I mean, lets get Taleb exactly right here: He basically says don't invest "moderately," -- like putting your large amounts of money in stocks, even index funds, is a bad idea.

Invest in both extremes, barbell style. Put MOST of it in something bulletproof (he goes with Treasury Bonds) and then the rest as big bets on long shots.

Really depends on you goals and also current financial security. I would rather receive 50.000$ than a 10% chance at 500.000$. But a richer person would probably choose the latter.

Sure, but one of the big points of "The Black Swan" is that your (and everybody's) percentages numbers are way less reliable than you think.

“things with a limited downside and unlimited upside”

Penny stocks and junk bonds, a classic recipe for attaining mega wealth.

That is how Warren Buffet got started, or as he called them, used cigarbuts.

It also helped that his father was a congressman and stock trader who brought Buffet around his finance friends throughout his youth and helped him start buying stocks as a young teenager.

Theoretically yes. Even putting it all on black in Vegas could work. But it doesn't mean you should do it. Any investment is inherently a gamble, some are riskier than others and some have a too small payoff for the risk.

That's a pretty big advantage rich people have as well: knowing they won't starve to death if they fail.