Retiring in 6 months (off TSLA options); Plan Review & Questions

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roguewarrior0
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Joined: Sat Feb 08, 2020 10:26 am

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by roguewarrior0 »

Peaceful wrote: Fri Mar 05, 2021 11:16 am
roguewarrior0 wrote: Fri Mar 05, 2021 11:07 am I have unwound all of my TSLA that is in my retirement accounts as there were no tax implications. On the taxable side, I still have the same position and am still planning to ride it out. Below is from the original post around my holdings

Taxable (unchanged)
Pre-Retirement ($3m) 35.3% of Portfolio
$4.533m 5,595sh Tesla (TSLA)
$2.23m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-$1.94m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.89m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)

TSLA = $571/sh
TSLA $550 6/17/22 call = $188

So to unwind my position would net out @ $383 share/price. My original cost basis was around $315. I would rather ride this out. I purchased TSLA as I believe it has long term viability. It ran to moon and is starting to come down again. However, I am still content to hold it 2022 before I convert this portion to the 3 Fund portfolio.
If you choose to continue to speculate with the TSLA options rather than close them out, it might be better off not to view them as part of your "retirement portfolio" at all. It seems to me "retirement" implies you're not actively trading with a substantial portion of your assets. So, you should have the "retirement portfolio" and the "active trading" portfolio. If you would be fine "retiring" on the "retirement portfolio" plus whatever you would net should the "active trading" portfolio might be worth in the worst-case scenario (not what you think the worst case scenario is, but the mathematical worst case scenario) then it's fine.
That is a GREAT idea. You are absolutely right and I hadn't thought of it that way. My TSLA optioned position "isn't active" in that I am buying/selling at all in the next 16 months, but has elements of active position.

That is new food for thought, and may actually change my early retirement plans based on that. Thanks for the light bulb moment. More to come once I have thought this over.
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CardinalRule
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by CardinalRule »

market timer wrote: Fri Mar 05, 2021 11:21 am
roguewarrior0 wrote: Fri Mar 05, 2021 11:07 am I have unwound all of my TSLA that is in my retirement accounts as there were no tax implications. On the taxable side, I still have the same position and am still planning to ride it out. Below is from the original post around my holdings

Taxable (unchanged)
Pre-Retirement ($3m) 35.3% of Portfolio
$4.533m 5,595sh Tesla (TSLA)
$2.23m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-$1.94m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.89m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)

TSLA = $571/sh
TSLA $550 6/17/22 call = $188

So to unwind my position would net out @ $383 share/price. My original cost basis was around $315. I would rather ride this out. I purchased TSLA as I believe it has long term viability. It ran to moon and is starting to come down again. However, I am still content to hold it 2022 before I convert this portion to the 3 Fund portfolio.
Should be a very interesting ride. I see TSLA just touched $550. It is a long way from now until June/Sep 2022. Good to hear that the retirement accounts have now been diversified.
Interesting indeed. OP has done great in any event, but I see that the June 550 call is at $99ish this morning, with TSLA at $560. So roughly $500 thousand value now for the 50 short contracts.
bugleheadd
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by bugleheadd »

So with Tsla going downhill, is this good or bad for OPs plan?
Normchad
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by Normchad »

You are my new hero! Congratulations!
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gobel
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by gobel »

roguewarrior0 wrote: Fri Mar 05, 2021 11:45 am
Peaceful wrote: Fri Mar 05, 2021 11:16 am
roguewarrior0 wrote: Fri Mar 05, 2021 11:07 am I have unwound all of my TSLA that is in my retirement accounts as there were no tax implications. On the taxable side, I still have the same position and am still planning to ride it out. Below is from the original post around my holdings

Taxable (unchanged)
Pre-Retirement ($3m) 35.3% of Portfolio
$4.533m 5,595sh Tesla (TSLA)
$2.23m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-$1.94m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.89m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)

TSLA = $571/sh
TSLA $550 6/17/22 call = $188

So to unwind my position would net out @ $383 share/price. My original cost basis was around $315. I would rather ride this out. I purchased TSLA as I believe it has long term viability. It ran to moon and is starting to come down again. However, I am still content to hold it 2022 before I convert this portion to the 3 Fund portfolio.
If you choose to continue to speculate with the TSLA options rather than close them out, it might be better off not to view them as part of your "retirement portfolio" at all. It seems to me "retirement" implies you're not actively trading with a substantial portion of your assets. So, you should have the "retirement portfolio" and the "active trading" portfolio. If you would be fine "retiring" on the "retirement portfolio" plus whatever you would net should the "active trading" portfolio might be worth in the worst-case scenario (not what you think the worst case scenario is, but the mathematical worst case scenario) then it's fine.
That is a GREAT idea. You are absolutely right and I hadn't thought of it that way. My TSLA optioned position "isn't active" in that I am buying/selling at all in the next 16 months, but has elements of active position.

