I find it sometimes very frustrating to read about all these people doing start-ups (who I am cheering to succeed - I have nothing against others succeeding, no matter how good their circumstances are) talk about the struggle and the hard work, etc. It's inevitable that either consciously or subconsciously you do a mental comparison between yourself and these people.
Sometimes, I tend to have questions such as "ummm... why am I not/did not follow similar path". I don't dwell to much on it as I catch myself and look at their background. For example, I will use the founder of one particular company (which I won't name). Let's see, father is CEO/founder of a medical company (ie. already no risk of any real failure - dad is available for a start-up capital and a job if things don't workout). He is graduating from Stanford (already higher chance of success, considering the reputation and connections that exist). I watch a presentation with the father and son and I just could not understand how this person felt they were taking a huge risk by doing their start-up versus "getting a job". He mentioned the risk and it really emphasized the vacuum some of these founders live in.
I will gladly give more respect to people such as Mark Cuban and many others like him who have built their companies from the start with real risk and real failure.
I wish the best of success for these people that do have these really good circumstances. Being able to leverage their good fortune to do a start-up is adding value to society but I tend to find it a bit too much sometimes when I read about the struggles of these people that have the good circumstances. I also feel it perhaps leads some people astray who should not do a start-up as the consequences of failure are extremely bad as they don't have the good circumstances to cushion the failures.