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need help with this Roth strategy
Old 01-22-2011, 09:49 PM   #1
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need help with this Roth strategy

I have been running some numbers based on Friday's closing price of Apple and I think I have a 100% safe way to convert $20,000 IRA to a Roth while only paying taxes on about $10,000 of it. This is kind of wacky, but here goes:

Using the options pricing at friday close:
Roth conversion account #1 $10,000 start
Sell 40 AAPL April 11 $325 calls for $20.45
Buy 40 AAPL April 11 $330 calls for $17.90
Net credit $10,200. Max loss $9800

Roth conversion account #2 $10,000 start
Sell 37 AAPL April 11 $325 puts for $17.95
Buy 37 AAPL April 11 $320 puts for $15.60
Net credit $8695. Max loss $9805

Scenarios
Apple closes below $320: Roth 1 worth $20,200, Roth 2 worth $195
Apple closes above $330: Roth 1 worth $200, Roth 2 worth $18,695
Apple closes between $320 and $330: Both Roths worth something, at magic number of $325 combined Roths worth $38,895 In this unlikely case, you would end up not saving any taxes, but then again, you have almost a 100% return.

Figure trading fees would be around $100 for each account. In a 28% tax bracket, you would pay $2800 in federal tax for the "good" account and recharacterize the one that lost back to IRA and pay no tax. If you had just done the conversion straight up, you would pay $5600 in tax. For the worst case of Roth 2 being the winner, you end up with a $18595 IRA for $2800 in taxes vs a $20,000 IRA for $5600 in taxes. If you back out the loss in the option play, you still are $1400 ahead.

Crazy? Seems foolproof, which makes me think it is foolish.
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Old 01-22-2011, 10:56 PM   #2
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I like your stab at financial engineering.

However, I think you need to be careful about the rules regarding the value of recharacterizations. I did a partial recharacterization in 2010 because I wanted to hit an exact $ amount on the conversion, and could only do a conversion as either straight cash or as a specific # of shares of a security (I did the specific # of shares.) After the fact, I had to get the brokerage to tell me how much I needed to recharacterize, or extra to convert, to hit the magic number (which I did with straight cash as it was a small amount), and it turned out that the recharacterization was different than simply the difference between how much had actually been converted and how much I had wanted to be converted, as the net value of the recharacterization was somehow based on the value of the security at the time of the original conversion (or something like that.) I have a hunch that this rule will obliterate your strategy - but then again maybe not.
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Old 01-22-2011, 10:57 PM   #3
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Originally Posted by 79protons View Post
I posted this on Bogleheads first, but they are all like "I don't understand...it doesn't involve Vanguard funds"

I have been running some numbers based on Friday's closing price of Apple and I think I have a 100% safe way to convert $20,000 IRA to a Roth while only paying taxes on about $10,000 of it. This is kind of wacky, but here goes:

Using the options pricing at friday close:
Roth conversion account #1 $10,000 start
Sell 40 AAPL April 11 $325 calls for $20.45
Buy 40 AAPL April 11 $330 calls for $17.90
Net credit $10,200. Max loss $9800

Roth conversion account #2 $10,000 start
Sell 37 AAPL April 11 $325 puts for $17.95
Buy 37 AAPL April 11 $320 puts for $15.60
Net credit $8695. Max loss $9805

Scenarios
Apple closes below $320: Roth 1 worth $20,200, Roth 2 worth $195
Apple closes above $330: Roth 1 worth $200, Roth 2 worth $18,695
Apple closes between $320 and $330: Both Roths worth something, at magic number of $325 combined Roths worth $38,895 In this unlikely case, you would end up not saving any taxes, but then again, you have almost a 100% return.

Figure trading fees would be around $100 for each account. In a 28% tax bracket, you would pay $2800 in federal tax for the "good" account and recharacterize the one that lost back to IRA and pay no tax. If you had just done the conversion straight up, you would pay $5600 in tax. For the worst case of Roth 2 being the winner, you end up with a $18595 IRA for $2800 in taxes vs a $20,000 IRA for $5600 in taxes. If you back out the loss in the option play, you still are $1400 ahead.

Crazy? Seems foolproof, which makes me think it is foolish.

