Similar situation as OP. My dad started the business (his 3rd overall) 22 years ago and it's been growing steadily since. My dad still does daily scans of our ERP. I run the business with him and we have 40 employees, and I too have had similar conversations with him.
While I'm sure there is a better way to do this (e.g. invest in BI, hire and train a person to do this etc.), the fact of the matter is no one else is as invested in your business as you. So you are wired to find issues (even if none exist). It might just be an old-school small business mentality, but it works.
At the same time, it's tied him to the business in a way that he doesn't know how to get out.
While I'm sure there is a better way to do this (e.g. invest in BI, hire and train a person to do this etc.), the fact of the matter is no one else is as invested in your business as you. So you are wired to find issues (even if none exist). It might just be an old-school small business mentality, but it works.
At the same time, it's tied him to the business in a way that he doesn't know how to get out.