The Hidden Obstacles in Business Sales

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 734 words

Most deals that fail do not fail on price. They fail after the price is agreed, on the details: the fine print in the purchase agreement, a buyer's financing, an advisor who turns every point into a fight, a seller with second thoughts, or results that slip during the process. These obstacles are hidden only because owners do not expect them. Each can be anticipated and most can be avoided.

The fine print after the handshake

The letter of intent (LOI) sets price and key terms, but the purchase agreement that follows runs to many pages. Representations and warranties, the statements of fact you make about the company, and the indemnification that makes you responsible if they prove untrue, are where many negotiations stall. So are the working capital target, the escrow or holdback of part of the price, and the scope of any non-compete.

Settle as many of these as possible in the LOI, so they do not become new battles later. Before you sign, ask your advisor and attorney which terms the buyer has left vague; vague language in the letter often becomes the hardest fight in the contract. What representations and warranties a business seller should expect explains them in plain terms.

Obstacles on the buyer's side

Buyers bring obstacles of their own, and most are visible early if you look for them:

• Impatience. Buyers who expected a quick purchase lose interest when due diligence takes longer than planned, and some give up on acquisitions altogether after a few months.
• No clear reason to buy. A buyer who cannot say why this company fits its strategy may never fully commit.
• Reluctance to pay for quality. Some buyers want an excellent company at an average price and keep trying to renegotiate.
• Financing that falls through. A buyer without a firm lender commitment or enough equity may be sincere and still unable to close.

Obstacles on the seller's side

Owners create obstacles too. Unrealistic price expectations are the obvious one. Less obvious is seller's remorse: second thoughts that surface as delays, new demands or reluctance to sign, and that are especially common in family companies where the business carries years of identity. Remorse is easier to prevent than to cure: settle your personal plans before going to market, and keep your family informed so doubts surface early rather than at the signing table.

Rigid terms cause trouble as well. An owner who insists on every dollar in cash at closing, when deals for similar companies normally include a seller note or an earnout, narrows the pool of buyers who can say yes. Finally, there is distraction. An owner absorbed by the deal can let sales, collections or staffing slide, and buyers watching the monthly results will notice.

Advisors who help and advisors who hurt

Attorneys, accountants and advisors on both sides can move a deal forward or bog it down. An advisor who treats every clause as a contest, misses deadlines or escalates small points can wear out the other side. Choose a transaction attorney who closes deals regularly and understands which risks are worth fighting over. You cannot choose the buyer's advisors, but you can ask early who they are and how the buyer expects due diligence to run. Agree with your team on priorities before negotiations begin, set a schedule for each round of drafts, and keep communication direct and prompt.

When to walk away

Not every deal should close. If a buyer keeps retrading, meaning trying to lower the price after the letter of intent, cannot show funding or changes the shape of the deal late in the process, it may be better to end talks and return to other buyers while your company is performing well. That is only possible if other buyers exist. A process that brings several qualified buyers into play at once makes walking away a real option rather than an empty threat, and that is central to how we approach sell-side representation.

How MDR & Associates keeps deals on track

We screen every buyer for funding before sharing details, negotiate several letters of intent at the same time and push to settle key terms early. A principal of the firm is in every negotiation, and we work alongside your own transaction attorney and CPA through due diligence and closing. To discuss a deal that has stalled, or one you are about to start, contact us.

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Questions owners ask next

What is retrading?

Retrading is when a buyer tries to lower the price or change terms after a letter of intent has been signed, usually citing something found in due diligence. Sometimes the finding is real. Disclosing known issues early, keeping results steady and having other interested buyers all reduce the risk.

How much of the price is usually held back after closing?

It varies with the deal, the buyer and the risks involved. Many agreements hold back part of the price in escrow for a set period to cover possible claims under the representations and warranties. Your attorney and advisor negotiate the amount and the duration; smaller, shorter holdbacks favor the seller.