Is it fair to expect someone in his position to have perspective?
I think if you ask him about the failure six months or a year later, a resilient person would be able to put it in perspective, but not while it's happening.
It is exactly clear to me how unhappy this sentiment makes startup people on HN, and that's fine. I take no offense.
Where do you draw the line and why there and not elsewhere? What's "proper pain"?
To be honest, I'm somewhat on your side and tend to take the "shut up and grow up already" mentality regarding people whining (suffering) about painful life events, but that view does not answer the above question reasonably, it just ends up denouncing whatever you personally cannot withstand or are annoyed with.
I personally don't get worked up about that kind of self commiserating sentences.
Please understand, though: it's not that someone is worse-off than this startup founder. There's always someone worse off. The unemployed factory worker is in a far better position than an impoverished rural Chinese farmer. It's that most people are worse-off than the startup founder. Even most Americans.