Fun, fun, fun! I'd rather set up a system than watch it (almost). As long as there are no 'fire-blocks' in the wall (pieces of 2x4 that are nailed in horizontally between the studs), you should be able to run the wire into the wall at the baseboard and out behind the speaker.

The best way to fish the wire with the smallest possible holes is to drop a length of beaded chain (like the kind used for ceiling fans, and can be found sold on a reel, or use several smaller lenghts joined by those little joiners) in the upper hole, pulled out of the lower hole by a strong magnet moved along the baseboard, connected to the speaker cable with a piece of string (it has to fit through your holes, obviously), and carefully pulled in, up, and out with the chain.

Larry