If he is ur best friend u should be Abel to tell him look man if u shoot another small buck ur not Gunba be alloud to hunt here any more u knew the rules and u broke them. If u break them again than ur gone. Tell him straight up and make it very clear to him. He should understand. If u have a few deer over 150 he should feel privileged to be Abel to hunt there and if he has that high of standards of a 150 inch deer and can't watch a Forky walk he's not a very good trophy hunter and he may not no what a 150 inch deer looks like. With that being said I would make it very clear to him now that if it happends again he's gone