[svdad]

couldn't agree more. "i only made a little money" -- enough to have started angel investing in 2004 after exiting paypal.

enough money to live in one of the most expensive places on earth, probably without having to work too much? check. a family and (apparently) happy marital relationship? check. moderately successful times working at important companies? check.

Sure, it's good to be ambitious and set high goals. But the dude needs to get a grip. If he wants to achieve more, fine. But there's no universal standard by which he's a "failure". At the end of the day it's up to him and he'd do well to admit it.

[jwhite]

A friend once took a 30 minute car ride with two successful people, both multimillionaires, back when that meant something. He asked them how much money they would need to feel financially secure. By the end of the trip they had bid each other up so far that they agreed that it would take a large multiple of their current net worths, just to feel truly safe and independent enough to retire.