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Wiki Selling TSLA Options - Be the House

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My 2 older boys had day off from the school. We spent the day at the skatepark with the new skateboard their grandmother bought my oldest for his birthday. I sold some 1225 CCs for tomorrow just before trying it again like old days when I was 14 and careless. I’m preparing my retirement by taunting the devil with bilateral wrist fractures.

I told myself I would only sell Puts if I ever got into option trading. However, my option was activated after the second greatest run up in the stock history. I could not help myself but to open strangles.

I have discussed a new strategy with my wife trying to use her engineering brain to average down my risk taking brain.

For a given week.
Monday: at the MMD sell puts 40% away from SP expiring on Friday. When the stock recovers sell CCs 40% above the SP. Open a safe strangle on both side using maybe 35% away of the covered calls from shares.
Tuesday: same thing but open a strangle 30% away from the new SP
Wednesday: 25% away
Thursday: 20% away
Friday: 15% away

I’m trying to set a simple safe strategy that my wife can follow the day I am too busy to even look at the stock price.

I’m trying to be safe from a 12% daily downturn and from a 12% run up. Safe from a drop of 17% over 2 days.

Please critic that strategy. I am trying to optimize the time spent following the stock/profit generated free of stress. High probability of success without having to manage rolling ITM BPS while not available in a doomsday scenario.
20% away the day before exp., and 15% the day of, will get you nothing. If you want to be that conservative, do 40% away the Thur./Fri before, 30% on the Monday/Tues. Reposition on Wednesday if it's worth it. Use $200 spreads with margin available to widen, or $300 to start with so they are easier to roll.
 
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20% away the day before exp., and 15% the day of, will get you nothing. If you want to be that conservative, do 40% away the Thur./Fri before, 30% on the Monday/Tues. Reposition on Wednesday if it's worth it.
Better yet, use your knowledge of TSLA. In mid December, 10-20% away for BPS, 30-40% for BCS. 10% for naked Puts. If P&D is good, keep it going until the week before earnings (then take cover).
 
I

My 2 older boys had day off from the school. We spent the day at the skatepark with the new skateboard their grandmother bought my oldest for his birthday. I sold some 1225 CCs for tomorrow just before trying it again like old days when I was 14 and careless. I’m preparing my retirement by taunting the devil with bilateral wrist fractures.

I told myself I would only sell Puts if I ever got into option trading. However, my option was activated after the second greatest run up in the stock history. I could not help myself but to open strangles since selling puts was riskier than selling covered calls after the run up.

I have discussed a new strategy with my wife trying to use her engineering brain to average down my risk taking brain.

For a given week.
Monday: at the MMD sell puts 40% away from SP expiring on Friday. When the stock recovers sell CCs 40% above the SP. Open a safe strangle on both side using maybe 35% away of the covered calls from shares.
Tuesday: same thing but open a strangle 30% away from the new SP
Wednesday: 25% away
Thursday: 20% away
Friday: 15% away

I’m trying to set a simple safe strategy that my wife can follow the day I am too busy to even look at the stock price.

I’m trying to be safe from a 12% daily downturn and from a 12% run up. Safe from a drop of 17% over 2 days.

Please critic that strategy. I am trying to optimize the time spent following the stock/profit generated free of stress. High probability of success without having to manage rolling ITM BPS while not available in a doomsday scenario. Feel free to share not advice on how to tweak it to make it more profitable, less risk, more fun, etc…

I am tempted to reduce all the percentage by 5% closer ITM when I place my trades however my wife would stay 50% away. I’m trying to find common ground here.
I have previously (and still do, to some degree) used delta to make my decisions along these lines. It adjust automatically as you near expiration and is an approximation of finishing ITM. I.e. a .10 delta option has an approximately 10% change of finishing ITM, and thus 90% of finishing OTM. Even better is to find your broker's information about PoP (probabilility of profit), ProbITM, or similar. That's a more exact reading on how the market is pricing the likelihood of being ITM/ OTM at expiration.

The problem (MHO) with % share price OTM is that it doesn't adjust to IV, so its easy to be too far to make it worth the time and effort, or too near to the sun. But that %OTM doesn't change fast, so its also something that you can update in your rules periodically. Delta also adjusts based on the IV climate.


One path I've gone down previously, and hope to try again in the future, is to work out to every other week options instead of weeklies. When I tried before I got too antsy about moves against me and returned to weeklies. But that's also a thought for you to consider, and either way, keeping the target income small makes for access to a lot lower risk (likelihood of event / ITM). When I went to the every other week positions, what I specifically did was used every other week for my expirations.

I.e. in a given month all of my options will use the first and third week of the month as their expiration (or the 1/3/5th; 2/4). That reduced the number of expiring positions I needed to keep track of. But as I said - that didn't work out for me and I've returned to weeklies.
 
Something I have been thinking about after these last few stressful weeks. Is there an easier way than weeklies? Something I could set and forget? I started looking at longer dated strategies to replicate weekly trading profits.

