*Disclaimer: Robbins Pellegrino is not nor does it claim to be a financial advisor. Please consult with your CPA, Financial Advisor or Tax Strategist. If you need a connection, send us a request.
Whether you’ve built your business from the ground up or you acquired and expanded it, cashing out can be both exciting and rewarding.
But before you start celebrating, there’s one critical factor you need to consider: taxes.
From capital gains taxes to hidden liabilities, understanding the tax implications of your sale can make a massive difference in how much money you actually get to keep.
If you’re not careful, taxes could eat up a significant portion of your hard-earned profits.
In this guide, we’ll break down the key tax considerations when selling a business, how different deal structures impact your tax bill, and strategies to minimize your tax burden.
How Business Sales Are Taxed
When you sell a business, the IRS doesn’t just see it as a single transaction.
Instead, it considers the sale of each individual asset within your business. This means different parts of your business could be taxed in different ways, impacting your overall tax liability.
Capital Gains vs. Ordinary Income
The tax treatment of your sale largely depends on whether your profits are classified as capital gains or ordinary income:
Capital Gains Tax: If you’ve owned your business assets for more than a year, they are typically taxed as long-term capital gains, with rates ranging from 0% to 20%, depending on your income bracket.
Ordinary Income Tax: Some parts of your sale may be taxed as ordinary income, which is taxed at a much higher rate—up to 37% at the federal level.
Since capital gains tax rates are generally lower, most sellers aim to structure their sale in a way that maximizes capital gains treatment.
Key Factors That Influence Your Tax Bill
1. Asset Sale vs. Stock Sale
How your business is sold plays a major role in how taxes are applied.
Asset Sale: This is when you sell the individual assets of the business (such as equipment, real estate, inventory, and intellectual property). Each asset is taxed differently, with some falling under capital gains and others as ordinary income.
Stock Sale: If your business is structured as a corporation, you may have the option to sell stock shares instead of individual assets. Stock sales typically result in capital gains treatment, which is more favorable for sellers.
Buyers, however, often prefer asset sales because they can claim depreciation deductions. This can lead to negotiations over the structure of the deal.
2. Purchase Price Allocation
The IRS requires both the buyer and seller to agree on how the purchase price is allocated across different business assets. This allocation impacts taxation:
Tangible assets (e.g., equipment, inventory) – Taxed as ordinary income
Real estate and goodwill – Taxed as capital gains
Consulting agreements or non-compete clauses – Taxed as ordinary income
Sellers typically prefer to allocate more of the price toward goodwill and capital assets to take advantage of lower capital gains rates.
Buyers, on the other hand, want more allocation toward depreciable assets.
Finding a balance is key to realizing a successful transaction.
3. Installment Sales vs. Lump Sum Payments
If you receive the full sale price upfront, you’ll owe all your taxes in the year of the sale.
But if you structure the deal as an installment sale, you may be able to spread out your tax liability over multiple years.
Lump Sum Sale: Full tax burden in one year
Installment Sale: Taxes are paid as payments are received, potentially keeping you in a lower tax bracket each year
This strategy can significantly reduce your overall tax rate and improve cash flow for the business.
4. Depreciation Recapture
If you’ve claimed depreciation deductions on business assets over the years, the IRS may “recapture” some of those tax savings when you sell.
Instead of being taxed as capital gains, depreciation recapture is taxed as ordinary income (up to 37%).
This applies to depreciated assets like buildings, equipment, and vehicles. If you’ve taken large depreciation deductions, be prepared for a higher tax bill on those items.
5. State and Local Taxes
Federal taxes aren’t the only concern—state and local taxes can add another layer of complexity.
Some states have high capital gains taxes, while others (like Florida and Texas) have no state income tax at all.
Before selling, consult your business broker and your CPA to understand the full tax impact based on your state’s laws.
Tax Strategies to Reduce Your Tax Burden
1. Structure the Sale for Capital Gains Treatment
Whenever possible, allocate more value to capital assets like goodwill. This helps ensure you pay the lower capital gains tax rate instead of ordinary income tax rates.
2. Use an Installment Sale
Spreading your payments over several years can help reduce your overall tax rate by preventing a large one-time tax hit.
3. Take Advantage of a Like-Kind Exchange (1031 Exchange)
If you’re selling real estate as part of the deal, you might be able to defer capital gains taxes by reinvesting in another like-kind property through a 1031 exchange.
4. Maximize Retirement Contributions Before the Sale
Before finalizing the sale, consider maxing out contributions to retirement accounts (like a 401(k) or SEP IRA). This reduces your taxable income for the year.
5. Work with Professionals
Selling a business is complex, and tax laws can be tricky. Your business broker should work with your CPA to help structure the sale efficiently and minimize your tax liability.
Common Tax Mistakes to Avoid
Not planning ahead – Waiting until after the sale to think about taxes can lead to unnecessary tax liabilities.
Underestimating depreciation recapture – This can cause a surprise tax bill if not properly accounted for.
Ignoring state taxes – Different states have different rules, and failing to plan for them can cost you.
Not consulting professionals – DIY tax planning can lead to costly mistakes.
Keep More of Your Hard-Earned Money
Selling your business is a huge milestone, but failing to plan for taxes can be a costly mistake.
By understanding the tax implications, structuring your deal wisely, and working with a professional, you can minimize your tax burden and maximize your profits.
Before signing any agreements, take the time to assess your tax situation. A little planning now can save you a fortune when tax season rolls around.
Thinking about selling your business? Contact us today to ensure you keep as much of your sale proceeds as possible!
About Robbins Pellegrino: Robbins Pellegrino is a Florida-based business brokerage firm led by Chandler Robbins and Joe Pellegrino, Jr. that is committed to redefining industry standards. We focus on creating meaningful partnerships and ensuring successful business transitions for both buyers and sellers. For more information, visit us at www.robbinspellegrino.com or call (239) 360-6273
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