Most philosophers are affiliated with universities these days, and few have other sources of income. I can think of two 20th Century philosophers who were successful outside of the university: Bertrand Russell and Sartre. Both wrote popular books.
Philosophers these days generally talk to other philosophers, and only a few nonphilosophers listen. Part of this is due to a lack of interest on the part of nonphilosophers, but part of it is also that philosophers aim to write for other philosophers rather than for a wider audience.
People in other fields, often without much formal training or background in philosophy, sometimes address philosophical issues and gain a popular audience. One who comes to mind is Michael Pollan, who explores the nature of reality and truth from the standpoint of food and comes to some genuine insights that intelligent people without philosophical background can understand.
Many modern stand-up comics, such as the late George Carlin, or Lewis Black, explore philosophical themes. Jon Stewart and Stephen Colbert have found two ways to reincarnate Socrates and the Socratic quest for knowledge.