For example, given a bullish outlook on the SP, one could:

Buy a March 2023 $700 call for $473
Sell a March 2023 $1200 call for $255

Entry cost: $21,810.00
Maximum risk: $21,810.00 (at TSLA$700.00)
Maximum return: $28,190.00 (at TSLA$1,200.00)
Max return on risk: 129.3% (95.9% annual)
Breakevens at expiry: $918.10
Probability of profit: 58.1% (I think this is actually closer to 100% with TSLA)

As far as weeklies, I assume for every $10,000 cash, I could conservatively make $200/wk selling BPS. So 70 weeks x $200 x 2 = $28,000

Two strategies that could arrive at the same point. Except one require maintenance and action every week, and one could be ignored for 2 years. I'm not sure if I would do something like this, but it sure is interesting.
 
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Know thyself. A fantastic example.

I agree that this IS real work. At least for me, I believe that to do this well, there has to be at least something about this that is fascination to fun about it. If this were work, in the sense of something that I was making myself do, then I wouldn't be doing it well.


NOT-ADVICE; just way that I see things. Worth working out your own examples to see if you agree.


The way I see rolling in general, and spreads more particularly... when a position is close to the money or in the money, and the purpose of the roll being considered is to buy time for the share price to turn around and the position to move back OTM (vs, a convenience roll - confirm the profit for this week, while opening the position for next week), then:

There is a balance between rolling too soon, and rolling too late that we're looking for. Of course if the crystal ball was always clear then it'd be easy, but the crystal ball is cloudy.

The factors that affect the roll - everything else being equal we'd like to roll with the time value as close to 0 as possible. The rationale is that on a roll we are buying out the time value remaining in the old position so we can sell the time value in the new position. The less time value in the old position, the less there is to buy out. Or a different way of thinking about the same thing - our earnings are in the time value; the less of there is remaining, the more that we've earned. That mostly means that the closer to expiration, the better.

The other factor is just how deeply ITM one goes. Generally speaking the quality of the available roll decreases as the share price approaches the short strike and continues getting worse as you go further and further ITM. It seems like the very best rolls are ATM or slightly OTM, but are still good enough that waiting a few extra days while going slightly ITM is a better tradeoff (time value melting away).

Too soon and you're buying out more time value than you want to (lower quality position to roll into), and too late may see you get too deeply ITM, thereby lowering the quality of the position you can roll to.

My own bias in this tradeoff is to roll early and for maximum strike improvement (subject to a net credit). There are two reasons for this:
1) The maximum strike improvement is going to get me the best protection if THIS move is a biggie. Most of them aren't, but if this is the one, then I'd like to have given myself the very best chance of staying ahead of it, so the shares can reverse.
2) I view the roll as buying time and that means I'll have a week (or more) of effectively no earnings. Earnings going to 0 for a week or more is way better than realizing losses. And since I'm in this for income, and I've got enough buffer from the weeks that win, one of the uses for those winning weeks is to allow for weeks with no income. Oh - and realized losses are bad, really bad, for income :D

Rolling early if the shares aren't gapping up and down will bias towards still OTM. If I'm close to expiration and OTM, then I might split the difference on the roll - find out my max strike improvement and then come back 1 strike so I get a bit of income that week while still providing lots of coverage if this is a BIG move against me.


From what I've seen high IV provides significantly better rolling choices, while also being an environment in which more rolls are needed (can't get something for nothing).

I learned at the beginning of the year when IV was high that I could get an effective roll while $80 ITM. Shares around 720 and strike around 800 on some puts, so 10% ITM at that point, where effective = credit + strike improvement available, whether I take the strike improvement or not. A month later with IV down, I no longer had an effective roll when $40 or $50 ITM. I don't have a formula here - I just regularly setup candidate rolls when its possible that I might be needing them soonish so I can see just what's available.

I learned that there are situations where a 1 week roll is barely or not effective, while the 2 week roll IS effective. Or 1 week vs 3 or 4 weeks. I personally choose to not roll out to more than 4 weeks, at least without a lot of thought about it. I've rolled out to 1 and 2 years before and really didn't like that dynamic. Once I'm up to 3-5 weeks to expiration then it might be time to take assignment (or the loss) and move on.

I've seen situations where the 2-4 week roll is much more than 2-4 1 week rolls. And heck - if you're deep enough in the doodoo, then I've rolled for as much as a month just to avoid the weekly work (and get a better credit).

When really deeply ITM on naked puts and calls, the time value will approach 0 much sooner than the day before expiration. I keep an eye on that and have been in situations where I was rolling 1 week ahead of expiration to avoid early assignment (a good time to be considering monthly rolls). That doesn't guarantee no early assignment - I just don't try to push time value really, really low. Probably around .30 to .50 is as close as I've gone (guessing at the number - it is at least directionally accurate).

And last that I can think of right now - spreads have different roll characteristics from plain short options. These are best seen in a really tight spread, but the dynamic applies to some degree to any spread. To the degree that a spread behaves like a short put|call, then the rolls that maintain the spread size should be expected to behave similarly or the same. From what I've seen this relationship holds pretty well through 1/4th of the way into the spread. So $50 on a $200 wide spread.

The spread stops rolling for a credit or strike improvement at the mid point.

Rolls past the midpoint of the spread are a net worsening of the position, either by paying a debit to maintain the strikes, worsening the strikes, and/or bringing more capital into the trade.

And somewhere in there - probably the midpoint and lower - adding more time to the roll doesn't change the quality of the roll that is available. I think that what's going on here is that the % change in time value for the long and short legs are now changing roughly the same, so whether you add 1 week or 4, the time value relationship between the two changes about the same, thus little or no extra value in more time. Maybe even a worse roll with more time - I haven't tested this though.
YESSS!! Thank you so much for the details!! You have addressed all the variables I've been racking my brain over.

