How Inexperience Can Impact Your Business Sale

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 732 words

Inexperience hurts a business sale in four predictable places: the financial story buyers are told, the accuracy of the marketing documents, confidentiality, and the terms negotiated after a letter of intent is signed. Owners selling on their own, and advisors who have closed few deals, tend to stumble in the same spots.

Credentials are not the same as deal experience. An MBA or a law degree teaches principles. It does not teach how a buyer's lender reacts to an add-back nobody can document, or how to hold a price when due diligence turns up something unexpected. Those lessons come only from doing many transactions.

Bring your finance lead in early

Serious buyers will want to meet whoever keeps your books, whether that is a CFO, a controller or an outside CPA. Due diligence, the buyer's detailed review of your records after the letter of intent, will produce a long list of financial requests, and the answers must be quick and consistent.

Involve that person before the company goes to market. They should reconcile the financial statements with the tax returns, close each month on time, and help prepare the recast that adjusts earnings for owner-specific and one-time expenses. Larger buyers often commission a quality of earnings report, an accountant's independent review of how reliable your earnings are. A finance lead who has prepared for it makes that review a confirmation rather than a renegotiation.

Get the numbers and the story right

The confidential marketing package is the buyer's first real look at the company, and small errors carry large consequences. A revenue figure that differs from the tax return, an add-back with no support or an important fact left out will not stay hidden. When the buyer finds it, trust drops, and lower trust shows up as a lower price, a larger holdback of the purchase price or a buyer who quietly moves on.

Every number in the package should trace to a source document, and every claim about the business should be one you can prove. The story should be accurate, current and consistent from the first page to the last.

Treat confidentiality as a process, not a form

Inexperienced sellers often treat the NDA as a formality, or share information before it is signed. That is how employees, customers, suppliers and competitors learn a company is for sale. The fallout is predictable: key people start looking for other jobs, customers hedge by trying other vendors, and competitors tell your accounts you may not be around much longer.

Confidentiality needs a sequence, not just a signature: a blind profile, a properly executed agreement, proof of funds, then staged release of information. Our answer on keeping a sale confidential from employees, customers and competitors covers the practical steps.

Where experience shows most: after the letter of intent

Many first-time sellers think the hard part ends when a letter of intent is signed. It is where much of the value is won or lost. The buyer usually gets a period of exclusivity, and your leverage falls. The working capital peg, the level of receivables and inventory you must leave in the business, is negotiated. Representations and warranties, the factual promises you make about the company, and indemnification, your obligation to cover losses if those promises prove wrong, are drafted. A buyer may try to retrade, meaning lower the price, using something found in diligence. An experienced advisor has seen each of these many times and knows which requests are normal and which are opportunistic.

How to judge an advisor's experience

• How many transactions has the firm closed, and how many like yours?
• Who will negotiate, and how many deals have they personally taken to closing?
• May you speak with owners the firm represented?
• How does the firm handle a buyer who tries to retrade?
• Is the firm a broker, an M&A advisor or an investment banker? The guide on choosing between a business broker, M&A advisor and investment banker explains the difference.

What MDR & Associates brings

Since 2008 the firm has closed more than 250 transactions, selling companies with about $500 million in total market value, with a success rate above 90%. Named examples are on the results page, and the people who negotiate are on the team page. A principal is in every negotiation, and the firm works alongside your own attorney and CPA. To discuss your situation, contact the firm.

Where this fitsSell your business in Texas →

Questions owners ask next

Can I sell my company myself if I already have a buyer?

You can, but you lose competition, which is what usually sets the price, and you take on the negotiation and diligence yourself while running the company. At minimum, hire an experienced transaction attorney and CPA. Many owners with one buyer still benefit from an advisor who tests the market.

What is a quality of earnings report?

It is an independent accountant's review of how reliable and repeatable a company's earnings are, looking at add-backs, revenue timing and working capital. Buyers often commission one before closing. Some sellers commission their own beforehand so there are fewer surprises.