Tax-Loss Harvesting Explained
The legal strategy that turns losing stocks into tax savings.
What is tax-loss harvesting?
Tax-loss harvesting (TLH) is the practice of selling investments at a loss to offset capital gains taxes. If you sold some stocks for a $10,000 profit this year, you owe capital gains tax on that profit. But if you also have $10,000 in unrealized losses elsewhere, you can sell those losing positions to cancel out the gain. Result: $0 in capital gains tax.
If your losses exceed your gains, you can deduct up to $3,000 in net losses against ordinary income each year. Any remaining losses carry forward to future years indefinitely.
The wash sale rule
The IRS has a rule to prevent abuse: the wash sale rule. If you sell a stock at a loss and buy a "substantially identical" security within 30 days (before or after the sale), the loss is disallowed. You cannot sell Apple at a loss and buy Apple back the next day.
But you can sell Apple and buy Microsoft. Different company, different ticker, still gives you large-cap tech exposure. This is where direct indexing gets powerful.
Why ETFs are bad at tax-loss harvesting
When you own an ETF, you own one single security. The only way to harvest a loss is to sell the entire ETF position. If SPY is up 15% for the year, you cannot harvest losses on the individual stocks inside it that went down. Those losses are trapped inside the fund wrapper.
Even in a strong bull market, some stocks within any index are down. In a typical year, 30-40% of individual stocks in the S&P 500 have negative returns, even when the index is positive overall. Every one of those losing positions is a potential tax-loss harvest that ETF holders cannot access.
How direct indexing supercharges TLH
With direct indexing, you own each stock individually. That means you can sell any losing position at any time to harvest the loss, then replace it with a similar (but not identical) stock to maintain your portfolio's overall exposure.
For example: you own 20 stocks replicating ITA (the defence ETF). Suppose Northrop Grumman drops 12% while the rest of the basket is up. You sell NOC, book the loss, and use that loss to offset gains elsewhere. To maintain defence sector exposure, you could increase your weight in Lockheed Martin or General Dynamics. You stay fully invested, stay diversified, and get a tax deduction.
A concrete example
Portfolio: $100,000 in a direct-indexed defence basket (20 stocks)
Scenario: After one year, the basket is up 8% overall. But 6 stocks are down, with combined unrealized losses of $4,200.
Action: You sell those 6 losers, book $4,200 in losses, and reinvest in similar defence stocks after 30 days (or immediately in non-identical substitutes).
Tax savings: At a 32% marginal tax rate (income above $191K), that $4,200 loss saves you $1,344 in taxes this year. Repeat annually, and the savings compound.
If you held the same stocks through an ETF wrapper, those losses would be invisible. The ETF is up 8%. No harvesting opportunity. You would owe full tax on any other gains you realized that year.
Who benefits most?
- High-income earners (32%+ marginal tax bracket) get the biggest dollar benefit from each harvested loss
- Active traders who realize capital gains frequently have more gains to offset
- Taxable brokerage accounts only. TLH does not apply in IRAs or 401(k)s since those accounts are already tax-advantaged
- Larger portfolios ($50K+) have more individual positions and more harvesting opportunities
If you are in the 22% bracket with a $15K portfolio in an IRA, tax-loss harvesting will not help you. If you are in the 32%+ bracket with $100K+ in a taxable account, it can save thousands per year. Read the full direct indexing vs ETF comparison for more on when direct indexing makes sense. To see the compounded cost of your current fund fees, use the ETF expense ratio calculator.
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