It is a fact of life: Many investors begin putting together their portfolios before they really know what they are doing. As they get more knowledge and experience under their belts, they are apt to realize that some adjustments are in order. The young investor who started out with a balanced portfolio may decide he really should be mostly in stocks, for example, or the investor who started out amassing a portfolio of individual stocks may decide that mutual funds are a better fit for her busy lifestyle.

In a similar vein, some investors may have started in a taxable brokerage account without regard for the tax-efficiency of their investments. A few unwanted income or capital gains distributions later, they realize that they should have been more focused on investments that limit those taxable distributions. On the short list of tax-friendly investments for stock investors are individual stocks, broad-market exchange-traded funds and index mutual funds, and tax-managed funds. For bond investors, municipal bonds, whose distributions are free from federal and in some cases state and local taxes, often make sense.

Trouble is, giving a taxable portfolio a tax-efficient makeover is not necessarily tax-free. That is because investors pay two sets of taxes: the taxes on income and capital gains distributions they receive during their holding periods as well as taxes on any appreciation they have enjoyed over that same time frame. An investor swapping an investment for a more tax-friendly option may make her portfolio more tax-efficient in the future, but she could incur capital gains taxes to do so.

The good news is that if she can account for the taxes she has already paid on distributions she received and reinvested during her holding period, she can offset—partially if not entirely—the taxes she will owe on her own gains. Thus, she may have no reason to put off making her portfolio more tax-friendly in the future.

Reinvested Capital Gains = Prepaying Your Taxes
A simplified example can illustrate how distributions can be costly, from a tax standpoint, in the year in which they are received, but those costs can help offset eventual tax outlays upon selling.

Say, for example, an investor sinks $100,000 into a mutual fund at the beginning of 2013. The fund appreciates by 10% ($10,000) that year and promptly makes a capital gains distribution of 5% ($5,500). Even though the investor reinvests that distribution back into the fund to purchase more shares, she is on the hook for capital gains tax on that amount; let us assume the gains are long-term and she pays a 15% capital gains rate on the $5,500 distribution ($825) for 2013. However, she can also increase her cost basis in the investment to account for the reinvested distribution; in essence, she has prepaid a portion of the taxes due for her fund’s appreciation. Her cost basis is now $105,500 and her holdings are worth $110,000. (Her reinvested capital gain is a wash from the standpoint of her account’s current value; the fund paid it out and she put it right back in. Had she spent that capital gain distribution rather than reinvested it, her cost basis would remain $100,000 and her holdings would be worth $104,500.)

In 2014, the fund has an even better year, gaining 25%. Her fund shares are worth $137,500 (her $110,000 portfolio value at the beginning of the year plus $27,500 in new appreciation). But some of the holdings in the fund hit the manager’s sell target, so the fund sells some of its stocks and makes another capital gain distribution—this time 10% of its net asset value, or $13,750 for our hypothetical investor. She again pays 15% in long-term capital gains tax—$2,062.50—on that distribution. But if she reinvests that distribution back into the fund, her cost basis would jump to $119,250 (her previous cost basis of $105,500 plus the reinvested distribution of $13,750).

In early 2015, she decides she is fed up with paying taxes on all of those unwanted distributions and wants to switch to a more tax-friendly portfolio mix. The long-term capital gains taxes due upon the sale of her fund would be the difference between her stepped-up cost basis of $119,250 and the current value of her shares, $137,500—or 15% of 18,250 ($2,737.50). That is not anything to sneeze at, of course, but if it means that her portfolio will be more tax-friendly on a going-forward basis, it may be a sacrifice worth making.

It is also worth noting that for some investment types, transitioning to a more tax-friendly portfolio will generate few tax implications. Taxable bonds and bond funds, for example, generate most of their returns via income distributions rather than capital appreciation; investors pay taxes on that income in the years in which they receive it. That means selling a taxable bond fund will typically not bring a big tax hit.

Additionally, investors whose equity funds have not performed especially well over their holding periods may find that their capital gains bills are not all that high after they sell. A mutual fund, for example, may have made big capital gains distributions in three of the past five years, but its five-year total annualized return is only about 7%. Many investors who hold this hypothetical fund in a taxable account have probably paid a good share of any taxes they will owe upon sale. Therefore, switching to a more tax-friendly holding, such as an equity ETF, may not be all that painful.

The Importance of Good Record-Keeping
The key to receiving the step-upped cost basis, however, is making sure you have good records on reinvested dividends and capital gains distributions. Beginning earlier this decade, investment firms have been required to track customers’ cost basis for them. (Brokerage firms began tracking cost basis for individual stock holdings in 2011; cost-basis tracking for mutual fund shares went into effect in 2012.) But if investors owned shares prior to those rules going into effect, the onus is on them to keep track of their cost basis and those reinvested capital gains distributions. Otherwise they will be paying taxes twice—first on the capital gains and dividend distributions they already received, and again when they sold and did not account for those reinvestments by increasing their cost basis.

For example, if the above-mentioned investor were transacting before the cost-basis rules went into effect and did not have a paper trail on her cost basis, including those capital gains distributions that she reinvested and paid taxes on, her cost basis would be her initial $100,000 investment, plain and simple. Upon sale she would owe capital gains taxes on the entire $37,500 of appreciation—$5,625, assuming she is in the 15% long-term capital gains tax bracket. But because she has already paid $2,887.50 in taxes on the distributions she received in 2014 and 2015—and she is not giving herself credit for them—her total tax outlay would be $8,512.50.

The bottom line is that for investors who have been keeping close track of their reinvested dividend and capital gains distributions—or who have only owned their investments since the cost-basis accounting rules went into effect—much of the cost of engineering a tax-efficient portfolio makeover may already be “sunk”; the taxes due upon sale may be less than they imagined. Undertaking a tax-efficient makeover and swapping into more tax-efficient investments may not cost them a lot in capital gains taxes, and, if their holding period is sufficiently long, could pay for itself many times over down the line.


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