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The MacTax with R. Duncan MacPherson, CPA

@themactax

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Specializing in 🇺🇸U.S.- 🇨🇦Canada tax services
We work with accounting firms and corporate owners in optimizing tax positions in Canada

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A deal can look fantastic on paper and start falling apart the minute due diligence gets serious.

That’s something I’m seeing more of in 2026.

Buyers are cautious. Capital is more selective. And when a Canadian acquisition involves messy documentation, questionable filing positions, or cross-border tax exposure that nobody can clearly explain, confidence in the deal can disappear quickly.

For sellers, that means your paperwork needs to support the story your financial statements are telling.

For U.S. buyers, it means knowing exactly what you’re acquiring before you inherit it.
→ Are the Canadian filings clean?
→ Can intercompany transactions be supported?
→ Is there hidden withholding, payroll, or GST/HST exposure?
→ Does the acquisition structure make sense after the deal closes?

Cross-border due diligence isn’t paperwork for paperwork’s sake. It can affect valuation, deal terms, purchase price adjustments, and whether the transaction gets done at all.

If you’re buying or selling a Canadian business, book a no-cost Cross-Border Tax Strategy Session. We’ll review the deal structure, diligence concerns, and potential tax exposure while there’s still time to address them.

#CrossBorderMA #TaxDueDiligence #CanadianAcquisitions by @themactax

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20 days ago

For CFOs, the most valuable tax conversations happen before the decision is finalized.

When your company is growing across the U.S. and Canada, tax can influence decisions far beyond compliance.

→ How you deploy capital
→ How you finance expansion
→ How cash moves between entities
→ How an acquisition should be structured
→ Where cross-border risk may be developing

The challenge is that many of these decisions happen quickly. By the time tax enters the conversation, contracts may be signed, money may already be moving, and some of the best planning options may be off the table.

That’s why I encourage CFOs to bring cross-border tax into the conversation earlier.

You want to understand the tax implications while you still have choices, not when you’re trying to unwind a decision that’s already been made.

If your company is operating in Canada, expanding there, or considering a cross-border transaction, book a no-cost Cross-Border Tax Strategy Session.

We’ll look at your current situation, where you’re headed, and the tax risks and planning opportunities worth addressing before your next major financial decision.

Comment “TAX STRATEGY” below to get started.

#CFOLeadership #CrossBorderTaxStrategy #USCompaniesInCanada by @themactax

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21 days ago

For CFOs, tax gets a lot more interesting when it stops being a year-end exercise.

When you’re responsible for the financial health of a growing company, especially one operating across the U.S. and Canada, tax starts showing up in decisions you’re already making:

→ Where should we deploy capital?
→ How should we finance our Canadian operations?
→ What does an acquisition do to our overall tax position?
→ How should cash move between entities?
→ Does our current structure still make sense for where we’re headed?

These aren’t questions you want answered after the deal is signed or the expansion is already underway.

I’ve seen the role of tax change considerably over the years. The strongest CFOs are bringing tax into the conversation early enough that it can actually inform the decision.

That means having a clearer picture of:

✓ Cash flow implications
✓ Cross-border tax exposure
✓ Financial and compliance risk
✓ Capital allocation opportunities
✓ The true economics of a transaction or expansion

Because for a CFO, the question shouldn’t simply be:
“What will this cost us in tax?”

It should also be:
“How should we structure this decision so it supports where the business is going?”

That’s where tax becomes a strategic function.

#CFOLeadership #CrossBorderTaxStrategy #StrategicTaxPlanning by @themactax

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22 days ago

How you fund your Canadian operation matters more than many companies realize.

Let’s say your U.S. parent needs to put additional capital into Canada. Do you fund it through debt? Equity? An intercompany loan?

On the surface, each option accomplishes the same thing: getting money into the Canadian business.

From a tax perspective, they can produce very different results.

The structure can affect interest deductibility, withholding taxes, cash flow, intercompany reporting, and eventually how efficiently you can move money back across the border.

This is why financing shouldn’t be decided in isolation by simply choosing whatever gets the cash there fastest.