Your position is called: 'iron butterfly' although a little bit unbalanced since you have 40 contracts on the call side and only 37 on the put side. See this link for description of iron butterfly. Iron Butterfly Explained | Online Option Trading Guide.

Like all investments, iron butterfly has a risk too, albeit limited. I do not trade multi-leg positions like this strategy, only simple calls and puts, so I can't comment on the risk and reward.
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Old 01-22-2011, 11:23 PM   #4
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I posted this on Bogleheads first, but they are all like "I don't understand...it doesn't involve Vanguard funds"(snip).
I have no comment on the proposed strategy—I don't know enough about options trading to know whether your idea is brilliant or boneheaded. But your characterization of the responses on boglehead.org is inaccurate, as anyone can see by reading the thread (which contains five comments as of this writing).

There were two responses questioning the idea. One wanted to know whether the transactions would be allowed in an IRA, the other questioned your description of the proposed trade as "100% safe". There was no mention at all of Vanguard funds, or of not understanding. You could have asked this without mentioning bogleheads at all, or simply said that you only got a few responses and wanted to hear more peoples' take on it. What is your reason for adding an unnecessary and inaccurate put-down to your question?
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Old 01-22-2011, 11:31 PM   #5
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But your characterization of the responses on boglehead.org is inaccurate, as anyone can see by reading the thread (which contains five comments as of this writing).
Ok, I removed the remark from the original post. I was just ticked off by a response there from a poster saying they stopped reading after the title yet wanted to take the time to reply to the message they had not read with a silly diatribe about investment risks.
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Old 01-22-2011, 11:34 PM   #6
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I like your stab at financial engineering.

I have a hunch that this rule will obliterate your strategy - but then again maybe not.

I haven't tried a recharacterization yet, but I am unsure what you mean. If I convert $10,000 in cash sitting in my traditional IRA to a Roth, then make the investment move in the Roth and it goes to near zero, why would I not be able to convert that account back to an IRA? I have not read any rule preventing this.
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Old 01-22-2011, 11:37 PM   #7
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Your position is called: 'iron butterfly' although a little bit unbalanced since you have 40 contracts on the call side and only 37 on the put side. See this link for description of iron butterfly. Iron Butterfly Explained | Online Option Trading Guide.

Like all investments, iron butterfly has a risk too, albeit limited. I do not trade multi-leg positions like this strategy, only simple calls and puts, so I can't comment on the risk and reward.
Excellent, thanks for the link. I guess every option strategy has a name by now. I googled iron butterfly and roth conversion and did not find any reference to anyone trying this.

I am not seeing the risk if it is indeed there. I understand the trade would likely have a moderate loss and commission charges, but these would be far far offset by the tax savings. If someone had a much larger IRA they wanted to convert, say $200,000 or something, this strategy would really shine, saving tens of thousands of dollars in taxes. Maybe it would get you on the bad side of the IRS though? They might get pissed and try to audit you somewhere else?
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Old 01-23-2011, 12:23 AM   #8
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Ok, I removed the remark from the original post. I was just ticked off by a response there from a poster saying they stopped reading after the title yet wanted to take the time to reply to the message they had not read with a silly diatribe about investment risks.
There are a lot of people who post on both boards.

Should we search Bogleheads.org to find out what you're saying about E-R.org? Or should we just search for the keyword "silly"?
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Old 01-23-2011, 01:29 AM   #9
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Excellent, thanks for the link. I guess every option strategy has a name by now. I googled iron butterfly and roth conversion and did not find any reference to anyone trying this.

