Unless he was wrote about it ahead of time, we have no way of knowing whether he also made a similar bet with another friend in a different conversation to say that housing prices were going to continue towards the moon. If he had also structured the bet in which he got his school payed for and seemingly no downside if he lost, then he could have guaranteed free school, and looked like Nostradamus either way.
So it's quite possible that this is selection bias at work, and he "flips coins" on a regular basis and only brags about the ones that come up heads.
The people who become notable are those who predicted an economic crisis, for decades before circa 2008, and once they got notoriety for that, have continued to predict doom for the subsequent decade. Eventually they either die or are right again.
IF s/he was confident about the prognosis, making really money in the marketplace would have given leverage x-fold higher than a bet between friends would allow.