Business listings are written by people who want to sell you a business. Nothing wrong with that, but it means your protection is not in the listing. It is in your questions, asked in roughly this order, before your deposit goes anywhere.
About the money
1. Can I see three years of financial statements and tax filings? Not a spreadsheet summary. Statements, and the filings that match them. Hesitation here ends the conversation.
2. What does the owner actually take home? You're buying seller's discretionary earnings, not the net profit line. Our valuation guide explains the add-backs; make the seller walk you through theirs, item by item.
3. How much revenue is cash, and can any of it be proven? Unprovable revenue is not revenue you should pay for. Full stop.
4. What happens to sales when the owner goes on vacation? The honest answer tells you how much of the business is the business, and how much is the person you're replacing.
About the lease
5. How long is left, and what are the renewal terms? Around Markham's plazas this question is the deal. A thriving shop with fourteen months of lease and no renewal option is a countdown, not an asset.
6. Does the landlord have to approve the transfer, and on what terms? Start this conversation early. Landlords can slow-walk assignments, and some use them to reopen the rent.
About the people
7. Who are the key employees, and do they know? If the kitchen manager or lead technician walks the week after closing, what exactly did you buy? Understand tenure, pay, and whether anyone essential is close to leaving.
8. Is any revenue concentrated in a few customers? One client at forty percent of sales is a risk you price in, or walk from.
About the seller
9. Why are you really selling? Retirement is common and often true, given how much of Canada's business ownership is heading for the exit. But cross-check the story against the trend line. People rarely retire from businesses that are getting easier and more profitable every month.
10. Will you stay for a transition, and for how long? A seller who refuses any handover period is telling you something.
11. What would you fix first if you were staying? Asked casually, this produces more truth than any document request.
12. Are there any debts, disputes or obligations that follow the business? Then have your lawyer verify the answer independently. That is not distrust; it is the process working. This is exactly the stage where the professionals earn their fees, and where a local business lawyer and accountant stop being optional.
Browse what's currently on the market in Markham & Richmond Hill businesses for sale, and take the questions with you.
About the Author
Guides & Lifestyle Editor
Daniel Tremblay was born and raised in Markham and has spent his career writing about outdoor recreation, civic life, and community resources across York Region. An avid hiker and trail runner, he has personally walked nearly every public trail in the Rouge National Urban Park and the York Regional Forest. His guides aim to give residents practical, on-the-ground information about the places, services, and routines that shape daily life in Markham and Richmond Hill.
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