A lot of my stress comes from whether I should roll for next week, 2 weeks, 4 weeks, etc. Then, it's the WHEN of rolling. Right now, my ITM BPS are hard to salvage at this share price range. I feel we are going sideways, with shaky support at the bottom, a cap at the top, leading to the risk of a drop and no real catalysts in near future. So I almost rolled my 11/19 ITM BPS today to next week due to the unknown. But I think I will shoot to roll as close to January, bit by bit, whether in 1, 2, 3, 4+ week increments. Hearing your experience of rolling a deep ITM put spread and salvaging it by rolling it further out helps me a lot. I now feel comfortable giving myself more time to roll out. It is also going to help my stress levels, making me a better trader.

I think my goal would be to roll when the share price will be back in the 1200s for multiple days, if not a week. Mainly due to volatility, I can see it touching 1200 then zooming down, making my OTM BPS, ITM in no time. If that happened Thur/Friday of the week of expiration, I'd be doomed.

When will TSLA be 1200? I'm not sure other than maybe late December/January when Q4 Earnings are released and Giga Berlin occurs. I'm there with the "cloudy crystal ball" analogy. I don't know what it'll be like next week, but looking at Max Pain for next week and the week after, it is not looking good. I know max pain is not a reliable indicator for share price other than for the current week. But the max pain next week is sitting in the 900s with not many calls; just a massive put wall in 1,000. For me, I don't want to play with the chance of this even breaking below 1,000. I rolled my BPS 11/12 to 11/26 yesterday on the hunch that it'd be better.

So far I have 11/19 and 11/26 ITM BPS. With the IV spike in the morning, I considered rolling my 11/19 out. Now, I'm considering doing it out to December if possible. If Friday there is a spike up, or there's a spike up next week, I will likely roll out, as close to January as I can to buy myself more time for the share price to rise and stabilize at the 1150s or 1200s. Of course, if Friday goes really well, Monday might be a great up day too, giving me a chance for my ITM BPS to expire worthlessly. But knowing TSLA, it can quickly drop 100 points in a day easily on no news. So I will shoot for rolling as close to January as I can over these next few weeks.

Really glad to hear your ITM BPS were salvaged somewhat. I panicked and BTC sold when I didn't need to, should've rolled, but I live and learn. I am practicing my own advice around managing "my inner critique", doing deep breathing paired with muscle relaxation exercises, etc. Happy to say mentally I am taking care of myself so I can take in this information, stay in the fight, and keep moving along. Last night was my first night of a straight 4 hours of sleep and feel better. I teach my clients these mindfulness, relaxation strategies and didn't think to use them until last night as my heart was racing in bed. A good deep breath while flexing my muscles for 10-20 seconds multiple times helped me relax to my "sleeping point".

Funny enough, I talked to Etrade and consulted with an active trading team member. That guy had also done a credit spread on TSLA, got fearful, and bought to close! I felt so relieved and happy to know how many people got caught in the same situation as me. Really normalized and validated the experience I've been going through and has really shut up my inner critique and made me more confident.

I appreciate you and everyone else here on the forum. You've all helped me feel more optimistic, empowered, and knowledgeable. Some have really gone out of the way to be extremely supportive and it's really meant a lot to me. So much so that it's given me the strength to keep on rolling, just when I thought I was down and out.

Thank you all and here's to a Happy Friday!
 
Closed my remaining spreads for this week for average 97% profit. Opened new positions for next week:

50x 760/860 1140/1240
20x 850/900 1250/1300
80x 870/920 1260/1310

Intend to initiate another batch of IC and/or naked puts early next week for 11/19 as well.

I very much believe we will see 900 before we see 1200 again. I also believe it’s going to be a very volatile few weeks ahead of us and intend to keep my strikes behind significant support/resistance lines (as opposed to just setting x% OTM).
 
I rolled all my at risk spreads to next week but this is something I have been pondering since yesterday.

Let’s say you have 1 -1100/1000 put spreads expiring tomorrow.

And let’s say we open flat tomorrow and bounce around a bit by $30+-

Would one be able to exit the position by rolling to 5 -1020/1000 puts at say 1pm expiring same day to help reduce the loss?

Assuming the stock closes OTM at 1040.

Right now it looks like the close would cost 3875 and the open would credit 615. Like i said I rolled this earlier this week. I originally sold it for 1400. So I think this would limit the potential loss of 4600 to 1860.

Is this correct?
 
Know thyself. A fantastic example.

I agree that this IS real work. At least for me, I believe that to do this well, there has to be at least something about this that is fascination to fun about it. If this were work, in the sense of something that I was making myself do, then I wouldn't be doing it well.


NOT-ADVICE; just way that I see things. Worth working out your own examples to see if you agree.


The way I see rolling in general, and spreads more particularly... when a position is close to the money or in the money, and the purpose of the roll being considered is to buy time for the share price to turn around and the position to move back OTM (vs, a convenience roll - confirm the profit for this week, while opening the position for next week), then:

There is a balance between rolling too soon, and rolling too late that we're looking for. Of course if the crystal ball was always clear then it'd be easy, but the crystal ball is cloudy.

