This sort of hubris has always bothered me about some entrepreneurial types. I understand "looking past limitations", "going against the odds", and "taking risks". But, I think: a) There are outside forces which you cannot control and which can drastically affect your business (even to the point of failure). To ignore them is foolish, IMO. b) I think failure is a key part of being an entrepreneur. It's how you learn and grow. Failure happens sometimes.
Also, I wish his points on humility were a little more thorough (and included points on failure). I'm not sure W. Churchhill and John Lennon even qualify as entrepreneurs.