I am not seeing the risk if it is indeed there. I understand the trade would likely have a moderate loss and commission charges, but these would be far far offset by the tax savings. If someone had a much larger IRA they wanted to convert, say $200,000 or something, this strategy would really shine, saving tens of thousands of dollars in taxes. Maybe it would get you on the bad side of the IRS though? They might get pissed and try to audit you somewhere else?
Many IRA accounts would not allow you to sell options regardless you have enough margin or not. Depending on the firms, selling 40 calls for a stock price of $325 which equals to (4000 X $325 = $1,300,000), would need margin from anywhere between 20 to 50% cash or equivalent in the account. With high volatility stock like AAPL, the margin requirement tends to be on the high side. Even with 25% margin requirement, you would need $325,000 in the account in order to place your short call trade.
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Old 01-23-2011, 01:50 AM   #10
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Ok, I removed the remark from the original post. I was just ticked off by a response there from a poster saying they stopped reading after the title yet wanted to take the time to reply to the message they had not read with a silly diatribe about investment risks.
Well, your title was "help me double check this 100% safe investment idea please". The commenter questioned whether any investment is 100% safe. Even if you stop reading after the first line of his reply, this is a valid question. If the responder over at bogleheads is right in suggesting that there is no such thing as a 100% safe investment, then it is possible for you to lose money on this trade. I would suggest not going ahead with the trade until you figure out how it could come out adversely for you, how much money you would lose if that happens, and verify that the trade is permissible in an IRA.
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Old 01-23-2011, 06:26 AM   #11
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Old 01-23-2011, 07:16 AM   #12
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Many IRA accounts would not allow you to sell options regardless you have enough margin or not. Depending on the firms, selling 40 calls for a stock price of $325 which equals to (4000 X $325 = $1,300,000), would need margin from anywhere between 20 to 50% cash or equivalent in the account. With high volatility stock like AAPL, the margin requirement tends to be on the high side. Even with 25% margin requirement, you would need $325,000 in the account in order to place your short call trade.
You are not on margin in this trade. You buy a put and a call to protect the put and call you sell and also you have cash in the account from the net credit you received from the sale in the event the stock moves past both of your put and call prices. Anyway, this is just a net credit spread, which is allowed at etrade in ira and roth at option level 3, which I am approved for.
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Old 01-23-2011, 08:04 AM   #13
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You are not on margin in this trade. You buy a put and a call to protect the put and call you sell and also you have cash in the account from the net credit you received from the sale in the event the stock moves past both of your put and call prices. Anyway, this is just a net credit spread, which is allowed at etrade in ira and roth at option level 3, which I am approved for.
I would be very careful here. Suppose you were assigned on the short call. You would find out the next business day, at which point you would exercise your long call. Because of the 3 business-day settlement on stocks, you could end up short the stock for one business day. Are you sure this would be allowed in an IRA?

Or on the put side you could end up long stock for one business day. How would you settle? What if you had to borrow for one day to settle? I'm pretty sure you can't borrow in an IRA.
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Old 01-23-2011, 09:00 AM   #14
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I would be very careful here. Suppose you were assigned on the short call. You would find out the next business day, at which point you would exercise your long call. Because of the 3 business-day settlement on stocks, you could end up short the stock for one business day. Are you sure this would be allowed in an IRA?

Or on the put side you could end up long stock for one business day. How would you settle? What if you had to borrow for one day to settle? I'm pretty sure you can't borrow in an IRA.
Hmmm...an interesting point. Since Etrade does allow this type of trading in an IRA, I assume that if you are assigned on the short call, they immediately also assign the long call for you such that the cash in the account used to secure the spread fully covers the difference. I don't think Etrade provides any margin or loan for an IRA, so where would the cash come from? You can't go negative in an IRA to my knowledge, so if they allow this type of trading, they must assume the responsibility to make sure it executes correctly. I will definately check into this.
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Old 01-23-2011, 03:48 PM   #15
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I have been running some numbers based on Friday's closing price of Apple and I think I have a 100% safe way to convert $20,000 IRA to a Roth while only paying taxes on about $10,000 of it. This is kind of wacky, but here goes:

Using the options pricing at friday close:
Roth conversion account #1 $10,000 start
Sell 40 AAPL April 11 $325 calls for $20.45
Buy 40 AAPL April 11 $330 calls for $17.90
Net credit $10,200. Max loss $9800

Roth conversion account #2 $10,000 start
Sell 37 AAPL April 11 $325 puts for $17.95
Buy 37 AAPL April 11 $320 puts for $15.60
Net credit $8695. Max loss $9805

Scenarios
Apple closes below $320: Roth 1 worth $20,200, Roth 2 worth $195
Apple closes above $330: Roth 1 worth $200, Roth 2 worth $18,695
Apple closes between $320 and $330: Both Roths worth something, at magic number of $325 combined Roths worth $38,895 In this unlikely case, you would end up not saving any taxes, but then again, you have almost a 100% return.

