Ask a founder how a particular process works and watch what happens. Most of the time, they can tell you, in detail, fluently, without hesitation. That fluency feels like mastery. It is usually a warning sign.
The cost of being the archive
When a founder is the one place all the institutional knowledge lives, the business has a single point of failure wearing a nice suit. Every exception gets routed through them. Every new hire's real onboarding is "go ask the founder." Every vacation becomes a stress test the business quietly fails. None of this shows up on a P&L. It shows up as a founder who cannot take two consecutive weeks off without the business visibly wobbling.
It does not feel like a systems problem from the inside. It feels like being indispensable. Those two things look identical until the day they do not.
What 'documented' actually means
Documentation has a bad reputation because most of it is theater, a binder or a wiki page written once, referenced never, already stale by the time anyone opens it. Real documentation is different: it is tied to the actual work, owned by whoever does the work, and updated as the process changes. It answers the question a new hire actually asks, not the question a compliance checklist assumes they will ask.
If the business only works because you remember everything, you have not built a business, but a very complicated job for yourself.
Where to start
You do not need to document everything at once, and trying to is how these efforts die. Start with three things: the process people ask you about most often, the task that only you know how to do, and the decision you make so automatically you would struggle to explain your own reasoning. Write those down first. They are the ones quietly costing you the most, and they are usually the fastest to get real leverage from once they are out of your head and into the system.
A business that depends on your memory is not more valuable because you are good at remembering. It is more fragile. Getting that knowledge out of your head is one of the highest-leverage things you can do this quarter, and one of the cheapest.