That is new food for thought, and may actually change my early retirement plans based on that. Thanks for the light bulb moment. More to come once I have thought this over.
Could you close the $550 covered calls right now for less than you paid, or move up the call price since the price has dropped a lot and you think it will go back up?

I'm trying to understand how the other two options work. From looking at the recent price, one could pay about $110 for the potential of $220 at expiration? So the price has to stay above at least $390 to avoid losing money?

btw were the covered calls in-the-money when you wrote them? I have read that there can be tax consequences, eg a constructive sale or suspension of the holding period when the options hedge out too much risk. Do you know/did you check if this affected you?
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canadianbacon
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by canadianbacon »

bgf wrote: Fri Feb 12, 2021 8:34 am you've done exceedingly well and should run to your broker like a masked man with a chainsaw is chasing you. i know that you think your covered calls are 'reasonably safe' but that is far more risk than you have any NEED to bear. i would close out all positions immediately that you do not intend to hold through retirement. tax consequences are completely irrelevant. you made bank, you pay the taxman. you, right now, with no need for more risk or gains can retire for the rest of your life. any legitimate threat to that, even if deemed 'reasonable', is too much. cut and run. live your retired life in peace.
This was very good advice.
Bulls make money, bears make money, pigs get slaughtered.
Frogster
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by Frogster »

pseudoiterative wrote: Thu Feb 11, 2021 9:03 pm
Another way to frame a decision is to focus on two competing goals of (i) retiring in July 2021 and (ii) retiring with enough assets to sustain $250k/yr withdrawals from a portfolio with 3% real return. TSLA share price is a factor completely outside your control. Suppose it were to drop to $100 / share before you could exit position. Which goal is more important? Retiring this year or retiring with enough assets to sustain $250k / yr? If former goal is more important, given your retirement expenses are largely in control of your family, is there a lesser withdrawal rate that would still be acceptable if you could guarantee a fixed retirement date in 2021 independent of whatever the TSLA share price does?

If latter goal of being able to sustain $250k / yr withdrawal is more important, suppose TSLA share price goes to $100. How many more years of corporate life would you need to work to regain that $7.5m pre-tax drop in net worth?
This is a great way to frame this kind of decision(s).
Last edited by Frogster on Sat Mar 06, 2021 2:15 am, edited 1 time in total.
an_asker
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by an_asker »

bgf wrote: Fri Feb 12, 2021 8:34 am you've done exceedingly well and should run to your broker like a masked man with a chainsaw is chasing you.
[...]
I just thought of something. A masked man today is less scary than an unmasked man ;-) I would run faster from an unmasked man, with or without a chainsaw :oops:
CDub
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by CDub »

roguewarrior0 wrote: Sat Feb 13, 2021 2:38 am
Worst case I can always pull the parachute as its dropping. If I close the position anywhere near $550ish, I am still golden.
Came here remembering this post and bgf’s warning to sell... looks like it’s back around $600. Surprised that you’re going to hold on to them! Then again, the initial bet was pretty risky so I suppose you have a higher risk tolerance than most around here.
Topic Author
roguewarrior0
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by roguewarrior0 »

Quick Update of my current Portfolio steps and what I am choosing to do.

I realize I still have a large exposure TSLA. Again I have the TSLA shares primarily done via Covered Calls thus I feel relatively safe. As you can see in the details, they are Covered @ $550 & $500 for 6/22 & 9/22.

At this junction, I do not plan on unwinding TSLA, because of taxes. I would actually rather delay early retirement and let TSLA to naturally unwind versus selling and taking the tax hit.

Here is what I see if I let them naturally unwind:

2022 September Expiration and TSLA shares called away (Long term capital gain)
  • $4.6m in taxable less LTCG
  • $4.2m after tax
2021 Close out
  • $3.36m less short term tax on 1m (-$370k)
  • $3m roughly
This is a HUGE delta for getting out early and being safe. I would rather work 12-15 more months and trust that I chose correctly w/ TSLA. Yes I know there is risk that TSLA goes down, but I believe TSLA has a strong business model. Put another way, I am willing to work an additional year with $1m+ with the Option naturally expiring. Gotta take that bet every day.



