Two & Three trick pony's are very rare, usually a guy gets over confident after his first win, put's it all in the pot, and assumes he's going to win the house. Just like poker, its a losers play.
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.