I've come to the conclusion that success in business is like the game Rochambeau (Rock, Paper, Scissors). People will argue to death whether it's a game of luck or skill, and often it gets very emotional, with people who've had success attributing it to skill and the rest attributing their lack of success to bad luck. In reality, it's neither. It's a game of <i>strategy</i> in the academic, game-design sense (interaction rather than individual skill as the driver of outcome) but often with very little information that would indicate what the good strategies are. Rochambeau has no randomizer (no dice or shuffled cards) and is a skill game <i>if</i> you can predict the other guy's moves. Iterated, it becomes somewhat of a skill game. Same with business. Iterated, both become games of making choices, often with no idea what good and bad choices are, because useful information is so thin on the ground. Business is obviously not "random" in a true sense, but it's obviously not a pure-skill game because so many idiots get lucky and a lot of really talented people (like DMC) don't. It's a game of making iterated choices, often with little or no information that would inform them, and the luck factor comes out of the opacity.<p>How does this relate to OP? DMC is a highly talented person, but he's in his mid-40s, he's worked in the supposedly meritocratic startup sector (and, as with trading, the definition of success in VC-istan <i>is</i> making money; if you've been in VC-istan for 2 decades and haven't made fuck-you money, you haven't won) and his net worth (as he admitted on Quora) is less than $1m. Given that, it's fair to say that he probably hasn't played his cards right. That doesn't make him unskillful or weak or "a loser"-- far from it, and I'm sure that none of those are true. It doesn't make him any less of a person, or any less smart, than the more successful people. It just makes it a good bet that if he could rewind to 20 and play from there again, he'd have a lot more success.<p>And ultimately, the reason why many of us are sitting here not being rich and outlandishly successful when people of similar or inferior talent smash $500m+ exits is that, when faced with a thousand identical-looking doors, one with a pot of gold behind it, they had the "insight" to pick door #467 while we picked #822 or #134 or #915. Some of us pick #467 at the next opportunity but, of course, the next time the pot of gold is behind #719.<p>I think the best thing to do is to back away from the VC-istan insanity, and pretend all that garbage doesn't exist. As long as I'm growing my skillset by 20 to 25% per year (which is not hard to do, because returns from increasing skill in technology are exponential) I feel like I ought to be happy with that. It can be difficult to be satisfied with this (first world problems) when you see unqualified idiots getting funded in enormous amounts, and then getting acquisitions and EIR gigs as welfare checks because they have powerful friends... so it takes some discipline and maturity not to be annoyed... but sanity is worth it.