Yes I did, in his remarks he said "that there's nothing pilots would rather do than fly", he went on to say "that pilots would fly for free".

I disagree with that.

I think he was being facetious. However, working for 20 grand is about the same as working for free.

I think you misunderstood his point. And I think he is 100% correct. Way too many people are willing to work for peanuts in this industry.

I wish someone had told me that about 14 years ago when I was deciding if i wanted to be a pilot or a doctor.

There's always risk. I don't see any difference in taking out a student loan to go through college and then struggling to find a job. Aviation can be tough; some people make it and some don't. Better to do something you love then something you hate.

Yeah that's kind of an extreme statement.

Extreme?
 

Maybe not so extreme as some may think. There was an airline called Gulfstream that charged First Officers nearly 20K to fly right seat. In the airline's early years, the FO was sitting in aircraft not requiring an FO at all. These pilots were not initially paid. That may have changed later though.
The fact that some will make it and others won't relates more towards the financial aspects of the profession rather than what be be implied towards the effort a person may commit.

They got bought out and are now Silver. Also they don't do that anymore.

I agree that Dave Ramsey tends to make extreme statements, and likes to be dramatic. However, he has a valid argument about going into deep debt for years. It's also sad that an entry level truck driver earns more than an entry level pilot.