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ConservagameR said:

Wasting all that PayPal money on electric cars and reusable rockets that'll both crash and burn..

It certainly hasn't sunk in yet. How long before the lightbulb illuminates?

And that was before he had tens of billions of dollars at his disposal.

Your post is like a half written sentence.

Just because someone has had success in the past, doesn't guarantee that they will in the future. 

There are plenty of factors that affect whether someone will be successful or a failure outside of their own decisions or who they are. 
Plenty of big companies have multiple wildly successful ventures, that find themselves with big failures.