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.

08/12/2026

The best time to start was 12 months ago

The second-best time is today.

If you're an Ontario business owner planning a sale in the next 12–24 months — the preparation window is open right now.

Most owners wait until a buyer appears. By then, the leverage is gone.

The Ontario Exit Timeline Blueprint shows you exactly what to do, in what order, starting this week.

Free download. Link in the comments.

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08/11/2026

The 7-day quick start that puts you ahead of 90% of Ontario sellers going to market this year

Most Ontario sellers going to market this year will wait until a buyer appears. Then scramble.

Here's what the prepared 10% do in the first 7 days:

Day 1: Create the Exit Binder folder structure.
Day 2: Upload last 3 fiscal years of financials and last 12 months of monthly P&L.
Day 3: Export A/R and A/P aging. Flag every account over 60 days.
Day 4: Pull last 4 HST filings and payroll remittance confirmations.
Day 5: Start the normalized EBITDA bridge.
Day 6: List top 10 customers by revenue. Calculate concentration percentage.
Day 7: Book calls with your accountant and corporate lawyer.

Seven days. Ten actions. No large investment required.

Free blueprint in the comments.

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08/10/2026

12 months from now, you could be at the closing table — or you could still be getting ready

Two Ontario business owners. Same industry. Similar revenue. Both planning to sell.

Owner A started preparing 12 months ago.

Month 1: Exit Binder built. Month 2: EBITDA bridge complete. Month 3: Working capital calculated. Month 4: Compliance clean. Month 5: Contracts inventoried, lease reviewed. Month 6: SOPs written, KPI dashboard built. Month 7: Deal structure mapped. Month 8–9: Data room complete. Month 10: Pre-List Gate passed. Month 11: CIM built, buyer list of 27 ready. Month 12: LOI received.

Owner B is still thinking about getting ready.

The sequenced path is available to every Ontario business owner who decides to take it.

That's what the Ontario Exit Timeline Blueprint is.

Link in the comments.

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08/07/2026

Pass the gate before you go to market

Before you approach a single buyer, score yourself across five areas:

Financial Gate. Compliance Gate. Legal Gate. Transferability Gate. Data Room Gate.

If any one of them is incomplete — that's where a buyer will find leverage.

Fix it first. Go to market once. Go to market ready.

The Ontario Exit Timeline Blueprint includes the full Pre-List Gate scorecard in Month 10.

Free download in the comments.

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08/06/2026

The buyer list most Ontario sellers never build — and why it costs them

Most Ontario sellers answer "who would buy my business?" with two or three names and stop.

A well-built buyer list should have a minimum of 20 vetted names across four categories: strategic buyers, adjacent industry operators, private equity and search funds, and strategic unknowns outside your industry.

Why does the buyer list matter? Because a competitive process is the most powerful tool a seller has.

An owner with one interested buyer has no leverage.
An owner with five engaged buyers has significant leverage.
The buyer who knows there are other NDAs signed closes faster and concedes more.

Build the list in Month 11, before a single call is made.

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08/05/2026

Marketing a business is not posting it online

Marketing a business is controlled disclosure.

Teaser → NDA → CIM → Management Meeting → LOI.

Each step is a filter. Each step releases more information to a more qualified audience. Each step protects your confidentiality — and your negotiating position.

Buyers who receive a well-sequenced, professionally prepared package move faster and offer more.

Buyers who receive a rushed CIM with an incomplete data room slow down and negotiate harder.

The preparation is the marketing.

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08/04/2026

How to build a buyer list of 20 vetted names — before you talk to anyone

The single most powerful tool a seller has in an Ontario M&A process is a competitive buyer universe.

One interested buyer: no leverage.
Five engaged buyers: significant leverage.

Here's how to build a list of 20 vetted names:

Direct competitors — who would benefit most from your customer relationships, geography, or capability?
Adjacent operators — businesses that don't compete with you but would benefit from what you do.
Financial buyers — PE-backed search funds are active in Ontario for $1M–$5M EBITDA businesses.
Strategic unknowns — who outside your industry might want what you've built?

Twenty names. Each with a one-sentence rationale.

Build the list before any outreach begins.

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08/03/2026

Going to market too early is one of the most expensive mistakes an Ontario seller can make

An Ontario business owner, $6M in revenue, had listed their business three months earlier. Three buyers had signed NDAs. All three had gone quiet.

I asked to see the CIM and data room.

The data room was a folder on Google Drive with 23 documents, none organized, three named "Final Final 2023 v3." The EBITDA bridge had two add-backs with no documentation. The lease assignment clause required 90 days notice to the landlord.

The business had been marketed before it was ready.

Three qualified buyers, none of whom would come back.

Going to market too early doesn't just delay your sale. It burns your buyer pool.

The Pre-List Gate is Month 10. Before any buyer outreach begins, score yourself across five areas: Financial Gate. Compliance Gate. Legal Gate. Transferability Gate. Data Room Gate.

If you can't pass all five — don't go to market. Fix the gaps. Then go.

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07/31/2026

Your data room is ready before the LOI — or it costs you

The LOI arrives with a 45-day diligence window.

That's not 45 days to build your data room. That's 45 days to answer questions from a data room you've already built.

There's a version of this where you're scrambling, slow to respond, and giving a buyer reasons to question your credibility.

And there's a version where you send a link and everything they need is already there.

The Ontario Exit Timeline Blueprint covers both phases of data room construction — Months 8 and 9.

Free download in the comments.

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07/30/2026

Why employment agreements with IP clauses matter more than most owners realize

A software-adjacent business in Ontario had built proprietary workflow tools — automation built by two developers over three years.

The buyer's diligence team found something in the HR folder: no signed employment agreements with IP assignment clauses for those two developers.

The intellectual property of the company's most differentiated asset had never been formally assigned to the corporation.

The deal triggered legal work that delayed close by six weeks. A price reduction was negotiated. The developers had to sign retroactive IP assignment agreements.

The fix — done properly in Month 9 — would have taken an afternoon: standardized employment agreements for all key staff, IP assignment clauses as standard, confidentiality and non-solicitation included. Signed. Filed. Done.

If your business has any proprietary technology or client systems built by employees or contractors — this is not optional paperwork. It's valuation protection.

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Toronto, ON

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