To be a single-digit employee, you had to start in the 70s -- i.e., 40 years ago. My friend -- I don't think it'd be appropriate to name him -- has "only" been there 30, which means he joined a healthy-sized Apple already 10 years into its life.
That says a lot. I would have jumped ship around 1995-1997. Things were bleak for Apple and everything they shipped software wise was buggy, behind the times,
In 1994. Apple was on top of the world. They were the number one or number two computer seller and the PPC Macs were introduce and then Windows 95 happened.