You sell your business once. The buyer across the table does this every week. Here is what I learned on the seller’s side of the table, some of it the expensive way.
1. Selling is like dating.
Every stage of a relationship shows up in an exit, except the ending. There is the romance of first meetings and a flattering offer. Then the power struggle of diligence, when the flaws come out. Then things settle, terms get agreed, and you commit at signing. In a relationship, the last stage is building something together. In a sale, that stage rarely arrives. After close, the person who courted you is often the person disputing your earnout.
2. Big numbers can dazzle.
The headline number is the maximum, not the expected. It adds up the upfront payment, the holdbacks and every earnout as if all of them pay in full. Each piece comes with conditions. Read the conditions before you celebrate the total.
3. Deal structure is everything.
Get as much as possible at close, and as little as possible tied to what the buyer does next. Money due later depends on targets, on the buyer’s decisions and on the buyer’s interpretation of the contract. All of it also depends on you meeting your own obligations, so know exactly what those are.
4. You are always on the record.
The buyer’s team is friendly because friendly gets answers. Over months you will build real rapport with them. That is their job: earn trust, then look under the surface. Anything you say in a call, a dinner or an email can come back later, out of context and against you.
5. The team will change.
Experienced buyers bring different specialists to each stage. The people who courted you are not the people who run diligence, and neither group runs integration. Don’t read the swap as a signal. It is the process.
6. The details count.
Big issues surface early. Small ones get collected and used late. Each minor finding gets noted, then stacked up to cut the price, withhold a payment, or force a settlement. No single item looks worth fighting. Together they can be.
7. What’s missing?
Buyers are trained to find gaps, and AI means they will find all of them. Diligence used to test samples. Now a buyer can process every contract, invoice and email you hand over, quickly and systematically. A missing or incomplete customer or vendor contract will not slip past. It will become a negotiating point.
,8. Whose certification?
If your products carry certifications, ask whether they survive the sale. Does the buyer use the same standard and the same certifying body? Can they sell your existing stock? On one sale of mine, the buyer claimed, incorrectly, that hardware units could not be sold because of certification issues. They pulled a line from one of my emails, used it out of context, and withheld $80,000.
9. They might see everything afterward.
Depending on the deal, the buyer may get your documents and email after close, and use them. That is how they found the email in point 8. Assume anything in your company’s systems will be read by someone looking for a reason not to pay.
None of this is a reason not to sell. It is a reason to prepare, and to have someone on your side who knows the buyer’s playbook. Start with a First Meeting.
