He also can talk to people he disagrees with without going into petty word fights. Despite his image he has a lot of humility, he knows and openly admits not to be the smartest man in the room. And to me comes across as a person eager to learn and hear new ideas.

I have learnt quite a lot about being good conversationalist by studying what and how he deals with guests.

He has casual (friends) episodes that are pretty repetitive but he also invites experts from all over. Those episodes are very entertaining.

(I dont use spotify so havent been following his podcast since the move)

Could being the operative word. We're talking about "blow a million dollars on random shit every year until you die and still have multiple millions left over" amounts of money. Why would anyone who doesn't already have hundreds of millions of dollars opt for that? The whole point of this tangent in the discussion is that he probably realized his time in the spotlight was limited, so any plan that assumes longevity is statistically unlikely to come to fruition.