Couple of bits that stand out that I don't get, like the above...And this below...
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So the strategy is basically to collect premium by selling farOTM puts on ES, yes? And each one of those "legs" is 50 options?
Who the hell is buying them? At what point did you sell those?
Above, you are showing a roll I guess from Sep 2022 puts to Jun 2023 puts...When did you roll that?
My main point is how can there be people buying such far OTM puts, (much less 50 of them?!?) you write today for the ES to be below 3000, and as low as 2550? That is some real damned pessimistic market outlook.
> And each one of those "legs" is 50 options?
You are misunderstanding the meaning of the label. The 50 you refer to is the instrument multiplier. You could not possibly be short of that many options, obviously, I am not Warren Buffet, LOL
Example:
ES FOP 20231117 4200 P CME 50 E-mini S&P 500 [EW3X3 P4200, 593587272, mult: 50]
(I always append the instrument multiplier in my labels, unless it is 1)
> So the strategy is basically to collect premium
No, the main idea is not to collect the premium. I have explained it many times. The idea is a continuous balance of long/short by modulating the position to collect those "scalps". Then there are additional sources contributing to the overall edge and causing that PNL slope of 570 days, as I have already explained many times.

How you roll is quite arbitrary, simplistically said, the main purpose of the "rollover" (or more precisely "information transfer") is "stop-loss-order recovery" and transfer of the trading information, so that it can be used strategically for the next orders. Clearly, always with an eye to the global payoff scenario.
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