Zoro looks like he’s teasing Usopp here, but really he’s just telling him it’s fine to be honest your weaknesses and limitations. Despite their gap in raw power, Zoro has a lot of respect for Usopp as a fellow warrior.
Nobody on the crew ever mocks Usopp for his fears, even if they don’t always take him entirely seriously.
From Volume 35 - Chapter 333 / Season 4 Episode 236. Luffy has won the battle. But unlike all his other victories, this one is no cause for celebration. Usopp, his crewmate, his friend, lies on the floor, beaten and humiliated. This is not an argument that can be made up with apologies and take backs. No, the crew must leave him along with the poor Going Merry. It's heavy, but this is the path of a captain.