A skateboard includes a motorized drive assembly and a motorized brake assembly, both operable with a wireless remote control to be carried by a rider. The drive assembly is free-wheeling permitting normal use of the skateboard in the event of battery depletion. The brake system includes a motor operable through a simple machine structure to move a brake pad against a brake disk mounted against a wheel. A self-adjustment mechanism presets the brake pad a predetermined distance from the disk prior to brake application. Motor enertia is relied on to store potential energy in a wheel axel in accordance with an associated method of operation.