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Not exactly in the spirit of this thread (which is about selling options and applying the wheel), but I wanted to share what I’m doing with long call options.

Made some pretty big moves today: Liquidated my rollover IRA and transferred the long option positions into the taxable account. Sold a few thousand TSLA shares and re-invested funds into short term call options and LEAPs. My current long call positions are now:

12/18/2020 520 C
12/24/2020 550 C
12/24/2020 600 C
12/31/2020 600 C
1/15/2021 650 C
2/19/2021 600 C
3/19/2021 500 C
3/19/2021 600 C
7/16/2021 600 C
9/17/2021 500 C
6/17/2022 400 C
1/21/2022 300 C
1/21/2022 500 C
3/18/2022 500 C
1/20/2023 200 C

I was planning on holding the shares and LEAPs long term to avoid a huge taxable event this year, but since inclusion announcement my plan has changed to take advantage of what seems to be a once in a lifetime opportunity to lever up prior to a rally, and i will just have to settle up with the tax man after the dust settles. I’m spreading the risk out by choosing different strike prices and mixing in a good portion of ITM calls and LEAPs, so even if I’m wrong about the expected share price movement timing, I’m not going to blow up my account.
 
Not exactly in the spirit of this thread (which is about selling options and applying the wheel), but I wanted to share what I’m doing with long call options.

Made some pretty big moves today: Liquidated my rollover IRA and transferred the long option positions into the taxable account. Sold a few thousand TSLA shares and re-invested funds into short term call options and LEAPs. My current long call positions are now:

12/18/2020 520 C
12/24/2020 550 C
12/24/2020 600 C
12/31/2020 600 C
1/15/2021 650 C
2/19/2021 600 C
3/19/2021 500 C
3/19/2021 600 C
7/16/2021 600 C
9/17/2021 500 C
6/17/2022 400 C
1/21/2022 300 C
1/21/2022 500 C
3/18/2022 500 C
1/20/2023 200 C

I was planning on holding the shares and LEAPs long term to avoid a huge taxable event this year, but since inclusion announcement my plan has changed to take advantage of what seems to be a once in a lifetime opportunity to lever up prior to a rally, and i will just have to settle up with the tax man after the dust settles. I’m spreading the risk out by choosing different strike prices and mixing in a good portion of ITM calls and LEAPs, so even if I’m wrong about the expected share price movement timing, I’m not going to blow up my account.
Whoa. I had to read that three times and I’m still not sure of even the order of magnitude of that trade. I hope that someday I will be able to own a few thousand shares, let alone risk them on options.:eek:
 
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Not exactly in the spirit of this thread (which is about selling options and applying the wheel), but I wanted to share what I’m doing with long call options.

Made some pretty big moves today: Liquidated my rollover IRA and transferred the long option positions into the taxable account. Sold a few thousand TSLA shares and re-invested funds into short term call options and LEAPs. My current long call positions are now:

12/18/2020 520 C
12/24/2020 550 C
12/24/2020 600 C
12/31/2020 600 C
1/15/2021 650 C
2/19/2021 600 C
3/19/2021 500 C
3/19/2021 600 C
7/16/2021 600 C
9/17/2021 500 C
6/17/2022 400 C
1/21/2022 300 C
1/21/2022 500 C
3/18/2022 500 C
1/20/2023 200 C

I was planning on holding the shares and LEAPs long term to avoid a huge taxable event this year, but since inclusion announcement my plan has changed to take advantage of what seems to be a once in a lifetime opportunity to lever up prior to a rally, and i will just have to settle up with the tax man after the dust settles. I’m spreading the risk out by choosing different strike prices and mixing in a good portion of ITM calls and LEAPs, so even if I’m wrong about the expected share price movement timing, I’m not going to blow up my account.

this info doesn't help with the market closed :p
 
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Whoa. I had to read that three times and I’m still not sure of even the order of magnitude of that trade. I hope that someday I will be able to own a few thousand shares, let alone risk them on options.:eek:


