The Smart Way To Decrease Taxes When Selling Your Business

Team Acquira
-  February 14, 2024
What You’ll Learn
  • How strategic tax planning influences the financial outcome of selling your business.
  • What tax implications, including capital gains, affect your proceeds from a business sale.
  • How different sale structures, like asset or stock sales, impact your tax liabilities.
  • Why timing your business sale is critical for minimizing tax burdens.
  • How to leverage Section 1202 Stock Exclusions and 1031 exchanges in tax planning.

When considering selling your business, understanding and minimizing tax liabilities becomes a crucial aspect of the transaction. 

It’s not just about how much you sell your business for, but also how much of that sale you get to keep after taxes. 

You want to maximize how much you put in your pocket, not how much you pay the government. 

This is where strategic tax planning comes into play, and with Acquira’s expertise, you can navigate this complex landscape more effectively.

Here’s a look at how to minimize taxes when selling your business.

You want to maximize how much you put in your pocket, not how much you pay the government.

Tax Implications of Selling Your Business

what is tax planning

When you sell your business, several types of taxes come into play, with capital gains tax being one of the most significant. 

The rate at which you’re taxed depends on various factors, including how long you’ve held the business and your income bracket. 

It’s essential to grasp these details as they directly impact the net amount you’ll receive from the sale. 

Besides capital gains, other taxes like income tax on the sale proceeds may also apply. Each of these can significantly affect your financial outcome.

Structuring the Sale of Your Business for Tax Efficiency

How you structure the sale of your business can greatly influence your tax liability. 

Broadly, sales can be categorized as asset sales or stock sales, each with its unique tax implications. 

An asset sale, while potentially more favorable for buyers due to step-up in basis on purchased assets, often leads to higher tax liabilities for sellers. 

In contrast, a stock sale might be more tax-efficient for a seller but less so for the buyer. 

Read more: What You Need To Know About Asset Vs. Stock Sale

The key is to balance these aspects to find a structure that meets both parties’ needs. 

Consulting with tax professionals – including the business experts at Acquira – is critical to tailor the most tax-efficient sale structure for your specific situation.

Three strategies—Charitable Remainder Trusts (CRTs), Installment Sales, and Opportunity Zone Funds—stand out for their ability to potentially reduce tax liabilities and maximize profits from your sale.

1. Charitable Remainder Trusts (CRTs):

CRTs serve as a dual-purpose tool for business sellers looking to minimize taxes while contributing to charity. 

When you use a CRT, you transfer a portion of your business into a trust before the sale. The trust then sells the business tax-free. 

You receive an income stream from the trust for a specified period, which can be for life or a set number of years. 

Upon the termination of the trust, the remaining assets go to the designated charity. 

The key benefit is the deferral of capital gains taxes when selling your business, along with receiving a charitable deduction and a steady income.

 However, this strategy requires careful planning and consideration of your long-term financial goals and charitable intentions.

2. Installment Sale:

An installment sale allows you to spread the receipt of funds (and therefore the taxes when selling your business) over several years. 

By receiving payments over time, you may reduce your tax rate due to lower taxable income each year, as opposed to a lump-sum payment that could bump you into a higher tax bracket. 

This approach is beneficial for managing cash flow post-sale and can be particularly advantageous if your income post-sale is expected to be lower than during your high-earning years.

3. Opportunity Zone Funds:

Investing in Opportunity Zone Funds is a relatively new strategy introduced by the Tax Cuts and Jobs Act of 2017.

If you reinvest your capital gains from the business sale into these funds, which are designed to spur economic growth in designated distressed areas, you can defer and potentially reduce these gains. 

The deferral lasts until you sell your stake in the fund or until December 31, 2026, whichever comes first. 

Additionally, if you hold the investment in the fund for at least ten years, you may be eligible for an exemption from taxes on any gains produced through the fund investment.

Planning and Timing For Selling Your Business

Strategic planning before selling your business is not just about getting the best price; it also involves smart timing to optimize tax liabilities. 

The timing of your business sale can significantly impact the taxes you owe, influenced by factors like holding periods and current tax laws.

Holding periods are crucial in determining the tax rate applied to your gains. 

For instance, assets held for more than a year typically qualify for long-term capital gains tax, which is generally lower than short-term capital gains tax.

 Therefore, understanding the holding period of your business assets can guide you to schedule the sale at a time that minimizes your tax burden.

Timing the sale also involves considering the current tax landscape. 

Tax laws and rates can fluctuate, and selling your business during a period of lower tax rates can lead to substantial savings. 

Additionally, consider the state of the market – selling in a strong market not only maximizes your return but can also influence the type of deal structure, potentially offering more favorable tax implications.

