Selling a business

Selling a Business Means You Should Expect the Unexpected

The surprises that catch sellers off guard, on price, confidentiality, consents, time and performance, and how to plan for each.

Small business owner packing a cardboard box in a sunny studio

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 761 words

Almost every sale hits something the owner did not see coming: an offer below the number in their head, a rumor among employees, a landlord or lender whose consent is needed, a flood of due diligence requests or a soft month at the worst moment. None of these has to end a deal. They do the most damage when they arrive as a surprise, so the practical answer is to plan for them before the company goes to market. An experienced advisor has seen each of them many times, and much of the value of that experience is knowing what comes next.

The number in your head versus the market

Many owners carry a price they picked up from a friend's sale, an industry rule of thumb or what they need for retirement. Buyers work from adjusted earnings and risk. For companies with $3 million to $100 million in revenue, value most often falls between three and seven times adjusted EBITDA, where EBITDA is earnings before interest, taxes, depreciation and amortization, and adjusted means one-time and owner-specific costs are added back.

Get a realistic range before you start, and ask which factors move you up or down within it. What is my business worth? walks through those drivers.

Owners also forget that the headline price is not what they take home. Debt is paid off at closing, advisors are paid, taxes come due, and part of the price may be held back or paid later. Ask your CPA to estimate your net proceeds early, so the number you measure offers against is the right one.

Five surprises and how to prepare for them

SurpriseWhy it happensHow to prepare
A rumor reaches employees or customersA buyer visit, an overheard call, a document left on a printerAgree in advance what will be said, by whom and when; keep a short, true statement ready
A landlord, lender or key customer must consentLeases, loans and some contracts require approval when ownership changesRead your lease, loan papers and top contracts now and list every consent clause
Due diligence takes more time than expectedBuyers and their accountants and attorneys ask for years of recordsBuild an organized document folder before marketing starts
The working capital target comes into playBuyers expect a normal level of receivables and inventory, less payables, to stay in the companyHave your CPA work out your typical monthly working capital early
Results dip during the saleThe owner's attention shifts from the company to the dealHand daily decisions to managers and keep sales activity on schedule

Your time is part of the price

Even with an advisor running the process, you will spend real hours on it: answering questions for the marketing package, meeting buyers, reviewing offers and supplying records during due diligence. Owners who prepared in advance, often through pre-exit consulting, spend less time and make fewer mistakes under pressure. Owners who did not often find themselves doing two full-time jobs at once.

The hardest part is keeping results steady. Buyers watch monthly numbers until closing, and a decline can reopen a price you thought was settled. Decide now who covers your usual work during the busiest weeks, and tell managers only what they need to know. Plan your personal calendar as well: long trips, elective surgery and major projects are better scheduled before marketing starts or after closing.

Keep one contingency plan for a leak

Even with blind profiles and confidentiality agreements, a rumor is always possible. Prepare a short, honest message for employees, a separate one for key customers, and name the single person who answers questions. Owners who respond calmly and quickly usually contain the story within days, while owners who go silent tend to make it grow.

Keep the statement true. Saying the company is looking at options to grow, or talking with possible partners, is often both honest and calming; flatly denying a sale you are pursuing damages trust if the deal later closes.

How MDR & Associates plans for the unexpected

In our first meeting we look for the surprises most likely to affect your sale: consent clauses, customer concentration, records that do not reconcile, dependence on the owner. We fix or disclose them early, so they do not appear late as reasons to cut the price. A principal of the firm is in every negotiation, and our VP of Client Engagement keeps you informed during marketing. Our process shows where each surprise tends to appear. Start with a free valuation snapshot for a realistic first range.

Questions owners ask next

What if a buyer's offer comes in well below my expectations?

Find out why. Ask which earnings figure and multiple the buyer used and which risks it priced in. Sometimes the gap is a misunderstanding that better data can fix; sometimes it is real. Several offers side by side show which it is, which is one reason to avoid negotiating with a single buyer.

Do I need my landlord's permission to sell my company?

It depends on the lease and on how the sale is structured. Many commercial leases require consent for an assignment or a change of ownership. Have your transaction attorney review the lease early, because a landlord who hears about the sale late can delay the closing.

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