Yeah it felt crazy moving around an amount of money that is 10x what my net worth just a few years ago. I wouldn’t have been in a position to do so had i not gone all-in on TSLA starting last August (just purchasing shares in the high 200s, eventually liquidating a Roth IRA and a 401k) and then gaining experience with options (mostly selling) this year thanks to this thread. I am now 100% in TSLA options, and hope to get back in to shares at some point in the future, and continue selling options for retirement income if i feel the share price is caught in a channel and stabilized after S&P inclusion.
 
this info doesn't help with the market closed :p

Sorry, i made these moves in the last hour of the day. Only had time to read through my brokerage history to tally up the positions after the market closed and i was enjoying a beer :)

I noticed i do have a good bit of dry powder left as its been held to secure the short put positions i still have:
TSLA 12/18/20 380 P
NIO 12/18/20 32 P
ZM 12/18/20 400 P

I believe this i because i have Reg-T margin in Schwab, and long option positions aren’t marginable securities, so i have to have actual cash set aside to back the put sales. I’ve applied for portfolio margin, and have been denied once, but owe the margin desk another call. Also planning on moving to Interactive Brokers in the near future for PM and more attractive margin rates.

I’ll likely close out these short put positions so I’m ready to load up on more calls on the next red day
 
Last edited:
Not exactly in the spirit of this thread (which is about selling options and applying the wheel), but I wanted to share what I’m doing with long call options.

Made some pretty big moves today: Liquidated my rollover IRA and transferred the long option positions into the taxable account. Sold a few thousand TSLA shares and re-invested funds into short term call options and LEAPs. My current long call positions are now:

12/18/2020 520 C
12/24/2020 550 C
12/24/2020 600 C
12/31/2020 600 C
1/15/2021 650 C
2/19/2021 600 C
3/19/2021 500 C
3/19/2021 600 C
7/16/2021 600 C
9/17/2021 500 C
6/17/2022 400 C
1/21/2022 300 C
1/21/2022 500 C
3/18/2022 500 C
1/20/2023 200 C

I was planning on holding the shares and LEAPs long term to avoid a huge taxable event this year, but since inclusion announcement my plan has changed to take advantage of what seems to be a once in a lifetime opportunity to lever up prior to a rally, and i will just have to settle up with the tax man after the dust settles. I’m spreading the risk out by choosing different strike prices and mixing in a good portion of ITM calls and LEAPs, so even if I’m wrong about the expected share price movement timing, I’m not going to blow up my account.

Big moves indeed! As they say, fortune favors the bold. Something I am pushing myself to learn. Best of luck to you!
 
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Big moves indeed! As they say, fortune favors the bold. Something I am pushing myself to learn. Best of luck to you!

There is a narrow window between FOMO / fortune favors the bold, and taking advantage of an investing conviction in a fashion that will move the needle.

For the latter notion, one of the best things I've learned is to make life changing investments in strong convictions. Back in '08 (ish), I found a company paying a 10.8% dividend, that had a multi-year history of increasing the dividend every quarter, with a cash flow / income that could practically be filled out for the year (capacity fully subscribed for the year). I looked at it for 2 weeks trying to figure out the catch. Couldn't find one and finally invested. For years afterwards, that investment worked EXACTLY as I expected it to, and felt like I knew, when I made the original investment.

Yay me. The problem, as I explained to any number of people over those years, is that I invested roughly 1 order of magnitude less than I should have. My learning - when those strong convictions come along, don't dabble. And those strong convictions are rare - I think 3 of them for me over the 30 years I've been investing (Intel, Oneok Partners, Tesla).

Good timing on that education, my next conviction came along 4 years later when we bought into TSLA. The investment today looks trivial, but back then it was the limit of what my wife and I were willing to put into 1 thing. That investment is ahead ~80X and is a big component of what enables retirement for me in a couple of months.

That 8 year old strong conviction around TSLA continues today, and I'm not dabbling. A good approximation is that something like 80-90% of our portfolio is tied up in TSLA and related (options) investments.

This can look like gambling pretty easily. And does to all of the financial advisors my wife and I have talked to. Their alternatives are what looks risky to me :)


Which leads to the narrow window between large investments in strong convictions, vs FOMO / fortune favors the bold investing. Simplistically, I define the difference in those two with long term buy and hold plus OTM option sales (stuff we're talking about in this thread) on the strong conviction side, and use of margin plus buying options on the FOMO / fortune favors the bold side.

