My approach to selling puts.

I am not sure this is correct. If I want to go long, I buy the underlying. Selling puts is a bet on stagnation in my view (neither long nor short).

Stagnation is only a small part of the P&L curve; all the rest of it, out to infinity, parallels a long position. For the purposes of @Overnight 's question, that was the closest equivalent.
 
I am not sure this is correct. If I want to go long, I buy the underlying. Selling puts is a bet on stagnation in my view (neither long nor short).
it depends on the volatility skew.. if there is put skew - i.e., indexes and most large caps - then selling OTM puts will give you a long term mathematical edge because of the pricing discrepancy between the selling price and the theoretical expected value.. options are priced based on probabilities, and those probabilities tend to hold true over the long term..

if the volatility skew is neutral or to the call side, there is no mathematical advantage to selling OTM puts versus longing shares, in the long run at least.. there are individual situations which would yield one to be better versus the other, but in the long run, after 1,000 trades, the edge will depend primarily on the volatility skew..

also, counterintuitively, selling covered calls against shares if you get assigned will, in the long run, negate the mathematical edge you gave yourself by selling puts.. this is because in put skew equities, while the puts are overpriced the calls are underpriced, and the two will wash out in the end.. you'd want to sell covered calls on equities with call skew, where the calls are overpriced..
 
I'm not as leveraged like you, but I do something that works similar concerning due diligence/value/balance sheet. I steal from someone else!! The Royce Family of Funds...RMT, RVT. They will do many things that you do. I usually will wait for a correction, then buy individual stocks from their funds. I'll then do covered calls (just me).

You have to be thick skinned to post here...If there is a hole, people will find it. You ready...A new Covid variant starts hitting and killing men and women in their 30s and 40s. Covid-19 hit more of the elderly/over weigh (in general). The Spanish Flu hit (killed) the young and healthy. Could they handle the claims? Do these companies cover life, property/casualty, and reinsurance?? If it's just life, you may want to dial back a bit...

I certainly appreciate that there is nothing new in my approach. Do others do anything better besides less leverage? What can I learn from them to improve?

Leverage ratio is for me opportunity driven and not risk driven. There are less opportunities now. I approach this matter more like a hedge fund than retail (some call it balls of steel, far from that).
 
Could you clarify nr. 3? Are you looking for special events when selling vol or is it a pure IV percentile/premium bet? Since you mentioned you assess events that the market got wrong by looking through SEC fillings I assume the former(?), or do you look through the sec fillings to look at their financial health/balance sheet only? Do you hold after the event has passed or do you sell after the IV Crush?

I do both but event driven stuff amplifies returns.

I obsess about all fillings looking for nuances. But the starting point is the balance sheet th n followed by the special situation or even drive.
 
it depends on the volatility skew.. if there is put skew - i.e., indexes and most large caps - then selling OTM puts will give you a long term mathematical edge because of the pricing discrepancy between the selling price and the theoretical expected value.. options are priced based on probabilities, and those probabilities tend to hold true over the long term..

if the volatility skew is neutral or to the call side, there is no mathematical advantage to selling OTM puts versus longing shares, in the long run at least.. there are individual situations which would yield one to be better versus the other, but in the long run, after 1,000 trades, the edge will depend primarily on the volatility skew..

also, counterintuitively, selling covered calls against shares if you get assigned will, in the long run, negate the mathematical edge you gave yourself by selling puts.. this is because in put skew equities, while the puts are overpriced the calls are underpriced, and the two will wash out in the end.. you'd want to sell covered calls on equities with call skew, where the calls are overpriced..

That's interesting.
 
What is the rough cost of hedging a given portfolio with 20% OTM SPX puts on a monthly basis?

Can someone give tradier a hand with this one perhaps?

This post seems to have attracted a number of experienced options traders now...
 
That's interesting.
next time you're looking at an index look at the prices for a call and put equal distance from the stock price.. in a perfectly efficient and neutral market, they would cost exactly the same, but you'll find the puts cost more.. in other stocks, especially HTBs and tech stocks around earnings season, you'll find call skew..

EDIT: as to the cost of hedging with SPX, i don't trade futures at all, so i wouldn't be the person to ask on that front..
 
I had a pretty good put-selling system using 20-day and 50-day ATRs but I have been overloaded with assignments the last month. I've got to sell puts for less juicy premiums. I now screen for stocks and ETFs with 94% DITM and sell puts at 6% ITM%.

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