Lack of Experience Can Be a True Deal Killer

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 737 words

Selling a company is a specialized job, and an owner who hands it to someone without deal experience, however smart and well-meaning, often ends up with a leak, a lower price or no sale at all. The mistakes are predictable: no confidentiality agreements, a marketing document that leaves out what buyers need, a lawyer who has never handled a sale, and buyers nobody checked.

The temptation is easy to understand. An experienced advisor's fee looks large, and a relative with a business degree, a trusted employee or the company's usual attorney looks like a way to save it. Here is what that choice tends to cost.

Confidentiality agreements are not a formality

An inexperienced intermediary often begins by telling interested parties the company's name. Without a signed confidentiality agreement (NDA), nothing stops a competitor from asking questions, a buyer from repeating what it heard, or word from reaching your employees, customers and suppliers. Once the news is out, it cannot be recalled.

Experienced advisors work in a fixed order: a blind profile that describes the company without naming it, then a signed NDA, then proof that the buyer can fund the purchase, and only then the details. Our answer on how buyers are screened before seeing confidential information walks through that order.

The marketing document sets the first offers

Serious buyers form their first view from the confidential information memorandum, the document that explains the business, its history, its customers and its financial results. A thin or careless one lowers bids or loses buyers entirely. It also has to be consistent: figures in the memorandum that differ from the tax returns will be found in due diligence and cost you credibility. First-time preparers tend to leave out the same things.

• A financial recast that adds back owner compensation and one-time costs, so buyers see true earnings.
• An explanation of large or unusual items, such as a sum the owner drew out of the company.
• Trends over several years rather than one year's statement.
• Where growth could come from under a new owner.
• An honest account of the risks, with the context that makes them manageable.

Using the wrong professionals

Your company's regular attorney may be excellent at contracts, leases and employment matters and still never have negotiated the sale of a business. Transaction work has its own conventions: representations and warranties, caps on indemnification, escrows, working capital adjustments. A lawyer learning them on your deal costs you in time and in terms given away. The same caution applies to your accountant: ask whether they have supported a seller through a buyer's quality of earnings review, the accounting firm's test of your reported profits.

The same goes for finance. Buyers expect to meet the person who runs the numbers, usually a CFO or controller, during due diligence. If that person has not been brought into the process and has no reason to stay through closing, the buyer's questions go unanswered, or the person leaves at the worst moment. A retention or stay agreement solves that.

Buyers who were never screened

Every conversation with a buyer who cannot or will not close wastes time and spreads the news further. Experienced advisors interview buyers, ask what they have bought before, and require a financial profile before sharing details. Inexperienced ones take every inquiry at face value, and the owner spends months talking with someone who never had the money.

For most owners, selling the company is the largest financial transaction of their lives. The savings from doing it without experience are small next to what a leaked sale, a weak document or one lost buyer can cost. Before sharing anything, an experienced intermediary gets straight answers to a few basic questions.

• What have you bought or run before?
• How will you pay: your own cash, a bank loan, investors or a mix?
• Who else takes part in the decision?
• What is your timeline, and why this company?

What we bring to the job

MDR & Associates has closed more than 250 transactions since 2008, and a principal of the firm is in every negotiation. Every company goes to market with a confidential marketing package, a financial recast and a professionally produced HD marketing video. We work alongside your own transaction attorney and CPA rather than replacing them, and we are paid only if the company sells, as our fee page explains. To start, contact us for a confidential discovery meeting.

Where this fitsHow a business sale works, step by step →

Questions owners ask next

Can my company's regular attorney handle the sale?

They can, if they have negotiated sales of companies your size. Ask how many purchase agreements they have handled for sellers in recent years. If the answer is few or none, keep them for company matters and hire a transaction attorney for the sale; the two can work side by side.

Is it worth selling without an advisor to save the fee?

Occasionally, when a buyer is already known and the terms are simple. More often the owner saves a fee but loses competition among buyers, which is what sets the price. With a success-fee-only advisor you owe nothing unless the company sells, so the real comparison is between net results, not fee versus no fee.