Current Portfolio - $8.6m
Summary:
  • Total Bond - $2.14m ~25%
  • Total Int'l Stock - $1.13m ~13%
  • Tota Stock - $942k ~11%
  • TSLA - $3.67m ~43%
  • MM/ Cash - 625k ~7%
Taxable -
Pre-Retirement ($3.36m) 35.3% of Portfolio

$3.36m 5,595sh Tesla (TSLA)
$1.77m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
$625k VMFXX
-$1.10m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.04m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)

$80k Google (GOOG)

$11k Total Bond Admiral (VBTLX)
$12k Total Int Stock Admiral (VTIAX)
$12k Total Stock Admiral (VTSAX)
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market timer
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by market timer »

roguewarrior0 wrote: Sun Mar 07, 2021 8:34 pmHere is what I see if I let them naturally unwind:

2022 September Expiration and TSLA shares called away (Long term capital gain)
  • $4.6m in taxable less LTCG
  • $4.2m after tax
2021 Close out
  • $3.36m less short term tax on 1m (-$370k)
  • $3m roughly
Of course, there is a third scenario worth modeling out: TSLA is not called away in 2022. The odds of this scenario are nearly 50%, and the calls you sold will expire worthless, but you'll owe STCG on the call premium.

Speaking of taxes, have you confirmed that the position is eligible for LTCG tax treatment if TSLA is called away in 2022? There are fairly complex eligibility conditions, e.g., the call was ideally out-of-the-money when sold. The rules here are quite complex, and you should check if you haven't already whether you qualify: https://www.fidelity.com/learning-cente ... ered-calls
This is a HUGE delta for getting out early and being safe. I would rather work 12-15 more months and trust that I chose correctly w/ TSLA. Yes I know there is risk that TSLA goes down, but I believe TSLA has a strong business model. Put another way, I am willing to work an additional year with $1m+ with the Option naturally expiring. Gotta take that bet every day.
Indeed, $1.2M after tax is a large delta; however, this is not due to taxation. Even assuming your tax calculation is correct, the true delta from a tax perspective is the difference between LTCG and STCG. Assuming your $1M gain were taxed at the LTCG rate of 20%, you'd owe $200K. If it were taxed at the LTCG rate, you'd owe $370K--the delta from a tax perspective is only $170K. The remaining delta of >$1M is the risk premium from retaining so much downside exposure to a volatile stock like TSLA for 15-18 months.
invest2bfree
Posts: 271
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by invest2bfree »

roguewarrior0 wrote: Thu Feb 11, 2021 2:35 pm I am planning to retire in July 2021 @ 47. Let me call out the elephant in the room. Yes, I have been ridiculously lucky with my market timing and have 90% of Portfolio in a single stock. This was lucky and it may go to badly in next 6 months, but ultimate I have attempted to hedge my luck by selling Covered Calls and using the Call Premium to pay off debt. Assuming TSLA stays north of $550 at Call expiration ($825 currently), (this gives me over 30% margin of safety), I will have a portfolio of $9.7m at retirement and unwinding of TSLA via Covered Calls. For the purposes of this discussion I am going to assume my TSLA shares will get Called away @ 550 and 500.

My goal now is to unwind my individual stock exposure to 3 Fund portfolio and go time tested plan and re-balance semi-annually. I expect to live off of $250k/year.


Emergency funds: 3 months ($60k) in money market (VMFXX)

Debt: none
Tax Filing Status: Married with 2 dependent children (17,16)
Tax Rate: 35% Federal, state: n/a
State of Residence: Texas
Age: 46

Desired Asset allocation: 75% stocks / 25% bonds
Desired International allocation: 15% of stocks

Current portfolio: $8.5m
Target portfolio @ retirement: ~$9.7m
Goal: Retire and not return to Corporate world
Retirement Withdrawals: $250k/yr
Other Assets: Own free/clear 3 homes ($1m value)
Other Assets: 2 of the homes above generate a total $3500/month in Rental income
Other Costs outside of $250k/yr:
  • 2021 2020 tax bill $300k
  • 2022 New Car $80k
  • 2022 2021 tax bill $300k
  • 2023 2022 tax bill $300k
  • 2024 New Car $25k


Current Portfolio

Taxable -
Pre-Retirement ($3m) 35.3% of Portfolio
$4.533m 5,595sh Tesla (TSLA)
$2.23m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-$1.94m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.89m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)

$80k Google (GOOG)

