Options Trading - Straddle Musings

Matt

Administrator
Staff member
People fear options trading, and rightly so. However, it can be a good tool for hedging stock positions, so when done correctly can be safer than being invested in a 'safe' manner such as in a passive index strategy.

One strategy that I am currently exploring is a straddle between taxable and advantaged accounts. In theory this is a very good way to create income safely. However, I am still wrapping my head around certain IRS regulations that pertain to this specific type of investment. Here's a good post on the topic for those interested: http://seekingalpha.com/article/1109941-stocks-options-taxes-part-vi-options-and-tax-straddles-covered-calls

Note - I WOULD NOT deploy this strategy at this stage due to uncertainty on the proper way to package the straddle. However, if we could determine that the call killed the trade, it may be interesting.

The theory:

Increase income from existing portfolio by selling covered call within IRA. This will:
  • Produce income from premium (good)
  • Reduces upside gain beyond a predetermined point (not good)
  • Trap your investment against stop limit/loss orders (not good)
Add in a Protective Put
  • Costs money to buy premium (not good)
  • Protects core stock/etf position across the IRA boundary (good)
What's it worth?
The with options that have similar dates and strikes (creating a hedge) vol is going to be an important factor. However, the vol will impact pricing both on the acquisition of the Put and the sale of the Call, so they may offset one another.

The key with building a straddle is that you need a market. A good stock to look at for this would be a well traded one. Let's consider Apple:

Market Price $127.23

Screen Shot 2015-04-06 at 12.13.41 PM.png

The Trade:
Sell $128 Calls for $157
Buy $127 Puts for $198
Net: Loss of $41

Note that both of these positions are considered out of the money at this moment.

Let's remember the overriding goal - to make more money! As such the above strategy isn't ideal, because the Net is a loss of $41. However, from a balance sheet perspective the following occurs:

Taxable Account -$198
Advantaged (EG Roth) Account +$157


As you can see, we can theoretically garner a capital loss of $198 and also create a capital gain of $157, but the gain is shielded. The challenge is determining whether the IRS will allow you to do this with regard to the straddle rules. If they did, then even a losing trade makes money, and also has the added value of shifting money into a Roth via investment gains.

What's more.. there will be trades that net a profit.. there are a few reasons that the puts are more expensive in the AAPL example above. The most obvious one is that the price of the stock $127.23 is closer to $127 than $128 and therefore has less far to travel to make the Put in the money.

Outcomes:
The beauty of a straddle like this is that there can only ever be 3 possible outcomes:
  1. The Put ends in the Money
  2. The Call ends in the Money
  3. Both the Put and the Call Expire
Because of this, you move away from randomness, and create three possible results, if all three are acceptable to you then it's a good trade.

In the case of AAPL:

1. If the Put ends in the money the Stock price has dropped below $127, this means that for 100 shares:
  • Stock loses $23+difference between $127 and Zero.
  • Call expires, adding $157
  • Put gains in value in direct proportion to the stock loss
  • Max Loss on Trade = $64
Proof
Max Loss stock price drops to $126
Buy AAPL at $12723
100*$126=$12600
Net Loss of -$123
Put Premium Value = -$98 ($100-198)
Call value (earned) = $157
Total Loss if Stock drops= -$64

2. If the Call ends up in the money the stock price has risen above $128 this means that for 100 shares:
Stock gains $77+ anything above $128
Put expires, losing $198
Call caps gain at $128, anything above is excluded.
Max Gain on trade $121

Proof Max gain price raises to $129
Buy AAPL at $12723
100*$129 =12900
Net gain of $177
Put premium paid -$198
Call value $57( $157-$100)
Total Gain if stock raises= $121

3. If both expire, the stock would be priced between $127-$128. The gain or loss would be related to the premium spread (-$41). It is possible for the stock to gain (eg end at $127.89) or decline in value (eg end at $127.11)

Note that I skipped over ATM prices for clarity in the above.

The goal of this strategy is to benefit most when the price ends somewhat flat. Note that the holding period for the investment is only 2 weeks in this example. Additionally, the value is that we are trading within an advantaged account, such as a Roth. This means that if the price rises (resulting in a trade execution) we don't need to worry about short term cap gains.

I think I'll put this one into the someday/maybe file as it can offer a lot of value, providing it is allowed by tax law!
 

Matt

Administrator
Staff member
Here's an example of a position close to the call price, thus creating a net profit from the call/put transaction:
Screen Shot 2015-04-06 at 1.19.25 PM.png

Sell @51 for $1.10
Buy @50 for $0.80
Net cost = profit of $30
 

MilesAbound

Level 2 Member
I'm a finance professional with good knowledge of this space... and I've no f'ing clue what you are talking about. Meaning this is crazy and definitely NOT "safer than 'safe'", which has to go down as crazy quote of the day. Possibly week, month and year. Maybe in the top 10 for decade ;)

If you become a financial advisor and actually sell this shit to your clients the only ones who will agree are those that don't understand what you are saying but just nod in agreement so they don't look stupid.

edit to add this should not be in investments as this has nothing whatsoever to do with investing. You should open up a new Gambling and/or Crazy Ideas forum for these kind of posts
 

MickiSue

Level 2 Member
We use covered calls as a way to increase the yield on our Roth IRAs. The best of all possible worlds, in that case, is a stock that stays flat, and allows you to sell covered calls on it, over and over.

I know a little about options trading--learning as we go slowly. But I have no clue what you are talking about either, Matt.
 

