The cynic always sounds smart and remains poor.
Why would cynics be poor? The OP mentioned "techies", many of whom have jobs paying 6 figures a year.
Sceptical people will be grounded by what we know to be true. They will explore new ideas but will not be swept up by them. We need people like that or we'll waste our time on flights of fancy. But we need the irrational optimists to explore new ideas too. It's a classic exploration vs exploitation trade-off.
The Cynic has enough if he has his cloak and found some food in the garbage can. He feels like he has enough. You might feel like that's not enough.
Conversely I might think the richest man in the world (by net worth) has enough. He feels like he needs more.
But it could be this too in some cases.
Some people do things unless they find a reason not to but so a skeptical person will only do things if they find a reason.
People who really feel they have enough might not see any reason to spend their time or effort placing bets, even on things they think are probable. But I don't think many people think that way.
Quite the opposite: it takes a lot of strong will and risk to talk against a hype. A kind of risk-affinity that unluckily rarely makes you rich. :-(