$11k Total Bond Admiral (VBTLX)
$12k Total Int Stock Admiral (VTIAX)
$12k Total Stock Admiral (VTSAX)

401k (96k) - 1% of Portfolio
$96k (1.29%) Vanguard 2040 Target (VFORX) (expense 0.05%)
Contributions: Max out
Company match: Yes, up to $8,750

Roth IRA at Vanguard = 0.1% of Portfolio
$12k Vanguard Total Intl (VTIAX) (0.11%)

Rollover IRA at Vanguard ($333k) - 4% of Portfolio
$328k Tesla (TSLA)
$5k Total Bond Admiral (VBTLX)


IRA at Vanguard (3.98m) - 46.8% of Portfolio
$5.21m (15.4%) 6,435sh Tesla (TSLA)
$278k (15%) Long 5 Calls @ $280 9/16/22 Tesla (TSLA)
-$216k (3%) Short 5 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.75 (4%) Short 59 Calls @ $550 6/17/22 Tesla (TSLA)
$264k (0.2%) Total Bond Admiral (VBTLX)
$12k (0.2%) Total Int Stock Admiral (VTIAX)
$12k (0.2%) Total Stock Admiral (VTSAX)


Wife's IRA Rollover ($1.17m) - 13.5% of Portfolio
$1.168m 1,440sh Tesla (TSLA)
$56k Long 1 Calls @ $280 9/16/22 Tesla (TSLA)
-$416k Short 14 Calls @ $550 6/18/21 Tesla (TSLA)

$41k Nividia (NVDA)

$276k Vanguard Total Bond (VBTLX)
$40k Vanguard Total Stock (VTSAX)
$18k Total Int Stock Admiral (VTIAX)


Wife's Roth IRA - ($7k) - 0.1% of Portfolio
$7k Vanguard Total Bond (VBTLX)


Anticipated Portfolio at Retirement 7/2021

Taxable (unchanged)
Pre-Retirement ($3m) 35.3% of Portfolio
$4.533m 5,595sh Tesla (TSLA)
$2.23m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-$1.94m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.89m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)

$80k Google (GOOG)

$11k Total Bond Admiral (VBTLX)
$12k Total Int Stock Admiral (VTIAX)
$12k Total Stock Admiral (VTSAX)

Retirement Accounts 64.7% of Portfolio
$2.25m Total Bond Admiral (VBTLX)
$1.35m Total Int Stock Admiral (VTIAX)
$2.4m Total Stock Admiral (VTSAX)

Target Asset Allocation
60% Equity (Stock & Total Stock Fund)
15% Total Intl Stock Fund
25% Total Bond Fund

The Tesla Covered Calls will prevent me to moving them to Index Funds until at earliest 6/2022 in my taxable brokerages.


Questions;
1) I realize 60/15/25 is really aggressive, but given the 45+ year retirement horizon I need a more aggressive plan. Also given 3% wd rate, it looks "safeish". ERN site seems to support that would work indefinitely, but still concerned. I would really appreciate feedback here?

2) With the tax implications of TSLA stock sale in my taxable brokerage, would it be better to continue delaying TSLA sale via rolling options (riskier) or bite the tax bullet (my current plan) and move into Index funds in my brokerage (primarily Total Stock in brokerage)?

3) Annual 250k usage, I plan on keeping the $250k that I use in MM (VMFXX) and replenishing that amount annually to MM (VMFXX). Is there a better vehicle to store funds for annual living expenses?

4) With $1m in upcoming liabilities ($900k tax, $100k car), would these monies best be served to be set aside in MM as well? My current plan is to have them invested in AA model I laid out (60/15/25).

5) Rebalancing - Do folks typically re-balance strictly based on calendar (for me January and July) or do you also potentially re-balance based on allocation changes? Example, Bond fund grows suddenly to represent 35% rather than 25% of overall portfolio and thus triggering a re-balance?
I wanted to get a followup from this poster.

Did he sell or he is waiting for the LTCG to kick in?

Tesla just down to $547 today.
60% VT, 40% BND.
Topic Author
roguewarrior0
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by roguewarrior0 »

I sold all of TSLA in retirement accounts. I am still holding TSLA in my taxable, as reflected below.


