboard. The skateboard system includes a board including a first end and a second end, the first end offset from the second end, and the second end defining a board plane. The skateboard system also includes a truck assembly attached near the first end of the board, and a caster assembly attached near the second end of the board. The caster assembly has a caster pin at an angle with respect to the board plane. Other embodiments are also disclosed.