The factors that affect the roll - everything else being equal we'd like to roll with the time value as close to 0 as possible. The rationale is that on a roll we are buying out the time value remaining in the old position so we can sell the time value in the new position. The less time value in the old position, the less there is to buy out. Or a different way of thinking about the same thing - our earnings are in the time value; the less of there is remaining, the more that we've earned. That mostly means that the closer to expiration, the better.

The other factor is just how deeply ITM one goes. Generally speaking the quality of the available roll decreases as the share price approaches the short strike and continues getting worse as you go further and further ITM. It seems like the very best rolls are ATM or slightly OTM, but are still good enough that waiting a few extra days while going slightly ITM is a better tradeoff (time value melting away).

Too soon and you're buying out more time value than you want to (lower quality position to roll into), and too late may see you get too deeply ITM, thereby lowering the quality of the position you can roll to.

My own bias in this tradeoff is to roll early and for maximum strike improvement (subject to a net credit). There are two reasons for this:
1) The maximum strike improvement is going to get me the best protection if THIS move is a biggie. Most of them aren't, but if this is the one, then I'd like to have given myself the very best chance of staying ahead of it, so the shares can reverse.
2) I view the roll as buying time and that means I'll have a week (or more) of effectively no earnings. Earnings going to 0 for a week or more is way better than realizing losses. And since I'm in this for income, and I've got enough buffer from the weeks that win, one of the uses for those winning weeks is to allow for weeks with no income. Oh - and realized losses are bad, really bad, for income :D

Rolling early if the shares aren't gapping up and down will bias towards still OTM. If I'm close to expiration and OTM, then I might split the difference on the roll - find out my max strike improvement and then come back 1 strike so I get a bit of income that week while still providing lots of coverage if this is a BIG move against me.


From what I've seen high IV provides significantly better rolling choices, while also being an environment in which more rolls are needed (can't get something for nothing).

I learned at the beginning of the year when IV was high that I could get an effective roll while $80 ITM. Shares around 720 and strike around 800 on some puts, so 10% ITM at that point, where effective = credit + strike improvement available, whether I take the strike improvement or not. A month later with IV down, I no longer had an effective roll when $40 or $50 ITM. I don't have a formula here - I just regularly setup candidate rolls when its possible that I might be needing them soonish so I can see just what's available.

I learned that there are situations where a 1 week roll is barely or not effective, while the 2 week roll IS effective. Or 1 week vs 3 or 4 weeks. I personally choose to not roll out to more than 4 weeks, at least without a lot of thought about it. I've rolled out to 1 and 2 years before and really didn't like that dynamic. Once I'm up to 3-5 weeks to expiration then it might be time to take assignment (or the loss) and move on.

I've seen situations where the 2-4 week roll is much more than 2-4 1 week rolls. And heck - if you're deep enough in the doodoo, then I've rolled for as much as a month just to avoid the weekly work (and get a better credit).

When really deeply ITM on naked puts and calls, the time value will approach 0 much sooner than the day before expiration. I keep an eye on that and have been in situations where I was rolling 1 week ahead of expiration to avoid early assignment (a good time to be considering monthly rolls). That doesn't guarantee no early assignment - I just don't try to push time value really, really low. Probably around .30 to .50 is as close as I've gone (guessing at the number - it is at least directionally accurate).

And last that I can think of right now - spreads have different roll characteristics from plain short options. These are best seen in a really tight spread, but the dynamic applies to some degree to any spread. To the degree that a spread behaves like a short put|call, then the rolls that maintain the spread size should be expected to behave similarly or the same. From what I've seen this relationship holds pretty well through 1/4th of the way into the spread. So $50 on a $200 wide spread.

The spread stops rolling for a credit or strike improvement at the mid point.

Rolls past the midpoint of the spread are a net worsening of the position, either by paying a debit to maintain the strikes, worsening the strikes, and/or bringing more capital into the trade.

And somewhere in there - probably the midpoint and lower - adding more time to the roll doesn't change the quality of the roll that is available. I think that what's going on here is that the % change in time value for the long and short legs are now changing roughly the same, so whether you add 1 week or 4, the time value relationship between the two changes about the same, thus little or no extra value in more time. Maybe even a worse roll with more time - I haven't tested this though.
FAQ post of merit. Still cogitating on this, but here are some more suggestions and questions when considering rolling. I’m wondering if rolling would be better in a rising or falling SP scenario, in a higher or lower variability time (morning oscillation or afternoon siesta), or whether it makes no difference. When rolling CCs are decoupled into multiple, sequential trades, it makes sense to BTC lower and STO higher (rising SP environment). However, when this BTC+STO occurs in single multi-leg trade, does direction matter? Maybe not.

A real world thought experiment, which seems to corroborate the thesis that one should roll before getting ITM: SP closed today, Thursday, at 1063.51. Assume you were worried about Friday’s 11/12 -c1100s @ $3.20 and wanted to roll. MaxPain shows IV & the Greeks after close:
50.897 IV0.166 delta0.007 gamma-2.683 theta0.179 Vega

The closest delta equivalent for 11/19 -c1170 @ $8.65, so ~$5.45cr
60.997 IV0.165 delta0.002 gamma-1.421 theta0.407 Vega
Notice, the higher IV-Vega but lower gamma/theta. Presumably, the higher IV is one reason for the higher premium for the same delta. One might choose such a roll if comfortable with current risk level. This is a nice $70 strike improvement, 6%/wk (much better than my $5/wk strike improvement for those far ITM 820 calls).

