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Taxes For Selling A Business: All You Should Know AS A Trader

Skylar Williams

Nov 16, 2022 15:46


When you sell your business, you may incur a hefty tax liability. After selling a business, it is difficult to prepare your taxes. After paying all applicable taxes, you may be left with less than half of the original purchase price. However, with forethought and planning, at least some of these taxes can be avoided, reduced, or postponed.

Must I pay taxes for selling a business?

When a business is sold, money is made. You presumably took use of tax deductions and credits to offset a portion of the costs associated with launching your business.


When you sell a business, you must pay taxes on the profit. In the majority of situations, the proceeds are taxed at the capital gains tax rate; however, certain assets may be taxed as ordinary income.

Does the Internal Revenue Service impose capital gains tax on the sale of a business?

The sale of a firm is subject to a capital gains tax by the Internal Revenue Service. You can expect to pay this type of tax on the proceeds from the sale of your company.

Nonetheless, make no mistake about it. The capital gains tax in this jurisdiction does not adhere to the same regulations as regular income tax. Unlike ordinary income tax, which is normally paid on the gross income or profits your business generates, capital gains tax is only levied on the net value reached since you acquired the business.

For example, if you bought business stock for $20,000 and then sold it for $30,000, you will have realized a $10,000 capital gain. This is what the IRS considers taxable income when calculating the capital gains tax on the sale of your business.

But that's not the end of the tale. It turns out that stock transactions aren't the only thing that triggers the capital gains tax on a business sale, and similar tax consequences might be expected even when selling an asset.

This frequently occurs in deals involving sole proprietorships. Since these corporations do not ordinarily issue stock, the capital gains tax is imposed directly on the net investment income generated from the sale of individual business assets.

This means that the IRS will not view your small business as a single capital asset that may be transferred, and it views each sole proprietorship as a collection of numerous smaller assets that can be sold separately.


And no exceptions exist. The IRS considers the tax basis of both physical and intangible assets, and this includes furniture, real estate, collectibles, machinery, property leases, copyright, patents, trademarks, goodwill, etc. Any loss in value is written off as an investment loss, while any increase in value might result in taxable capital gains.

However, this structure is not limited to sole proprietorships, and it is also applicable to C Corporations that opt to conduct asset sales rather than stock transactions. The Internal Revenue Service imposes capital gains tax based solely on the net worth of each exchanged item.

However, if you are attempting to sell a partnership business, you may wish to reconsider your strategy. You can avoid the hassle of assigning a sale price to each partnership asset by transferring your whole partnership share as a single capital asset. Consequently, you will ultimately file a capital gains tax return based on the acquisition price and the partnership's corresponding adjusted basis.

Reduced tax liability is the effect of capital gains

For tax reasons, when you sell your business, you are truly selling a collection of assets. Some are tangible (such as real estate, equipment, and inventory), while others are intangible (such as goodwill, accounts receivable, and a trading name).

Unless your business is incorporated and you sell a stock, the purchase price must be assigned to the transferred assets. According to IRS regulations, the buyer and seller must use the same allocation, and thus the allocation must be discussed and included in the sales contract in writing.

Price allocation between assets can be a contentious matter. The buyer desires that as much money as possible be allocated to goods that are already deductible, such as a consulting arrangement, or to assets that can be swiftly depreciated. This will boost the company's cash flow by lowering its tax liability in the crucial first years of operation.

On the other hand, the seller desires that as much money as possible be allocated to assets on which the gain is considered capital gains, as opposed to assets on which the gain must be treated as ordinary income. This is because the tax rate on long-term capital gains for non-corporate taxpayers is significantly lower than the highest individual maximum tax rate. Selling that the majority of small business owners who successfully sell their companies are in high tax bands, this rate differential is crucial for minimizing tax liability.

Any gains on assets held for less than a year, inventory, or accounts receivable are taxed at the standard rate. Amounts paid according to non-compete agreements are taxable as ordinary income to the recipient and can be amortized over 15 years by the purchaser unless the IRS successfully claims that they are actually part of the purchase price. Amounts paid under consulting agreements constitute ordinary income for the consultant and are now deductible for the client.

What are capital gains (and losses)?

The buildings, machinery, equipment, and vehicles that your business possesses are examples of capital assets. It can be invested or employed to generate a profit. You can sell a capital asset for a gain or loss. The difference between the original purchase price (known as the basis) and the selling price is either a capital gain or a capital loss.

