Introduction to Tax Loss Harvesting

Learn more about this potential money saving practice and get to know the do’s and don’t’s of the trade.

Nobody likes to own a losing investment. It can be difficult to convince yourself to sell it because of the sunk cost fallacy. You have to admit that you’ve made a mistake and didn’t have the ability to predict the future. Who likes being wrong? But once you get over yourself, there is a silver lining in that Uncle Sam will share in your losses. Up to $3,000 per year in net investment losses can be deducted form your ordinary income. For a typical lawyer, that’s worth $1,000 to you. If the losses exceed $3,000, you can carry over the deduction and apply it to your future tax returns.

But an intelligent investor can take advantage of market downturns to generate losses on long-term assets without losing a dime. Here’s how you do it.

Tax loss harvesting – how to do it

Step 1) Purchase investments in a taxable account that you intend to hold for a long time. This is not about market-timing, speculating, or purchasing specific types of investments just for the sake of implementing tax loss harvesting. Buy the things you would have bought anyway.

Step 2) When the assets decline in value, instead of freaking out and selling the investment for a loss, you simply “harvest the loss”. This generates a paper loss for you which allows you to take the tax benefits for selling the “losing” investment but does not impact your long-term investment results. How do you do that? By swapping the current investment with one that is highly correlated but not identical. The result is that your portfolio hasn’t changed (you swapped one highly correlated asset for another) yet you still have generated a tax loss which you can claim on your taxes.

Example of tax loss harvesting

Let me give you an example.

On March 1st you purchased $10,000 of Vanguard Total Stock Market Index Fund (VTSAX). On July 1st you’ve noticed that the market is currently down 10% since you made your investment on March 1st. So on July 1st you exchange your shares in VTSAX for the Vanguard Large Cap Index Fund (VLCAX). The new fund has a correlation of close to 99% to the old fund, so you have essentially traded one investment for another. However, this exchange is not considered “substantially identical” by the IRS. You’ve now booked a loss of $1,000. Given a 33% federal tax bracket, you will save $333 on your federal taxes. If the market continues to trend down, you can do it again. The only caveat is that you’ll have to remember that you cannot make an investment in VTSAX for at least one month or the “wash sale” rule will eliminate the tax break.

What’s the Wash Sale Rule?

From IRS Publication 550:

A wash sale occurs when you sell or trade stock or securities at a loss and within 30 days before or after the sale you:

  1. Buy substantially identical stock or securities,
  2. Acquire substantially identical stock or securities in a fully taxable trade,
  3. Acquire a contract or option to buy substantially identical stock or securities, or
  4. Acquire substantially identical stock for your individual retirement account (IRA) or Roth IRA.

If you sell stock and your spouse or a corporation you control buys substantially identical stock, you also have a wash sale.

Critics of tax loss harvesting

Some investors are quick to point out that you’ll end up paying more taxes later because you’ve lowered your basis in the investment. That is absolutely correct. In the example above, you’ve lowered your basis in the investment from $10,000 to $9,000, so when you ultimately sell the investment you will be required to pay taxes on any gains above $9,000 (rather than $10,000).

There’s still some reasons why this is a good idea.

First, you’re deferring taxes and there’s inherent value in tax deferral strategies (some even say that a tax deferred is a tax avoided). By taking the tax break today, but paying taxes in the future, you’re taking advantage of the time value of money by having access to the extra funds today which could be invested themselves and earn compound returns. Also, don’t forget that there are strategies to flush out capital gains from your portfolio, such as donating appreciated stock to charity rather than giving cash directly.

Second, there’s tax arbitrage in deducting at your regular federal tax income rate (33% in the example) and paying future capital gains at a 15% rate. That’s an 18% savings right there that should be encouraging for anyone looking to minimize taxes.

While many young lawyers may have no need for a taxable account, since they should be focused on maximizing retirement accounts, there may not be much reason to take advantage of this strategy. For me, I’m focused on maximizing retirement accounts and saving for a down payment, so there’s not much point for a taxable account for me. However, if you have a taxable account, dips in the markets are a great time to take advantage of tax loss harvesting.

Now you also understand what the roboadvisors (Betterment, Wealthfront, etc.) are doing through their algorithms to generate the extra portfolio returns by tax loss harvesting automatically for you.

Joshua Holt is a former private equity M&A lawyer and the creator of Biglaw Investor. Josh couldn’t find a place where lawyers were talking about money, so he created it himself. He knows that the Bogleheads forum is a great resource for tax questions and is always looking for honest advisors that provide good advice for a fair price.

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    Seven thoughts on Introduction to Tax Loss Harvesting

    1. This is an incredibly helpful post. Is there a way to confirm if my investment is substantially or not substantially identical to an alternative investment? I have VTI right now and am considering selling it for VOO. Thanks!

      1. Great introduction to TLH, BigLaw.

        The tax arbitrage can be much, much better if you can keep earned income low enough to remain in the 15% federal income tax bracket, where capital gains are zero. With the right portfolio, it’s not that difficult to do, particularly in an early retirement scenario with a large taxable account to spend from.


        1. Agreed, which gives you a great opportunity to negate the decrease in basis obtained through the tax loss harvesting. If your income is sufficiently low in early retirement (or if you are taking some time off between jobs and have a low income year), you can also take advantage of tax gain harvesting, but that’s a subject of a future post.

      2. VTI holds 3677 stocks compared to 514 for VOO. That may have changed a bit since written, but I can say with certainty that the IRS cannot and would not consider substantially identical. I swap back and forth between the mutual fund versions routinely for TLH purposes.

      3. @MMA – I’m not aware of any guidance from the IRS on what is “substantially identical” but agree with @PoF that swapping between VTI and VOO is fine. Tax loss harvesting is widespread and I have yet to see any cases where the IRS has argued that a particular correlated asset is in fact substantially identical. It’s just not something that they care about, unless you sell and then re-purchase the exact same security.

        Here’s the guidance from Publication 550:

        Substantially identical. In determining whether stock or securities are substantially identical, you must consider all the facts and circumstances in your particular case. Ordinarily, stocks or securities of one corporation are not considered substantially identical to stocks or securities of another corporation. However, they may be substantially identical in some cases. For example, in a reorganization, the stocks and securities of the predecessor and successor corporations may be substantially identical.

        Similarly, bonds or preferred stock of a corporation are not ordinarily considered substantially identical to the common stock of the same corporation. However, where the bonds or preferred stock are convertible into common stock of the same corporation, the relative values, price changes, and other circumstances may make these bonds or preferred stock and the common stock substantially identical. For example, preferred stock is substantially identical to the common stock if the preferred stock:

        * Is convertible into common stock,

        * Has the same voting rights as the common stock,

        * Is subject to the same dividend restrictions,

        * Trades at prices that do not vary significantly from the conversion ratio, and

        * Is unrestricted as to convertibility.

    2. Great post! Finally a simple guide to follow for tax loss harvesting. How did you come up with switching VTSAX to VLCAX? In other words, how did you know that the IRS will not consider the two to be “substantially identical.”

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