You (and by extension YC) always seem to mostly focus on the success stories of the alumni/group. Have you or will you consider talking about the failures? If you can't do it, is there a reason why?
It turns out that most people (and certainly most journalists) want to talk about/write about the success cases.
I'll think about how to best do this.
In the startup world we have to be comfortable making mistakes, but I really want those to be new, interesting mistakes.
Speaking from experience.
Better for recursive 'winning entrepreneurs' to play it like sam, and dole out their money to 100 different excellent candidates, and then manage the winners, and try to cull the losers early.
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Harvard spends a lot of time on case history, and a lot of time on losers. But in general once you have been an entrepreneur its pretty quick to spot a loser or a winner.
For first time young guys with a good idea, and the right experience '25 years' is about right, 2 or 3 founders is right, backed by a good CPA and law-firm is rarely mentioned but this can be more key than TECH, as fighting the legal hassles and avoiding taxation are more important than how much money you make, its all about much money you walk away with when the game is over.
Very few people play second rounds, I think most lose their health, and of course most fail, and you don't hear about them. These few people who continue to play VC, are in the game for the love of it, the connections of SV and such, for most people the dream is to get out and grow wine grapes, or just get far from the rat race.
I think most 'winners' end up like the WOZ, they just retire early and spend their lives doing as they wish, very few become like Jobs and try be a control freak until death. I think a normal person gets very bored with managing people after a certain point. Even fewer 'winners' become VC enablers, again we only hear about the winner's. Most 'winners' are smart enough to know that making money is easy, keeping it is hard, so said Carnegie of steel in the 1800's.
With all the startups you see, what are the common patterns to failing? A missing skill, lack of belief, timing, weak message etc?
If appropriate, how to recognise the warning signs to correct and avoid being the next failure.
Andy Grove (Intel) used to say "Only the paranoid survive", so true,
I used to be amazed that the first thing startup's did was try to imitate the god's with furniture and building's, and the trappings's of wealth. I think your first $10M gross you need to stay lean&mean, complacency is the opposite of paranoia.
In a interview with B-Gate he said his recurrent fear early on was making payroll, cash-flow is a real problem. Keeping the expenses low, and keeping lots of cash on hand to make that payroll in good & bad times is a key often missed, of course a few times the VC's may step in to make that payroll, but that's not really a startup, its more of a parent paying the bill's.
I think a key is getting all the employees to understand that their 24/7 task is to do activity's that bring in the money, when this is done the money flows. Money is the blood of politics and business, if you see a 'failed' biz, its because their revenue came to a halt.
I'd do it myself but lost some bookmarks in a recent crash/restore cycle.
I think it will help to talk about folks whose initial companies went under, and then succeeded later. Or failed later and kept on going.
(That being said I do agree with the implication of the question, that learning from failure is important and may need greater discussion.)