A guy gettin lots of air on a skateboard at a skatepark
A man asleep on his snowboard.
A man cannot be asleep and on a snowboard at the same time.  Also a skateboard and a snowboard are not the same thing.
The man cannot be getting air on a skateboard and asleep at the same time.
The first sentence is about a man catching air on a skateboard which is impossible to do while sleeping, so the second sentence is clearly about somebody else sleeping on his snowboard, which is also contradictory to the first sentence because skateboards and snowboards are used for two different sports. One has wheels, the other does not.