How to Minimize Capital Gains Tax When Selling Your Business

Team Acquira
-  April 12, 2024
What You’ll Learn
  • The significance of capital gains tax when selling your business.
  • Strategies for minimizing capital gains tax, including holding periods and 1031 Exchanges.
  • How Qualified Small Business Stock exemptions can provide tax relief.
  • How investing in Qualified Opportunity Zones can reduce tax liabilities.
  • Ways to reinvest proceeds to defer or reduce capital gains tax.

When considering the sale of a business, many entrepreneurs focus solely on valuations, buyer negotiations, and potential returns. However, there’s a critical financial aspect that often gets overlooked: the capital gains tax. 

Understanding how capital gains tax could impact the proceeds from your business sale is essential, as it can significantly affect your financial future. 

Ignoring or underestimating this tax obligation could lead to unexpected financial strains and diminished returns on your investment.

Hence, savvy business sellers pay meticulous attention to capital gains tax as part of their exit strategy.

What is Capital Gains Tax?

Capital gains tax is a tax levied on the profit realized from the sale of a capital asset, which includes property, stocks, and businesses. 

In simpler terms, it’s the tax you pay on the difference between what you sold the asset for and what you originally paid for it, including any investments made to improve it over time. 

While it might seem straightforward, calculating capital gains tax can get complex, depending on various factors such as the duration of asset ownership, additional investments in the asset, and the current tax laws.

Understanding how capital gains tax could impact the proceeds from your business sale is essential, as it can significantly affect your financial future. 

Capital Gains Tax on Business Sale

how to avoid capital gains tax on sale of business

When it comes to selling a business, capital gains tax becomes especially important if you’re trying to maximize profit from a sale. 

That’s because the tax liability can vary based on the structure of the business—be it a sole proprietorship, partnership, or corporation—and how the sale is structured. 

Read more: Everything You Need To Know About Business Valuation

Generally, the tax rate for long-term capital gains (assets held for over a year) is more favorable than short-term capital gains. 

The long-term capital gains tax rate in the United States is 0%, 15%, or 20% on most assets held for longer than a year.

However, additional taxes like the net investment income tax or state-level taxes could also apply.

The potential tax liability from a business sale is often substantial. 

It’s essential to consider this when negotiating the sale price and payment terms. Sometimes, structuring the sale as an installment sale or using other financial strategies could provide tax benefits.

It’s highly advisable to consult with tax professionals and financial advisors experienced in business transactions.

How to Avoid Capital Gains Tax on Sale of Business?

Now let’s look at ways to help offset capital gains from a business sale to maximize profit.

Holding Periods

The duration of your ownership of the business can significantly influence your capital gains tax rate. Assets held for more than one year are generally subject to lower capital gains tax rates, ranging from 0% to 20%.

Assets held for a shorter period are subject to higher short-term capital gains tax, which aligns with your ordinary income tax rate. Therefore, timing your sale after you’ve held the business for over a year can offer tax advantages.

Qualified Small Business Stock

The Qualified Small Business Stock (QSBS) exemption can be a boon for eligible small business owners. If you’ve held C-Corporation stock for over five years, you may be eligible to exclude a portion or even all of the gain from federal tax, up to certain limits. This provision aims to incentivize long-term investment in small businesses and can result in substantial tax savings.

1031 Exchange

Named after Section 1031 of the Internal Revenue Code, a like-kind exchange allows you to defer capital gains tax by reinvesting the proceeds from your business sale into a similar asset or business. While this strategy is more common with real estate, it can apply to certain business assets as well, provided they are used in a trade or business.

Invest in a Qualified Opportunity Zone

The Tax Cuts and Jobs Act introduced Opportunity Zones to incentivize investment in economically distressed communities. By reinvesting your capital gains into these zones, you can defer and potentially reduce your tax liability. The longer you hold the investment, the greater the tax benefits, which can include a step-up in basis or even complete tax exclusion after ten years.

Sell to Your Employees

Selling your business to your employees via an Employee Stock Ownership Plan (ESOP) can offer specific tax advantages, including the potential to defer or avoid capital gains tax. An ESOP sale can be an excellent way to transition out of business ownership while ensuring its continuity.

Use a Charitable Remainder Trust

By placing the business in a Charitable Remainder Trust, you can sell the asset tax-free, with the proceeds providing you with an income stream while also benefiting a charity of your choice. This can reduce your immediate capital gains liability while serving a philanthropic cause.

