What the work
looks like.

An entrepreneur had built a portfolio of seven quick-service restaurant locations across four operating companies over fifteen years. Every dollar of profit — from operations, real estate, and investments — sat inside the operating companies. There was no holding company, no family trust, no estate freeze. If a lawsuit hit one location, it could reach the assets of all four corporations. If the owner died, the entire $27 million in value would be taxed on the terminal return — a potential tax bill exceeding $7 million.

The accountant knew something needed to be done but did not have the capacity to design or implement a restructuring of this complexity. The file was referred to Cedar Group.

We designed a reorganization involving four butterfly transactions to separate non-business assets from the operating companies, ten estate freezes to lock in the current value of every entity, a new holding company to consolidate investment assets, and a family trust to multiply the lifetime capital gains exemption across five family members. The entire restructuring was coordinated across eleven entities — tax, legal, and valuation working from the same table.

A husband and wife built a manufacturing business over 25 years. It was worth $7.1 million. They wanted to sell — not to an outsider, but to their daughter and a long-time employee, each taking 50%.

This is the kind of deal that sounds simple until you look at the tax. Because the daughter was not at arm's length with her parents, the sale triggered a rule called section 84.1 — which could have converted the entire capital gain into a taxable dividend, more than doubling the tax rate on the proceeds. The parents also wanted to use their lifetime capital gains exemption, which required a pre-close reorganization to crystallize the exemption before the shares changed hands.

We built a multi-tab deal model covering every step of the reorganization: stock dividend for LCGE crystallization, section 85 rollovers into new holding companies, an intercorporate dividend to extract retained earnings tax-efficiently, and a structured closing sequence that satisfied both buyer and seller counsel. The total model coordinated six entities, two law firms, and a 14-step reorganization sequence.

When a founder died, she held shares in two private companies worth a combined $2.3 million. Canadian tax law treats death as if you sold everything at fair market value — her terminal tax return owed tax on the deemed capital gain. Then, when the estate tried to get the money out of the corporations, it would be taxed again as a dividend. Two layers of tax on the same money. The estate was facing over $400,000 in total tax.

There is a solution — called a post-mortem pipeline — but it has to be implemented within one year of the date of death. The accountant handling the estate knew about the pipeline but had never executed one. He referred the file to us with eight months remaining on the clock.

We modeled the three layers of tax (terminal return, dividend to estate, corporate tax on underlying assets), identified the optimal pipeline structure, and coordinated the implementation — including a loss carryback election and a capital gains bump on the real property. The duplicate tax was eliminated entirely.

A chiropractor was selling the shares of her professional corporation to a buyer. The deal was straightforward — until we looked at the balance sheet. Her father had loaned the corporation $200,000 when she first bought the practice, and she had personally contributed another $15,000 over six years. Neither loan was properly documented. The father wanted to forgive his loan before the sale closed.

Forgiving a shareholder loan has tax consequences. If done incorrectly, the $200,000 forgiveness could be taxed as income to the corporation, and the father would lose the ability to claim a capital loss. The sale was weeks away. Her own accountant flagged the issue but did not know how to resolve it in time.

We restructured the loan treatment before closing — ensuring the forgiveness was handled in a way that avoided the income inclusion, preserved the father's loss position, and did not create a surprise for the buyer's due diligence team.

A technology company had not filed its GST/HST return for four years. The company had $580,000 in input tax credits sitting on the table — but under the Excise Tax Act, ITCs expire if not claimed within four years of the reporting period. The deadline was literally the next day.

To make things more complicated, the company was already under an active GST audit by the CRA. Filing a four-year-late return during an active audit is high-risk — it invites scope expansion and additional scrutiny.

We filed the return electronically on the last possible day to preserve the ITCs. We then developed a strategy for the remaining outstanding returns: filing them through the CRA's Voluntary Disclosures Program to minimize penalties, while preparing the client for the upcoming audit interview with fully reconciled books.

A real estate investor with five rental properties held everything inside one corporation. He wanted three things: protect the properties from a potential lawsuit against his dental practice, reduce the tax his family would pay when he eventually sold or passed away, and start splitting income with his spouse and children.

His accountant handled the annual compliance but had never designed a reorganization. He came to us after hearing about estate freezes on The Advisors Table Podcast.

We incorporated a holding company, rolled the investment assets out of the operating corporation on a tax-deferred basis, established a family trust with his spouse and three children as beneficiaries, and completed an estate freeze — locking in the current value of the business at today's amount. All future growth accrues to the trust and the next generation. We also reviewed his life insurance to ensure he had enough coverage to fund the tax bill on death, and explained how a post-mortem pipeline could eliminate the duplicate tax when the time comes.

A Canadian resident received a $268,000 distribution from an offshore trust administered by a global bank. He did not report it on his personal tax return — he believed the distribution was a tax-free return of capital. CRA's foreign source matching program flagged the amount and sent a letter: explain or we reassess.

The issue was not whether the money was taxable — it was what kind of money it was. Trust distributions can be capital (tax-free), income (fully taxable), or a mix, depending on how the trust documents characterize them. The bank's confirmation letter confirmed CRS reporting was completed but did not clarify the character of the distribution. Without that classification, CRA would default to treating the full amount as income.

We analyzed the trust deed, the distribution records, and the section 94 non-resident trust rules to determine whether the trust was deemed resident in Canada. We then prepared the response to CRA with a characterization of the distribution supported by the trust documentation and the relevant sections of the Income Tax Act.