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In a recent CNBC interview, Black Swan author Nassim Nicholas Taleb gave a categorical advice about investing in the Corona period. “It is very unwise to do any form of investment without some form of tail risk hedge.”

I understand the concept of hedging tail risk. But how is it done in practice?

Suppose I have 100 Apple (AAPL) shares and want to hedge my tail risk. The current share price is around USD 350.

So would I buy 100 deep out of the money Put options with a strike price of say USD 75 which expire in 12 months, for USD 84 (USD 0.84 per option)? I wonder if there is any kind of best practice or rule of thumb.

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    $\begingroup$ You may find this April 2020 story bloomberg.com/news/articles/2020-04-09/… illuminating. Calpers had a tail-risk hedge for 3 years, but got rid of most of it just as the markets began to react to the COVID-19 pandemic. $\endgroup$ – Dimitri Vulis Jun 27 at 12:08
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    $\begingroup$ "Taleb telling you to worry about long tails" has about the same level of information content as "the sun will probably rise tomorrow morning". What else would he say, unless he suddenly decided everything he has done so far is wrong??? $\endgroup$ – alephzero Jun 28 at 0:54
  • $\begingroup$ This is a little bit of an older paper (2 pages) but it provides a consice overview and hopefully it will help a little cboe.com/micro/buywrite/benchmarks-fact-sheet.pdf. This one is a little more detailed before 08 the PUT index seemed to perfom better than it does now: citeseerx.ist.psu.edu/viewdoc/… $\endgroup$ – Jorisdrees Jun 29 at 10:47
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With difficulty and high costs and secretively. Successful ones are the ones that are able to do it more cheaply. This is also the reason for their secretiveness: prices would go up.

The costly but straightforward approach would be to buy equity index puts. However, I don't think anyone here can or will explain how you can tail hedge at scale significantly more cheaply and effectively. To support this negative answer, I offer this:

In May 2020, there was a Twitter fight between Nassim Taleb (of Black Swan and tail hedging fame) and Cliff Asness (co-founder of 143 billion hedge fund AQR) on this very subject. The fight started after a report by AQR on their blog claimed the strategy happened to work in March 2020 during the (first?) COVID-19 sell-of but was expensive to maintain during all the periods before this. They conclude that over longer periods, buying portfolio insurance isn't a good investment.

Taleb claims that tail-risk hedging can be done and should be done but I'm not aware of him or anyone else giving a general guide on how they exactly do it or point out where the AQR research paper went wrong.

What you can, is do an analysis (company, scenario, macro or something else) and try to figure out where tail risks are underpriced in the market and buy the protection (for example John Paulson's bet against the housing market). In my opinion, this has more in common with active investing than hedging.

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    $\begingroup$ That sounds like a wise, albeit somewhat disappointing answer. What about buying deep out of the money put options (as in my example), which are usually cheap? $\endgroup$ – twhale Jun 27 at 19:24
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First off, I agree with the comments and answers already here. "Simple" tail hedging is expensive in the long run and WILL lose you money. Best example is the CBOE Put Protection index (PPut). Even through COVID-19 it barely outperformed the SPX and that was the mother of all tail risks. In all other market phases you basically buy reduced volatility for quite a lot of return. Cheap tail hedging that will not lose you money is pretty much the holy grail of portfolio management and as such priceless information.

Hedging in general needs good timing to be profitable and options are not the best options as they are expensive. A different way to hedge (non tail-risk specific) is buying an inversely correlated asset (i.e. bonds, gold). But frankly the easiest and most straight forward way to hedge is just to reduce exposure and have cash to buy when the price has fallen.

Oh and yea Nassim just sells you quite obvious information literally everyone in the business knows and makes it seem incredibly complex and special. But in reality because its known it does not help at all. I mean, of course, after this run in this situation everyone wants to protect against "the second wave" but not loose performance if it goes up. And who knows that better than the people selling options. So those options are priced to perfection plus a little so the sellers make money.

