Case Study: The Deal That Almost Fell Apart During Due Diligence

Truforte Business Group - Brokers Blog

Case Study: The Deal That Almost Fell Apart During Due Diligence

How a Broker’s Preparation Saved One Deal While Another Collapsed

The following is a fictional case study created for illustrative purposes. Due diligence is often where deals succeed or fail, even after a letter of intent has been signed. Issues that surface during this stage, whether financial, legal, or operational, can spook buyers or give them leverage to renegotiate. Understanding what buyers look for during the acquisition process can help sellers avoid last-minute surprises.

We compare two Florida deals that each hit a bump during due diligence, and how differently each situation was handled.

Deal A: Proactively Managed Through the Bump

  • Buyer’s due diligence uncovered a lease assignment clause that needed landlord approval
  • Broker had already contacted the landlord in advance and had preliminary approval documented
  • Buyer’s concerns were resolved within a week with clear documentation
  • Deal closed on the original timeline

In Deal A, a retail business sale in Fort Myers, the broker anticipated that lease assignment could be a sticking point and addressed it before it ever became a problem during due diligence. When the buyer raised the question, the answer was already on file.

Deal B: Reactive and Nearly Collapsed

  • Buyer’s due diligence uncovered undisclosed equipment liens the seller had not mentioned
  • Seller had no documentation ready to explain or resolve the liens
  • Buyer lost confidence and threatened to walk away entirely
  • Deal was saved only after two weeks of scrambling and a price concession

Deal B, a manufacturing business sale in Lakeland, hit a significant snag when liens surfaced that the seller had not disclosed upfront. The scramble to resolve the issue delayed closing and cost the seller leverage in the final price negotiation.

Factor Deal A (Proactive) Deal B (Reactive)
Issue Found Lease assignment clause Undisclosed equipment liens
Preparation Addressed in advance Not disclosed upfront
Resolution Time 1 week 2 weeks
Outcome Closed on schedule Closed with price concession

Why This Happens

Almost every deal encounters at least one issue during due diligence. The difference between a smooth close and a near-collapse usually comes down to whether the seller and broker anticipated the issue or were caught off guard by it. Buyers are far more forgiving of a known issue with a documented resolution than an undisclosed surprise that raises questions about what else might be hidden. A thorough pre-listing review, similar to what we cover in our preparation-focused case studies, helps surface issues before a buyer ever does.

Lessons for Business Owners

Before listing your business, work with your broker and advisors to identify potential due diligence issues, such as lease clauses, liens, permits, or contracts, and resolve or document them proactively. This single step can be the difference between a smooth closing and a deal that nearly falls apart. Our team at Truforte Business Group helps sellers get ahead of these issues well before a buyer’s due diligence team finds them. Learn more about our process for selling a business today.

Related Case Studies

For more real-world (fictional) examples of how deal factors affect outcomes, see: Case Study: How Clean Financial Records Change a Business Sale, Case Study: The Million-Dollar Difference Good Financial Records Made, Case Study: Add-Backs That Increased a Business Sale Price by $700,000.

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