1. Define what you are actually buying
Decide on sector, size and role before you look at listings. A $400k owner-operated trades business and a $6M distribution company are different jobs, not different price tags.
Set a realistic budget: total capital available, how much can go to the down payment, and how much must stay in the business as working capital after closing.
2. Get financing pre-arranged
Most Toronto acquisitions are funded with a blend: buyer equity, a Canada Small Business Financing Program or bank term loan, a vendor take-back note, and sometimes equipment or receivables financing.
Goodwill cannot be repossessed, so lenders price on cash flow and collateral coverage. Knowing your approved structure before you make an offer is what keeps a deal from dying at the financing condition.
3. Sign the NDA and read the CIM properly
Sellers release detail only under confidentiality. Expect a confidential information memorandum with three to five years of financials, a customer profile, staffing and lease terms.
Recast the earnings yourself. Seller's discretionary earnings and adjusted EBITDA both include add-backs — confirm every add-back is genuinely non-recurring or personal.
4. Price it against real market evidence
Main Street businesses in the GTA typically transact on a multiple of seller's discretionary earnings; middle-market companies trade on an EBITDA multiple that rises with size, recurring revenue and management depth.
Customer concentration, owner dependence, lease security and equipment condition move the multiple more than the headline revenue figure does.
5. Make a structured offer, not just a number
A letter of intent should set price, deal structure (asset vs share purchase), the diligence window, exclusivity, and how the seller stays involved through transition.
Asset purchases limit inherited liability; share purchases can preserve contracts, licences and tax attributes. In Ontario the choice affects HST, land transfer exposure and employee continuity — decide it with your accountant before the LOI, not after.
6. Run due diligence on the GTA specifics
Financial: bank statements against reported revenue, payroll records, WSIB standing, CRA account balances and HST filings.
Legal and regulatory: municipal business licensing with the City of Toronto, zoning and permitted use, AGCO liquor or gaming licences, TSSA equipment registrations, environmental history on industrial sites.
Commercial: lease assignment rights and remaining term (often the single biggest risk in a retail or restaurant deal), key customer contracts, and whether staff and management will stay.
7. Close and take over deliberately
Coordinate the landlord consent, financing advance, insurance, payroll transfer and supplier accounts to land on the same day.
Plan the first ninety days: how customers and employees are told, who holds the relationships, and what the seller's transition or training period actually covers in writing.