The Superforecaster approach absolutely should account for this, and to some degree does. You won't see anyone who has done superforecaster training saying things like "It is 99% likely X will win a two horse race election" before any votes have been cast.
1. Taleb says the stock market systematically under-prices risk when in reality probabilities have fat tails, or high kurtosis.
2. Taleb took advantage of this by buying OTM puts which were being undervalued compared to the real risk. He's now "F you" rich, awesome.
(correct me if I'm wrong on these two assumptions)
The next question I have is, now that the cat's out of the bag, does this strategy still work? Is it possible that the market could over-value tail risk, making it a losing proposition to run this strategy (at least on certain stocks).
And if so, how do you know when that deep OTM put option is over or under priced?
I recall Taleb spent a lot of time talking about the problems but was light on actual details of how to make this strategy work out in practice (though it's been a few years since I've read some of his earlier books).
Markets, and people generally, don't work like that. The exact logic varies with strategy but, in this case, people like strategies that involve picking up quarters in front of a steamroller (i.e. selling deep OTM options).
These strategies sell exceptionally well with retail investors. French investment banks, in particular, are known for absolutely loving these strategies. And they blew up hundreds of thousands of Korean investors a couple of years ago with this stuff (and they did this in 2008 too...people really love these strategies and French banks really love blowing up retail investors).
A slightly more trenchant example is tech stocks. These are high momentum stocks, we know that high momentum is extremely cyclical and will eventually blow up (i.e. like option selling) but people do it because they think they will be able to jump out before it goes wrong (spoiler: they won't).
So yes, there is always a price at which something stops working but it is very unlikely we are at that point with this strategy. Implementation of this strategy varies. Empirica (or whatever they are called) apparently do something clever, I know someone doing this who just buys 10-15% OTM puts (and does some kind of simple backtesting/valuation)...but the basic idea is: what is the probability of the price falling this much, what do I gain if this hits, what do I lose if it doesn't. You can get very complex with modelling volatility, if you are trading volatility then that is relevant...for this strategy, you have no real idea when it is going to occur (the PM I know who was buying puts was doing it for three or four years before this happened, they still a lost a bit in the drop but, importantly, they didn't have to sell anything so have had a great year (up 10-15% with very little net exposure to markets).
The problem is in conflating the two.
His investment strategy, as I understand it, is to capitalize on that confusion. Which is exceptionally hard work, in spite of a summary of Taleb's idea.