Employing strategies like delaying the sale to qualify for long-term capital gains tax or aligning the sale with favorable tax environments can markedly enhance your financial outcome. 

Strategies to Minimize Tax Liability

Let’s delve into several more strategies that can help you keep more of your hard-earned money from the sale.

Section 1202 Stock Exclusions

Section 1202 of the Internal Revenue Code is a gem for business sellers. 

It allows you to exclude up to 100% of the capital gains from the sale of qualified small business stock (QSBS) held for more than five years. 

The exclusion is capped at the greater of $10 million or 10 times the adjusted basis of the stock. 

To qualify, your business must be a C corporation and meet other specific requirements, such as asset limits and type of business activity. This is particularly attractive for early investors or founders who have significant gains in their business.

Like-Kind Exchanges (1031 exchanges)

A 1031 exchange, named after Section 1031 of the IRS Code, is a powerful tool for deferring capital gains taxes. 

It allows you to exchange business assets or real estate used for business for similar or “like-kind” properties without incurring immediate tax liabilities. 

This strategy is particularly beneficial if you plan to reinvest in another business or real estate property. 

It’s vital to follow specific rules and timelines, and typically, a qualified intermediary is used to facilitate these transactions.

Employee Stock Ownership Plans (ESOPs)

Selling your business to an ESOP allows you to defer or even avoid capital gains taxes. 

An ESOP is an employee benefit plan that gives workers ownership interest in the company. 

If you sell your business to an ESOP and reinvest the proceeds in securities of U.S. companies, you can defer the tax on the gain. 

This option not only provides tax benefits but also contributes to employee motivation and retention, as workers become direct beneficiaries of the business’s success.

However, it should be noted that setting up an ESOP can be incredibly complex so it’s best to seek professional help when setting it up.

Maximizing Deductions and Credits

Business sellers can significantly reduce their tax liabilities by strategically utilizing deductions and credits. 

A prominent option is the Research and Development (R&D) tax credit. 

If your business has invested in developing new products, processes, or software, or in enhancing existing ones, you may be eligible for this credit. 

It’s designed to encourage innovation and can lead to substantial tax savings. 

Documenting your R&D expenses meticulously is key to claiming this credit effectively.

Other deductions to consider include depreciation of business assets, expenses incurred during the process of selling the business (like legal fees, broker fees, and marketing expenses), and interest deductions on business loans. 

Utilizing these deductions requires careful documentation and sometimes strategic timing of expenses and sales. 

FAQs About Taxes When Selling Your Business

What should I consider for post-sale tax planning?

Consider long-term investment strategies for your sale proceeds to manage potential taxes. Consult with a financial advisor on diversifying investments, estate planning, and charitable giving to optimize tax benefits and ensure financial stability post-sale.

How do I pay the least in taxes when I sell?

To minimize taxes, consider strategies like structuring the sale for tax efficiency, utilizing capital gains exemptions, and timing the sale to align with favorable tax conditions. Engage a tax professional to tailor these strategies to your specific situation.

Can I pay no tax when I sell?

Completely avoiding taxes on a business sale is unlikely, but you can significantly reduce tax liabilities. Explore options like Section 1202 exclusions for small business stock, reinvesting proceeds into Opportunity Zone Funds, or using Charitable Remainder Trusts (CRTs) to defer and minimize taxes.

What’s the best time to sell my business?

The ideal time to sell your business is when it’s performing well, showing strong financials, and the market conditions are favorable. Aligning the sale with low capital gains tax rates and personal readiness for transition also contributes to optimal timing.


Selling a business involves strategic planning to ensure maximum financial benefit and minimal tax liability. 

The key is understanding the right timing, employing effective tax strategies like Section 1202 Exclusions, 1031 Exchanges, or ESOPs, and leveraging deductions and credits such as R&D tax credits. 

Remember, each business’s circumstances are unique, so it’s vital to consult with financial experts to tailor a plan that fits your specific needs, ensuring a profitable and smooth transition.

Are you a small business owner looking to get the most out of your sale by reducing your tax liability? If so, reach to Acquira for a FREE business valuation to see how our industry professionals could help you get the most out of your exit. 

Key Takeaways

  • Effective tax planning is key to maximizing proceeds from selling your business.
  • Understanding capital gains taxes when selling your business and its impact on your sale’s net amount is crucial.
  • Sale structuring significantly affects your tax obligations; choose wisely.
  • Optimal sale timing can lead to significant tax savings.
  • Utilizing specific tax strategies like Section 1202 Exclusions can greatly reduce tax liabilities.
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