Tax Planning before the Sale of your Business

Tax Planning before the Sale of your Business

In preparing to sell your business, the earlier the better applies. Some planning is best done years before:

  • Start with an appraisal to determine the most probable selling price (MPSP);
  • Identify drivers to increase the business’s value; and
  • Get advice from a tax lawyer or accountant to take advantage of available opportunities for paying no more tax than necessary.

I have asked Jay Humphrey of Jay C. Humphrey Professional Corporation to comment upon one of the meaningful tax benefits available to owners of small businesses – the lifetime $830,000 capital gains exemption on the sale of shares of a qualifying small business corporation.


While the tests for determining whether a sale of shares does or does not qualify for the exemption are technical, a rule of thumb is that the corporation must be operating an active, rather than passive, business and the assets owned by the corporation at the time of sale must generally be assets used in the active business.

A corporation’s stock portfolio acquired with retained earnings would typically be seen as “passive” assets, while inventory and equipment would be considered to be “active” assets. It is possible to clean up a non-qualifying corporation prior to the sale so that the seller can nonetheless qualify for the capital gains exemption.

“It is key to remember that only individuals (including as beneficiaries of certain trusts) can qualify for the exemption, notes Humphrey. “If there is a holding company between the operating company and the ultimate owner, the sale could only qualify if the individual sold shares of the holding company which in turn owns the operating corporation. The problem is that holding companies often hold passive or other assets that the business owner does not want to sell and that the buyers do not want to buy.”

“There are structures that may allow an owner to obtain the $830,000 exemption and also enjoy the benefits of a holding corporation, including creditor-proofing and the payment of tax-deferred corporate dividends out of the operating corporation. Business owners should speak with their advisers to see if such a structure is appropriate in their particular circumstances”.

There is usually a 24- month hold rule to claim the capital gains exemption, with a notable exception. An entrepreneur selling an unincorporated business may claim the lifetime $830,000 capital gains exemption on the sale of shares of a qualifying small business corporation by first transferring their business to a corporation and then selling their shares of that corporation.

Claiming a capital gains reserve

A seller who accepts a promissory note for a portion of the purchase price payable over a number of years should be able to claim a capital gains reserve so that the timing of the obligation to pay income tax on the portion of proceeds not yet received is matched with the actual receipt of cash. The capital gains reserve rules require a minimum of 20% of the capital gain to be recognized in the year of sale and the four following years. Keep in mind that the test in the reserve rules is not that an amount has not actually been received, but that it is not yet payable. If the note that a vendor takes back is payable on demand without any restrictions, no reserve would be available as the Canadian Revenue Association (CRA) would argue the whole amount is immediately payable.

From a buyer’s perspective

From a buyer’s perspective, give careful consideration to using a newly incorporated corporation to acquire the shares of a target corporation. If you buy the founder’s shares which had an initial subscription cost of one hundred dollars, which is often the case, only that amount will be allowed to be repaid to you tax-free from the target corporation even though your cost to purchase the shares was their current market value.

“Using a new corporation to acquire the target should allow the tax-free removal of retained earnings of the target in amounts up to the purchase price through inter-corporate dividends to the new corporation and then a return of capital or debt to the owner of the new corporation”, said Humphrey.

Next issue we will focus on the Canada Small Business Loan program, which finances asset purchases rather than share purchases The program is at odds with the capital gains exemption, which requires a sale of shares, and so we will consider approaches that attempt to bridge that gap. Why these two federal programs work directly against one another I do not know, but proper structuring may assist in finding a solution that is the best compromise for buyer and seller.

by Greg Kells