Selling a Business Tax Considerations


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If the potential tax implications of selling your business seem daunting, a crucial first step is to have a business valuation performed.

This process of business valuation is not only an assessment of your company’s worth, assisting in determining an appropriate selling price, but it’s also a tool that can aid in forecasting the potential tax consequences of the sale.

The valuation, when carried out effectively, can often unearth strategies to mitigate your tax burden, such as strategic timing of the sale or utilization of certain tax provisions.

In the course of this article, we will endeavor to provide you with a comprehensive understanding of these considerations, helping you to make an informed decision when it comes to selling your business and navigating potential tax implications.

Learn more information about selling a business by downloading the BizBuySell Guide to Selling Your Small Business. Or if you’re buying a business, for more information download the BizBuySell Guide to Buying a Small Business.

How are Business Sales Taxed?

Business sales are taxed on the principle of capital gains, essentially the profit that you make from the sale of your business. The capital gains tax rate corresponds to your standard income tax rate, rendering capital gains as a form of income.

It’s important to note that the amount of capital gains may push you into a higher tax bracket, depending on the other income you have accrued throughout the tax year.

selling a business tax

What Is a Capital Gain?

Simply put, a capital gain refers to the profit realized from an investment, which in this case, is your business. This can culminate in a capital gain when the sale of the business yields a profit, or a capital loss when it results in a deficit.

A capital gain or loss is established by the difference between your initial investment in the business and the final selling price.

Certain factors, like equipment depreciation or the cost of capital improvements, can affect the size of the capital gain and thereby your tax liability.

For instance, if you initially bought a business for $200,000, invested an additional $100,000 in upgrades, and sold it for $350,000, your capital gain would be $50,000.

It’s important to note that capital gains tax rates may vary based on the length of time the investment was held.

Capital Gains Tax on Selling a Business

Capital gains are generally taxed as ordinary income, yet the IRS draws a line between short-term and long-term capital gains. For those who’ve owned a business for less than a year before selling, your capital gain is taxed at your ordinary income tax rate.

If you’ve owned the business for over a year, the capital gain tax rate for long-term capital gains applies, which is currently 15%.

Strategies like specifying which part of the sale price applies to different business assets, such as inventory or real estate, can help reduce your overall tax bill.

This often involves the gradual sale of capital assets in an installment sale, thereby reducing the immediate tax impact.

Additionally, if reinvested properly, certain capital gains can qualify for tax deferment, such as through 1031 exchanges in real estate transactions.

selling a business tax

7 Tax Considerations Before the Sale of a Business

Various tax strategies and considerations come into play when selling your business.

1 . A Stock Sale or an Asset Sale?

In a stock sale, the buyer acquires an ownership stake in the business by purchasing the seller’s shares. This method is typically employed in transactions involving C corporations and S corporations, given their structure.

Alternatively, an asset sale involves the disposal of the company’s capital assets, including physical property such as buildings and equipment, which by definition hold value beyond a single year.

Choosing between a stock sale or an asset sale carries different implications for the calculation and taxation of capital gains. Guidelines for short and long-term capital gains rates apply variably to stock and asset transactions.

Therefore, understanding these differences is crucial when considering the most tax-efficient approach for selling your business.

The choice between these two types of sales can significantly impact the net profit from the sale, underscoring the need for careful financial and tax planning.

2. Establishing Value of Business Assets

When calculating the value of business assets, such as a piece of machinery, it’s crucial to include the associated costs beyond the purchase price. These costs may involve installation and employee training expenses.

Keeping meticulous records of these costs can significantly aid in reducing your capital gains taxes. However, it’s important to note that routine maintenance costs can’t be factored into this calculation.

Understanding and accurately documenting these costs is essential when preparing to sell your business assets, as it can help minimize potential tax liabilities.

3. Purchase Price Allocation

Purchase Price Allocation, or PPA, is a method that business owners use to calculate the fair market value of a business. This strategy is particularly common during mergers and acquisitions.

The buyer “allocates” the purchase price among the various assets and liabilities of the company. At the same time, the seller computes the value of net assets, utilizing “good will accounting” to factor in the value of intangible assets, like the business name and logo.

