What do you consider when a person works from the bottom up?

I overhead my boss say in a business related meeting he worked from the very bottom. Partly could be BUT in his early 20s he also married the daughter of a wealthy realtor whose both daughters inherited massive properties of restaurant/hotel, which he became partner of through her. So really, working your way up (for me) is defined entrepreneurs who built themselves using their own strength, risks and finances.

Trump also used his poor excuse of building his empire by just ONLY getting $1Mil. from his father, as if it was 100 bucks