Utilize Installment Sale

Structuring the sale as an installment sale can spread your capital gains over multiple years, potentially reducing your annual tax liability and allowing for more manageable tax payments.

Offset Gains with Losses

If you have capital losses, you can often use them to offset your capital gains, reducing your overall tax liability.

Review Business Asset Classes when Allocating Purchase Price

When selling your business, how you allocate the purchase price among various asset classes can impact your tax burden. Working with a tax advisor to optimize this allocation can result in significant savings.

Non-Grantor Trust

A non-grantor trust is a distinct legal entity responsible for its own income taxes, unlike a grantor trust where the grantor bears the tax liability. By strategically utilizing non-grantor trusts, individuals can distribute income to multiple beneficiaries, often at lower tax brackets. This structure can be particularly useful for offsetting capital gains taxes, as it allows for income and gains to be taxed at potentially more favorable rates.

Reinvestment Options

how do you avoid paying taxes when selling a business?

Another potential avenue for offsetting capital gains is to consider a variety of reinvestment options. 

One effective approach is to invest the proceeds into tax-advantaged accounts like Individual Retirement Accounts (IRAs) or 401(k)s. 

These accounts often allow for tax-deferred growth, meaning you won’t pay taxes on the earnings until you withdraw the funds. 

This not only provides a tax shelter but also encourages long-term saving for retirement.

You could also consider using the proceeds to fund a new business venture. 

Depending on the structure and expenses of the new business, you may be able to write off initial costs, thereby reducing your overall taxable income. 

Plus, investing in a new enterprise could offer the potential for future earnings that exceed what you might get from more traditional investments.

Diversification is another excellent strategy. 

Instead of pouring all the proceeds into a single venture or investment vehicle, spreading the funds across a range of assets can provide not only a balanced portfolio but also opportunities for offsetting gains with losses, which can be an effective tax strategy.


Who Must Pay Capital Gains Tax?

Essentially anyone—individuals, corporations, or other entities—who realizes a profit from selling a capital asset like property or stocks is required to pay capital gains tax. The rate can vary based on how long the asset was held.

Who Doesn’t Pay Capital Gains Tax?

Certain income brackets or special circumstances might exempt someone from paying capital gains tax. For example, some taxpayers in lower income brackets do not have to pay tax on long-term capital gains.

What Happens If You Don’t Report Capital Gains?

Failure to report capital gains can result in hefty fines and potential legal repercussions. Tax authorities have robust systems for detecting unreported income, including gains from asset sales.

How Acquira Can Help

When it comes to selling your home service business, Acquira offers a streamlined, efficient solution that alleviates many of the frustrations typically associated with traditional brokers. 

Traditional business sales methods can consume a great deal of time and energy, not to mention the emotional toll of entrusting your legacy to someone else. 

Acquira simplifies this complex process by partnering with business owners for quick, straightforward exits that not only protect the essence of your business but also ensure its long-term viability.

Additionally, Acquira offers a distinct edge in minimizing capital gains tax through strategic financial planning. By carefully assessing the worth of your business and working closely with you, Acquira can provide expert advice on the optimal timing for sale, asset allocation, and reinvestment strategies. 


If you’ve spent years (or more likely decades) growing your business, you want to maximize your profit when you sell. Getting the most out of the exit requires careful consideration of capital gains. 

Addressing this tax liability effectively can make a significant difference in your financial future. 

Strategies like the judicious timing of the sale, leveraging possible Qualified Small Business Stock exemptions, considering 1031 Exchanges, or investing in Qualified Opportunity Zones can offer tangible tax benefits. 

Moreover, the structuring of the sale and how you choose to reinvest the proceeds can have a lasting impact on your tax liability and overall financial health.

Are you a business owner looking for a convenient way to sell your business while maximizing value? Use our free valuation calculator to see how healthy your business is. If you meet our specific criteria, we may want to buy your business at a fair market value with no fees for you. If you don’t happen to meet those requirements, we can introduce you to our network of preferred brokers to help ensure you get the best value for your business. Simply fill out the form below to get started.

Key Takeaways

  • Timing is everything: assets held for over a year often have lower tax rates.
  • Various financial tools and structures, such as 1031 Exchanges and Qualified Small Business Stock, can offer significant tax benefits.
  • Reinvestment strategies, including tax-advantaged accounts and new business ventures, can minimize tax impact.
  • Consult expert services like Acquira for strategic financial planning to both expedite the sale and minimize tax liability.
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