Im not saying everything Solly does is fantastic, but a negative mind will never give you a positive life.
Try to focus on the good things he has done, and tell him your opinion when he is wrong.
And when you tell him your opinion, give him an alternative way and a reason for why your method is better, and he will consider your opinion.
There is a fine line between being realist and being negative. In investing world, too much positive will lead you to your destruction, we have seen this many times, especially during bubbles. I rather be little pessimistic and be cautious than be too optimistic and just focusing "on the good things he has done." You can't just simply pretend the problem is not there when it is right in front of you. Honesty is the key on investing, if he did something good, tell him that and vice versa. If he is smart enough, he will learn from it, good or bad.
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