What we have learned advising owners through a transaction they will only go through once.
Valuation
A multiple of revenue is a shorthand, not a valuation. Your accountant's number is built for tax, not for a buyer. And the offer a competitor made your neighbour tells you about their company, not yours. Value is a range produced by a method, and the method should be shown to you.
Preparation
Seven questions a buyer's diligence will ask, in the order it asks them: can the financials be reconciled, are the add-backs defensible, how concentrated is the revenue, does the business run without you, who succeeds you in each role, are the contracts assignable, and is any of it written down.
Structure
A full sale, a recap that lets you take chips off the table and keep a second bite, a strategic sale to someone who wants what you built, a management buyout that rewards the team. Each pays differently, taxes differently, and asks something different of you after close.
Timing
The work that moves value — reducing concentration, building a bench, getting out of the critical path — takes quarters, not weeks. An owner who starts eighteen months out has options. One who starts when the buyer calls has a deadline.
Process
Not just a higher headline number. Competition improves terms, shortens exclusivity, reduces the retrade risk, and gives you a genuine alternative when a buyer tests you late in diligence. One interested party is not a process.
After
Most regret after a sale is not about price. It is about identity, about the people who stayed, and about not having planned the next thing. It belongs in the plan from the start, not in the last week before close.