I hear about this kind of this semi-regularly. It’s crazy to me that simply asking people for money can put someone in the top ~20% of earners. He probably made more than most people giving him money. It throws the incentives all out of whack for being a productive member of society.
I get more judgemental about the people mostly lucking into wealth. Stuff like the gymbro type that land a VP sales role selling stuff that basically sells itself, or relying on all the hardwork of the other people who built the sales tools. Or the small to medium CEOs who act important when they do very little. For example that guy that set a $70k minimum wage at his company but goes around giving paid speeches about it to enrich himself. Even many of the startup people here - you got lucky and picked a winner while there's plenty of others who worked just as hard on equally good ideas that didn't catch the same lucky break/timing. People asking for money and getting it... does it really matter if it's the guy washing your windshield at the light or trying to start up a company that might not do anything for society?