This will start a little technical (and seemingly off-topic), but should quickly get relevant and may cause you to see some things in a new light.

To begin, we need to discuss synthetic securities, and I will use stocks as the easiest one to understand. Suppose you have a non-dividend-paying stock that is trading at $50 (we could use any security that has options on it but for simplicity I will use the term “stock” throughout this piece, but you could replace it with the generic term “the underlying” with no loss of applicability if you like). If you wanted to “own” (replicate) the upside of that stock over the next three months, you could buy a call with a $50 strike price maturing in three months. If you wanted to “own” the downside of that stock over the next three months (I know it sounds weird – why would you want to do that? – but stay with me) you would sell a put with a $50 strike price maturing in three months. You could also purchase a t-bill that matured in three months at $50. (You’ll see why that matters shortly.)

Now, the interesting thing is that we can create any one of these instruments with any three of the others. For example, the stock we have been discussing is exactly equal to being long the call, short the put, and long the t-bill. Mathematically, it looks like this:

S = C – P + T

Any value that the left of the equation goes to in three months the right side will match perfectly. These relationships must hold because if there were an inequality, it would allow a risk-free arbitrage opportunity. For example, if the stock was too expensive you could short the stock and go long the instruments on the right and arbitrage the difference.

The interesting part is that with simple algebra we can rearrange this equation. For example, we can move the call option to the other side like this:

S – C = T – P

The left side of this equation is covered call writing (long the stock, short the call) which is widely considered a relatively safe “widows and orphans” type strategy. Perhaps you have noticed though that it is exactly the same as buying T-bills and selling naked puts on stocks – a strategy that most folks would consider insanely risky!

We can also rearrange to remove the risk of the stock. Suppose we are long the stock, short the call (we sold the upside), and long the put (we bought protection against the downside):

S – C + P = T

This is a really tight collar and as you can see gives you T-bill returns. (Before you get clever ideas, the tax laws would consider this a constructive sale of a stock position.)

Now in real life there are complications like dividends and the fact that the options are usually purchased out of the money. These changes make the math complicated but don’t change the underlying reality – when you do covered call writing, you are effectively buying bonds and selling naked puts, or, as the saying goes, picking up nickels in front of a steamroller.

I don’t think it changes the overall point that this “conservative” strategy is actually extremely risky, but there are two reasons that selling calls can add a little value. (The same holds for selling puts for that matter – because of the equation above I can make puts out of calls or calls out of puts by combining with stocks and T-bills – just rearrange the equation – and “put/call parity”, as it is called, exists.) First, the price of the option is based on expected volatility and historically the expected volatility is higher than the volatility that is actually realized. In short, options are probably a little bit too expensive on average (though Nassim Taleb, of Black Swan fame would argue the opposite and I’m not sure he’s wrong) so selling them (as in a covered call writing strategy) might earn a small premium. Second, there is a well-known effect called the “volatility smile” where if you graph the strike prices of the option on the x-axis and the volatility of the stock implied by the market prices on the y-axis it should be a straight line, but it generally forms a “smile” which just means that the further away from the current market price the strike price is (i.e. the more out-of-the-money or in-the-money an option is), the more expensive it is (options on stocks with higher volatilities are more expensive). Thus, out-of-the-money options are potentially too expensive. There isn’t a clear reason why this should be so, but it may be related to people’s preference for lottery-type payoffs and willingness to insure against catastrophic losses even at higher prices. Here is a graph of the volatility smile:

In short, I would caution against using covered-call-writing as a strategy unless you were also comfortable with owning a bond portfolio and writing naked puts – it’s the same thing!

By default we set up every taxable (i.e. non-retirement) account to have margin but we almost never use it. (You don’t want retirement accounts to have debt at the account level because it gives rise to UBTI – unrelated business taxable income – which is taxed at the high trust rates, but you get no basis in the IRA for it. In essence you end up getting taxed twice on the income. Leverage in the underlying investment – debt that a company holds, or a leveraged ETF – is This is why leveraged ETFs are sometimes used (but not y us): leverage in the underlying investment is fine from a tax perspective.)

If you have a diversified portfolio with both stocks and bonds (as almost everyone should) and then you add leverage through margin interest you are essentially long fixed-income and short fixed-income but almost certainly paying on the spread. It is far better to liquidate bonds (for temporary needs) or a portion of the portfolio as a whole (for longer-term needs). Nonetheless we occasionally have clients in margin for the following reasons:

1. The client needs/wants funds right away and it is worth a few days of margin interest expense to them rather than waiting for the trade to settle.

2. The client needs/wants funds and all the positions in the account have large short-term gains. This usually only happens when it has been less than a year since the client came on board or tax loss harvesting was done and the market subsequently moved up nicely. If the gain will be long-term in 10 days (for example) it might make sense to send them the funds, putting the account into margin for the 10 days, and then liquidate the position to repay the margin loan after the taxes are more favorable. For example, assume a 10% unrecognized gain, a 20% differential in long and short term tax rates, and 7% margin interest rate, and a need for $100,000. 20% of the $10,000 gain is $2,000. 7% of $100,000 for 10/365 of a year is $192. Obviously the larger the gain and the shorter the period until it becomes long-term the more this makes sense.

3. Similar to the previous item, if it is December and the client’s tax rate will be lower the following year it might make sense to use margin. For example, suppose the gains are long-term, but they are in the 15% LTCG bracket this year, but will be in the 0% LTCG braket next year. There is a 15% difference in the rate by waiting until the next year to sell.

