Nov 02

I’ve been known to use the expression, “Don’t let the tax tail wag the investing dog.” I stand by that remark. If you own a stock and it’s time to sell since it no longer is a stock your own criteria would justify, by all means, sell it. Holding it for an extra month to get long term favored gains may result in a greater loss than the missed long term treatment.

That said, the strategy of tax loss harvesting can help you boost your returns a bit depending on your timing. Let’s look at how this can work for you. First, you need to understand taxation of long term capital gains. There’s a zero percent rate for gains on sales of stocks (including mutual funds) held for over one year. But, there’s a catch. This great rate applies to those in the 10% or 15% brackets. If you take a peek at my last post, you’ll see that, in 2016, for a couple, the 15% bracket ends at $75,300. Add the exemptions and standard deduction, totaling $20,700, and this is an even $96,000, gross income. Less than 25% of households had more than this much income in 2014 according to the latest census data, so this strategy will help most of my readers. Last, understand the rules regarding wash sales. If you sell a stock or fund at a loss and purchase “substantially identical” funds or ETFs with 30 days, this triggers a wash sale. Earlier this year, Michael Kitces wrote an in depth article, Does Tax Loss Harvesting “Almost” Substantially Identical Mutual Funds And ETFs Trigger A Wash Sale Problem? For my purposes, selling an S&P tracking fund or ETF and buying a larger index, whether tracking the top 1000 or 1500 stocks should suffice.

You’re looking at your brokerage statement, and find you have 2 funds, one showing a $3000 gain, the other a $3000 loss. A contrived, simple example. For this discussion, we’ll assume they are generic, say S&P 500 index, and a broad Small Cap fund. If you sold both of these, and bought other funds this year, the loss and gain cancel, no tax due, no tax savings. Instead, sell the losing fund this year, buying into another fund reflecting your desired asset allocation. Now, you have a $3000 (the maximum you can take each year) loss, and you’ll see $450 more in your tax refund when you file. At the end of the following year, review your holdings, and if you won’t have a loser to sell in the next year, sell the one with the gain, and buy into another to keep your allocation to your goals. This move will raise your basis to the new, higher level, and should the market fall from this new level, you’ll have another chance to sell for a loss.

Let’s look at how this strategy could have been implemented over the decade from 2000 to 2009.


This is the ‘lost decade’ for the S&P, a remarkable 10 years that resulted in the S&P losing 9% of its value. You can click on the chart above to take a look, full size, or go to MoneyChimp and look at the returns for 2000 through 2009. In this crazy decade, we can take advantage of the market’s volatility by taking the losses along the way, and reinvesting this money. This example starts with a $30,000 investment account all reflecting the return of the S&P. For each year from 2000 though 2003 we are able to deduct a $3000 loss and get $450 back when filing. Note, even though 2003 had a gain, the S&P index dropped 40% in the 3 years from 2000 to 2002, and by shifting from one fund to another, there were $12,000 were of losses to claim over the 4 years. In the next few years, basis is increased by swapping funds. Here’s a chart illustrating this –


You can see, the ‘regular’ return reflects the buy and hold, but ‘taking losses’ adds $450 each year we are able to take the $3000 loss. $3000 is the maximum you can take each year again ordinary income. Typically, losses first offset gains, but in our example, we’ll only take losses when they can be deducted against ordinary income. In this decade shown, losses are taken in each year from 2000 to 2003, and again in 2008 and 2009. The gains up to 2007 are used to increase basis by swapping funds, so in 2007, your basis is $36,697. Another fund swap in 2008, results in loss of over $13,000 letting you spread the deduction over the next 4+ years, so even though 2010 and 2011 showed gains, you are still taking a loss and adding $450 into the account.

The result of this annual effort is a 10% swing, instead of losing 9% for the decade, we are up just over 1%. To be fair, with expenses, we’d be just about at break-even, vs being down 9% plus expenses. Another way to look at it is that the return was improved by a full 1%/yr just from this strategy. No magic here, just using the rules of our tax code to write off losses against ordinary income, but take the gains tax free.


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Nov 18

Remember New Coke?

Remember Qwikster?

My Spidey senses tell me that Intuit’s TurboTax product is about to have its own moment of marketing mishap. Now. As a tax nerd, I don’t put my TurboTax on the shelf after I file my return. I open it regularly to plan my year. Since one of my goals is to avoid paying more tax than I have to, I use it to plan my stock sales, Roth conversion, if any, and forecast my tax bill well in advance of April 15th. It’s been a ritual of mine to buy the new tax year software the weekend it’s out, usually the weekend after Thanksgiving. This year, as I started to look to see a product release date, I found that the versions offered had their contents revised.


(Right-click to open in new screen)

You can see, the Deluxe version no longer handles any stock transactions, i.e. Schedule D, or any rental property details, Schedule E. Last, with part time blogging income, I need to file a Schedule C, which is now a Home and Business offering.

Here’s my concern – people are creatures of habit. When was the last time you “read the fine print”? We buy what we’ve bought and rarely catch the changes until it’s too late. Unfortunately, in this case, it with be a painful process, realizing your return wont have the forms you’re expecting and you need to upgrade the software (hopefully that option will be available, to pay the difference and move on) or buy the right one for your needs. The 2014 version was just released, and Amazon reviews are already running negative, 8 reviews so far with 7 showing One Star.