Previous
Taxable -
Pre-Retirement ($3m) 35.3% of Portfolio
$4.533m 5,595sh Tesla (TSLA)
$2.23m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-$1.94m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$1.89m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)


The only changes are in the values:

Taxable's as of 5/19/21 are
$3.125m 5,595sh Tesla (TSLA)
$1.2m Long 40 Calls @ $280 9/16/22 Tesla (TSLA)
-0.782m Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$0.680m Short 50 Calls @ $550 6/17/22 Tesla (TSLA)


With the time going by as well as downturn in TSLA, my net worth is currently actually higher. This is due to the time erosion of Options I am short (theta) as well decrease in overall TSLA options Premium.

In the ideal scenario for me, TSLA will be BELOW $550 in June 2022 and BELOW $500 September of 2022. So I am staying the course until 2022 to let it play out.

Currently my Portfolio sits at around $8.9m today and will now be $10.1m in 2022 (assuming my TSLA shares get called away) so net worth has increased since I originally posted. Additionally, I have decided to postpone my retirement from July 2021 to ~Feb 2022. This will give me some additional time to get healthcare squared away (additional doctor, dentist, optometry visits paid by company insurance) as well get another 401k match on the books for 2022.

I am glad that the forum suggested to close out TSLA in my retirement accounts. I moved those into traditional 3 fund portfolio, primarily Total Bond Fund. My inner demon is telling to leverage this "dry powder" in retirement accounts to take advantage of this dip and resume my Option strategy, but so far I have resisted.
manuvns
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by manuvns »

TSLA might be down to 200's be ready!
Thanks!
Slacker
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by Slacker »

OP:. How much did you start with in January 2020? How much money did you put up initially to start this TSLA adventure?
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roguewarrior0
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by roguewarrior0 »

6/1/2019 - Portfolio was 2.396m
12/31/2019 - Portfolio was 3.146
6/1/2020 - Portfolio was 4.027
12/31/2020 - Portfolio was 8.498
5/17/2021 - Portfolio - 8.909 (likely lower as of today)


As to some of the other posts:

"Might be 200's" - I am not going to overreact because TSLA could go down to the 200's. I believe TSLA is a solid company and will continue to grow. It still sells every car it makes with no discounting. That is just ridiculous. If it did drop back to the 200's, I am more likely to backup the truck and buy more of it.

"Risks of change to LTCG's tax rate" - Similar to previous posts. If that does pass, I will deal with it.

I have zero belief it would pass retroactively to 2021, never been done in history. Trump's tax changes were on a go forward basis. Given the ever increasing budget deficit (not taking politically sides), I believe Trump Tax breaks will have to be revoked at some point, whether by Biden or someone else. However regardless what side of aisle you sit, I think we will agree that Dems & Repubs CAN'T agree on anything. So I am more willing to bet very little gets done in the next 4 years so nothing drastic will happen.

Worst case is something is sent through "reconciliation" which won't be too huge. Again, I plan to stay the course through 2022. 8 more months until I put in my notice so I have ways to shift gears. Good news is my spending has not grown just the nest egg.
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by 3CT_Paddler »

If anybody can give you relevant advice on this forum, it might be Market Timer. He stared down bankruptcy with risky investing decisions in 2008 and lived to tell the tale (and came out a little wiser). His 2008 blow by blow thread might be a top 5 all time Boglehead thread.
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Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by LadyGeek »

I removed a post conjecturing on Biden's tax plan proposal. Speculation about future legislation is prohibited by forum policy, see: Unacceptable Topics
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This forum is focused on investing that is directly actionable to personal investors. We don't hold debates on conjecture.

The whole point of the policy is to (1) eliminate contentious disagreements that result from these discussions and (2) keep investors from making bad decisions. Proposed legislation changes many times between the time it's introduced and signed into law.

The best approach is to make your decision about current law. When the law changes, make your decision at that time.
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Topic Author
roguewarrior0
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Joined: Sat Feb 08, 2020 10:26 am

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by roguewarrior0 »

I wanted to post an update. I have decided to postpone my retirement until 2/2022. I also have given in to propensity for TSLA Covered Call Strategy and jumped back into TSLA during the recent pull-back. I realize it doesn't follow Boglehead strategy, but I am taking advantage of the current situation. We will see if I have chosen poorly. During the pullback, I sold off my bonds and went back in.

TSLA now represents 76.59% of my portfolio. I own 13,052 shares + 46 Long Calls and am short 166 Call Contracts.

I still plan on reverting to 3 Fund Portfolio once I retire. Estimated Target Portfolio assumes my shares get Called away.

Here is my updated portfolio.

