You will sell your business once. The buyer across the table has bought a dozen, the broker has closed hundreds, and the lender has underwritten thousands. You are the only amateur in the room, and the room is built to extract value from amateurs. The good news is that the costly mistakes are not exotic. They are a short, knowable list, and every one of them is cheaper to avoid than to negotiate around.
You are the amateur at the table
Selling a business is not a skill most owners ever get to practice. You build something over ten or twenty years, and then, exactly once, you try to convert it into cash. Everyone else in the transaction is a professional repeat player. The private-equity buyer runs a deal model for breakfast. The broker has a playbook for every objection you will raise. The buyer-side advisor is paid to find every reason your number is too high. You walk in with conviction about what the business is worth and almost no feel for how the process actually moves money from their side of the table to yours, or away from it.