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The parent is a concrete example of selection (or survivor) bias. Picking post factum one case which turned out to be right (and ignoring unknown but possibly large number of cases which turned out to be wrong and faded into the dark pit of obscurity) does not help you predict anything.
Consider a forecast: the stock market will crash. No idea when, but at some point it will. It is a safe prediction to make? Yes, it is. Is it a useful prediction? No, it is not.
Taleb's advice is good for burnishing one's reputation as a psychic. It's not so good for making actionable forecasts.
To recall a well-known remark by Paul Samuelson,
ETA: So the guy sold his Washington DC condo in 2004? That looks to have been a pretty poor decision.
Did you just link to the change in the housing market over the past year? Washington Post:
My link:
Let's subtract the $1000 he paid for the best argument against the existence of a housing bubble. On the face of it, you appear to be arguing with a man who... (read more)