An alternative roll for minimal credit is 11/19 -c1255 @ $3.25
68.698 IV0.065 delta0.001 gamma-0.817 theta0.207 Vega
Presumably, one might choose such a strike to reduce risk, forgoing one weekly premium, especially if the SP is expected to move quickly. This is a $155 strike improvement (14%/wk).

Not to derail from TSLA too much, but I finally opened a small taxable brokerage account, that is currently limited to options level 1, worse than my IRAs.:mad: I’m only allowed to sell CCs, and I can’t trade TSLA since the account is much smaller than $106,351.00. I’m currently experimenting with QS and LCID, and really enjoy the actual roll function. After a month, I’ll request level 2, then maybe try to get 2+, so that I can trade spreads. Watching QS today reminds me of TSLA these past few weeks. I will definitely be practicing my rolling skills (sold a 11/19 -50cc today, SP near $40, IV near 100, up 16% today).
 
I rolled all my at risk spreads to next week but this is something I have been pondering since yesterday.

Let’s say you have 1 -1100/1000 put spreads expiring tomorrow.

And let’s say we open flat tomorrow and bounce around a bit by $30+-

Would one be able to exit the position by rolling to 5 -1020/1000 puts at say 1pm expiring same day to help reduce the loss?

Assuming the stock closes OTM at 1040.

Right now it looks like the close would cost 3875 and the open would credit 615. Like i said I rolled this earlier this week. I originally sold it for 1400. So I think this would limit the potential loss of 4600 to 1860.

Is this correct?
Your numbers look right, if it closes above 1040.
Max risk is 10k, minus premium of 1400, max loss is 8600.
5x a 20 spread has same max risk, and your premium becomes 1400-3875+615=-1860, so total loss could be 11,860. However, if it stays OTM, then you are only out 1,860.
 
Something I have been thinking about after these last few stressful weeks. Is there an easier way than weeklies? Something I could set and forget? I started looking at longer dated strategies to replicate weekly trading profits.

For example, given a bullish outlook on the SP, one could:

Buy a March 2023 $700 call for $473
Sell a March 2023 $1200 call for $255

Entry cost: $21,810.00
Maximum risk: $21,810.00 (at TSLA$700.00)
Maximum return: $28,190.00 (at TSLA$1,200.00)
Max return on risk: 129.3% (95.9% annual)
Breakevens at expiry: $918.10
Probability of profit: 58.1% (I think this is actually closer to 100% with TSLA)

As far as weeklies, I assume for every $10,000 cash, I could conservatively make $200/wk selling BPS. So 70 weeks x $200 x 2 = $28,000

Two strategies that could arrive at the same point. Except one require maintenance and action every week, and one could be ignored for 2 years. I'm not sure if I would do something like this, but it sure is interesting.
You forgot compounding in your second calculation.
2% per week ~>1.02^70 = 3.9997 => 10k -> 40k, not 28k.
 
Something I have been thinking about after these last few stressful weeks. Is there an easier way than weeklies? Something I could set and forget? I started looking at longer dated strategies to replicate weekly trading profits.

For example, given a bullish outlook on the SP, one could:

Buy a March 2023 $700 call for $473
Sell a March 2023 $1200 call for $255

Entry cost: $21,810.00
Maximum risk: $21,810.00 (at TSLA$700.00)
Maximum return: $28,190.00 (at TSLA$1,200.00)
Max return on risk: 129.3% (95.9% annual)
Breakevens at expiry: $918.10
Probability of profit: 58.1% (I think this is actually closer to 100% with TSLA)

As far as weeklies, I assume for every $10,000 cash, I could conservatively make $200/wk selling BPS. So 70 weeks x $200 x 2 = $28,000

Two strategies that could arrive at the same point. Except one require maintenance and action every week, and one could be ignored for 2 years. I'm not sure if I would do something like this, but it sure is interesting.

It's an interesting approach.

Some food for thought - I think that something the weeklies strategy gets you (especially if you have the discipline to not be in the market 100% of the time) that the above strategy doesn't is flexibility. If you're selling BPSs 20% OTM and the stock craters 20% in a week, you can go an additional 20% OTM the very next week, and the week after that, and continue to make money even in a longterm bear market (like the 2007-09 market). You also can have some exposure to extra volatility during some events, which can be incredibly lucrative.

Whereas with a vertical spread strategy, if you're unlucky enough to open the positions at a time when we're entering a longterm correction, you just might be SOL. However, the length of time you've chosen (~16 months) mitigates that risk for sure - and the risk could be further defrayed by choosing even longer-dated instruments. Also, there's something to be said for not having to manage positions so frequently.
 
So if I'm understanding it, rolling a ITM BPS may be best to do later in the week, like Thursday, rather than a Tuesday?
Short answer - no. Rolling an ITM BPS is best done earlier rather than later in the week. You may still get a reasonable roll on Thursday depending on IV, but into Friday the P+ loses a lot of value while the P+ for next week is still expensive. This makes rolling an ITM BPS very expensive as it gets close to expiry in the final week.
 
Short answer - no. Rolling an ITM BPS is best done earlier rather than later in the week. You may still get a reasonable roll on Thursday depending on IV, but into Friday the P+ loses a lot of value while the P+ for next week is still expensive. This makes rolling an ITM BPS very expensive as it gets close to expiry in the final week.
Thank you so much for explaining! I have ITM BPS expiring 11/19. I am worried about....anything at this point. I may look
Know thyself. A fantastic example.

