Having watched a good number of Elon Musk interviews, I wish more interviewers would ask more direct questions. Asking Elon general questions usually results in fairly similar responses to what you have heard before or read in his biography.
He has always said the chances of SpaceX succeeding was very slim - but at what point(after any particular technical achievement) he realized the this might work out.
Wasn't Falcon 1 a test bed for Falcon 9? I remember one when Tom Mueller called Elon Musk to say the a full length Merlin burn was completed without melting the engine. That was a big milestone.
I am pretty sure there have multiple of this yahoo moments successively - that made him believe that SpaceX will be able to succeed.
I've heard from interviewers that he's notoriously difficult to interview. He doesnt trust reporters and usually has certain questions they cant ask him.