Weight of man and paint = 160 + 5 = 165 total pounds.
Gravitational force is independent of the path taken so we can ignore the radius of the silo.
Work done = total weight x height
The problem says he climbs to the top so overall height is 90 feet
Work = 165 lbs x 90 ft = 14,850 ft-lbs
5(-2) = -10, so 5(-2)(-11) = (-10)(-11) = 110