An accountant calculates possible taxes for a business sale.


Selling a business can be an overwhelming process, and one of the trickiest parts is navigating the complex world of tax implications. If you’re contemplating selling your business, understanding how to calculate taxes can save you from unwelcome surprises and costly mistakes. In this comprehensive guide, we will simplify the intricate process of calculating taxes on the sale of a business. The journey may be complex, but with the right knowledge, it’s navigable.

Understanding the Basic Terminologies

Before diving into the tax calculations, it’s essential to familiarize yourself with some key tax terms and concepts.

A. Capital Gains

When selling a business, tax obligations primarily revolve around capital gains. This is the profit you make from selling assets more than their purchase cost.

B. Cost Basis

The cost basis is the original value of an asset for tax purposes. Usually, this is the purchase price, but it can be adjusted for factors like depreciation.

C. Business Structures

Different business structures – sole proprietorship, partnership, LLC, or corporation – come with distinct tax implications when selling. It’s crucial to understand these differences.

Recognizing Types of Assets in a Business Sale

When selling a business, you’re actually selling a combination of assets. The types of assets involved in the sale will significantly impact your tax obligations.

A. Asset Sale versus Share Sale

In an asset sale, you sell the individual assets of the business, while in a share sale, you sell your shares of the company. The tax implications differ significantly between these two options.

B. Tangible and Intangible Assets

Tangible assets include physical items like equipment, inventory, and property, while intangible assets include non-physical items like customer lists, brand recognition, and goodwill. The tax treatment for each asset type varies.

C. Depreciation

Depreciation refers to the reduction in the value of an asset over time, which impacts your tax obligations.

Distinguishing Between Long-term and Short-term Capital Gains

The duration for which you’ve held the business assets before selling them impacts your tax obligations.

A. Long-term Capital Gains

If you’ve held your business assets for more than a year before selling, any profit from the sale will be treated as long-term capital gains, typically taxed at a lower rate.

B. Short-term Capital Gains

Profits from assets held for less than a year are considered short-term capital gains, which are usually taxed at a higher rate.

Understanding Cost Basis and Its Role in Tax Calculation

The cost basis is instrumental in calculating capital gains tax. You subtract the cost basis from the sale price to determine your capital gain.

A. How to Determine Cost Basis

To determine the cost basis, consider the purchase price and any additional costs incurred, such as improvements to the assets.

Calculating Capital Gains Tax on Business Sale

Once you’ve determined your capital gains and understood your cost basis, you can calculate the capital gains tax.

A. Step-by-step Guide

  1. Determine your capital gains by subtracting the cost basis from the sale price.
  2. Identify whether your capital gains are short-term or long-term.
  3. Apply the appropriate tax rate to your capital gains to calculate the capital gains tax.

B. Impact of Business Structure

The structure of your business can affect the tax calculation. For instance, corporations may be subject to double taxation.

How Installment Sales Affect Tax Liability

An installment sale is when the buyer makes payments over time, rather than paying the full purchase price upfront. This method can spread your tax liability over multiple years.

A. Deferring Tax Liability

When you receive payments over time, you only pay taxes on the income received each year. This can lower your overall tax bill by spreading it over a longer period.

B. Reporting Installment Sales

Installment sales are reported using IRS Form 6252. Each year, you report the part of the payment you received, and only that portion is taxed.

Tax Reduction Strategies

With strategic planning, you can reduce the tax liability when selling your business.

A. 1031 Exchange

Under Section 1031 of the tax code, you can defer capital gains taxes by reinvesting the proceeds from the sale into a similar type of business within a specific timeframe.

B. Charitable Giving

Donating a portion of the sale proceeds to charity can reduce your taxable income.

C. Seller Financing

If you finance the sale of your business to the buyer, you can spread out your tax liability over several years, similar to an installment sale.

Importance of Professional Advice

Navigating the tax landscape when selling your business can be a daunting task. Thus, professional advice is critical. That’s where a Certified Exit Planning Advisor (CEPA) can come into play. A CEPA, like the team at Proxxy, can provide the guidance you need throughout the process, ensuring consistency in what can often be a multi-year endeavor.

Whether you’re contemplating a merger, acquisition, investment, or scale financing, a CEPA can help you assess your readiness to sell and your business’s appeal to potential buyers. This preparation does more than just ready you for a potential sale—it improves your company’s operations today, allowing you to scale efficiently.


Selling a business is more than a transaction—it’s a complex journey filled with numerous decisions that carry substantial tax implications. By understanding the fundamental tax concepts, recognizing the types of assets involved, distinguishing between long-term and short-term capital gains, and employing tax reduction strategies, you can navigate this journey with confidence. While the process might seem overwhelming, remember that guidance is available. The right expertise can not only make the journey manageable but can also set your business up for enduring success, whether you decide to sell or not.

Navigating the world of tax implications when selling your business can be complex. However, with the right preparation and advice, you can navigate this process confidently and maximize your profits from the sale. By taking the time to understand these concepts and work with experienced professionals, you’ll be well-positioned for a successful business sale.


Checklist for Calculating Taxes on the Sale of a BusinessDone
Understand the Language of Tax
Understand the Concept of Profits and Gains
Understand the Original Value (Cost Basis)
Understand the Types of Businesses
Recognize What You’re Really Selling
Understand the Difference Between Share Sale vs. Asset Sale
Identify the Physical vs. Abstract Assets
Understand the Impact of Depreciation
Understand the Difference Between Short-term vs. Long-term Capital Gains
Understand the Importance of Cost Basis in Tax Calculation
Determine the Cost Basis
Understand the Math Behind Capital Gains Tax
Calculate Capital Gains
Identify the Type of Gains (Short-term or Long-term)
Apply the Corresponding Tax Rate
Understand the Impact of Business Structures on Tax Calculation
Understand How Installment Sales Affect Tax Liability
Understand Tax Deferral in Installment Sales
Learn to Report Installment Sales
Learn and Implement Tax Reduction Strategies
Understand and Utilize 1031 Exchange
Consider Charitable Contributions
Understand the Benefits of Seller Financing
Seek Professional Advice
Work with a Certified Exit Planning Advisor (CEPA)
Assess Readiness to Sell and Business Appeal
Understand How Preparation Can Improve Current Operations

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