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№ 389 Case Study — Buying & Selling a Business

Old supplier invoices almost cost Lorna her buyer

A two-year-old billing dispute with a supplier surfaced during due diligence on Lorna's Brantford business, and the real fix turned out to have nothing to do with a courtroom.

Buying & Selling a Business9 min readBrantford, OntarioClearing disputes before marketing
All Buying & Selling a Business case studies
ClientLorna, selling her Brantford cleaning-supply distribution business after a health diagnosis
The issueA two-year-old unresolved supplier invoice dispute was flagged during the buyer's due diligence and threatened to derail the sale
ServiceReviewed the payables, negotiated a settlement with the supplier, and documented a release the buyer could rely on
ResolutionThe dispute was closed and the sale completed, but Lorna gave up a real amount of money and eight weeks she did not have to spare

The situation

By the time Lorna called our office, thirty-four thousand dollars in disputed supplier invoices had been sitting untouched on her payables ledger for close to two years, and the accountant working for her prospective buyer had just found every one of them. The buyer's team would not put anything in writing until the dispute was resolved, and Lorna had roughly eight weeks before a scheduled heart procedure that made the timing of any sale close to non-negotiable. She had not planned for the invoices to matter to anyone but her and her supplier. Now they were the reason her sale might not close in time, and every day spent arguing about the past was a day she did not have to spare before her surgery.

Lorna had run a small janitorial and cleaning-supply distribution business out of a Brantford warehouse unit for eleven years, selling mop heads, degreasers and paper stock to office cleaning contractors across the region. It was a modest business, worth somewhere in the low-to-mid six figures on a good day, but it was the thing she had built on her own after a divorce left her starting over in her forties. Until a cardiac diagnosis six months earlier, she had no plan to sell it at all.

The dispute went back to a shipment from one of her larger suppliers, a wholesaler run by a man named Rajesh, whose company had billed her twice for a container of paper products after a warehouse mix-up on his end. Lorna had refused to pay the duplicate invoice. Rajesh had refused to withdraw it. For two years, neither side did much more than exchange the occasional terse email, and it cost Lorna nothing while the business stayed hers. An unpaid, disputed invoice sitting quietly on a ledger has no real consequence for a business that is not being sold.

That changed once she found a buyer. Anjali, a delivery courier looking to leave shift work behind, was buying the business together with her husband, a factory technician who had spent years wanting to run something of his own. Anjali's accountant flagged the standing dispute during a routine review of the payables and would not sign off on the deal without a resolution. What had cost Lorna nothing for two years was, all at once, standing between her and a sale she needed to close before her surgery.

What the review found

We started by asking Lorna for every piece of paper connected to the dispute: the original invoices, the duplicate, her email exchanges with Rajesh, and her own accounting records showing what had actually been received against what had been billed. The picture that emerged was not complicated. Rajesh's company had genuinely shipped one container of paper stock, but a warehouse error on his end had generated two invoices for it, and neither he nor Lorna had ever sat down to compare the shipping records against the billing records properly. It was a bookkeeping mistake dressed up as a two-year standoff.

That mattered, because it meant Lorna was almost certainly right that she did not owe the second invoice, but it also meant this was never a dispute that needed a courtroom to resolve. A lawsuit over thirty-four thousand dollars in a business sale worth a few hundred thousand would likely have taken most of a year and cost a meaningful fraction of the disputed amount in legal fees on both sides, money and time Lorna did not have with a surgery date on the calendar.

The review also turned up a second, smaller problem. Because the dispute had sat unresolved for so long, it was unclear from the paperwork alone whether Rajesh's company still considered the account open, or whether some informal understanding between him and Lorna had quietly settled it years earlier without anyone writing it down. That ambiguity was its own risk for a buyer, because an open account with no documented resolution can resurface as a claim against the business long after the sale closes, regardless of who was actually right about the underlying invoice.

What the review told us, in short, was that Lorna did not need to win an argument about who owed what. She needed a clean, written resolution that a buyer's lawyer could look at and be satisfied the account was closed for good. That reframed the whole problem, from a fight Lorna might eventually win in principle to a piece of paper she needed in hand within eight weeks.

There was one more thing the review surfaced, and it was the piece that ultimately shaped our advice more than the dollar figure did. Rajesh's company was not a large one, and pushing him toward formal legal proceedings over an amount that a fuller reconciliation would likely reduce substantially risked turning a minor supplier into a hostile witness in the middle of a due diligence process, at exactly the moment Lorna needed her supplier relationships to look stable on paper. A buyer reviewing a business for sale reads an active lawsuit against a current supplier as a warning sign about the seller's operations generally, independent of who is actually in the right. Avoiding that appearance was worth almost as much to the sale as resolving the dispute itself.

