Paulie was stealing from Rocky all along
You remember Rocky V when Paulie had signed some paper and Rocky lost all his money? Then obviously Paulie was stealing from Rocky all along! How else do you explain all his money in Win Win?
Furthermore, why did he hide to Rocky that he had a daughter? My theory is that she was the daughter of Drago's ex-wife from Rocky IV, and he didn't want Rocky to know that for obvious reasons.