I started thinking about it and just in the last 20 years this guy has at different times (and many times overlapping):
-Managed 2 different restaurants
-Owned a restaurant
-Owned a little used car dealership
-Owned a little paper where people advertise things they want to buy and sell
-Worked in Management for a chain of local convenience stores
-Driven a truck for an oil and gas company
-Been a substitute teacher
-Reffed HS basketball games
Contrast that to someone like me who has worked for two companies in the last 20 years, and only one at a time.