Tax Implications In the Sale of A Business

Tax Implications In the Sale of A Business

One of the major considerations in structuring a sales transaction is the tax consequences to both the Seller and the Buyer. Like other terms of the agreement, what may be good for the Buyer, may not necessarily be good for the Seller, or vice versa.

From a tax standpoint, the best strategy is to minimize the total taxes paid on the transaction, taking into consideration what the seller’s taxes may be now and what the Buyer will ultimately have to pay.

We have chosen to take a look at tax considerations from a Federal tax standpoint. One should always keep in mind, there may be state and local tax considerations. As always, we urge you to seek the advice of your own accountant prior to entering into any agreement.

Buyer’s Issues

A Buyer is going to want to structure a sale as to reduce the after-tax cost of acquiring the business. As a result, a primary concern will be the allocation of the acquisition cost. The Buyer will want this cost to be allocatable to assets than can be expensed or depreciated quickly. In some instances the business may have a net operating loss (NOL) or tax credit carryforward that the purchaser may want to use for future use. To the extent a transaction can be structured favorably to preserve any carryforwards or minimize any future restrictions, may translate into a Buyer’s ability to pay more for that business.

Seller’s Issues

The Seller will want to structure the sale in a manner as to minimize taxes paid from the gain of the sale of the business. Timing of the taxable gain is certainly of concern. As an example, if the Seller finances a portion of the transaction or accept’s purchaser’s stock, the Seller wil want the transaction structured so that any tax paid on the gain is delayed until receipt of the installment payments or the sale of the stock is received.

A send issue relates to the nature of the gain (ie.,capital gain versus ordinary income). The tax rate on capital gains is less than the tax rate on ordinary income.

Stock Versus Asset Sale

The consideration of what will be sold-the individual assets of a business or the stock in the corporation- can be paramount in determining the structure of a transaction. For the Buyer, this decision determines the tax basis in the assets to be acquired. For the Seller, this decision will affect not only the absolute amount of the gain, but its timing and character.

A stock sale causes no change in the legal entity. There is no change in the tax entity. The tax basis of the corporation’s assets remains unchanged, and all the corporation’s tax attributes, including methods, tax year, corporate tax election, are preserved. Existing carryforwards are available to the purchaser.

With an asset sale, the corporation’s tax identity does not transfer to the purchaser. The acquired assets receive a new tax basis which is equivalent to the purchase. There are no NOL carryforwards or other favorable tax attributes available to the purchaser.

The tax implications of a stock sale are fairly straightforward, unless it involves the sale of a subsidiary. The Seller’s gain or loss is the difference between the amount received on the sale and the shareholder’s tax basis in the stock (generally, the amount the shareholder paid for the stock initially).

The Seller’s tax basis in a company’s stock is typically quite different from the company’s tax basis. If a shareholder expects a sizeable gain on the sale, they will usually favor a stock sale rather than an asset sale. This is because the gain from the asset sale is taxed twice- the corporation must pay taxes on the gain from the sale of the business, and the shareholders pay taxes again when the net proceeds are distributed to them.

The purchase of stock, from a Buyer’s perspective, can under certain circumstances, be less than desirable. After all, the Buyer is required to assume the existing tax basis of a company’s assets even though they may have paid far more for those assets. If the Buyer had bought assets instead, the value of the acquired assets could have been “stepped up” to their purchase price.

The absence of a “step-up” can have a considerable affect to the Buyer. As an example, if the appreciated assets have short lives (eg., equipment, inventory, or receivables), of if the purchaser intends to liquidate the corporation or to sell some of the appreciated assets in the near future, the lower tax basis may result in a significantly higher future tax liability.

Tax-Free Reorganization

There are occasions where business owners see an advantage in combining forces with another entity rather than selling out completely. Continuity of ownership and continuity of the business are the essential elements of tax-free reorganizations. In order to meet the “continuity of interest” test the shareholders of the target company must receive equity in the acquiring company. The IRS likes at least 50% of the equity of the target company to be exchanged for stock in the acquiring company. Absence of meeting this continuity requirement, the merger will not be considered tax-free, and the corporation will have a taxable gain to the extent that the value of stock and cash they receive exceeds their basis in their old stock.

The business merger must fit into one of five basis structures in order to avoid current taxation.

Statutory Mergers

This is the most flexible form of tax-free reorganization. To the extent that shareholders of the target company receive stock of the surviving corporation, they do not realize a gain or loss on the transaction. They are, however, subject to taxation on any other consideration received (cash, dividends). The holder of debt securities in the target corporation can exchange those securities for debt securities in the surviving corporation tax-free, but only to the extent that the principal does not exceed the principal amount of the debt securities transferred.

The surviving corporation usually assumes a tax basis of the target corporation=s assets equal to the basis that the target corporation had in the assets.

The same rules generally apply when a subsidiary operation is formed by the acquiring company to house the target company. The IRS likes 70% of the fair market value of the gross assets and 90% of the fair market value of the assets to be acquired. If stock is issued it must be of the subsidiary’s parent.

Stock for Stock

Under this transaction, shareholders of one corporation surrender their stock solely in exchange for the voting stock of the acquiring corporation (or the voting stock of its parent). Immediately, the corporation must own 80% of the voting and 80% of the non-voting stock of the target company. Because they received solely voting stock in the acquiring company, the shareholders recognize no gain or loss. The acquiring company’s basis in the stock of the acquired company is equal to the basis that the shareholders had in their stock. And because this is a stock transaction, there is no change in the acquired company itself so that its basis in its assets and most of its tax attributes carry over.