This is a simplistic split, and I know it's not 100% true.

One instance is that I rarely buy options (calls on TSLA), where rarely is <<annually, and yet I occasionally find situations that I find so compelling that I do buy calls on TSLA. This happens to be one of those situations, and if I go another 5 years before I see a similar setup, then I'm not worried about that, won't be surprised, and I'm going to chase after what might happen. I.e. - I DO have a strong conviction about buying and owning calls for about a month or 2 right now (and I'm in at what I consider strong conviction levels - roughly 1% of portfolio - for this kind of investment).

I do understand the available risks, positive and negative, of doing this or deciding not to do this; and I make my own decisions, and experience the consequences of those decisions. And if I get enough of these negatively wrong, then I'll need to go find another job when I've retired and don't want to do that. Which means negative consequences for me are high, and I am VERY motivated to get these safely right.
 
@adiggs for reference how much did you pay for the Jan c700s? I am thinking on getting some more calls if I get an opportunity next week. thanks

The Jan 700s were $5.18 when I got them. I got into 4 of my 5 purchased call positions the morning after the S&P announcement - prices and IV were already starting to go up, but they hadn't really gotten started at that point.


I went for January on 3 positions (500, 700, 800) for 2 reasons. The first is that I expect I'll be closing them 2-4 weeks before expiration (sometime after Dec 21), and that means that the time decay won't yet be taking really big bites out of the premium.

The other reason is that account is taxable, and I'm hoping for the share price to be flat or still in a bit of an upward curve (end of year window dressing?) through the end of the year, so I can sell them and put the tax event into 2021. It's not a huge deal to close in 2020 - I like to think about taxes, but I don't let taxes dominate a decision.

Oh - and those 800s I consider to be something of a reach, where I'm looking for pretty high leverage to generate outsized returns. I also know that they probably won't.


A lesson I learned about taxes (indirectly) ... I'm reminded of a fun day at lunch, back in the 90s. I was part of a group of people that would get together to play bridge over lunch. One of those days, I was sitting around chatting with Dave and a few other folks. Dave was sad / moaning about the 6 figure tax bill he had to deal with that year, due to options he'd received previously that had appreciated so much.

Many small violins played for Dave that day.

The point being that if I have a 6 figure tax bill for 2020, it's because something has gone very right for me :)

Maybe I can swing a 7 figure tax bill some year - that'd be awesome!
 
@adiggs for reference how much did you pay for the Jan c700s? I am thinking on getting some more calls if I get an opportunity next week. thanks

Another thought relative to your question - one of my positions is a 12/4 expiration call. I sort of expect to close it at some point next week (so still a week or week and a half from expiration), and use those proceeds to establish a 12/11 position.

My thinking on that 12/4 position was I could get them more cheaply than further out options, and though it won't capture all of the S&P 500 inclusion move, it'll capture the first couple of weeks (working well so far), and if that's working well, then I can 'roll' the position week to week and capture the movements I expect right into and maybe a little past inclusion.

I also have a 12/8 position, with a similar thought process.


(and remember - I'm about as bad of an example of buying calls as you can find. I know I have the wrong fundamental mentality, and I struggle with shifting to something more amenable for buying options. And I'm bad at picking direction, magnitude, and timing on <3 month stuff. So I only do something like this when it seems like I've got a spotlight shining in my eyes, guiding me to this :D)
 
Whoops! Fat fingered one of my covered calls. :eek: Thought I had set it to expire on 20 Nov, but instead it expires 27 Nov. As I also had set up the same call on Friday, I now have two 540 strike 27Nov calls.

Going to try and close out the accidental one sometime early next week. There are a lot of 500 calls, so a strong draw for MMs, but that SP500 though... :eek: Might be a 100 shares shorter than I intended!
 
Whoops! Fat fingered one of my covered calls. :eek: Thought I had set it to expire on 20 Nov, but instead it expires 27 Nov. As I also had set up the same call on Friday, I now have two 540 strike 27Nov calls.