What we did

  1. Requested Rajesh's own shipping and billing records directly. Two years of letters between Lorna and Rajesh had gone nowhere partly because each side was arguing from its own version of events, so rather than continue that pattern, we asked his company directly for its warehouse logs and invoicing history for the shipment in question. Working from his own paperwork rather than Lorna's let us show, in a way he could not easily dispute, that only one container had actually gone out despite two invoices being generated against it.
  2. Calculated the true amount actually owed, if any. The thirty-four thousand dollars on Lorna's ledger was a disputed total, not a proven one, and treating it as real would have meant negotiating from a weaker position than the facts supported. Once the shipping records were compared line by line against payments Lorna had already made, the account turned out close to even, with only a small residual amount genuinely outstanding on either side, far less than the figure sitting on the books for two years.
  3. Opened a direct settlement conversation with Rajesh's company instead of threatening litigation. Given the size of the true dispute and the time pressure Lorna was under, we called Rajesh's office and proposed a straightforward cash settlement to close the account, framing it as a practical fix both sides had avoided for two years rather than a legal fight either side stood to win outright.
  4. Negotiated a modest payment from Lorna to close the account cleanly. Rajesh's company agreed to withdraw the duplicate invoice in exchange for a payment in the low thousands covering the genuinely outstanding balance, a fraction of the thirty-four thousand dollars that had appeared on paper, resolved in a phone call and a follow-up letter rather than a year of litigation.
  5. Drafted a written release and confirmation the account was fully settled. The practical fix, a phone call and a modest payment, was not itself the legal work. The legal work was turning that informal agreement into a signed release stating the account was closed, with no further claims by either side, in language a buyer's counsel could rely on without independent investigation.
  6. Provided the release and supporting reconciliation to Anjali's accountant. A signed release on its own would still have invited questions about why the account had sat disputed for two years before finally settling in an eight-week rush, so we sent it together with a short summary of the shipping and billing reconciliation. That gave Anjali's team a documented paper trail showing exactly how the dispute had been resolved and why the payables were now clean, which is what let them sign off without asking Lorna to explain the history herself.
  7. Confirmed the timeline against Lorna's surgery date. A dispute this size could have been pushed harder for a marginally better number if time had not mattered, so throughout the file we tracked how many weeks remained before Lorna's procedure and used that clock to decide when to keep pressing and when to settle. Prioritizing the settlement conversation over a longer fight for the last few thousand dollars reflected what actually mattered to Lorna, which was closing on time, not closing for the maximum amount.
  8. Advised Lorna against disclosing the settlement as an ongoing dispute in the sale documents. Once the release was signed, the account was legally closed, so we made sure the purchase agreement's representations described it accurately as a resolved and settled matter rather than as a lingering contingency, which avoided giving the buyer a reason to reopen the price discussion or ask for a further holdback against a risk that no longer existed.

The outcome

The account closed within three weeks of Lorna's first call to our office, well inside the eight-week window she had before her surgery. Anjali's accountant accepted the signed release and reconciliation without further questions, and the sale proceeded to closing on the timeline Lorna needed, with the disputed invoices no longer appearing anywhere on the business's books.

The loss was real, even if it was contained. Lorna paid a settlement in the low thousands to close an account that a fuller investigation, given enough time, might have shown she owed little or nothing on at all. She also paid for the legal work to document the release properly. Set against the alternative, a lawsuit that would have cost more in fees than the settlement itself and taken far longer than she had, it was the right trade, but it was still money out of a sale she was already making under difficult circumstances.

What made the difference was recognizing early that the legal question and the practical question were not the same problem. Rajesh and Lorna could likely have settled the underlying billing error themselves at any point in the previous two years with a single phone call. What they could not do without help was turn that settlement into something a buyer's advisor would accept as final, in writing, within a deadline that mattered. That distinction, between fixing the problem and protecting the fix, is often where the real legal work in a business sale actually sits.

Lorna's surgery went ahead as scheduled, roughly a month after closing. She has said since that the hardest part of the whole process was not the settlement itself but the two years beforehand, when she let a manageable disagreement sit unresolved simply because nothing was forcing her to deal with it. A dispute that costs nothing to ignore rarely stays that way once a sale, an estate, or any other transition puts a deadline on it.

What you can learn from this

  • A stale, unpaid dispute that costs you nothing today can become an obstacle the moment you try to sell. Resolve old billing disagreements with suppliers or customers well before you list a business, not after a buyer's accountant finds them.
  • Not every dispute needs to be won outright to be handled well. When time is short, a fair settlement that closes the account cleanly is often worth more to you than a stronger legal position pursued too slowly and too expensively.
  • Before assuming a dispute is complicated or entrenched, compare the underlying shipping or delivery records against the invoices themselves. Many long-running billing disputes turn out to be bookkeeping errors rather than genuine disagreements about what was owed.
  • An informal settlement is not the same thing as a documented one. If a buyer's advisor needs to rely on a resolved dispute, get it in writing with a signed release stating the account is closed, not a verbal understanding between the parties.
  • When a health deadline or any other hard closing date is driving a sale, tell your advisor as early as possible. It changes which trade-offs are worth making and how quickly a lingering dispute should be settled rather than fought to a better number.
This case study is entirely fictional. It does not describe any real client, file, or matter handled by Treadstone Law, and it is not a real file with details changed. All names, people, properties, businesses, dollar amounts, dates, and events are invented, and any resemblance to a real person, business, or situation is coincidental. Fictional scenarios like this one illustrate the kinds of legal issues people in Ontario commonly face and how a lawyer can help. They are general information, not legal advice — no two matters unfold the same way, and nothing here predicts the outcome of any real case. Reading a case study does not create a lawyer-client relationship. If you are facing something similar, speak with a lawyer about your specific circumstances.

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