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  • $\begingroup$ For me as a novice, your answer is very helpful. I originally studied economics and had to go through all the math of asset pricing theory, including options. But it sank away and am brushing it off now. Incidentally, I also studied philosophy. And from that perspective I find Taleb wonderful. It is now clear to me that his ideas about hedging tail risk cannot be implemented easily and cheaply. But philosophically, I think his ideas are very relevant - because they also apply outside the market. And they are relevant and useful there, I find. $\endgroup$ – twhale Jun 28 at 11:11
  • $\begingroup$ This isn't the most extreme of tail risks, but then in a really extreme tail risk scenario, the markets aren't going to be working anyway. $\endgroup$ – Acccumulation Jul 13 at 23:43
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Taleb equates famous put sellers like Niederhoffer with all derivative traders who short derivatives, so does this guy with an axe to grind, https://steadyoptions.com/articles/how-victor-niederhoffer-blew-up-twice-r124/ They are ignorant of risk management a naked put need not be more risky than buying a share, but I am not in the business of educating. I keep it to myself, thanks. This is the basis of his famous quotes, eat like mice, shit like elephants, and also behind the famous sucking up nickels in front of a steam roller, lovely quite picturesque, good to scare people off because as every economist worth his salt knows once an arbitrage is exploited there is no super-profits just marginal revenue. Which is my main beef with Tom Sosnoff everything he says is pretty spot on, and he is more honest than Taleb, but if everyone trades the way he recommends as he shows on his tasty trade channel, there would not be much money to be made from trading that way, in fact there would end up being more option sellers than buyers he should think that through some time. Most people even Finance MBA's on Wall street have a very limited financial literacy they are focused on orthodoxy, as the economist J K Galbraith coined it, the conventional wisdom, he said that facetiously. As Shakespeare wrote, "there is more in heaven and earth than is dreamed of in your philosophy, Horatio!"

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    $\begingroup$ Why don't you put all your comments and the second answer into one answer? You can edit the answer after submitting it, you know? $\endgroup$ – Hans Jun 28 at 2:51
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    $\begingroup$ Please put everything into one answer. What you're doing now won't work as the order will get messed up. $\endgroup$ – Bob Jansen Jun 28 at 10:03
  • $\begingroup$ That is not how this site works, the whole community gets to vote on your contributions, subverting this is against rules. I urge you to follow the rules to create a pleasant experience for everyone. $\endgroup$ – Bob Jansen Jun 29 at 6:57
  • $\begingroup$ It is not subverting as you suggest , it is protecting my free speech. As others are not making it a pleasant experience for everyone, I would suggest you take a long hard look at your rational for that statement. What are there motives for there subjective evaluation? Do you know? $\endgroup$ – nhoj Jul 18 at 7:22
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It is not that difficult to know when to use remedial action against high levels of market downside volatility and when not to , I refer you to William Ziemba's recent publication on this How to Predict Stock Market Crashes, Ziemba and Ed Thorp and there associated professors, have for many years published many brilliant publications way way beyond Fama French Markowitz and all of that. They are the kings of Kelly Investing and Ziemba has quietly published the real deal about finance along with Thorp, the stuff that Wall street desperately does not want you to know at any cost. Extreme Value theory is mathematically complex so is runs detection and change point detection. But if you seriously wish to trade like a real quant not watch squiggly lines on a map and jump up and down punching buy buy sell like a crazy monkey, then so be it , do the hard yards or stick with something easy, buy and hold and go play golf. I am quite amazed people do not find this useful information considering that 90% of orthodox finance has largely proven to be fallacious, and especially seeing as the question raised a particularly specious and dubious claim by Taleb, ignorance knows no bounds.

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  • $\begingroup$ Thanks a lot. Could you please put all your answers and comments in one answer? That would make it much easier to read all your thoughts in one go. Thanks! $\endgroup$ – twhale Jun 29 at 13:34

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