Mastering Tax Loss Harvesting to Offset Capital Gains

Thayer Partners Thayer Partners November 17, 2025

Unlock the full potential of your investment portfolio by strategically leveraging tax loss harvesting to minimize your capital gains tax burden.

Understanding the Essentials of Tax Loss Harvesting

Tax loss harvesting is a strategic approach for investors looking to optimize their portfolios and reduce their tax liability. At its core, this technique involves selling securities at a loss to offset realized capital gains elsewhere in your portfolio. By doing so, you can directly reduce the amount of taxes owed on gains, freeing up capital for future investments.

Understanding which assets to sell and when to realize losses is crucial for tax planning. Tax loss harvesting is generally performed near year-end, allowing investors to take full advantage of their annual capital gains and losses when filing taxes. This process can be especially beneficial for business owners and executives managing complex portfolios.

Identifying Opportunities for Tax Loss Harvesting in Your Portfolio

The first step in successful tax loss harvesting is reviewing your portfolio for under-performing assets. Look for investments that have declined in value since purchase and are unlikely to recover in the near term. These losses can be strategically realized to offset gains from other high-performing assets, reducing your overall tax burden.

It’s important to consider the broader context of your investment strategy. For business owners and executives, this often means working closely with financial advisors to identify loss harvesting opportunities without disrupting long-term growth objectives or liquidity needs.

Implementing Effective Tax Loss Harvesting Strategies

Effective tax loss harvesting is about more than simply selling losing assets. It requires a disciplined approach, balancing short-term tax benefits with long-term investment goals. One common strategy is to realize losses on specific lots of securities while maintaining your desired market exposure by purchasing similar—not identical—assets to avoid the IRS wash-sale rule.

Executives and business owners should plan harvesting activities in coordination with year-end financial reviews, ensuring that any realized losses align with corporate cash flow requirements and personal financial objectives.

Navigating Common Pitfalls and IRS Rules

The IRS wash-sale rule is a critical consideration in tax loss harvesting. This rule disallows a loss deduction if you purchase a substantially identical security within 30 days before or after the sale. Failing to account for this can negate the intended tax benefit and complicate your tax reporting.

Staying compliant requires careful tracking of all transactions and a thorough understanding of IRS regulations. Business owners and executives should engage experienced tax professionals to avoid common pitfalls and ensure all moves are legally sound.

Maximizing Long-Term Benefits with Professional Guidance

While tax loss harvesting can yield significant short-term tax savings, its greatest value often lies in its impact on long-term wealth accumulation. By regularly assessing your portfolio and strategically realizing losses, you can manage your tax liability while maintaining your investment strategy.

Given the complexity of tax regulations and the unique needs of business leaders, partnering with a trusted financial advisor is essential. Professional guidance ensures you’re leveraging every available opportunity while navigating evolving tax laws and aligning decisions with your broader financial goals.

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This material prepared by Thayer Partners is for informational purposes only.  It is not intended to serve as a substitute for personalized investment advice or as a recommendation or solicitation of any particular security, strategy or investment product.  Thayer Partners is a Registered Investment Adviser. SEC Registration does not constitute an endorsement of Thayer Partners by the SEC nor does it indicate that Thayer Partners has attained a particular level of skill or ability. The material has been gathered from sources believed to be reliable, however Thayer Partners cannot guarantee the accuracy or completeness of such information, and certain information presented here may have been condensed or summarized from its original source.  Thayer Partners does not provide tax or legal or accounting advice, and nothing contained in these materials should be taken as such.

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