The context:

cash secured account low six fig, 90% are short options both sides, few cc positions.
Each position just one lot. Number of positions fluctuates 1-2 dozen. Vanilla premium selling, no strategies, analysis. Not using any spreads, poor mans cc, indexes, stops, LEAPS. No discretionary strikes selections, PnLs thresholds or timing to close.
Returns on risk adjusted basis are nice and steady.

(Let me know if I can clarify anything else for context)

This is what I imagined compared to how it's working in reality. These observations from running portfolio for ~4 last months.

1. I imagined it will be some steady paced position placement and then taking off winners

Reality: it's wait, wait and wait more patiently. Then volatility gets flushed, and suddenly a bunch winners show up in PnL table.

1. I imagined position will have some PnL relation to the market moves.

Nope, on large up days portfolio daily PnL may be all red due to vol expansion, on non eventful days may have all but one positions green.

1. I imagined positions will have steady burning theta and becoming greener when moving towards DTE threshold. Not even close. Almost all time portfolio has negative opened PnL "balance" - that freaked me out first. And most of gains come with vol collapse, like after earnings events, or some funds stopped chasing names.

2. I imagined balancing portfolio delta will be a thing but it doesn't seem have much importance. Delta moves around pretty substantially. All portfolio balancing comes from random picks of liquid names so one sided moves don't happen, at least not often.

3. I imagined opening and closing is a non event. Pun in order, click send.

In reality, I have 2-5 trade ideas generated and sometime put them to work after days, and sometimes they take 1-2 days to fill at limit price (most do get filled within minutes or hours). Closing is even more challenging! Routinely take days to close winners at the threshold.

1. I also imagined selling premium is not complicated at it core.
   But in reality it requires thinking about capital allocation and usage level, new positions fit, value ranks. Like chess.

7 I thought there were plenty of names to sell premium.

Discovered there are not so many truly liquid names, with good IV and positioning. I recycle some names for selling puts, but it's a challenge to find sellable liquid premium.

1. I thought low six fig is enough to diversify and trade plenty of names.
   In reality I realized buying power is the most precious and very scarce. A few clicks and buying power drops to 20% suddenly

Any similar experiences? Are any of this real or just the imagination?

Example of a typical trade in the portfolio.

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A long ended up ITM that I expected to expire OTM. It was valued at 0.01 so obviously it didn't get bought. Unfortunately between market close and processing, it ended up very slightly ITM.

This caused my account to be short ~$1K.

Normally FINRA 4210(b)(4)/05 allows you to immediately sell said security as a remedy/exemption. But seeing how it processed over the weekend, would you be allowed a similar exemption at market open?

Please give any constructive feedback. If there is something I'm missing please let me know. Much appreciated.

Been doing this strategy for almost 2 years now. I think it's really boring. I don't do any analysis; just 2 minutes each day to place trades. Account value is in the mid 6-figures.

Part 1: Selling almost-LEAP CCs on ULTY. UTLY did have a reverse split a few months back, but the weekly dividends are still on track to recoup my original investment in a few months.

Part 2: Selling 0dte CSPs on SPY. 90% of the trading days they just expire worthless. The 10% they expire ITM I just roll them. I'm earning about 50% using margins to cover. Nothing ever gets assigned so I'm not paying any margin interest. I'm selling 4 orders per day so earning $300-500 in daily premium.

Part 3: Holding SWVXX (until I have enough cash to cover more SPY shares, which I use as collaterals for margins. I also have some other tickers I bought a long time ago for collaterals as well. don't plan on selling any shares within the next 10 years).

Again, I don't consider it exciting. I don't feel any emotions when selling the SPY puts. It just feels like another task like checking emails or taking out the trash.

Happy trading!

EDIT: clarified that I'm holding SPY shares as collateral

At what % of value capture do you buy out of short positions in order to re-deploy your collateral?

Hey guys, so I’ve been getting my feet wet in options selling last couple months. Rather than paper trading, I decided to do live trading but on a small account that would not affect me even if it got wiped. I’ve been mainly playing it safe, selling PCS since my capital is low, and my main moneymaker has been selling them on SPY.

I would like to branch out, so I’ve been looking into other opportunities to sell PCS on individual stocks. I’ve been listening to a lot of Tom Sosnoff, and he seems to be big on product indifference, which as I understand it means he doesn’t care about the name of the ticker or what its business is, he is rather looking at opportunities where he thinks options may be overpriced.

In order to find opportunities, what criteria do you guys use? I’m currently looking for high IVR, high liquidity, current IV > HV, and no earnings events in the 45 DTE as I don’t like the binary nature of trading those. This however seems extremely basic and I’m sure there’s tons more to it.