The key-person risk that does not show up in the financials Most small businesses have a person who is the API. Every question routes through them: the schedule, the exceptions, the pricing calls, which employee can do which job. It works, which is exactly why it hides. It is also the part of the value that leaves when they do. For a few seasons that person was me. I am the GM of a multi-base outdoor recreation company in Idaho. Before we rebuilt it, weekly planning took twenty to forty hours, most of it me answering questions the software could not. It takes two to four now. If you are looking at a business before close, this is what I would try to measure: 1. In one normal week, how many questions reach the key person that someone else could answer if the information lived somewhere? 2. Where do the rules live? Not the data. The rules: who is qualified for what, what cannot be scheduled together, which customers get exceptions. 3. What happens if that person is unreachable for two weeks in peak season? Ask the staff, not the seller. 4. Which recurring decisions get made at night, because the day goes to answering questions? 5. What does the software store, and what does a person store about what that data means? If the answers all point at one head, that is not a reason to walk away. It is the first ninety days of work, and it is fixable. The long version: justinsmith.build/writing/i-was-the-api/