When I’m looking at a cross-border structure, I want to understand where the company is going, how the Canadian operation is expected to grow, and what leadership may want to do with that capital later.

Because the question isn’t only “How do we fund Canada?”

It’s also “What does this decision mean for us two or three years from now?”

That’s a much more useful conversation to have before the money moves.

If you’re funding or expanding Canadian operations, it’s worth understanding the tax impact before the money moves.

Book a no-cost Cross-Border Tax Strategy Session and let’s review your current structure, financing plans, and potential opportunities across both sides of the border.
Comment “TAX STRATEGY” below to get started.

#CrossBorderTaxStrategy #USCompaniesInCanada #InternationalTaxPlanning by @themactax

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23 days ago

There’s a point in a company’s growth when tax can’t just be something the accounting team handles at year-end.

Especially when you’re operating across borders.

As your business expands into Canada, the decisions your executive team is already making, where to invest, how to structure operations, how money moves between entities, where people are hired, can all create tax consequences.

That’s why I think there’s one tax conversation every leadership team should be having regularly:

Does our current tax strategy still support where this business is going?

Not where it was two years ago. Where it’s going next.

Are you structured properly for the next stage of growth? Do you understand where cross-border exposure is developing? Is tax being considered before major decisions are made? And does everyone involved, finance, legal, operations, leadership, know when tax needs to be brought into the conversation?

These are much better questions to ask in a strategy meeting than after CRA or the IRS sends a letter.

For larger companies, good tax governance gives leadership better information before committing capital, entering markets, making acquisitions, or changing operations.

Tax may be complicated, but the executive question is pretty straightforward: Is our tax strategy keeping up with our business?

#TaxGovernance #CrossBorderTaxStrategy #InternationalTaxPlanning by @themactax

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24 days ago

Growth changes the financial conversation.

When you’re entering a market like Canada, it’s easy to focus on what the expansion will cost today: people, operations, infrastructure, compliance.

But I think the better question is:

Will the financial decisions we’re making today give us more options as we grow, or fewer?

The right structure can help preserve cash flow, make it easier to reinvest profits, support future acquisitions, and give leadership more flexibility when new opportunities arise.

That’s why I’ve always viewed tax and financial planning as part of the growth strategy, not something that happens after the numbers are in.

A good strategy protects what you’ve already built.
A great one gives you room to build what’s next.

#CrossBorderTaxStrategy #CanadaBusinessExpansion #FinancialStrategy by @themactax

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a month ago

A Canadian acquisition can look great on paper and still come with tax problems you won’t discover until after closing.

I’ve seen U.S. buyers spend enormous amounts of time analyzing EBITDA, valuation, and growth potential while some very important questions get far less attention.

Are the GST/HST filings clean?
Are intercompany charges properly documented?
Is there withholding or payroll exposure sitting in the background?
And perhaps most importantly, are you buying the company in a structure that actually makes sense from both sides of the border?

Once the deal closes, your negotiating leverage changes considerably.

That’s why I tell U.S. acquirers to treat tax diligence as part of the deal economics, not simply another compliance box to check.

If we uncover $500,000 of potential tax exposure before closing, that information can affect the purchase price, representations, indemnities, or even the structure of the transaction.

Find it afterward, and you may have simply inherited a very expensive problem.

If you’re considering acquiring a Canadian company, bring your cross-border tax advisors into the conversation while you still have options.

#CrossBorderMA #TaxDueDiligence #CrossBorderTaxStrategy by @themactax

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a month ago

The finance leaders I talk to are asking different questions about cross-border growth than they were a few years ago.

They’re looking beyond, “Are we compliant?”

They want to know how tax decisions will affect cash flow, capital allocation, financing, an acquisition, or the next phase of expansion.
And that makes sense.

Once a company is operating across the U.S. and Canada, decisions around entity structure, intercompany transactions, financing, and where capital is deployed start affecting much more than the tax return.

They can influence how efficiently the business operates and how much flexibility leadership has when the next opportunity comes along.

That’s why I’m seeing tax brought into strategic conversations earlier, particularly among companies with ambitious growth plans.

There will always be compliance work to do. But the real value comes when tax planning helps leadership make a better business decision before the decision is made.

