Whatever your motivation for selling your business, you'll only get
one chance to maximize the return on your years of hard work. Do it the
right way and you could get the price you want and reduce the impact of
capital gains and estate taxes. Do it the wrong way and you might end up
with a hefty capital gains tax bill and estate-planning headaches.
You can increase your chances of a successful sale if you coordinate
your efforts and work closely with a financial professional from the
very moment you start thinking about selling your business. A financial
professional, with the assistance of a qualified appraiser, can help you
place an accurate value on your business interest and provide the
critical insight and expertise needed to steer you through a complex and
Consider your potential buyers. Are you planning
to place your business on the market for anyone who's interested? Or, do
you want your business to stay within your family? If so, do family
members have the means to buy it? Might your senior managers or other
employees be interested in purchasing your business interest? Dealing
with succession issues early in the sale process is important. Once you
have, the next step is to determine the most advantageous way to sell
the business. Here's a brief overview of some of these options.
Stock versus Assets
While buyers may prefer to buy assets, if
you're selling an incorporated business, you generally can get a better
tax deal by selling stock. In the case of a business asset sale, you may
have to pay taxes twice – a corporate capital gains tax on the sale of
the assets (at the same rate as for the corporation's ordinary income)
and an individual income tax on any corporate distributions received by
the stockholders. Selling stock, instead, allows you, as a shareholder,
to pay tax only once, at the more favorable 15% capital gains rate.
There is no corporate level tax.
Owners of small businesses can get an even better deal. If you sell
your business interest as Qualified Small Business Stock (QSBS) and buy
other QSBS, you may be able to roll over your gain tax free. (Additional
requirements apply.) Alternatively, you can exclude 50% of the gain
from your taxable income if you held the stock for more than five years
and meet other tax law requirements. The remaining gain is taxed at a
maximum rate of 28%. In general, gain qualifying for the 50% exclusion
cannot exceed $10 million or 10 times the QSBS's base disposed of during
the year (whichever is greater).
With an installment sale, you ask the buyer for a
downpayment and a note covering the balance of the purchase price. You
report taxable gains as you receive payments from the buyer, rather than
all at once in the year of sale. You also must report the interest
payments you receive on the note as ordinary income. When correctly
structured, an installment sale can "freeze" the value of the business
at its sale price for tax purposes. So, if the business continues to
increase in value, your estate will not owe taxes on any appreciation
generated after the date of the sale.
Private Annuity Sale
Under this type of arrangement, the buyer of
your business agrees to make periodic payments to you for life in
exchange for your interest in the business. This approach guarantees you
a lifetime income and is taxable to you under special rules. Moreover,
the annuity arrangement removes the value of the business from your
estate for tax purposes.
To help maximize your financial return on the sale of your business,
consult a financial planning professional before you put your business
on the market.