Hindsight is 20/20. Entrepreneurs should understand that if you swing for the fences that failure is likely. It's about the risk/reward tradeoff. These risks should be understood, mitigated as much as possible, and accepted before undertaking any venture. The bullet points you mentioned are a part of that risk. There should be no regrets if one has thought through them.

Yes, there are arrogant people swinging for the fences. But there are others who have thought through it. My 2 cents.