Assets for Stock

This type of tax-free reorganization is commonly referred to as a “C” reorganization. All the assets of the target company are acquired solely for voting stock of the acquiring corporation (or parent company). The acquiring company is generally permitted to assume the liabilities of the target company.

In order to qualify, the acquiring company must acquire substantially all of the assets of the target company. A small amount of cash or assets can be left to take care of dissenting shareholders. There is no taxable gain or loss for shareholders of the target company. Any cash or other asset distribution to shareholders is taxable.

Even though this is basically an asset sale, the acquiring corporation generally takes the basis that the target company had in those assets. There is no new basis in the acquired assets.

Reverse Triangular Merger Under an “E” reorganization, the subsidiary of an acquiring company is merged into the target company, with the target company surviving. This preserves the legal existence of the target. To qualify, the acquired company must continue to own “substantially all” of its assets, and the assets of the acquired corporation, and the shareholders of the target company must exchange stock of the target company (at least 80% of the voting stock) for voting stock of the parent.

Capital Gains vs. Ordinary Gains

For individuals, capital gains are taxed at rates below the maximum rate for ordinary income. An individual’s deductions for capital losses are limited to $3,000 annually plus any capital gains.

In a stock sale, any gains or losses are generally capital gains or losses. In a sale of assets, much of the gain may be ordinary income. Ideally, the sale agreement will identify the assets purchased and the amount allocated for each item. Most of the assets, including inventory, equipment, will result in ordinary income. Some items, such as goodwill, most real property (real estate), and any appreciation over the original cost of the equipment, will qualify as capital gains.

The identification and valuation of “intangible” assets can be significant in negotiating terms. Goodwill is an intangible that has capital gain treatment for the Seller. The buyer can generally amortize purchased good will over l5 years.

Non-Compete Agreement

It is many times advantageous to both the Buyer and Seller to allocate a reasonable portion of the total consideration being paid to a covenant not to compete. It is common to have the proceeds attributable to the non-compete be paid directly to the shareholders of a corporation, thereby avoiding a corporate level tax on that portion of the price, even in an asset sale. The non-compete payments are taxable to the Seller(s) as ordinary income. The Purchaser is generally entitled to amortize the non-compete payments over l5 years.

Other Allocations

A portion of the purchase price may also be assigned to such items as customer lists, databases, favorable leases, backlogs, technology, etc. These items can be amoritzed over l5 years with a resulting tax deduction for the purchaser.

Net Operating Losses

If the Buyer purchases a company’s stock, that company=s tax attributes are retained. There are special considerations when the target company has net operating loss carryforwards. The tax code does put a limitation on the amount of the carryforward and generally those carryforwards are canceled if the business of the company is discontinued during the first two years following a change in ownership. Typically the NOLs and certain built-in losses of an acquired company can only be used to offset future income of that company, not taxable income of other businesses of the Buyer that are included in the Buyer’s consolidated return. However, if the acquired company continues to have losses, the buyer may file a consolidated tax return and may offset current losses against current profits.

Generally, the Section 382 limitation is calculated by multiplying the total value of the company by the tax-exempt long-term bond rate at the ownership change. In some instances, the time is takes to take advantage of the loss carryforwards makes sense. In some instances, it’s not worth the effort.

Installment Gains

If the Seller finances a portion of the transaction, the installment sales method of income recognition may be available to defer the payment of taxes. Under this method, the seller recognizes gains on the sale only as the proceeds are received, not when the transaction takes place. There are several restrictions. Gains from inventory, publicly traded securities, or depreciation recapture are not eligible for installment reporting. If the installment receivable is greater than $5 million as of the end of the year of the sale, interest is charged on the taxes deferred.

Use of the S Corporation

The “S” Corporation is basically a non taxpaying entity. The income or loss of an S corporation is taxed directly to the shareholders the same way that partnership income or loss is taxed directly to the partners. No second layer of taxation occurs when an S corporation sells its assets.

To be eligible to be an S corporation, the corporation must have only one class of stock, no more than 35 shareholders, all of whom are U.S. citizens or U.S. residents, and have no subsidiary of which it owns 80 percent of more.

Excess Debt

There are restrictions on the deduction of interest on obligations that claim to be debt obligations, but are, in reality, equity. Concern over highly leveraged transactions have caused Congress to place additional restrictions on the deductibility of interest expense.

Before you commit to a purchase or sale of your business we strongly urge you to consult with your accountant, financial advisor, and attorney. Taking the proper precautions, including developing an understanding of how structuring a transaction one way will effect the other side, will lead to a much smoother process, perhaps saving you considerable dollars down the road.

Selling a business is not a simple transaction. You can sell assets or your can sell stock. You can sell all or a portion of the business. Receivables may be included in a sale or the owner may retain both receivables and payables. There are also many ways to structure financing and what may be good for one buyer may not be good for another.

Talk to your accountant now.

Understand the tax consequences of a sale and how a deal might be structured to maximize your return after taxes. And, be prepared to provide your accountant and attorney information on the ins and outs of running your type of business and what a buyer might expect.

Unless you have broad experience instructing these type of transactions, get the advice of someone who does.


Grimes, McGovern & Associates provides expert advice during all phases of a transaction. Contact us today for a confidential consultation: John McGovern, CEO, [email protected], (212) 255-9700.


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