Going to try and close out the accidental one sometime early next week. There are a lot of 500 calls, so a strong draw for MMs, but that SP500 though... :eek: Might be a 100 shares shorter than I intended!

I hate it when that happens!

My version of that was buying (to open) some calls when I was trying to sell (to open) them. Thankfully I noticed that the sign on the number of contracts was positive instead of negative, and was able to close that position almost immediately - only lost $100 on the round trip, and consider that to be a cheap experience and reminder on the importance of double (triple?) checking order tickets.
 
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The Jan 700s were $5.18 when I got them. I got into 4 of my 5 purchased call positions the morning after the S&P announcement - prices and IV were already starting to go up, but they hadn't really gotten started at that point.


I went for January on 3 positions (500, 700, 800) for 2 reasons. The first is that I expect I'll be closing them 2-4 weeks before expiration (sometime after Dec 21), and that means that the time decay won't yet be taking really big bites out of the premium.

The other reason is that account is taxable, and I'm hoping for the share price to be flat or still in a bit of an upward curve (end of year window dressing?) through the end of the year, so I can sell them and put the tax event into 2021. It's not a huge deal to close in 2020 - I like to think about taxes, but I don't let taxes dominate a decision.

Oh - and those 800s I consider to be something of a reach, where I'm looking for pretty high leverage to generate outsized returns. I also know that they probably won't.


A lesson I learned about taxes (indirectly) ... I'm reminded of a fun day at lunch, back in the 90s. I was part of a group of people that would get together to play bridge over lunch. One of those days, I was sitting around chatting with Dave and a few other folks. Dave was sad / moaning about the 6 figure tax bill he had to deal with that year, due to options he'd received previously that had appreciated so much.

Many small violins played for Dave that day.

The point being that if I have a 6 figure tax bill for 2020, it's because something has gone very right for me :)

Maybe I can swing a 7 figure tax bill some year - that'd be awesome!

Thanks. Yeah I have been letting taxes dominate my decisions and sometimes I don't make short term trades because of that. I wish I could give the tax money to family members instead; I just feel bad about it is hard to explain. I really need to change that mind set.

I was able get some short term options on the morning of the inclusion but not enough to make a big difference in my portfolio if the inclusion goes the way that many of us are thinking that it's going to go.

On you other post, yeah I usually do really bad with some short term options. I really try to avoid short term options and way OTM but with the current situation it seems that there is a good chance that it will work in our favor.
 
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There is a narrow window between FOMO / fortune favors the bold, and taking advantage of an investing conviction in a fashion that will move the needle.

For the latter notion, one of the best things I've learned is to make life changing investments in strong convictions. Back in '08 (ish), I found a company paying a 10.8% dividend, that had a multi-year history of increasing the dividend every quarter, with a cash flow / income that could practically be filled out for the year (capacity fully subscribed for the year). I looked at it for 2 weeks trying to figure out the catch. Couldn't find one and finally invested. For years afterwards, that investment worked EXACTLY as I expected it to, and felt like I knew, when I made the original investment.

Yay me. The problem, as I explained to any number of people over those years, is that I invested roughly 1 order of magnitude less than I should have. My learning - when those strong convictions come along, don't dabble. And those strong convictions are rare - I think 3 of them for me over the 30 years I've been investing (Intel, Oneok Partners, Tesla).

Good timing on that education, my next conviction came along 4 years later when we bought into TSLA. The investment today looks trivial, but back then it was the limit of what my wife and I were willing to put into 1 thing. That investment is ahead ~80X and is a big component of what enables retirement for me in a couple of months.

That 8 year old strong conviction around TSLA continues today, and I'm not dabbling. A good approximation is that something like 80-90% of our portfolio is tied up in TSLA and related (options) investments.

This can look like gambling pretty easily. And does to all of the financial advisors my wife and I have talked to. Their alternatives are what looks risky to me :)


Which leads to the narrow window between large investments in strong convictions, vs FOMO / fortune favors the bold investing. Simplistically, I define the difference in those two with long term buy and hold plus OTM option sales (stuff we're talking about in this thread) on the strong conviction side, and use of margin plus buying options on the FOMO / fortune favors the bold side.

