I know a lot more poor people who are insecure as hell. This fella may have his insecurities, like all of us, but it's far from anything remarkable. Probably trying to build a "brand" of this new era of millionaires, Bilerian etc...
Rich people, just like poor, sometimes are weak psychologically and can't handle/deal with some areas of life, regardless of wealth, sometimes they commit a suicide. You can be rich as fuck, but very unlucky in love sphere, depression may follow and a suicide. I'd rather be insecure and rich, than insecure and poor tho'...
How do you know its not anything remarkable? The same was probably said about Robin Williams, and he wound up hanging himself.
I don't know the guy, so I can't say if his insecurity is "remarkable" or not. Its impossible to know just from a video. It may or may not be. Again, one cannot tell inner emotional experiences just from a video. Hell, he may be the happiest man alive!
And, yes, I think most would agree that they would rather be rich and insecure than poor and insecure. That is obvious. What is not obvious is that he can't be insecure because he is rich.
As Twain said, "Everyone is a moon, and has a dark side which he never shows to anybody."