I agree that this IS real work. At least for me, I believe that to do this well, there has to be at least something about this that is fascination to fun about it. If this were work, in the sense of something that I was making myself do, then I wouldn't be doing it well.


NOT-ADVICE; just way that I see things. Worth working out your own examples to see if you agree.


The way I see rolling in general, and spreads more particularly... when a position is close to the money or in the money, and the purpose of the roll being considered is to buy time for the share price to turn around and the position to move back OTM (vs, a convenience roll - confirm the profit for this week, while opening the position for next week), then:

There is a balance between rolling too soon, and rolling too late that we're looking for. Of course if the crystal ball was always clear then it'd be easy, but the crystal ball is cloudy.

The factors that affect the roll - everything else being equal we'd like to roll with the time value as close to 0 as possible. The rationale is that on a roll we are buying out the time value remaining in the old position so we can sell the time value in the new position. The less time value in the old position, the less there is to buy out. Or a different way of thinking about the same thing - our earnings are in the time value; the less of there is remaining, the more that we've earned. That mostly means that the closer to expiration, the better.

The other factor is just how deeply ITM one goes. Generally speaking the quality of the available roll decreases as the share price approaches the short strike and continues getting worse as you go further and further ITM. It seems like the very best rolls are ATM or slightly OTM, but are still good enough that waiting a few extra days while going slightly ITM is a better tradeoff (time value melting away).

Too soon and you're buying out more time value than you want to (lower quality position to roll into), and too late may see you get too deeply ITM, thereby lowering the quality of the position you can roll to.

My own bias in this tradeoff is to roll early and for maximum strike improvement (subject to a net credit). There are two reasons for this:
1) The maximum strike improvement is going to get me the best protection if THIS move is a biggie. Most of them aren't, but if this is the one, then I'd like to have given myself the very best chance of staying ahead of it, so the shares can reverse.
2) I view the roll as buying time and that means I'll have a week (or more) of effectively no earnings. Earnings going to 0 for a week or more is way better than realizing losses. And since I'm in this for income, and I've got enough buffer from the weeks that win, one of the uses for those winning weeks is to allow for weeks with no income. Oh - and realized losses are bad, really bad, for income :D

Rolling early if the shares aren't gapping up and down will bias towards still OTM. If I'm close to expiration and OTM, then I might split the difference on the roll - find out my max strike improvement and then come back 1 strike so I get a bit of income that week while still providing lots of coverage if this is a BIG move against me.


From what I've seen high IV provides significantly better rolling choices, while also being an environment in which more rolls are needed (can't get something for nothing).

I learned at the beginning of the year when IV was high that I could get an effective roll while $80 ITM. Shares around 720 and strike around 800 on some puts, so 10% ITM at that point, where effective = credit + strike improvement available, whether I take the strike improvement or not. A month later with IV down, I no longer had an effective roll when $40 or $50 ITM. I don't have a formula here - I just regularly setup candidate rolls when its possible that I might be needing them soonish so I can see just what's available.

I learned that there are situations where a 1 week roll is barely or not effective, while the 2 week roll IS effective. Or 1 week vs 3 or 4 weeks. I personally choose to not roll out to more than 4 weeks, at least without a lot of thought about it. I've rolled out to 1 and 2 years before and really didn't like that dynamic. Once I'm up to 3-5 weeks to expiration then it might be time to take assignment (or the loss) and move on.

I've seen situations where the 2-4 week roll is much more than 2-4 1 week rolls. And heck - if you're deep enough in the doodoo, then I've rolled for as much as a month just to avoid the weekly work (and get a better credit).

When really deeply ITM on naked puts and calls, the time value will approach 0 much sooner than the day before expiration. I keep an eye on that and have been in situations where I was rolling 1 week ahead of expiration to avoid early assignment (a good time to be considering monthly rolls). That doesn't guarantee no early assignment - I just don't try to push time value really, really low. Probably around .30 to .50 is as close as I've gone (guessing at the number - it is at least directionally accurate).

And last that I can think of right now - spreads have different roll characteristics from plain short options. These are best seen in a really tight spread, but the dynamic applies to some degree to any spread. To the degree that a spread behaves like a short put|call, then the rolls that maintain the spread size should be expected to behave similarly or the same. From what I've seen this relationship holds pretty well through 1/4th of the way into the spread. So $50 on a $200 wide spread.

The spread stops rolling for a credit or strike improvement at the mid point.

Rolls past the midpoint of the spread are a net worsening of the position, either by paying a debit to maintain the strikes, worsening the strikes, and/or bringing more capital into the trade.

And somewhere in there - probably the midpoint and lower - adding more time to the roll doesn't change the quality of the roll that is available. I think that what's going on here is that the % change in time value for the long and short legs are now changing roughly the same, so whether you add 1 week or 4, the time value relationship between the two changes about the same, thus little or no extra value in more time. Maybe even a worse roll with more time - I haven't tested this though.
Forgot to mention my current situation:

BPS:
11/19
4x: 1135/1110
7x: 1130/1090
5x: 1135/1125

11/26:
4x: 1050/1080
20 x : 1125/1100

I don't if this changes things. As I'm not "that far out the money". I know its' NOt ADVICE. But this is my predicament. I am somewhat close to the share price. I just need it to break past 1100... My fear is that it drops down to 900s and we hit a huge lull like Q1.

