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Plan for taxes
when selling out
The often-overlooked impact of capital
gains taxes can spell the difference between a good deal and a bad one
Capitalizing on a strong economy and
favorable capital gains tax rates, many business owners have
decided that now is the right time to sell out. If you’re among
them, please heed this piece of advice: Don’t overlook the tax
issues related to the sale of your business. Major tax
consequences can turn what looks like a good deal into a bad one.
Assets vs. stock. From a tax standpoint, one of the biggest
questions in selling your business may be whether to sell the assets or
sell the stock. If you choose the former, whether the entity is a C
corporation or an S and whether it has always been that type of
corporation will have significant tax implications for you.
Sale of stock. The advantages to you of a stock sale are its
simplicity and favorable long-term capital gain treatment, assuming you’ve
held the stock for more than 18 months.
For federal income tax purposes, assuming long-term capital gain treatment
applies, the excess of the amount you receive over your basis in the stock
is taxed at a maximum rate of 20%. Your buyer gains control of the
corporation in a simple transaction, and you receive favorable tax
treatment.
If stock is to be sold, an installment sale might be attractive to you and
the buyer. The buyer doesn’t have to obtain outside financing, since
you’re financing the purchase, and the interest rate you negotiate with
the buyer will probably be higher than what you could earn with other
investments.
More important, in an installment sale the taxable gain is recognized as
you collect the payments.
Sale of assets. Generally, the sale of assets and subsequent
liquidation of the business is not in your best interests.
The impact is especially unfavorable if you own a C corporation. Any gain
on the sale of assets will be taxed to the corporation, and when the net
assets are distributed in liquidation, you will be taxed on the amount by
which the proceeds received exceed the stock basis.
If you own an S corporation, you avoid the double taxation of earnings
(but if your S corporation was converted from a C corporation within 10
years before the sale, you may be subject to additional tax).
Nontaxable reorganization. If you meet certain complex
requirements, you may be able to sell your corporation tax-free or at a
substantial tax savings. There are three types of such corporate
reorganizations:
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a merger or consolidation,
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a stock-for-stock exchange, and
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the transfer of substantially all assets for
stock.
To meet the requirements of a tax-free reorganization, you must end up
with a substantial equity interest in the acquiring corporation. The basis
of the stock you receive in the corporation that acquires yours is a
carryover from the stock of your acquired corporation. You defer the gain
until you sell your shares in the acquiring corporation, and you can time
that sale to take advantage of favorable changes in tax rates.
Asset diversification vehicle. Under an asset diversification
vehicle (ADV), you set up a partnership to buy your corporation’s stock.
You then form a 20-year charitable remainder unitrust and contribute to
the trust a 99% interest in the partnership.
When you sell, only 1% of the sale price is taxable. You become liable for
further capital gains tax only when the trust distributes the sale
proceeds and their earnings to you over the trust’s 20-year life.
Intra-family sale. The intra-family sale technique allows you to
reduce your capital gains tax liability by selling your business to your
children, who in turn sell to the buyer. The children contract to pay you
an annuity based on the fair market value of the company for the rest of
your life.
No capital gain is triggered when the children sell the stock to the
buyer. That is because the children are entitled to a tax basis equal to
the present value of the amounts they agree to pay to you, as those
amounts are paid. This technique enables you to pay your capital gains tax
in installments as you receive payments from your children.
Based in Mesa, Arizona, and serving closely held businesses in the East Valley,
the Phoenix area and throughout Arizona, Schmidt Westergard & Company, PLLC, is
an independent full-service tax, audit, accounting and business advisory firm
focusing on the middle market.
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