You can increase the base of business equipment by updating it or reduce it by taking specific deductions and depreciation. The cost at acquisition plus these modifications result in an adjusted basis for selling equipment. The difference between this adjusted basis and the selling price is either a gain or a loss on the sale.

How does the capital gains tax function?

All capital gains are subject to capital gains tax. Depending on how long these profits are retained, they are taxed differently than regular income. The gain is considered long-term if you own an asset for more than a year before selling it, and short-term assets are those held for one year or less.

You must segregate short-term and long-term capital gains on all assets sold during the year to determine your capital gains tax rate using your net short-term and/or long-term capital gain (or loss).

Generally, a net short-term capital gain is taxed as ordinary income at your marginal tax rate. For the majority of taxpayers, the maximum net long-term capital gain is 15%. However, there are exceptions for high earners.

How are business sales taxed?

First, the sale of a firm is not often treated as the sale of a single asset by the Internal Revenue Service. The company's assets are instead treated as though they were being sold separately, with very few exceptions.

Then, there is the question of whether the sale of business assets will result in long-term capital gains or regular income. The distinction between the two has significant tax ramifications.

The proceeds are considered long-term capital gains when you sell an asset you've owned for more than a year. The maximum capital gains tax rate for the majority of taxpayers is 15%.

Any gains that are considered "ordinary income" are subject to taxation at the taxpayer's standard rate. More than twice as high as the rate on long-term capital gains is the maximum federal income tax rate for individuals, which is now 37%.

Tax considerations for the sale of a business

Here are the most important factors to consider when selling a business in the present tax climate.

1. Sale Type

Initially, it is essential to determine if the transaction will be a stock sale or an asset sale. There can be substantial tax differences between these two transaction forms, making this the first and most crucial consideration when selling a business.

In the case of a stock sale (assuming an S or C corporation), the transaction and any potential profit are not passed via the business. Instead, it is recorded at the shareholder level and taxed once (likely at the L/T capital gains rates for people plus their resident state tax rate).

Typically, a stock sale is not preferable for a buyer because its basis in the company purchase is fixed in time. In other words, the buyer is ineligible for immediate tax deductions upon the acquisition until they

Sell their stock to a third party in the future.

In contrast, in an asset sale, the buyer receives tax deductions over time or, in some cases, the whole of the year of the sale, based on the allocation of the sales price to the assets. Due to the quick tax benefits, asset sale structures are typically preferred by buyers.

2. Entity Type

Additionally, tax effects differ across C corporations, S corporations, and partnerships. Each entity has its own specialized tax provisions that can affect a sale's gain and subsequent tax obligations.

In one of many possible situations, C businesses selling assets for a profit would be liable to double taxation — first at the corporate level and again when the after-tax gains are paid to shareholders and taxed as dividends. It is common practice for some of the asset gains to be taxed at ordinary rates (up to a maximum of 37%) and some at long-term capital gains rates if the selling party was a pass-through business (S corp or partnership). The ordinary rate gain part can be derived via a frequent tax loophole known as depreciation recapture to offset the preceding owner's depreciation cost benefits at the same ordinary tax rate.

In contrast, partnerships have no idea of selling shares. Moreover, even if the intention is to purchase a partnership interest (or partnership units), tax rules require that the transfer be considered as a sale of partnership assets to the owners. Occasionally, this circumstance has been misconstrued as a pure capital gain sale on equity units comparable to corporate shares. Thus caution is advised. In actuality, the gain from the sale of a partnership is treated as regular income in a number of special circumstances.

3. Purchase Price Allocation

In asset transactions, the purchase price allocation can be the subject of the most intense negotiations between the parties. This is especially true for companies that rely heavily on equipment. The ordinary income tax looms big in these transactions, which might result in negative tax consequences for the seller.

For instance, a buyer may seek to acquire manufacturing equipment with an allotted purchase price of $10 million. According to the new tax regulations, the tax is entitled to a basis step-up for the purchased assets and can take advantage of first-year bonus depreciation of 100%. However, if the seller has already claimed full depreciation on the equipment, he or she may be left with a small or nonexistent tax basis. Therefore, the seller's gain on the equipment would be subject to depreciation recapture and taxed at the standard 37% federal rate.

Given that the Internal Revenue Service classifies goodwill and customer-based intangibles as capital assets, any tax made from selling them would be subject to the lower federal capital gains rate of 20%. This example promotes a seller bias to allocate a larger portion of the purchase price to intangibles and a smaller portion to regular assets, such as equipment in the preceding case.

