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AFO2023-11-29T12:21:46+00:00

Key Benefits of Year-End Tax Loss Harvesting

Written by: Susan Smith (CFA) & John Smith (CFP)
Reviewed by:
Rob Santos
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Rob Santos

Chief Executive Officer

As CEO and founder of Arrowroot Family Office, I specialize in the overall management of the firm. I also work with affluent families on providing bespoke family office services, which include tax-efficient advisory and financial planning, M&A advisory, family governance and process advisory, and philanthropic initiatives.

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In a perfect world, investors would only see gains when checking their accounts. But in the real world, the stock market can be volatile and doesn’t always trade on a straight upward trajectory. No one wants their investments to decline, but when the market does trade lower, it’s possible to convert those losses into valuable tax assets. This process is called tax-loss harvesting and involves selling underperforming investments to create capital losses, which can offset current-year taxes or be carried forward. This process typically occurs at year-end when investors review their annual portfolio performance and the potential tax implications.

The chart below explains how tax-loss harvesting works. It compares two portfolios that start with a $100,000 value and generate both a $10,000 gain and a -$5,000 loss during the year. In Scenario A, the investor realizes the $10,000 capital gain by selling the profitable investment but doesn’t sell the unprofitable investment with a -$5,000 loss. The result is a net $10,000 capital gain, which, at a 25% tax rate, would incur a $2,500 tax liability. In Scenario B, the investor realizes the $10,000 capital gain but also sells the investment with a -$5,000 loss. The investor has both a $10,000 capital gain and a -$5,000 capital loss, which offset to create a net $5,000 capital gain. At the same 25% tax rate, the investor faces a $1,250 tax liability, saving $1,250 in taxes.
Tax-loss harvesting offers tax advantages for investors with significant capital gains or losses, but there are special considerations. The IRS created the wash sale rule to discourage investors from selling securities at a loss solely for tax deductions. The rule states that if you sell a security at a loss, you can’t purchase the same or a “substantially identical” security within 30 days before or after the sale. Additionally, tax-loss harvesting is only applicable to taxable investments, not tax-advantaged retirement accounts. Finally, it’s important to keep in mind that the trading costs of selling and buying a new security could offset a portion of the tax benefits.
In summary, when done correctly, tax-loss harvesting can convert market selloffs into tax benefits. It’s a tool you can use to sell investments and rebalance portfolios in a tax-efficient manner, but it shouldn’t outweigh other financial considerations, jeopardize your long-term goals, or cause you to sell an attractive long-term holding. However, when the opportunity arises and you’re reviewing portfolios, tax-loss harvesting can be a powerful tool to rebalance and diversify a portfolio.
This material contains opinions of the author, but not necessarily those of Arrowroot Family Office LLC or its subsidiaries. The opinions contained herein are subject to change without notice. Forward looking statements, estimates, and certain information contained herein are based upon proprietary and non-proprietary research and other sources. Information contained herein has been obtained from sources believed to be reliable, but are not assured as to accuracy. No part of this material may be reproduced or referred to in any form, without express written permission of Arrowroot Family Office, LLC. There is neither representation nor warranty as to the current accuracy of, nor liability for, decisions based on such information. Past performance is not indicative of future results.
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  • 4553 Glencoe Ave, Suite 200, Marina del Rey, CA 90292
    (833) 224-2249
  • 2 Boars Head Ln, Suite 110, Charlottesville, VA 22903
    (626) 712-2090
  • 1107 Investment Blvd, Suite 160 El Dorado Hills, CA 95762
    (916) 384-0050
  • 725 Barclay Circle, Suite 215, Rochester Hills, MI 48307
    (248) 453-5252
  • 950 Broadway, Suite M100, Tacoma WA 98402
    (253) 858-2427
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Arrowroot Family Office LLC is a registered investment adviser with the U.S. Securities and Exchange Commission (“SEC”). Registration with the SEC does not constitute an endorsement by the SEC, nor does it imply that AFO has attained a certain level of skill or ability. Content should not be construed as legal or tax advice, AFO is not engaged in the practice of law or accounting.


AFO Form ADV (Part 2A & Part 2B)

AFO – ADV Part 3 Form CRS

    Terms & Condition | Privacy Policy | Web Accessibility

Copyright © 2025 Arrowroot Family Office – All rights reserved.

  • 4553 Glencoe Ave, Suite 200, Marina del Rey, CA 90292
    (833) 224-2249
  • 2 Boars Head Ln, Suite 110, Charlottesville, VA 22903
    (626) 712-2090
  • 1107 Investment Blvd, Suite 160 El Dorado Hills, CA 95762
    (916) 384-0050
  • 725 Barclay Circle, Suite 215, Rochester Hills, MI 48307
    (248) 453-5252
  • 950 Broadway, Suite M100, Tacoma WA 98402
    (253) 858-2427

Services

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