John McCubbin

John McCubbin Exits. Capital. Structured outcomes. Most entrepreneurs only go through one exit in their life. Raven Capital operates inside that cycle.

That makes it high-stakes, complex, and far too often — poorly structured. I work at the intersection of business exits, capital formation, and private market deal execution. Through Raven Capital, my role is to bring clarity, structure, and execution discipline to that process — so decisions are made cleanly, tax leakage is minimized, and value is not left on the table. Alongside exit advisory, I work with deal sponsors and operators raising capital for real estate and real asset opportunities. These are typically proven operators who need structure, investor alignment, and execution support to move from opportunity to funded deal. There is a capital cycle that sits underneath everything I do:



Create value → structure it → realize it → redeploy it. I typically work in two scenarios:



Business owners preparing for exit or transition who want to maximize value, reduce tax leakage, and avoid costly structural mistakes during a once-in-a-lifetime liquidity event. Deal sponsors and operators with validated opportunities who need capital structure, investor coordination, and execution support to bring deals to completion. This is not passive advisory work. It is active involvement in structuring outcomes that move capital. Unclear situations are diagnosed. Complexity is reduced into decisions. Value is captured and protected. Then capital is redeployed with intent. Faith shapes my personal operating principles around integrity, stewardship, and accountability — but the work itself is grounded in outcomes: better exits, better structures, and better capital deployment. If there is one consistent theme, it is this:



When structure is right, capital moves cleanly. When capital moves cleanly, value compounds. What we say will happen, happens.

09/15/2026

12 contractors. $380,000 in modelled CPP/EI exposure. One very difficult diligence conversation.

A buyer's tax diligence team was reviewing an Ontario professional services business.

The company had 12 contractors working with them for an average of 26 months. Each was paid monthly by e-transfer. None had formal written contracts. Several used company-supplied equipment. Two had email signatures with the company domain.

The buyer's counsel flagged all 12 for contractor misclassification risk. Their analysis: if CRA were to reclassify these workers as employees, the retroactive CPP and EI contributions — plus penalties and interest — could represent up to $380,000 in exposure.

The deal was restructured. A specific indemnity was added. The escrow was $180,000, held for 24 months.

Here's the test a buyer's team applies to every contractor relationship: long-term exclusive arrangement, employer-supplied tools, fixed hours, paid regularly like a salary, company email address — all misclassification risk signals.

The fix — done properly in advance: written subcontractor agreements, HST registration numbers collected, insurance certificates on file, proper invoices for every payment, documentation of independent business indicators.

None of that is expensive. All of it is standard practice. But it has to be done before a buyer's team arrives.

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09/14/2026

HST is the most-tested area in Ontario M&A diligence

If there's one area where Ontario sellers consistently underestimate buyer scrutiny, it's HST.

It's transactional. It's traceable. It's easy to test against your invoices and GL.

And incorrect HST treatment — overcharging, undercharging, weak ITC support, out-of-province classification errors — is one of the most common triggers for escrow demands in Ontario private sales.

The Hidden Tax Traps Guide covers HST errors in detail — including exactly how to build a reconciliation package that holds up under buyer scrutiny.

Free download. Link in the comments.

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09/11/2026

How to HST-proof your business before going to market

HST/GST diligence in an Ontario M&A transaction has four components. Most sellers have addressed none of them before they go to market.

1. Revenue stream mapping. Map every revenue stream to its correct HST treatment — taxable, exempt, or zero-rated. Confirm place-of-supply rules for out-of-province clients.

2. Invoice testing. Pull 20–30 invoices from different periods. Does each show your HST number? The correct rate? The tax amount separately stated?

3. ITC support. For every significant ITC claimed, make sure you have the supplier invoice and documented business purpose. For mixed-use items, confirm the personal-use percentage is calculated and applied consistently.

4. GL reconciliation. Reconcile your HST returns to the general ledger and financial statements. The tie-out should be clean and explainable. Document any differences with a written explanation.

A seller who has done this work in advance hands the buyer a clean HST reconciliation package on Day 1 of diligence.

A seller who hasn't spends three weeks answering questions under pressure and negotiating holdbacks.

The time to do this is now.

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09/10/2026

Four words that protect your HST position

"Here's our reconciliation package."

Four words that change the tone of an HST diligence conversation.

When you can hand a buyer's tax team a clean, organized package — revenue stream mapping, GL reconciliation, ITC support, invoice samples — before they ask for it, you signal something important:

This is a well-run business. There is nothing to find here.