This is a simplistic split, and I know it's not 100% true.

One instance is that I rarely buy options (calls on TSLA), where rarely is <<annually, and yet I occasionally find situations that I find so compelling that I do buy calls on TSLA. This happens to be one of those situations, and if I go another 5 years before I see a similar setup, then I'm not worried about that, won't be surprised, and I'm going to chase after what might happen. I.e. - I DO have a strong conviction about buying and owning calls for about a month or 2 right now (and I'm in at what I consider strong conviction levels - roughly 1% of portfolio - for this kind of investment).

I do understand the available risks, positive and negative, of doing this or deciding not to do this; and I make my own decisions, and experience the consequences of those decisions. And if I get enough of these negatively wrong, then I'll need to go find another job when I've retired and don't want to do that. Which means negative consequences for me are high, and I am VERY motivated to get these safely right.

I appreciate your posts and insight in this thread.

I am trying to learn to trust my judgment and research more, especially when opportunities present themselves. My whole life I have been extremely risk adverse and conservative with money. Some early losses in the market years before TSLA came along made me wary of even putting any money back in. I "took a gamble" and bought some shares of TSLA back in 2018, but my fear of the macros got the best of me and I sold everything after Covid at $820. I sat on the sidelines and missed the big runup. Right around the time of the split I had an "awakening" that my risk aversion would always hold me back from achieving my financial goals and the opportunity cost was tremendous. Had I trusted my judgment on TSLA, my portfolio would have been 10x where it is today.

So I started over in September after spending the better part of a month immersed in options/investing education. I am now about 90% invested in TSLA and plan to HODL for the next 5-10 years (or more) while selling options for an extra boost. I really love the "income" idea of the selling puts and calls with the wheel strategy. Holding back some cash in reserve to cover these puts allows me to remain somewhat conservative, while I continue to expand out of my comfort zone with very limited calls and a few leaps - and keep adding shares with option profits. I'm don't have any delusions that this will be easy, there will be setbacks, but I am committed to the effort.

One of the most helpful pieces of advice that I came across during my self education learning options was something to the effect "risk tolerance is like a muscle, it must be exercised and built up". I am pushing myself to do that. I do find the more education and experience I have, the easier that becomes.
 
Sorry, i made these moves in the last hour of the day. Only had time to read through my brokerage history to tally up the positions after the market closed and i was enjoying a beer :)

I noticed i do have a good bit of dry powder left as its been held to secure the short put positions i still have:
TSLA 12/18/20 380 P
NIO 12/18/20 32 P
ZM 12/18/20 400 P

I believe this i because i have Reg-T margin in Schwab, and long option positions aren’t marginable securities, so i have to have actual cash set aside to back the put sales. I’ve applied for portfolio margin, and have been denied once, but owe the margin desk another call. Also planning on moving to Interactive Brokers in the near future for PM and more attractive margin rates.

I’ll likely close out these short put positions so I’m ready to load up on more calls on the next red day

Unfortunately, most brokerages will not extend portfolio margin against underlying option positions. Only on equity or cash positions.
 
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So I started over in September after spending the better part of a month immersed in options/investing education. I am now about 90% invested in TSLA and plan to HODL for the next 5-10 years (or more) while selling options for an extra boost

For me at least, this 5-10 year holding period (or for me, 10+ years as of today, updated from 10+ years, 8 years ago) is critical to everything else being done here. That 10+ year holding period arises from my own assessment and investment thesis regarding Tesla.

I mention this to encourage you to think about what you see in the company, that leads you to a 5-10 year investment horizon. I don't personally fill out long form expected quarter or annual earnings predictions. That level of detail is extremely important to some investors. Put another way, I do perform my own level of financial due diligence and I consider some level of that necessary, but I don't need to predict each line item.

My primary financial due diligence has to do with fraud or other bad use of money by the company (I haven't seen any evidence of that, but I am always on the look out for it). A particular form of this I look for, is a dynamic where senior leadership and my personal interests as a long term shareholder differ. More crassly - is the senior leadership busy figuring out how to loot the company for their personal gain? I see this in other companies, and they don't get my investment.