Figure trading fees would be around $100 for each account. In a 28% tax bracket, you would pay $2800 in federal tax for the "good" account and recharacterize the one that lost back to IRA and pay no tax. If you had just done the conversion straight up, you would pay $5600 in tax. For the worst case of Roth 2 being the winner, you end up with a $18595 IRA for $2800 in taxes vs a $20,000 IRA for $5600 in taxes. If you back out the loss in the option play, you still are $1400 ahead.

Crazy? Seems foolproof, which makes me think it is foolish.
this looks very interesting and i hope it works (i would like to do it myself) but i am concerned about the recharacterizing working. will it have to be done before the options expire? if so, how fast can a recharacterization be accomplished? if you wait till they expire will the irs accept that you recharacterize $10K worth of TIRA to Roth conversion with a few hundred $? that just doesnt seem to pass my logic test, but the success of this seems to depend on it.
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Old 01-23-2011, 04:12 PM   #16
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this looks very interesting and i hope it works (i would like to do it myself) but i am concerned about the recharacterizing working. will it have to be done before the options expire? if so, how fast can a recharacterization be accomplished? if you wait till they expire will the irs accept that you recharacterize $10K worth of TIRA to Roth conversion with a few hundred $? that just doesnt seem to pass my logic test, but the success of this seems to depend on it.
No, the recharacterization would be done after expiration or after you have sold the spread (you can actually buy and sell spreads as a single entity to my limited knowledge). Evidently the IRS doesn't have a problem with you losing $10,000 and recharacterizing a few $ back.

I am not as keen on performing this idea now that it has been pointed out that the bid/ask spread might make getting the iron butterfly legs at the prices I outlined harder and thus less likely to have a great savings benefit. I guess there would still be the chance of hitting the middle price exactly and ending up with two Roths almost double in value though. This has to be a small chance...probably around 5% or so. 95% chance you end up with one Roth near zero and the other roth at 80% to 90% return.

I am going to proceed with a modified strategy where I split my IRA into three Roths and make two fairly bullish plays by buying call LEAPS on something (maybe AAPL and CSCO) and one bearish play by buying LEAP puts on something high priced that might tank in a general market correction (like NFLX or LVS). I generally believe the market will trend up (historically it does), and with the LEAPS I will have time to capture this hopefully in two of the plays while protecting them with the puts. I don't have any protection if the market stays exactly flat for a year though...that was the beauty of the iron butterfly...
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Old 01-23-2011, 05:47 PM   #17
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No, the recharacterization would be done after expiration or after you have sold the spread (you can actually buy and sell spreads as a single entity to my limited knowledge). Evidently the IRS doesn't have a problem with you losing $10,000 and recharacterizing a few $ back.
do you have a source for this, something from the irs or some CPA?

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I am not as keen on performing this idea now that it has been pointed out that the bid/ask spread might make getting the iron butterfly legs at the prices I outlined harder and thus less likely to have a great savings benefit. I guess there would still be the chance of hitting the middle price exactly and ending up with two Roths almost double in value though. This has to be a small chance...probably around 5% or so. 95% chance you end up with one Roth near zero and the other roth at 80% to 90% return.
you can specify how much credit each spread will produce in your buy order.
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Old 01-23-2011, 06:20 PM   #18
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Old 01-23-2011, 06:26 PM   #19
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do you have a source for this, something from the irs or some CPA?


you can specify how much credit each spread will produce in your buy order.

Some key points from the IRS document 590:

"You can convert a traditional IRA to a Roth IRA. The conversion is treated as a rollover, regardless of the conversion method used. Most of the rules for rollovers, described in chapter 1 under Rollover From One IRA Into Another , apply to these rollovers. However, the 1-year waiting period does not apply. "

So that is good. It means you can convert (rollover) your traditional IRA into any number of separate Roth accounts without incurring the normal 365 waiting period. Check!

This next part is the key part about the recharacterization, straight from document 590.