That signal is worth money. Every item a buyer has to dig for erodes their confidence and increases their appetite for escrow protection.

Build the reconciliation package before the LOI.

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09/09/2026

The ITC problem most Ontario owners don't see coming

Input Tax Credits are legitimate and valuable. But in M&A diligence, ITCs are one of the most-tested items on the buyer's checklist.

The rules around ITC eligibility are specific: you need a valid supplier invoice, the invoice must show the supplier's HST registration number, the invoice must show the tax amount separately, and the expense must have documented business purpose.

For mixed-use items — a vehicle used partly personally, a home office, a phone — the personal-use portion disqualifies that portion of the ITC.

If a buyer's team finds ITCs claimed without valid invoices, or ITCs on items with undocumented business use — that's an exposure item.

Test 20–30 of your largest ITC claims before any buyer does.

09/08/2026

The out-of-province revenue problem that triggered a $140,000 escrow demand

An Ontario service business had grown to serve customers across Ontario, Quebec, and British Columbia.

When the buyer's tax team ran their HST review, they found something the seller's accountant had never flagged: the business had been charging Ontario HST — 13% — on services delivered to customers in Quebec and British Columbia. The correct treatment? GST only — 5% — for out-of-province customers under place-of-supply rules.

The buyer's position: "We can't quantify this exposure. It could trigger reassessments, client complaints, or refund demands. We need protection."

The result: a $140,000 escrow holdback, to be released 24 months after closing.

The fix — done 12 months earlier — would have been a revenue stream mapping exercise with a tax advisor. One afternoon of work.

Proactive disclosure with a documented plan is infinitely more valuable than a buyer discovering the issue on their own.

When you disclose proactively, you control the narrative.
When a buyer discovers it, they control the escrow.

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09/04/2026

The CRA Status Summary — one page that protects your price

There's one document that consistently reduces buyer anxiety about tax history:

A one-page CRA Status Summary.

Filed periods. Last assessed date. Current balance. Any open items and their status.

One page. For every program account. Prepared by your CPA. Filed in your diligence binder before any NDA is signed.

It signals that you run a tight operation. It answers the question before it's asked. And it removes one of the most common triggers for expanded indemnity language in the purchase agreement.

The Hidden Tax Traps Guide covers how to prepare it — and the other 16 traps. Free download in the comments.

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09/03/2026

The 4-step CRA cleanup that takes less time than you think

One of the most consistent themes in Ontario M&A diligence: sellers are surprised by what shows up on their CRA accounts.

Here's the four-step cleanup and how long each step actually takes.

Step 1: Pull CRA statements of account for every program account. (30 minutes)
Log into CRA My Business Account. Download statements for T2, GST/HST, PD7A payroll, T4/T4A. Look at the balance, last assessed period, and any arrears.

Step 2: Confirm filing status for every period. (1–2 hours with your CPA)
No period should be outstanding or unassessed.

Step 3: Reconcile any discrepancies. (Varies)
Confirm all payments have been applied to the correct period. Find any surprises now — not when the buyer's team finds them during diligence.

Step 4: Document the cleanup. (1 hour)
Keep payment confirmations and filed return confirmations in your Diligence Binder. Create a one-page CRA Status Summary.

Total time for a typical business with clean filings: 3–4 hours. Dramatically less painful than a 36-month tax indemnity negotiated under deal pressure.

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09/02/2026

Payroll arrears — even small ones — are a hard stop for some buyers

Payroll source deductions are considered "trust" amounts by CRA. Directors can face personal liability for unremitted source deductions in certain circumstances.

This means a buyer moving to exclusivity who sees payroll arrears — even small ones, even from two years ago — may treat them as a deal-structure issue, not just a cleanup item.

The solution: reconcile your payroll remittances to your T4 summaries and the general ledger for the last 24 months. Confirm no gaps, late filings, or outstanding balances.

Do it now. Not after the LOI.

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09/01/2026

What 'filed' and 'assessed' mean — and why the difference matters

Most Ontario business owners assume that once a tax return is filed, it's done.

In M&A diligence, there's a meaningful distinction:

Filed means you submitted the return.
Assessed means CRA has reviewed it and confirmed the balance.

A return that's been filed but not yet assessed is an open item from a buyer's perspective. They don't know if CRA will assess it as filed — or reassess it at a higher amount.

In a share sale, that uncertainty belongs to the buyer after closing. So they protect themselves. Broader indemnity. Longer survival period.

Confirm your filings are assessed — not just submitted. Pull your CRA statements of account and verify.

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Toronto, ON

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