Cool is a matter of perspective. But according to literally anyone, he doesn't look cool. It would be easier to just fling himself to the bottom of the hill, no sled at all, but that would hurt, and besides. He wouldn't get to laugh at Eddy and Mickey's way down.

"What, scared you're gonna lose this one?" He taunts back. Neither of them are winning. He sits back up on the board, and begins scooting his way down, heels digging into the earth instead of his hands. This is a terrible idea, and he's getting a mouthful of cottonwood, but it's all in the name of momentum.