4. State Considerations

Finally, evaluating state tax consequences and savings options is essential.

When selling a business, federal taxes frequently take the majority of consideration. As a result of tax reform reducing federal tax rates, state taxes now constitute a much larger portion of the tax pie chart. The apportionment of any goodwill from the sale of an asset among numerous states and the seller's residency during the year of the transaction are noteworthy state-level issues.

On the latter point, a business owner in a high-taxed state with a buyer "on standby" to purchase their business may be tempted to move their principal residence to a state with no income taxes once the deal is finalized (such as Florida or Nevada). Nonetheless, state residency requirements are tight, as are tax audits of residents. In addition to residing in the new state for the majority of the tax year, a taxpayer who wishes to relocate must also take actions that firmly establish them in the new state's economy, such as changing their voter registration, obtaining a driver's license, or joining local organizations that require live attendance.


In all situations involving the sale of a business, a tax expert should be consulted regarding the numerous tax nuances and particulars. Selling a successful business should be a joyous occasion; do not allow an unexpected tax bill to mar the occasion.

Tax planning strategies for small businesses

When selling a business, it is essential to structure the transaction to minimize tax liability. A few straightforward initial measures might generate life-altering wealth. There are three typical approaches:

1. Sell Via a Charitable Remainder Trust

When you set up a CRUT, such as a Charitable Remainder Trust, you can sell your successful company without paying any taxes.

How does it work? Your first move should be to establish a trust to hold legal title to your business (of which you are in control as trustee and beneficiary). Next, you wait for the proper moment to sell the company. As a tax-exempt organization, you can rest assured that the CRUT will not charge you or the beneficiary any capital gains tax on the sale of any valuable asset, including shares in a company, that you contribute to the trust. You may reinvest the entirety of your sale revenues rather than sending a significant portion to the federal and state governments. You will receive annual dividends from the trust, and whatever is left after the trust terminates will be donated to a charity of your choosing.

2. Use An Installment Sale

Let's say you sell a company and make $250,000 in profit. It's likely that you will owe taxes on any additional $250,000 in taxable income that you report on your tax return for a single year. You'll have a lot more taxable income this year, so your effective tax rate will be considerably higher than normal, and second, you'll have to pay these taxes right away, in April.

However, if you don't want to seek a tax-exempt trust, you can use what is known as an "installment sale" to stretch the earnings over a number of years. This is accomplished by offering "seller finance" or, in essence, an installment plan for the purchase of your business. In addition, they will give you a portion of the purchase price this year as a down payment and the rest in installments over the next few years.

Importantly, with an installment sale, you only owe income taxes on the amount the purchaser pays you in a given year. If the payments are made over an extended period of time, you can dramatically reduce your marginal tax rate. In addition, you may charge the buyer interest on the business sale.

There are two primary dangers: first, you become a lender. You may have to foreclose on the business if the buyer fails to make the installment payments, but you will likely not recover everything you are owed. You will not be able to reinvest the funds and gain additional investment growth because you are receiving lower payments over time (though you will get those interest payments, which can make up for some of that growth).

3. Invest in Opportunity Zone Funds

In an effort to encourage investment in housing, small companies, and infrastructure in economically depressed areas, the U.S. government designated numerous places as Opportunity Zones in 2017.

When you invest the capital gains on the sale of an appreciated asset in Opportunity Zones, you can take advantage of a number of tax advantages, including complete tax deferral until 2026 and complete tax exemption on profits that occur within the Opportunity Zone investment.

When do you pay capital gains tax?

You must pay capital gains tax on the sale of business capital assets. From the viewpoint of the IRS, your business typically consists of multiple assets, and it consists of smaller assets that are sold individually. (As explained below, if you're selling your share in a partnership or a company, things are handled differently.)

Here is where business taxes become even more complicated. Not all of your business's assets will be taxed at the capital gains rate, and the regular income tax rate, which is higher for many people, might be applied to a portion of your assets. For instance, inventory sales and accounts receivable are taxed at the standard rate.


The IRS provides recommendations for determining the value of each asset, but for the vast majority of goods, there are aspects of price allocation that would benefit from professional guidance.


Before selling your business, you should fully comprehend the tax ramifications of your decisions. Working with a professional can help you negotiate some of the most complicated tax issues and identify a tax-reduction strategy.