4. The client anticipates putting the funds back before too long and doesn’t want to disturb their asset allocation (paying transaction fees to sell and then repurchase later) and paying taxes on gains. For example, suppose a client has a bonus coming (with very high probability)  in 60 days, but they find the “perfect” house to buy now and don’t want the opportunity to get away. It might make sense to take funds out of the account (causing it to go into margin) to purchase it and then replace the funds shortly when the bonus arrives.

In most cases, there are even better sources of short-term funds than margin interest – a HELOC (Home Equity Line Of Credit) for example – but sometimes it does make sense to use margin, temporarily.

Financial Professionals Winter 2019

The optimal savings vehicles are client-specific, both in what they may have available to them, and in what would be prudent for their specific situation.  Nonetheless, in general, this is usually the right order (exceptions and other issues at the end) for a typical client who expects to be in a lower tax bracket in retirement than they are now:

1. Tax-deductible, employer-based retirement plans (such as a 401(k) plan) to the extent of any match – a match just can’t be beat!
   • For a married couple, priority of funding must consider:
     • the better match
     • the better investment options (but if the spouse with poor options is changing jobs soon it can be rolled over to an IRA so it doesn’t matter as much)
     • the longer deferral (the younger spouse will have lower RMDs in retirement if desired)

2. HSA savings account – tax-deductible on the contributions and tax-free withdrawals (if used for medical expenses) later (ideally in retirement).

3. Tax-deductible, individually-controlled retirement accounts (such as a traditional IRA) – broad investment options and generally more favorable “exceptions” if early withdrawal became necessary.
   • For a married couple fund the younger spouse’s first.

4. Tax-deductible, employer-based retirement plans (such as a 401(k) plan) from the match (see #1 above) to the limit.
   • For a married couple, priority of funding must consider:
     • the better investment options (but if the spouse with poor options is changing jobs soon it can be rolled over to an IRA so it doesn’t matter as much)
     • the longer deferral (the younger spouse will have lower RMDs in retirement if desired)

5. Tax-free retirement vehicles (such as Roth IRAs).
   • For a married couple fund the younger spouse’s first (this currently doesn’t matter, as there are no RMDs, but the law could change)

6. If education funding is desired see College Funding.

7. If tax-inefficient investments (such as taxable fixed income) will not fit inside the previous options on this list see Asset Location Strategy (the five items at the end).

8. Taxable investments (regular brokerage accounts).

Important caveats and other comments:

1. I have ignored liquidity needs in the list above.  Of course short-term liquidity may take precedence over some of the options listed and funding #5 (since original contributions can be withdrawn without penalty) prior to #2-4 might make sense.  (Though probably not in place of #1.)

2. I have ignored the “investment” opportunity of reducing debt.  There may be behavioral and psychological issues that would impact the order, but from a purely financial perspective, there is low-rate (typically mortgage) debt and high-rate (typically consumer) debt:
   • High-rate debt should generally be paid after #1, but it will depend on the specific situation.  (Perhaps the client can both pay off the debt in a reasonable time frame and fund retirement vehicles.  If they are going to max out the retirement plans every year going forward, they probably want to use them now too, not just after the debt is gone, since there is no “catch-up” when fully funding.)
   • Low-rate debt should probably be paid down at #6 or #7 (in that order) if either is applicable.

3. Investing in human capital (education or skills), particularly for a younger person, might be a better investment than many of the options above.  (Though probably somewhere below #1.)

1. Fixed income is held for risk reduction, not return enhancement. It is the ballast that allows the ship of your portfolio to withstand the financial storms that periodically roil the markets.
2. It is conventional wisdom that “correlations go to one” in times of stress, but this is incorrect. Correlations between risky investments go up, but the correlations between risky assets (stocks) and safer assets (investment-grade bonds and cash) go down in periods of market stress.  Thus, the fixed income portion of a portfolio should include only the safest categories of bonds.
3. A fixed income portfolio should be equally weighted between nominal bonds and inflation-protected bonds to hedge unexpected inflation, unless the investor has exposures elsewhere that should be hedged (e.g. a very large pension with no COLA, or a real-estate portfolio with long-term, fixed-rate financing and short-term leases).
4. If foreign bonds are used in a portfolio they should be currency hedged.
5. Since liquidity in the bond market is higher for large (institutional) transactions than for smaller (retail) transactions, (inexpensive) bond funds, rather than individual bonds, are typically better for retail investors.
6. Due to interest being recognized immediately and as ordinary income, fixed income is ideally held in tax-sheltered accounts. If that is not possible, alternative exposures might be advantageous.  In addition, some alternative exposures might be better than traditional fixed-income investments regardless.  Here is a list of alternative types of fixed income grouped by when/why they should be considered:
   1. Better tax treatment but lower return (so benefits correlate with tax-bracket and interest-rates):
      1. Municipal bonds.
      2. Variable annuities (a plain-vanilla, inexpensive wrapper solely to defer income taxes).
      3. Permanent life insurance.^*
   2. Better tax treatment without any reduction in return (so advantageous if fixed income would otherwise be held in a taxable account):
      1. Non-deducible contributions to IRAs or other retirement plans (defers interest that would otherwise be taxable annually).
   3. Potentially higher returns (tax treatment is not a primary factor):
      1. Debt reduction if the after-tax interest rate on the debt is higher than an equivalent-duration bond with no credit risk.^*
      2. Social Security delayed-claiming (equivalent to purchasing TIPS).^*
      3. Pension annuitization rather than taking the lump sum is equivalent to purchasing fixed income.^*
      4. Human capital investment (additional education and training), particularly for younger individuals.^*

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^*Other factors, in addition to just taxes and rate of return, will affect the prudence of this option.