The first video says that Thiel is answering the question "What do you make of people celebrating Luigi?" and his response was "There may be things wrong with our healthcare system, but you have to have an argument and find a way to convince people" and that shooting random CEOs "isn't going to work".

Somehow I'm supposed to be led to believe this makes Thiel come across as stupid. My only guess as to how is because the OP must think that shooting CEOs in the street is an obvious rational good and that opposing such is idiocy, or reactionary fascism (in leftist usage, a synonym for idiocy), or so on.