If your company is growing across the U.S. and Canada, when does your tax team typically enter the conversation, before or after the strategy has already been decided?

#CrossBorderTaxStrategy #FinanceLeadership #InternationalTaxPlanning by @themactax

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a month ago

It’s easy to think of your Canadian operations as a separate tax issue.

The IRS may see things differently.

When a U.S. company operates in Canada, decisions made north of the border can influence the company’s U.S. tax position too, including foreign tax credits, intercompany transactions, financing, and how profits move between the two countries.

This is where cross-border planning gets complicated. A decision that makes sense from a Canadian tax perspective may create an unexpected consequence in the U.S., and vice versa.

After more than 30 years working on both sides of the border, this is one of the things I remind companies of constantly: you have to look at the entire picture.

If you’re operating in Canada and aren’t sure how your current structure is affecting your overall tax position, let’s take a look at it together.

Drop “TAX STRATEGY” below or DM me to book a no-cost Cross-Border Tax Strategy Session to review your current structure, identify potential exposure, and uncover planning opportunities across both countries.

#CrossBorderTaxStrategy #USCompaniesInCanada #InternationalTaxPlanning by @themactax

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a month ago

Growth into Canada can look great on a spreadsheet.

Then the business actually starts growing.

More transactions. More reporting. More money moving across borders. More decisions involving finance, tax, operations, and compliance.
That’s where finance leaders need to think beyond “How do we enter Canada?” and start asking “Will the way we’re building this actually scale?”

I’ve seen companies create structures that work perfectly well for the first stage of an expansion, but become cumbersome once revenue grows and the Canadian operation becomes more sophisticated.

A scalable strategy considers the next stage from the beginning: how the operation is financed, how cash moves, whether your systems can support cross-border reporting, and who owns the decisions as complexity increases.

You don’t have to predict exactly what the Canadian business will look like five years from now.

But you should build it in a way that gives you options when you get there.

Getting into Canada is one milestone. Building an operation that can grow there without creating unnecessary financial friction is the bigger goal.

#CrossBorderTaxStrategy #CanadaBusinessExpansion #InternationalTaxPlanning by @themactax

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a month ago

The most expensive time to start thinking about tax is after the business decision has already been made.

I see this more often than you might think.

A company enters Canada, signs the agreement, moves money between entities, hires employees or restructures operations. Then someone asks:

**“What are the tax implications?”**

There may still be options, of course. But there are usually a lot more options before the transaction happens.

For companies operating across the U.S. and Canada, tax can influence how you structure an investment, deploy capital, manage cash flow, price intercompany transactions, and ultimately bring profits back home.

That’s why I prefer to be involved while the strategy is still being discussed, when we can actually evaluate different paths rather than simply calculate the tax consequences of a decision that’s already been made.

Your tax advisor shouldn’t always be the person you call after the fact.

**Sometimes the most valuable question they can answer is, “What happens if we do it this way?”**

#CrossBorderTaxStrategy #StrategicTaxPlanning #InternationalTaxPlanning by @themactax

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2 months ago

As companies grow, tax has a funny way of showing up in places you didn’t expect.

You open another entity. Enter a new market. Move money between subsidiaries. Consider an acquisition. Change how you compensate people.

Individually, each decision may seem manageable.

But once you’re operating across the U.S. and Canada, those decisions start interacting with each other, and that’s where **tax governance** becomes much more than a compliance exercise.

A strong tax governance framework gives leadership a consistent way to evaluate decisions before they’re made. Who needs to be involved? What are the cross-border implications? What needs to be documented? How does this affect cash flow, risk, and the company’s longer-term plans?

For larger, growing businesses, that discipline can become a genuine competitive advantage.

You’re able to evaluate investments with better information, move into new markets with fewer surprises, and make decisions knowing someone has considered how the pieces fit together.

After more than 30 years working in cross-border tax, I’ve found that the companies that handle complexity best aren’t trying to eliminate it.

**They’ve simply built a better way to manage it.**

And as your business grows, that becomes increasingly valuable.

#TaxGovernance #CrossBorderTaxStrategy #CorporateTaxPlanning by @themactax

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2 months ago