The Beauty of Options - Portfolio Insurance at a Discount

I mainly observed this empirically where my basic BS calculations wouldn’t match what happens during large market swings, without understanding of why or what specifically fails, but simply deriving my own Greek-free correlations and models. While some people like Ron Bertino and the guy running SJOptions do seem to calculate how Vega changes differently across calendar expiry dates with underlying’s movement, and I’ve seen some mentions of “True Vega” or maybe “Dynamic Vega” with reference to Nassim Taleb’s book “Dynamic Hedging”, so possibly that book contains more info (I don’t have it).
Generally BS doesn’t even predict volatility smile, so it’s been adapted/utilized to more realistic market conditions.
While what I have observed is that, for example, as IV swings wildly and then settles at a high level, some of my ratio spreads keep changing value for a brief time even while the IV already settles and stops changing too much. This cannot be explained by any greeks or calculations.
I even had DOTM ratio spreads offset by equivalent back ratio spreads set couple weeks apart (both about 3 months out), and at one point they were both losing money as if both using completely different models or calculations. Though the following day they’ve equalized to the point of making sense again.
Some people would interpret this as market makers conspiring to kick them out their positions. While I was actually wondering whether MM’s options inventory doesn’t play a role here. I’ve also noticed very small differences between pricing of weekly vs monthly DOTM options, as if they’re handled by different MMs, but I’m not sure.
Though AFAIK for those reasons some quants seem to study vol surfaces empirically rather than trying to calculate them using BS or other static models (?).
While I’ve sometimes spent 15+ hours a day staring at options chains and I’d like to think I’ve derived some conclusions that I can use, while still suspecting that MMs may have more control than some people may think, and can for example set opening DOTM options prices after a market crash at whatever price levels they need and how it may affect their own positions/inventory (thus producing or skewing the vol smile), not at levels that can be pre-calculated. This may produce various inefficiencies as well as risks. Though I may be dumb and wrong, so I write software that assumes that I am dumb and derives its own correlations and conclusions empirically, without my personal opinions/biases, and I get much better (actually amazing) results when I remove Greeks as variables.
Interesting comments.

I have some DOTM options and recently their prices were all over the place, not making any sense (BSM wise) or tied to underlying prices. Didn't auto stop loss, decided the best thing to do was just let them settled down before took any action.
 
By the way, for those of you saying that is this an overall portfolio, or just portfolio insurance for other trades/investments, let me just say this. Do insurance company's make money? Hello? Yes. This portfolio is an insurance company during normal market conditions. It is also a policy holder when all hell breaks lose. It's a pretty good situation for the overall portfolio.

I'm really amazed that some of you made it through kindergarten graduation. You did make it through kindergarten, right?
 
Booby, portfolio insurance is an overlay. A vol-overlay. Not a janky one lot account that wouldn't buy a Model 3 Tesla.

AIG.
 
Booby wins.
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By the way, for those of you saying that is this an overall portfolio, or just portfolio insurance for other trades/investments, let me just say this. Do insurance company's make money? Hello? Yes. This portfolio is an insurance company during normal market conditions. It is also a policy holder when all hell breaks lose. It's a pretty good situation for the overall portfolio.

I'm really amazed that some of you made it through kindergarten graduation. You did make it through kindergarten, right?
I am one that didn't make it through kindergarten.

No matter how hard I tried I couldn't make your portfolio insurance worked (for SPY), going back 25 years.
 
Without taking sides, I see dest having provided a lot of real trades over time and Bobby showing a single strategy, and not going to comment on his strategy other than it looks overly complicated. But I don’t think Bobby wins in a competition . I just don’t see it happening.
 
Without taking sides, I see dest having provided a lot of real trades over time and Bobby showing a single strategy, and not going to comment on his strategy other than it looks overly complicated. But I don’t think Bobby wins in a competition . I just don’t see it happening.
I beat him once when he said I didn’t have on the positions in my account. I beat him twice when he rescinded his challenge. He’s a pussy.
 
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