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THERE’S A CHANGE coming in the way many of us invest. But for background, it’s important first to look at a related—though seemingly mundane—investment concept known as tax-loss harvesting.
To understand how tax-loss harvesting works, consider a simple example. Suppose you purchased a stock in your taxable account for $10, and it subsequently dropped to $8. That would be unfortunate, but there’d be a silver lining: You could sell the stock to capture the $2 loss for tax purposes and then reinvest the proceeds in another stock.
Like most topics in personal finance, tax-loss harvesting is the subject of some debate. Detractors argue that the tax benefit is something of an illusion. Continuing with the above example, critics would point out that a tax-loss harvesting trade would cause the investor’s cost basis to drop, and that, in their view, would negate any benefit.
Why? The new stock’s basis would be $8, whereas the original stock’s basis was $10. That’s important because it means that when the new stock is eventually sold, the taxable gain will be $2 greater than the gain would’ve been on the original stock. And that additional $2 of gain would perfectly offset the $2 loss that was captured earlier. It’s for this reason that some compare tax-loss harvesting to a shell game: They argue that it can shift a gain from one year to another, but never truly eliminate it.
In a narrow sense, the critics have a point. But there are many cases in which harvesting losses can yield tangible benefits. Suppose you’re in retirement and taking regular withdrawals from your portfolio. In that situation, tax-loss harvesting could help you moderate the capital gains on those withdrawals.
Continuing with the example above, if you took a $2 loss on one investment, you could pair that with a $2 gain on another investment. That would allow you to free up cash from your portfolio without any net tax liability. In that way, tax-loss harvesting can help retirees keep a lid on their tax bill when drawing down a taxable account.
Even before retirement, tax-loss harvesting can be a benefit. That’s because even the most dedicated buy-and-hold investor will want to make changes to their investments from time to time, if only for rebalancing. And that’s another key benefit of tax-loss harvesting. It can help investors rebalance—and thus manage risk—more tax-efficiently.
Those are the benefits of tax-loss harvesting. But you might notice a fly in the ointment. After the strong market we’ve enjoyed over the past decade, it might be hard to find holdings with any losses to harvest. Over the past 10 years, the S&P 500 has risen 250%. Even international stocks, which are seen as laggards, have gained nearly 70% over that period. That would appear to be an obstacle to tax-loss harvesting. In other words, it’s hard to harvest losses if there are no losses to harvest. For index fund investors, this is indeed a challenge.
But now imagine that if, instead of owning a broad-market index like the S&P 500, you instead owned each of the 500 stocks individually. Then, as you looked across your portfolio, there would be both winners and losers. While Nvidia has gained 25,000% over the past 10 years, stocks like Walgreens, Warner Brothers and American Airlines have each dropped more than 50%. Forty stocks, in fact, have lost money over that period. Nearly 300 of the 500 stocks in the S&P index have gained less than the index’s overall average. If you owned these stocks individually, they’d offer opportunities to take withdrawals from a portfolio more efficiently than if you owned the index only in the form of a fund.
Wouldn’t it be cumbersome, though, to own 500 stocks individually? That brings us to a strategy known as direct indexing. It’s a way to own the individual stocks in an index, and to conduct regular tax-loss harvesting, without needing to manage the portfolio yourself. Direct indexing has existed for decades. But in the past, because of the cost, it only made sense for the wealthiest investors.
In recent years, however, brokerage commissions have largely been eliminated, and new competitors—including Vanguard Group—have helped bring down the cost. As a result, these services now cost as little as 0.15% or 0.2% a year. Yes, that’s more than a comparable index fund. But according to at least one study, the tax benefits can easily offset that cost.
In addition to the tax benefit, direct indexing offers two other advantages. First, it offers the ability to customize a portfolio. Suppose there’s an industry that runs counter to your values—tobacco, for example. With a direct indexed portfolio, you could own all of the stocks in the S&P 500, with the exception of Altria and Philip Morris, leaving you with your own custom S&P 498. With direct indexing, you could also overweight selected industries.
Another benefit of direct indexing: Suppose you have a large holding in a single stock—Apple, for example. Because of the risk, you might want to diversify. But if you bought an S&P 500 index fund—ordinarily a good way to diversify—that would pose a problem, because 7% of any dollars invested in the S&P 500 would be allocated to Apple, further increasing your exposure.
But with direct indexing, you could construct a portfolio that included all of the stocks in the index except Apple. A further benefit: Over time, losses produced by the direct indexing strategy could be used to offset gains as you whittled back your Apple shares.
Are there downsides to direct indexing? As noted earlier, there’s the cost. In addition, some people dislike the idea of holding hundreds of individual stocks; it seems messy.
Another downside of direct indexing is that the tax benefits are front-loaded. Over time, as the market rises, there will be fewer losses available to harvest. Still, I believe direct indexing can continue to provide tax benefits far into the future. Even if, after a decade or two, most stocks in a portfolio have gains, there’ll always be some stocks that have gained more than others.