Worksheet 1-3. Determining the Amount of Net Income Due To an IRA Contribution and Total Amount To Be Recharacterized






1.Enter the amount of your IRA contribution for 2010 to be recharacterized1. 2.Enter the fair market value of the IRA immediately prior to the recharacterization (include any distributions, transfers, or recharacterization made while the contribution was in the account) 2. 3.Enter the fair market value of the IRA immediately prior to the time the contribution being recharacterized was made, including the amount of such contribution and any other contributions, transfers, or recharacterizations made while the contribution was in the account 3. 4.Subtract line 3 from line 24. 5.Divide line 4 by line 3. Enter the result as a decimal (rounded to at least three places)5. 6. Multiply line 1 by line 5. This is the net income attributable to the contribution to be recharacterized6. 7.Add lines 1 and 6. This is the amount of the IRA contribution plus the net income attributable to it to be recharacterized7.


Example.
On April 1, 2010, when her Roth IRA is worth $80,000, Allison makes a $160,000 conversion contribution to the Roth IRA. Subsequently, Allison requests that the $160,000 be recharacterized to a traditional IRA. Pursuant to this request, on April 1, 2011, when the IRA is worth $225,000, the Roth IRA trustee transfers to a traditional IRA the $160,000 plus allocable net income. No other contributions have been made to the Roth IRA and no distributions have been made.
The adjusted opening balance is $240,000 ($80,000 + $160,000) and the adjusted closing balance is $225,000. Thus the net income allocable to the $160,000 is ($10,000) ($160,000 x (($225,000 – $240,000) ÷ $240,000)). Therefore in order to recharacterize the April 1, 2010, $160,000 conversion contribution on April 1, 2011, the Roth IRA trustee must transfer from Allison's Roth IRA to her traditional IRA $150,000 ($160,000 – $10,000). This is shown on the following worksheet.

Worksheet 1-3. Example—Illustrated






1.Enter the amount of your IRA contribution for 2010 to be recharacterized1.160,0002.Enter the fair market value of the IRA immediately prior to the recharacterization (include any distributions, transfers, or recharacterization made while the contribution was in the account) 2.225,0003.Enter the fair market value of the IRA immediately prior to the time the contribution being recharacterized was made, including the amount of such contribution and any other contributions, transfers, or recharacterizations made while the contribution was in the account 3.240,0004.Subtract line 3 from line 24.(15,000)5.Divide line 4 by line 3. Enter the result as a decimal (rounded to at least three places)5.(.0625)6. Multiply line 1 by line 5. This is the net income attributable to the contribution to be recharacterized6.(10,000)7.Add lines 1 and 6. This is the amount of the IRA contribution plus the net income attributable to it to be recharacterized7.150,000


Timing. The election to recharacterize and the transfer must both take place on or before the due date (including extensions) for filing your tax return for the year for which the contribution was made to the first IRA.

Extension. Ordinarily you must choose to recharacterize a contribution by the due date of the return or the due date plus extensions. However, if you miss this deadline, you can still recharacterize a contribution if:
  • Your return was timely filed for the year the choice should have been made, and
  • You take appropriate corrective action within 6 months from the due date of your return excluding extensions. For returns due April 15, 2010, this period ends on October 15, 2010. When the date for doing any act for tax purposes falls on a Saturday, Sunday, or legal holiday, the due date is delayed until the next business day.

Appropriate corrective action consists of:
  • Notifying the trustee(s) of your intent to recharacterize,
  • Providing the trustee with all necessary information, and
  • Having the trustee transfer the contribution.
Once this is done, you must amend your return to show the recharacterization. You have until the regular due date for amending a return to do this. Report the recharacterization on the amended return and write “Filed pursuant to section 301.9100-2” on the return. File the amended return at the same address you filed the original return.
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Old 01-23-2011, 07:34 PM   #20
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Some key points from the IRS document 590:

"You can convert a traditional IRA to a Roth IRA. The conversion is treated as a rollover, regardless of the conversion method used. Most of the rules for rollovers, described in chapter 1 under Rollover From One IRA Into Another , apply to these rollovers. However, the 1-year waiting period does not apply. "

So that is good. It means you can convert (rollover) your traditional IRA into any number of separate Roth accounts without incurring the normal 365 waiting period. Check!
thanks for all the great info but i am not finding this in IRS Pub 590 and because of that 1-year waiting period on rollovers it is kinda key that it does not apply to a TIRA conversion to a Roth.
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