100% this. It's something I struggle with myself. I'm privileged in a lot of ways and that leads me to downplaying my own struggles fairly frequently. It's a bad habit I've spent years trying to break with mixed results. Suffering is not a competition or a zero-sum game. All pain is valid.
Not "bit" in the humour sense, but a good portion of his behaviour was specifically to prove a point. It was both performative and genuine simultaneously.
No amount of money will ever give you the sense of meaning and purpose these dudes lack. Money is ony useful as a tool. As an end in itself it is completely empty, a hollow pursuit that will never fill that void inside no matter how much cash and toys you try to cram into it.
Money removess a lot of the barriers to happiness, but it is no guarantee of it. If the things making you unhappy have nothing to do with material conditions, it's not going to do anything for you. If anything, it's just going to isolate you further.