Jesus isn't an investor, and he probably hates people getting a ton of money from doing it because they have a ton of money to put into it.
This doesn't make sense. Of course Jesus is an investor. He invests in human beings. And his reward is their salvation.
Maybe we read different Bibles, because I am left with the impression that "not sinning" was a goal but it was pretty low on the list because Jesus knew that even his followers would fail, but he encouraged them to try their hardest, and he was way more concerned with his followers being humble, meek, modest, and taking care of the poor and that specifically a rich man just is not going to get into Heaven.
I am amazed that, of all the things Jesus said, what you got from it was that not sinning is not important and that rich people are not going to get into heaven. You say we read different bibles but those assertions make it suspicious whether you actually read the bible at all.
Jesus would not send someone to hell or to heaven based on the size of their paycheck. He would be an evil man if he did so.
As for the importance of being humble, meek and modest, you are correct. Those teachings are found in the Sermon on the mount. It was the same sermon in which he said (speaking of the Law or the commandments):
19 Whosoever therefore shall break one of these least commandments, and shall teach men so, he shall be called the least in the kingdom of heaven: but whosoever shall do and teach them, the same shall be called great in the kingdom of heaven.
20 For I say unto you, That except your righteousness shall exceed the righteousness of the scribes and Pharisees, ye shall in no case enter into the kingdom of heaven.
It is also the same sermon in which he extended the law against adultery wherein he claimed it was a sin to even have lustful desires toward someone that is not your spouse. Even being angry with someone was enough to prevent someone from entering heaven. It is also the same sermon that ends the first part with these words:
48 Be ye therefore perfect, even as your Father which is in heaven is perfect.
Now for someone for whom not sinning was a low priority he certainly had a funny way of conveying that message.