This is the predicament I'm in...hold for a few weeks...vs. just jumping forward to January's earnings report.
 
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You forgot compounding in your second calculation.
2% per week ~>1.02^70 = 3.9997 => 10k -> 40k, not 28k.
For those hitting 2%/week, I suggest one considers excluding compounding from return calculations, as well as not actually compounding the results. Especially if you're using spreads (which is how I've been able to get to 2%/week) then whatever the spread size is you've got a relatively reachable maximum loss available. I.e. - a +800p/-900p spread only needs to reach $800 or lower share price for a max loss, while the same capital devoted to cash secured puts needs a share price of $0 for a max loss.

A max loss when you're compounding your results means that 1 max loss and the account is blown up (at least to the degree that the portion of the account devoted to the trading strategy anyway).

An example:
Start with $1M. Let's assume $100 wide spreads, so 100 of these right off the bat.
week 1 - earn 2%; now you've got 1,020,000.
week 2 - sell 102 contracts, earn 2% using the expanded pool; now 1,040,400.
week 3 - sell 104 contracts, earn 2%; now 1061200
week 4 - sell 106 contracts. collect 2% ($21k) and experience a max loss (1,060,000). Now you've got $21k + $1200 = $22,200

Admittedly if you weren't compounding then you'd be earning $20k/week and in week 4 you'd lose $1M and be left with $80k, so you really really want that max loss to wait for 50 weeks :). But the idea stands - compounding keeps 100% of your capital at risk which means that one's exposure to a black swan doesn't get better over time.


If the weekly results are good enough then compounding those results creates better and better results, but it doesn't help build a buffer for handling a max loss (or something similar).
 
Thank you so much for explaining! I have ITM BPS expiring 11/19. I am worried about....anything at this point. I may look

Forgot to mention my current situation:

BPS:
11/19
4x: 1135/1110
7x: 1130/1090
5x: 1135/1125

11/26:
4x: 1050/1080
20 x : 1125/1100

I don't if this changes things. As I'm not "that far out the money". I know its' NOt ADVICE. But this is my predicament. I am somewhat close to the share price. I just need it to break past 1100... My fear is that it drops down to 900s and we hit a huge lull like Q1.

This is the predicament I'm in...hold for a few weeks...vs. just jumping forward to January's earnings report.
I honestly don't really know what I would do. If you were to simply BTC these positions, would the time value lower the actual loss to be less than a max loss? My guess is that if the loss were smaller, then it wouldn't be much smaller.

With today's close at 1063 it looks like the only position here that isn't a max loss is the 1050/1080 and that one is close.


So I'm pretty sure that there aren't any rolls for a credit that retains the current strikes - you'd be rolling to a worse strike for the credit, or you'd be rolling for a debit to keep the strikes. And you'd still be at a max loss. The way I see it rolling a max loss is throwing good money after bad. Eating the max loss will hurt, but it also lets you start next week with a clean slate and start earning back the losses.

One idea - if they're already max loss and you've still got time, then I don't see a downside to just letting them run - maybe we get that spike back up to 1150 and you're partying in the aisles :) After all - there isn't a bigger than max loss as long as you trade the position as a spread. So a further move down doesn't change anything.


One of the ideas I've seen floated is to buy your way out of the short put and keep the long put(s). The idea makes sense to me but the 2 times I've tried it:
- bunch of extra work keeping tabs on the long puts and picked up an extra dime or 3 per share; totally not worth the energy and time (to me)
- bunch of extra work and the shares moved against me. Ended up with a loss on both sides (much less than a max loss, but larger than simply closing the spread).

Then again I didn't start with the insurance already ITM. If you felt strongly about the shares continuing down, and doing it soon, then this approach might dig you out fast. If you're wrong then you might swing a bigger than max loss! (So I'm not a fan - but that's not advice).


Good luck with these - lets root for a pop up to max pain tomorrow at 1110!
 
I honestly don't really know what I would do. If you were to simply BTC these positions, would the time value lower the actual loss to be less than a max loss? My guess is that if the loss were smaller, then it wouldn't be much smaller.

With today's close at 1063 it looks like the only position here that isn't a max loss is the 1050/1080 and that one is close.


So I'm pretty sure that there aren't any rolls for a credit that retains the current strikes - you'd be rolling to a worse strike for the credit, or you'd be rolling for a debit to keep the strikes. And you'd still be at a max loss. The way I see it rolling a max loss is throwing good money after bad. Eating the max loss will hurt, but it also lets you start next week with a clean slate and start earning back the losses.

One idea - if they're already max loss and you've still got time, then I don't see a downside to just letting them run - maybe we get that spike back up to 1150 and you're partying in the aisles :) After all - there isn't a bigger than max loss as long as you trade the position as a spread. So a further move down doesn't change anything.


One of the ideas I've seen floated is to buy your way out of the short put and keep the long put(s). The idea makes sense to me but the 2 times I've tried it:
- bunch of extra work keeping tabs on the long puts and picked up an extra dime or 3 per share; totally not worth the energy and time (to me)
- bunch of extra work and the shares moved against me. Ended up with a loss on both sides (much less than a max loss, but larger than simply closing the spread).