Matt

Administrator
Staff member
Meaning this is crazy and definitely NOT "safer than 'safe'", which has to go down as crazy quote of the day. Possibly week, month and year. Maybe in the top 10 for decade ;)
The essence of this concept is to hedge a position, including an index. People consider indexing 'safe' due to the diversification of it. The reality is that indexing is still a rollercoaster ride which can mean that your investment can drop 30% or more in a given year. Hedging that is 'safer than safe'...

I've no f'ing clue what you are talking about.
I have no clue what you are talking about either
Its really simple:

  • You hold a long position within an IRA.
  • You sell a covered call against it to create additional income (means you cap upside, but you guarantee a payment, called the premium)
But if you do the above in an IRA you cannot protect against catastrophic loss, because you have to first exit the call before you can (if you wanted to) sell the long position with a stop loss. The reason for this is IRA rules will not allow an uncovered call.

So you add in:

  • A married put
That's it.. all you are doing is reducing the risk of selling covered calls on your long stock position.

That is not crazy talk!

The part that I'm looking at is an IRS ruling on it all... if you take the above and transact the Put step within a taxable account, you could (rules permitting) capture capital losses from every time the put dies worthless. If you can build that properly (the regs are a little complex) then you can effectively buy losing positions in taxable (buy losses) and 'earn' winning positions in advantaged.

This is a pretty simple concept, the catch is whether you can do it in a manner that is approved or not.

edit to add this should not be in investments as this has nothing whatsoever to do with investing. You should open up a new Gambling and/or Crazy Ideas forum for these kind of posts
Crazy Ideas, yes! Gambling - no... I put this up as a sounding board post to hear some insight on. I would not attempt this(and stated so in big red letters in the post) without approval from the IRS.
 
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Someone

Level 2 Member
Tax is not my area of expertise, BUT I do have a little experience with options, and I like to learn about the tax stuff...

You are talking about creating a collar with the put leg in a taxable account, and the call and underlying in a tax advantaged account. If you go ask the IRS for their opinion (great idea! try it and let us know what they say) I'm guessing they will tell you your basis in the underlying is increased by the price you paid for the put, regardless of which account it is held in, and that you can't deduct any loss in the scenario you created.

Also, what would you do if your put goes ITM? Sell it right before expiration? You mentioned indexes, so maybe you're thinking of cash-settled options, but if you were dealing with individual stocks (like AAPL and TWTR in your examples) you wouldn't have the shares in the taxable account to sell.
 

Matt

Administrator
Staff member
Tax is not my area of expertise, BUT I do have a little experience with options, and I like to learn about the tax stuff...

You are talking about creating a collar with the put leg in a taxable account, and the call and underlying in a tax advantaged account. If you go ask the IRS for their opinion (great idea! try it and let us know what they say) I'm guessing they will tell you your basis in the underlying is increased by the price you paid for the put, regardless of which account it is held in, and that you can't deduct any loss in the scenario you created.

Also, what would you do if your put goes ITM? Sell it right before expiration? You mentioned indexes, so maybe you're thinking of cash-settled options, but if you were dealing with individual stocks (like AAPL and TWTR in your examples) you wouldn't have the shares in the taxable account to sell.
Saw something on a related topic here http://www.irs.gov/Businesses/Passthrough-Entity-Straddle-Tax-Shelter

First, the Service may disallow Taxpayer's loss under § 165(c)(2) by asserting that the loss was not incurred in a transaction undertaken for profit. See Smith v. Commissioner, 78 T.C. 350 (1982) and Fox v. Commissioner, 82 T.C. 1001 (1984)(disallowing losses from straddle transactions).
I think it would likely be a fight, and perhaps better than the IRS would be a good tax lawyer... and accepting that embarking in this strategy may involve tax court :)

Regarding the ITM put - you'd not need the shares, but yes, I would suggest closing out at the 11th hour.
 
Let's put this way:
You can make consistent money month over month selling calls or puts to other people. Many people have done this.
However, your entire gains would be wiped out in a black swan event. Black swan event is supposed to happen once in ten thousand years but happens every year or two in the market !!

If you are holding the right puts (or calls but rare), you can make money for a lifetime. In this scenario, you bleed money monthly but make up all of the losses and some when a big event happens.
 

Someone

Level 2 Member
I think it would likely be a fight, and perhaps better than the IRS would be a good tax lawyer... and accepting that embarking in this strategy may involve tax court :)
Which isn't as terrible as you make it sound... but like everything else we talk about on this board, the benefits have to outweigh the costs. If you aren't netting at least $20k extra from this strategy, that tax attorney's invoices are going to hurt.
 

Matt

Administrator
Staff member
Which isn't as terrible as you make it sound... but like everything else we talk about on this board, the benefits have to outweigh the costs. If you aren't netting at least $20k extra from this strategy, that tax attorney's invoices are going to hurt.
This is a HNW/UHNW play. I was speaking with some relatives on Easter about finance and they talked about no risk option strategies... they didn't outline what they were being pitched, but this is one that I felt might fit the bill.

The key to this idea is that you are constantly shifting money into the Roth via covered call inflows. If you have enough of a position to make that sizeable, then you can easily be moving beyond what you yourself could fund to such an account. I see it as a play similar to a backdoor Roth.

FWIW I'd say a private letter ruling might be a better solution, though it may cost more..
 
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Matt

Administrator
Staff member
Let's put this way:
You can make consistent money month over month selling calls or puts to other people. Many people have done this.
However, your entire gains would be wiped out in a black swan event. Black swan event is supposed to happen once in ten thousand years but happens every year or two in the market !!

If you are holding the right puts (or calls but rare), you can make money for a lifetime. In this scenario, you bleed money monthly but make up all of the losses and some when a big event happens.
In my example, you would not make up losses in a black swan event, you would simply be hedged, and not lose very much.
 
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