What I suspect you're not getting is that $50K/day is NOT 350x more rewarding-feeling than $1K a week. He can't just sit around and bask in some wonderful "I win" feeling, laughing off the haters.
There's an important point where you start making the money you need, then another where you start making the money you want (to reduce your future risk, to take reasonable good care of your parents as they age, etc.).
But the number going up beyond that doesn't give you anything good; it just makes you more of a target, separates you from everyone you interact with, gives you a heavier responsibility, makes it harder for you to just live the modest, comfortable life you were hoping for.
Money is not a goal in itself; or rather, only for the profoundly short-sighted. It's an enabler. If it's making him a target, and alienating him... why should he want that?
-- Edited: somehow I had the idea he was a teenager; corrected that.