I’ve been a user of TurboTax since filing my first return in 1985. We’re having our 30th anniversary with this next purchase. For the last decade, I’ve taken advantage of the ability to produce multiple returns, using my copy to print returns for my daughter, mother-in-law, sister and sister-in-law. I’m not going to quibble over a change that I read about and can adjust to. But I’ll sit back and watch how the reviewers are already having their say and see how my friends at TurboTax respond.

Update (11/22) – The reviews on Amazon continue to mount –


The one star reviews are all focused on the price increase. Unfortunate, I hope TurboTax jumps on this to stop the potential loss of customers.

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May 26

It’s that time of year again, graduation time. And that’s why today’s round up starts with The Most Important Piece of Financial Advice for College Graduates. I’m not going to spoil the punchline, but I will say, I agree with the article’s advise, and college grad or not, you’ll be a bit wiser for reading it as well.


Above is an image of the new sized fries that are soon to be sold in Japan. It weighs in at 350 grams (just over 3/4 lb) and will sell for 490 Yen ($5 or so). Rumor has it that Mayor Bloomberg is already planning a to launch a pre-emptive strike, writing a law limiting the size of a portion of fries that can be sold in New York City.

The Weakonomist asked Has The Recession Made Us More Informed About Economics? I was asking a similar question after the crash of 2000. And of course I remember the banking crisis of the early ’80s, you know, the Resolution Trust Corp? But I digress. We’ll see if this generation learns any of lessons the prior ones missed.

Next, the Debt Princess tell us What NOT to Do: Live in Denial. It seems the Princess has made a few mistakes and she’s working to right size her financial life. Jessica writes from the heart, and writes in the hope that her story will help others to avoid the mistakes that she’s made. An article that might help you look at your own choices more closely.

Kay Bell offered her take on the Senate’s Inquisition of Apple’s Tim Cook at Apple lauded on Capitol Hill at hearing about its low U.S. taxes. Kay’s not quite as sympathetic to Apple as I am, but I offer her article as a counterpoint to my opinion, and because Crossfire is no longer on the air.

As much as I love a bargain, and often fill a space in the closet with half price laundry soap or TP, it’s good to know What NOT to stock up on in your stockpile! An excellent tutorial at Couple Money on the items you should buy with caution.  I agee with the caution on buying too much fish, meat, etc, so keep an eye on your supermarket sales cycle, usually six weeks from one chicken sale to the next.

And to wrap up the week, at Money Under 30, Can In-Store Health Clinics Save You Money? I’ve found the Minute Clinic at CVS to be a great service, a time saver for me and a savings on the system. No need to go to my doctor’s office for a flu shot. Have you visited your local drug store clinic?

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May 07

After I wrote The Step Transaction Doctrine at my companion site, RothMania, I received a number of emails asking about situations where this might apply. Here’s an example of another disallowed series of transactions:

A) A son and wife are in a high tax bracket. Enough so the AMT effect causes there long term capital gain to be taxed at 22.5% (really 15% plus extra due to AMT). They gift the son’s parents $50,000 in appreciated stock.
B) The parents, who are in a low bracket, sell the shares and have no tax due as there’s no cap gain tax if you are in the 10 or 15% bracket.
C) Parents then gift their son and his wife $50,000, the proceeds of the sale.


In a Q&A a few years back my favorite IRA author Ed Slott offered a definition of the Step Transaction Doctrine:

The step transaction doctrine can be a bit complicated, but essentially, when applied it treats what are actually several independent steps as if they were a single transaction for tax purposes. 

There are three different tests which have been used to determine if the step transaction doctrine should apply. One test, commonly referred to as the “binding commitment test” applies when there is a commitment to complete a later step in an overall transaction at the time the first step is made. Since an IRA contribution (deductible or not) does not require that one convert the contribution to a Roth IRA, this test is a non-factor here.  

Another test that is used to determine if the step transaction doctrine should be applied is the “mutual interdependence test.” This test looks at each step in an overall series of steps and determines if a specific step is meaningless unless the later step(s) actually occurs. Since a non-deductible IRA contribution is clearly beneficial (read “not meaningless”) on its own, this test is also a non-factor.  

The third and final test, known as the “end result test,” is the most applicable for this discussion. Under the end result test, the steps in a transaction are looked at to see whether the series of steps were really just predetermined steps of a single, overall transaction, aimed at achieving a specific outcome. Do clients make IRA contributions with the idea that they will later convert them? Sure. So is it possible for IRS to raise issues with this strategy in the future? Yes, but it’s not a likely scenario.

You can see that each of these events, taken alone, is perfectly legitimate. It’s only when they are combined in this way that the IRS combines the transactions and would go back to our Yuppie couple along with a tax bill.
The key thing to ask yourself is whether each event was legitimate, and in this case, there’s really no bona fide gift to anyone, the transactions are simply tax avoidance. Will you get caught? That’s the wrong question. You see, once you start asking what your chances are, it’s a slippery slope. Best to avoid deals that look like this regardless of what your ‘advisor’ tells you. At RothMania, a reader’s brother has a tax attorney who was encouraging him to skirt this rule, either that or the lawyer was completely ignorant of it. In either case, I’d stay clear of any advisor who makes such proposals.  If it sounds too good to be true, it might just be tax evasion.

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Apr 06


The tax code has gotten out of control, more than 70,000 pages. Some like to say that it’s ten time the size of the Bible, although I tend to stay away from religion, and prefer to compare large books to War and Peace. My latest guest post at Turbo Tax might help you with a few Last Minute Tax Tips if You’re Still Working on Your Tax Return. Check it out and ask a question if you’d like.

One week to go!

written by Joe \\ tags: ,