Result: At any given time, if you were looking to take a withdrawal, there’d still be a tax benefit even if none of your holdings had losses. You could cherry pick from among your holdings to limit the gains on each sale. Moreover, to meet charitable goals, you could donate the most appreciated shares, such as Apple or Nvidia, thus sidestepping the gains.
Another potential risk with direct indexing is that a portfolio can ossify over time. Without the benefit of new cash, the ability to make changes can become constrained by unrealized gains. And this can cause a direct indexed portfolio to slowly drift away from its benchmark. This is where mutual funds have an advantage. Because there are always investors coming and going, mutual funds have the benefit of being able to deploy new cash on a daily basis, and that gives them the ability to stay right in line with an index.
For these reasons, I don’t recommend direct indexing as a substitute for index funds. But I do see it as a good complement. It is, I think, a strategy well worth considering.
Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam’s Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
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Selling and buying makes this strategy an actively managed index fund, no?
I like to defer capital gains; ideally forever. This can be accomplished if shares are donated to charity or passed on in an estate.
Here’s an example… I had shares in a regional bank, that got clobbered back in 2023. I sold those shares at a loss and got the deduction in my 2023 tax return. I simultaneously bought shares in a different bank that was also way down. Since that purchase those shares are up over 100%. I just gave them to my church.
I got a tax deduction for the capital loss in 2023, and a tax deduction for a charitable contribution in 2025. And no capital gains tax ever.
That is how it works…
I am a direct indexer. But my index is only 25 stocks. I own them in roughly equal parts, so each is about 4% of my portfolio. By comparison, the VOO (Vanguard’s S&P 500 ETF) holds it’s 26th stock at 0.53%. The DIA (SPDR Dow Jones ETF) holds 30 stocks, but the top 9 represent 52%. It is also widely followed. I believe my risk profile falls somewhere between the S&P 500 and the DJIA, as does my return. I do not harvest tax losses for the reasons Adam mentions, but I do intentionally pick shares to sell and give, with a goal to minimizing total tax burden (over my life expectancy.) I also rebalance by tax status across accounts (roth, traditional, and taxable.)
Rebalancing, of course, means selling the winners and buying the losers :-). Changing my direct index is a different choice than rebalancing.
As you might guess, I am happy with my choice, which of course has its own history, although I regularly recommend a balance between a dividend ETF and a broad market ETF to others, and fully expect to move that direction if I have any say about it when I can’t easily direct index any more.
Doesn’t this idea of selling off the losers mean that you are selling when they are low, rather than selling the winners that might be at a high point?
I’m not in a place where I’m looking to sell off myself but it seems like it would be a better strategy to sell high rather than selling low.
It’s important to distinguish between selling diversified funds and selling individual stocks. A diversified fund should rebound. An individual stock may fall and never recover.
I agree with Adam’s sensible advice about tax loss harvesting. I have an account with Wealthfront (a robo-advisor) that offers harvesting for ETF portfolios or direct indexed stocks. I see the benefits of harvesting in my 1099 at the end of every year.
One note. If folks work in a position in which they have to disclose investment holdings for ethical reasons, direct indexing can be a nightmare. Holding every stock in an index presents conflict of interest issues that can disqualify someone from a job or assignment. Most ethics rules exempt holdings in ETFs or mutual funds that are managed independently.
That’s a great point — one I’ve never heard mentioned before. If you work in journalism or in the securities industry, life is much easier if you stick with mutual funds and ETFs.
I wanted to get into direct indexing in my taxable account to benefit from tax loss harvesting opportunities as you state. My issue, which you also mention, is rotating out of a reasonable portion of my taxable portfolio will leave me with sizable taxable gains. Also, I’m retired, so not producing new savings to invest.
I believe I understand tax loss harvesting, I’ve done it myself on occasion. But am I correctly understanding that you are suggesting owning 500 individual stocks? Vanguard’s explanation of direct indexing is directed at advisors, not individuals. I neither have nor want an advisor, and I certainly don’t want to buy individual stocks, never mind 500.
It’s fun to read about this, thanks Adam. I’ll stick with my cheap, old school Vanguard Admiral index mutual funds. For sustained tax savings we’ll Roth convert about a third of my traditional IRA starting next year. More if the stock or bond markets drop.
I have 2 questions, besides the tax-loss harvesting consideration, is it better to direct indexing in a Roth vs taxable account? If I am a buy and hold investor, and the index would eventually be in positive position over time.
The other question, which index is better? S&P 500 vs Dividend growth?
If you’re a buy & hold investor, you’re likely better off sticking with index funds rather than direct indexing. You can employ portfolio “tilts” by adding value or dividend growth or small-cap index funds to your broad market index funds, to achieve certain goals. Or you can just keep it simple and own the broad market.
There’s no reason to do tax loss harvesting in a Roth or traditional IRA. It’s a strategy to minimize / avoid capital gains taxes. But transactions in both types of tax-advantaged accounts are immune to cap gains on trades. And withdrawals are either tax-free (Roth) or taxed at your ordinary income tax rate (trad). The tax basis of the holdings in the accounts are irrelevant. Tax loss harvesting is only for taxable, ordinary brokerage accounts