This process aids in providing a more complete picture of the business’s worth. Additionally, a PPA often undergoes reviews by banking institutions to validate the accuracy of the allocation.

Understanding this process is crucial for both parties involved, as it directly affects the financial dynamics of the transaction, including taxation.

4. Type of Entity

The percentage of interest that individuals hold in businesses such as partnerships and corporations is treated as capital gain income when they sell that interest.

It’s a fundamental aspect of business tax law that applies to various forms of business organizations.

However, tax implications can considerably vary depending on the type of entity. For example, a sole proprietorship might face different tax rules compared to a limited liability company or a corporation.

Understanding these nuances is crucial. It not only impacts the capital gains tax rates but also the overall financial planning and decision-making process for both business owners and potential investors.

Here’s a quick comparison:

Type of EntityTax Implication on SaleCapital Gains ImplicationNotes
C CorporationShareholders pay capital gains when they sell stock. If the entire C corporation is sold, corporate tax may apply.Capital gains tax applies to the profit made from selling the stock.Double taxation can occur: first at the corporate level if the corporation sells its assets, and then at the individual level when shareholders sell their stock.
S CorporationTransaction can be structured as stock or asset sales. The corporate structure can remain intact, implying no additional corporate tax implications.If selling as a stock sale, capital gains tax applies to the profit made. In an asset sale, it may result in ordinary income.S Corporations allow pass-through taxation, meaning the corporation's income, losses, deductions, and credits can pass through to shareholders for federal tax purposes.
PartnershipCapital gain is due on the individual's partnership assets. An individual can sell his percentage of partnership interest to a buyer.Capital gains tax applies to the profit made from selling the partnership interest.Capital gains tax on partnerships can be complicated by the fact that partnerships distribute both income and capital gains to their partners, which may be taxed differently.

5. Tax-Free Stock Exchanges

In tax-free stock exchanges, the buyer swaps their own company’s stock for that of another company. It’s a strategic move used often in the business world.

The exchanged stock should comprise between 50-100% of the total stock owned by the buyer. It’s a way to acquire a company without an immediate cash outlay.

A variation of this strategy involves a corporation issuing new shares in exchange for money or other forms of property.

This approach is flexible and can be leveraged to expand a company’s capital base, or acquire necessary assets or services.

6. Income Tax Rates

The personal tax rates, potentially as high as 37%, can exceed the maximum long-term capital gains rate, currently set at 15%. Despite a capital gain being taxed at a lower rate, it’s still considered income and can influence the tax basis applied to your personal taxes.

This aspect, along with the ability to distribute the income earned over time, contributes to the popularity of installment sales when divesting assets.

Although not completely tax-free, installment sales provide a more flexible, tax-efficient method of asset disposal.

7. State Considerations

Small business owners need to understand that tax obligations don’t stop at the federal level; state and local taxes can also play a significant role.

Take Florida, for instance, where residents enjoy a lack of personal income tax. However, corporations in Florida are subject to a corporate income tax, making it essential for business owners to plan accordingly.

In contrast, places like New York City present a different taxation landscape, imposing a city income tax on top of other state and federal obligations.

Understanding these differences can greatly influence the financial outcome when selling a business.

selling a business tax

Tips for Small Business Owners

The process of selling a business can be intricate, even more so when you’ve dedicated considerable time and effort into building a successful small business.

Navigating this complex process is crucial to ensure you don’t miss out on potential savings during the sale.  So knowing how to sell a business is extremely important. Here’s our best advice:

Consider Hiring a Tax Advisor for Your Business Sale

Hiring a tax advisor can provide immense value, especially if you are planning a business sale in the foreseeable future.

By involving them early in the process, they can guide you on potential steps to alter your business structure to yield maximum tax benefits, and better prepare for the sale.

If Your Business is a Sole Proprietorship, Sell Assets Separately

For sole proprietors, selling assets individually can be an effective strategy. It can help maintain your annual earnings at a stable level, ensuring that your taxable income remains consistent.