I do consider it necessary for investing to have at least a statable conceptual understanding of what each line in those financial statements means :)


You need to know why that 5-10 year window is meaningful to you. Without that, it's just a randomly chosen window that lacks the conviction and belief that will make it easy to hold through a 50% drop, because the only thing a 50% drop means is a buying opportunity. In my posting history, you'll be able to find multiple posts from when the shares had gone from $350 to $180 (or so) pointing out that for long term buy and hold investors, there was no difference at that point in time between a $350, $180, or a $800 (or even $2000) share price (all pre-split of course). They were all the same, and they were all meaningless - because they were all trivial next to the long term expected share price.

It also means you need to be in the financial state where you can hold through that 50% drop (we've seen these a few times over the last 5-7 years; I expect we'll see at least a few more over this decade. So if you're ready for retirement and need to be living off of your portfolio, or otherwise need money from the portfolio in a shorter time horizon, then that 50% drop might not be survivable.


My own investment thesis started 8 years ago after test driving one of the very first Model S's. It was the first test drive car to arrive in Portland, and was probably in the first 5,000 Model S's ever built. It was so far beyond anything I had ever ridden in, much less driven, that it blew my mind. It also created the conscious realization - the product matters. And when the product is so much better than anything else, it would require a monumental screw up somewhere else in the business to not succeed. That was good enough for me for the initial investment, but not enough by a long stretch for an all-in investment. I also liked that I was supporting a business that I thought had a glimmer of a chance of advancing a renewable energy economy, but there are other companies in that category - none of which I have invested in.

I liken my own reaction to what others have described as their iPhone moment. I never had that experience, as I've only reluctantly adopted smart phones at all, much less an early iPhone. The characteristic is that there is a world before, and an recognizable (and better) world after, that moment.

Characteristics of my investment thesis have to do with just how badly the competition is performing, the irrelevance today of whether competition is competent or not (the market is so big, we've got several years of everybody growing as fast as they want to / can, before actual competition sets in amongst the participants), and the number of different markets that Tesla is entering - each gargantuan in size.

All of which today, leads me to see 10+ years of reckless growth (in joke for those that have been around long enough :D) in front of Tesla. And that, plus the rate at which Tesla is going to convert revenue into gross margin, and from there into profit, leads me to believe that the 2030 Tesla may well be the single largest industrial entity in the world, the most profitable industrial entity, or that the world has ever seen. And all in a good cause. And a very rough estimate of what EPS might be, a reasonable to conservative $/EPS, and a company valuation that would follow from that. You can see the #s I think are possible in some of @FrankSG blogs if you haven't read those.


That's my investment thesis, not something I plan to get into in more detail in this thread. My point is that it's at least concrete and detailed in my own mind. Oh - and the selling of options enables me to get some income, which is necessary for me. :)


I am trying to learn to trust my judgment and research more, especially when opportunities present themselves. My whole life I have been extremely risk adverse and conservative with money. Some early losses in the market years before TSLA came along made me wary of even putting any money back in. I "took a gamble" and bought some shares of TSLA back in 2018, but my fear of the macros got the best of me and I sold everything after Covid at $820. I sat on the sidelines and missed the big runup. Right around the time of the split I had an "awakening" that my risk aversion would always hold me back from achieving my financial goals and the opportunity cost was tremendous. Had I trusted my judgment on TSLA, my portfolio would have been 10x where it is today.


A few ideas that have helped me with managing risk - the first is to understand / realize that EVERY decision, and every non-decision, carries with it risks and rewards, costs and benefits. Understanding both is the first risk mitigation strategy - sometimes the non decision, or the "conservative" decision, is in fact the most risky choice available. One example most people know about, is investing in cash. The returns frequently lag inflation, so you're guaranteeing long term loss of buying power. Cash looks like the most conservative, when in fact over a longer holding period, it's the most risky.