Current Age: 46
Current portfolio: $9.63m
Target portfolio @ retirement in 2022: ~$11.1m
Goal: Retire and not return to Corporate world
Retirement Withdrawals: $250k/yr
Other Assets: Own free/clear 3 homes ($1m value)
Other Assets: 2 of the homes above generate a total $3500/month in Rental income
Other Costs outside of $250k/yr:
2022 New Car $80k
2022 2021 tax bill $100k
2023 2022 tax bill $400k
2024 New Car $25k


Current Portfolio: $9.63m

Taxable Accounts- $5.286m - 55%

$790k - Cash

$4.514m 7,320sh Tesla (TSLA)
$1.426m Long 41 Calls @ $280 9/16/22 Tesla (TSLA)
-$932k Short 45 Calls @ $500 9/16/22 Tesla (TSLA)
-$836k Short 50 Calls @ $550 6/17/22 Tesla (TSLA)
-$102k Short 17 Calls @ $700 12/17/21 Tesla (TSLA)


$119k Google (GOOG)

$52k Total Bond Admiral (VBTLX)
$39k Total Int Stock Admiral (VTIAX)
$40k Total Stock Admiral (VTSAX)


Retirement Accounts- $4.344m - 45%

$3.534m 5,732sh Tesla (TSLA)
$174k Long 5 Calls @ $280 9/16/22 Tesla (TSLA)
-$104k Short 5 Calls @ $500 9/16/22 Tesla (TSLA)
-$196k Short 49 Calls @ $550 6/17/22 Tesla (TSLA)

$461k COIN
$223k GBTC
$78k NVDA

$23k Total Bond Admiral (VBTLX)
$32k Total Int Stock Admiral (VTIAX)
$75k Total Stock Admiral (VTSAX)
randybobandy
Posts: 159
Joined: Fri Oct 05, 2018 10:51 am

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by randybobandy »

Thanks for the update, hope all goes well for you!

--Randy Bo Bandy
Grammar and spelling matter. | Quoting the OP isn't a necessity.
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market timer
Posts: 6461
Joined: Tue Aug 21, 2007 1:42 am

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by market timer »

As a spectator, I find this very interesting. However, an an investor, I'd never have the guts to do this. I'm reminded of William Bernstein's quote: "When you've won the game, stop playing."
bovineplane
Posts: 168
Joined: Wed Jul 26, 2017 5:24 am

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by bovineplane »

3CT_Paddler wrote: Thu May 27, 2021 12:18 pm If anybody can give you relevant advice on this forum, it might be Market Timer. He stared down bankruptcy with risky investing decisions in 2008 and lived to tell the tale (and came out a little wiser). His 2008 blow by blow thread might be a top 5 all time Boglehead thread.
3C_Paddler - I may have missed this thread, any chance to get a link?

OP - I can only say your thread and regular updates are fascinating. This is the stuff some people dream of. Having the capital conviction and timing to do something like this. No matter the outcome, rooting for you. If only to live vicariously through the updates.
random_walker_77
Posts: 1542
Joined: Tue May 21, 2013 8:49 pm

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by random_walker_77 »

bovineplane wrote: Sat Jun 19, 2021 8:26 am
3CT_Paddler wrote: Thu May 27, 2021 12:18 pm If anybody can give you relevant advice on this forum, it might be Market Timer. He stared down bankruptcy with risky investing decisions in 2008 and lived to tell the tale (and came out a little wiser). His 2008 blow by blow thread might be a top 5 all time Boglehead thread.
3C_Paddler - I may have missed this thread, any chance to get a link?
Here's Market Timer's epic thread: viewtopic.php?f=10&t=5934
(there's a link to it from the thread on favorite posts: viewtopic.php?f=9&t=143500)
Ramjet
Posts: 1024
Joined: Thu Feb 06, 2020 11:45 am
Location: Ohio

Re: Retiring in 6 months (off TSLA options); Plan Review & Questions

Post by Ramjet »

random_walker_77 wrote: Sat Jun 19, 2021 3:00 pm
bovineplane wrote: Sat Jun 19, 2021 8:26 am
3CT_Paddler wrote: Thu May 27, 2021 12:18 pm If anybody can give you relevant advice on this forum, it might be Market Timer. He stared down bankruptcy with risky investing decisions in 2008 and lived to tell the tale (and came out a little wiser). His 2008 blow by blow thread might be a top 5 all time Boglehead thread.
3C_Paddler - I may have missed this thread, any chance to get a link?
Here's Market Timer's epic thread: viewtopic.php?f=10&t=5934
My all-time favorite thread on Bogleheads
VT & HFEA
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