When the COVID-19 pandemic first hit, economic uncertainty caused many business owners contemplating a sale — as well as many prospective buyers — to put their plans on hold. Now that there’s some light at the end of the pandemic tunnel, interest in buying and selling businesses seems to be picking up.

If you’re thinking about selling your business, be sure you understand the tax implications. The way that your business (as well as the transaction) is structured can impact your tax bill and, therefore, your net proceeds from the sale. Here are some issues to consider.

Stock sale vs. asset sale

If your business is a corporation (either an S corporation or a C corporation), deciding whether to structure the transaction as a stock sale or an asset sale may have a significant impact on its tax treatment. Generally, a stock sale is preferable from the seller’s perspective. That’s because when shareholders sell their stock, the profits generally are taxed at favorable long-term capital gain rates — currently a top rate of 20%, compared to a current top rate of 37% on ordinary income. In contrast, asset sales usually generate a combination of ordinary income and capital gains, depending on how the purchase price is allocated among the business’s various assets.

From the buyer’s perspective, on the other hand, an asset sale is usually the structure of choice. A buyer of stock generally inherits the corporation’s basis in its assets. If the corporation has already taken significant depreciation deductions on those assets, there may be little or no basis for the buyer to write off. But a buyer of assets generally receives a basis equal to the portion of the purchase price allocated to each asset, generating valuable tax write-offs.

Entity type

The seller’s form of business is another important consideration. If the seller is a C corporation, for example, a potential drawback of an asset sale is double taxation.

First, the business pays corporate tax on any gains from the sale. Then the shareholders are subject to a second tax when the sale proceeds are distributed to them as dividends. (Note: It may be possible to defer the second tax by having the corporation hold and invest the sale proceeds.) Double taxation isn’t an issue for stock sales. The buyer acquires the stock directly from the shareholders, so there’s no entity-level tax.

Double taxation usually isn’t a concern for S corporations. As pass-through entities, their income is taxed directly to shareholders at their individual tax rates. So, there’s no entity-level tax, even if the transaction is structured as an asset sale.

There’s a possible exception for a business that had previously been taxed as a C corporation but later elected S corporation status. Depending on how much time has passed, asset appreciation during the business’s time as a C corporation may be subject to two levels of tax.

Partnerships (including limited liability companies taxed as partnerships) don’t have stock, but it’s possible for the owners to sell their partnership or LLC membership interests to a buyer. It’s important for the sellers to understand, however, that this isn’t the same as selling stock for tax purposes. A sale of partnership or LLC interests is treated essentially as a sale of the underlying assets, typically resulting in a mix of ordinary income and capital gain to the sellers.

Allocation of the purchase price

When a transaction is structured as an asset sale, the allocation of the purchase price among various assets has significant tax implications for both buyer and seller. Often, the parties have conflicting interests, which can lead to intense negotiations on this issue. Keep in mind that the parties’ allocation of the purchase price isn’t binding on the IRS, though the IRS generally will respect the parties’ agreement so long as it bears a reasonable relationship to asset values.

Sellers generally prefer to allocate as much of the purchase price as possible to goodwill and other intangible assets that generate lower-taxed long-term capital gains. And they prefer to allocate as little as possible to equipment and other depreciable assets. Why? Because previous depreciation deductions taken on these assets are subject to “recapture” at ordinary income tax rates. Buyers, on the other hand, prefer to allocate as much of the price as possible to these assets because they can depreciate them quickly or in some cases claim 100% bonus depreciation in the first year.

What about state taxes?

Business owners usually focus on the federal tax implications of a sale, but don’t ignore state taxes. Now that federal tax rates are lower than they’ve been in the past, state taxes may take on added significance. If you’re contemplating relocating or retiring to another state, it may make sense to consider moving before you start selling the business, especially if the new state has low, or even no, income tax.

Before you attempt this strategy, however, be sure to consult your tax advisor. Changing your domicile and residence for tax purposes isn’t like flipping a switch. You’ll need to take several specific actions to demonstrate your intent to establish a permanent place of abode in the new state, such as obtaining a driver’s license, registering to vote, and becoming involved with local organizations and activities.

Keep in mind, also, that there may be rules about the number of days spent in the state, so if you do all of the above to show that you’re a resident of your new state, there are other factors. For instance, if you live in your “old” state most of the year and spend only a few months in your new state, you could find that, at least for tax purposes, you’re deemed as a resident of both states.

Knowledge is power

To successfully negotiate selling your business, it’s critical to understand the tax implications. Armed with this knowledge, you can assess the impact of various transaction structures and purchase price allocations on your net proceeds from the sale and potentially adjust the purchase price accordingly. Contact us to help guide you through the sale of your business.

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Thompson Greenspon

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