The other thing I like to keep an eye on are the tail risks, both up and down, and the consequences that would attach. An example position I have open - I've got a pile of covered calls for Sept 2022 at an 840 strike. I figure there is a reasonably good chance those will be in the money. I don't really want to get assigned on those, but I got a pile of cash up front - about $5k/contract/month (EDIT: $500/contract/month - moved a decimal point in my favor!) - I will have a choice to roll; and even if I just take assignment with the shares trading at $1500, then I'll still end up with an account that is >2x what I have today, where today is already "enough". In fact my overall portfolio will likely be at least 2x of "enough" in that circumstance.

Therefore, for me, the possibility that the shares WON'T advance that far is actually a larger risk due to lack of income and cash flow, than the risk the shares take off to $1500. More specifically, it's a shift from a growth mindset, to an income and growth mindset (plus an unwillingness, today, to sell shares for living expenses :D).


Not all risk / reward, cost / benefit, decisions are equal. And if you ever think that the benefit / reward of selling options is a no-brainer or free money, remember that the market has much bigger and smarter participants than you or I will ever individually be, and they are focused on mining out every penny of gains available. If this really were free money, they would take it all until the risk and reward had balanced out again.
 
Thanks. Yeah I have been letting taxes dominate my decisions and sometimes I don't make short term trades because of that. I wish I could give the tax money to family members instead; I just feel bad about it is hard to explain. I really need to change that mind set.

I was able get some short term options on the morning of the inclusion but not enough to make a big difference in my portfolio if the inclusion goes the way that many of us are thinking that it's going to go.

On you other post, yeah I usually do really bad with some short term options. I really try to avoid short term options and way OTM but with the current situation it seems that there is a good chance that it will work in our favor.

Risks and rewards, costs and benefits. I'm not a tax expert, but I don't know of any circumstances in current US tax code in which you spend more in taxes than you received in income / revenue. The timing might be bad for a particular year, but that's a different issue.

Therefore, big tax bills come from big earnings. One particularly twisted(?) way of looking at it - the bigger the tax bill, the bigger the available humble brag. As in "can you believe it - I HAD to pay 8 figures in taxes this year; oh whoa is me". (cue tiny violins)
 
I had sold some Dec 370 puts - closed those out this morning for about 83% profit. I would normally open new covered puts - something like a Dec 450 put (effectively rolling up). I am instead considering some additional calls. Maybe something like those 610s for this week @juanmedina :)

I am seriously considering purchasing some calls for this week. The thinking would be to close tomorrow or more likely Wed (not hold to Friday) and again capture more of the immediate potential move up this week. I still think there is upside from here, even this week.

EDIT to add:
I decided to purchase an 11/27 550 call position at about $5.45, and a 12/11 600 call position at $10.39. This set me up with purchased calls expiring each week now through Dec 18. I will evaluate as I go - I sort of expect to open a position for the week after the monthly expiration as well.

For the position this week, I expect to close tomorrow or Wednesday (don't want to wait for expiration day).

For the rest of the positions I'm thinking in terms of closing the week before expiration, so the 12/4s might also be closed this week.
 
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I had sold some Dec 370 puts - closed those out this morning for about 83% profit. I would normally open new covered puts - something like a Dec 450 put (effectively rolling up). I am instead considering some additional calls. Maybe something like those 610s for this week @juanmedina :)

I am seriously considering purchasing some calls for this week. The thinking would be to close tomorrow or more likely Wed (not hold to Friday) and again capture more of the immediate potential move up this week. I still think there is upside from here, even this week.

EDIT to add:
I decided to purchase an 11/27 550 call position at about $5.45, and a 12/11 600 call position at $10.39. This set me up with purchased calls expiring each week now through Dec 18. I will evaluate as I go - I sort of expect to open a position for the week after the monthly expiration as well.

For the position this week, I expect to close tomorrow or Wednesday (don't want to wait for expiration day).

For the rest of the positions I'm thinking in terms of closing the week before expiration, so the 12/4s might also be closed this week.

:p I end up buying 12/24 c580s to follow Frank's trade and I also bought some January c700s. I am officially done buying calls for the S&P inclusion. If we get a squeeze for instance to $800-700 what would you guys do with your shares? I think if I could get $200 for some January 23 c1000s I would sell some of them. I would also sell my other DITM options and maybe stay cash with those and sell puts.. decisions decisions