Gary's father: "There are much bigger things to come…I think he has a very good chance to replace Oprah."
Don't you just love this?
At least one other guy talked his way to the top.
More accurately he talked his way from the near-top to the very top.
This article also mentioned Gary's father had a 4 million dollar wine business.
And no, he didn't make it from the show directly, but the show made his brand name a lot more valuable, and made it a lot easier for him to make money from his businesses. And his true worth is probably far less than that. A lot of people claim in the $150m-$250m range. It's hard to estimate a guy whose worth is primarily not in equities.
If you haven't already, watch his first appearance on Conan: http://www.viddler.com/explore/djsteen/videos/69/
Presumably because it wasn't very successful? Even by the low standards of rev3.