It provides a way to manage tax obligations without overwhelming financial fluctuations.

Consider Selling to Employees

Transferring your business to employees through a long-term installment sale or an employee stock ownership plan can be an advantageous approach. This sale could be extended to all current employees or a selected group of key personnel.

Not only does this ensure continuity of the business and job security for valued employees, but it also allows them to have a stake in the business’s future success.

selling a business tax family

Think About Gifting Some of the Business Sale Money to Family

Distributing some of the sale proceeds to family members can be a delicate task and may even instigate family disputes. For instance, if only one child is involved in the business, should they be the sole recipient of the gift, or should it be equally shared among all siblings?

Should the proceeds be protected for direct family members only, and if so, should such terms be articulated in prenuptial agreements?

Such decisions necessitate guidance from tax and legal advisors, especially as baby boomers reach retirement and need robust exit strategies.

Structure the Deal as an Installment Sale

Installment sales can be structured in two primary ways:

  • Cash plus Seller Financing – The buyer pays a lump sum portion of the sales price and signs a promissory note for an installment purchase.
  • Earn Out – The seller is paid as a “consultant” and stays with the business for 2-3 years, earning a salary.

Consider an Opportunity Zone

You can reinvest the capital gains from your business sale into a Qualified Opportunity Fund within 180 days of the transaction.

The benefits increase over time: if held for five years, 10% of the gain is tax-free. An additional 5% is excluded if held for seven years; after ten years, the total gain is tax-exempt.

Leverage Retirement Plans as Part of the Sale

If you’re nearing retirement, consider incorporating your retirement plans into the business sale strategy. You can contribute a portion of the sale proceeds to a qualified retirement plan like a 401(k) or an IRA.

This move could potentially defer taxes on those funds until retirement, depending on the type of plan and your age. It’s important to consult with a financial advisor to understand the implications and benefits of this strategy, as well as to ensure compliance with IRS rules and contribution limits.

This approach not only helps in tax planning but also secures your financial future post-business sale.

Do I have to pay taxes on the sale of my business?

Unless your business is operating at a loss, you’ll need to pay taxes on the sale proceeds. However, there are strategies available to defer the tax impact over several years, such as utilizing installment sales for certain assets.

The amount of tax depends on the structure of your business (sole proprietorship, partnership, corporation), the nature of the assets sold, and the gain realized from the sale. Tax rates vary based on long-term capital gains and ordinary income rates.

How much tax do I pay on the sale of my business?

Your tax liability will depend on whether you pay short or long-term capital gains rates. The short-term rate aligns with your tax bracket, while the long-term rate is fixed at the capital gains rate, currently at 15%.

How do you avoid paying taxes when selling a business?

To maximize tax savings, hire a tax advisor who understands the dynamic tax codes. Several other methods can help reduce taxes, including:

You can also reduce taxes by:

  • Selling assets using installment sales
  • Owner financing
  • Gifting to family
  • Selling to employees

How are capital gains calculated when selling a business?

Capital gain is calculated by deducting the original purchase price from the sale price. There are several ways to reduce your tax bill, like claiming deductions for capital improvements and equipment purchases.

If the business entity was held for less than a year, the tax amount aligns with the owner’s personal income tax bracket. If held longer, the current capital gains tax rate, 15%, is applicable.

How do I report the sale of my business on tax return?

To report the sale of your business on your tax return, use IRS form T2125, the Statement of Business or Professional Activities. This form provides the necessary framework for accurately documenting your business activities and sale.

It requires detailed information about the sale, including the date, sale price, and any associated expenses. Additionally, the form allows you to report income or losses from the business operations prior to the sale.

Ensure all information is accurate to reflect the true nature of the business sale.

selling a business tax irs

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Lisa Price Lisa Price is a freelance writer living in Barnesville, Pennsylvania. She has a B.A. in English with a minor in journalism from Shippensburg State College (Pennsylvania). She has worked as a trucking company dock supervisor, newspaper circulation district manager, radio station commercial writer, assistant manager of a veterinary pharmaceutical warehouse and newspaper reporter.

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