Then again I didn't start with the insurance already ITM. If you felt strongly about the shares continuing down, and doing it soon, then this approach might dig you out fast. If you're wrong then you might swing a bigger than max loss! (So I'm not a fan - but that's not advice).


Good luck with these - lets root for a pop up to max pain tomorrow at 1110!
Absolutely thank you! There's still next week. I HOPE it spikes up to 1150 and I will be partying so hard!! I'm just...so close!! Hoping max pain comes through for 1110! Then I may roll my 11/19 out further to buy myself more time. Again, like you said it's hard to know what to do. Just know what strategy to deploy. I will have to keep my eye on the 11/19s as I imagine rolling Monday/Tuesday would be my last bet if things go south.

I think my goal would be to have my spreads ITM or OTM then BTC them...

Again, really appreciate your insight and positivity! Helps keep me going!:D

Funny enough, I found an old journal entry back when I sold my first CC 4 months ago and was languishing about losing $3,000 when my portfolio was half what it is now. It is nice to see how far TSLA has come in those 4 months, so that has given me a smile :)
 
Absolutely thank you! There's still next week. I HOPE it spikes up to 1150 and I will be partying so hard!! I'm just...so close!! Hoping max pain comes through for 1110! Then I may roll my 11/19 out further to buy myself more time. Again, like you said it's hard to know what to do. Just know what strategy to deploy. I will have to keep my eye on the 11/19s as I imagine rolling Monday/Tuesday would be my last bet if things go south.

I think my goal would be to have my spreads ITM or OTM then BTC them...

Again, really appreciate your insight and positivity! Helps keep me going!:D

Funny enough, I found an old journal entry back when I sold my first CC 4 months ago and was languishing about losing $3,000 when my portfolio was half what it is now. It is nice to see how far TSLA has come in those 4 months, so that has given me a smile :)
some NOT-ADVICE..
I was able to save a $50 wide bps when my long strike was atm by going full butterfly with it.. the credit I got for that $50 wide bps was so big that it reduced my max loss to almost nothing. In the end I closed both spreads for a slight profit.

Now trying this again, I have +p1050/-p1100/-c1100/+c1150 expiring today.. I will close the bcs and roll bps to next week. I am prepared to widen the bps if needed to roll for credit.

Mind you, these are experimental small positions for me, only 2 contracts..
 
It's an interesting approach.

Some food for thought - I think that something the weeklies strategy gets you (especially if you have the discipline to not be in the market 100% of the time) that the above strategy doesn't is flexibility. If you're selling BPSs 20% OTM and the stock craters 20% in a week, you can go an additional 20% OTM the very next week, and the week after that, and continue to make money even in a longterm bear market (like the 2007-09 market). You also can have some exposure to extra volatility during some events, which can be incredibly lucrative.

Whereas with a vertical spread strategy, if you're unlucky enough to open the positions at a time when we're entering a longterm correction, you just might be SOL. However, the length of time you've chosen (~16 months) mitigates that risk for sure - and the risk could be further defrayed by choosing even longer-dated instruments. Also, there's something to be said for not having to manage positions so frequently.
An advantage I see in the vertical spread strategy is the protection it provides against SP decrease, as the OTM short leg would then lose a lot of value (even with long dated options).

One could then decide to BTC this short leg for cheap, so generating a profit on this short leg transaction (somehow compensating the long leg unrealized loss), and transforming the vertical spread in a call. Needs cash or margin obviously.

This call could then be kept as is, or transformed into short term (weekly LCC / diagonal) or long term (LCC until LEAP expiration / vertical) spread, when the SP increases again.

Hope this makes sense.

Cheers

PS:
Thank you all for the incredible not-advices, I increased my shares count by 50% in the last 12 months thanks to options selling.

PPS:
And sorry for the SNAP debacle, I lost a full month options trading profit even by being 20% OTM.
This bad experience made me change my strategy and I STO far-OTM (30%+) weekly spreads now. And I only trade TSLA now.
Small profits, but less stress, and lower risk. May reduce the width if / when the SP settles a bit.
 
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Thank you so much for explaining! I have ITM BPS expiring 11/19. I am worried about....anything at this point. I may look

Forgot to mention my current situation:

BPS:
11/19
4x: 1135/1110
7x: 1130/1090
5x: 1135/1125

11/26:
4x: 1050/1080
20 x : 1125/1100

I don't if this changes things. As I'm not "that far out the money". I know its' NOt ADVICE. But this is my predicament. I am somewhat close to the share price. I just need it to break past 1100... My fear is that it drops down to 900s and we hit a huge lull like Q1.

This is the predicament I'm in...hold for a few weeks...vs. just jumping forward to January's earnings report.
Some digging your self out of the hole and survival strategies:
1. Downsizing- close some positions with losses and use the monies to further close other positions

2. If you have shares to sell or margin, you could convert some of the BPS.
Roll the short leg which is at a loss to Jan 24 Leap Put and get as much premium as possible
The current long leg should have some profit, so close it
Use the premium from the leaps to further close other BPS positions

3.if you have shares , sell Jan 24 CC for 1900+ strikes and get premium. Use premium to close loosing BPS

I think for weekly sell strategies, one should stay on top of max loss/return at all times. For like 1000$ gain at 2%, max loss will be like 50K. So how much monies can account afford to lose per week should be factored in before thinking of annual returns by compound interest.+ personally trying to keep weekly amount the same and using proceeds to offset margin, for other strategies

Cheers!!
 
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