We also must remember the context of the story of the rich young man. The Gospels says that Christ saw the young man, loved him, and then told him to sell what he had, give it to the poor, and follow him. It was a personal command to the young man. Just as not everyone is called to make a religious Vow of Poverty, not everyone is called to this life.
Now, it is not necessarily true to say that Jesus doesn’t like money. It isn’t that he doesn’t like it, but rather he doesn’t care about it. Money has no impact upon salvation and is simply a tool of this world. The poverty of Christ is the attachment to things or money. Do not seek money for money’s sake. This is what Mt. 6:24 and Lk. 16:13 are trying to explain. Money is intended to be used. To what end that money is used is the real question. Billionaire Bob can live within his vocation by still keeping his money. It may be that Christ is calling Bob to provide jobs for many people through investments in companies or directly employing. I know of some very rich people (not necessarily billionaire, but close) who are some of the most spiritually poor people I know. They are generous to the poor and use their money for investment in start-up companies so they can expand and in turn hire more people or in direct ownership of failing companies to turn them around and allow their employees to keep their jobs. Inversely, I have met people who are below the poverty line who covet money only for the sake of having money. There people are spiritually richer than those financially blessed people I mentioned earlier.
Yes, it is harder to live a spiritually poor life when you have a great deal of money, but it can be done without giving away everything outright.
