Trump sure likes to have people think of him that way, i.e. as a self-made man in the fashion of Andrew Carnegie.
In reality, there was nothing "self-made" about him, nor was he a "free market" entrepreneur. His father was a millionaire contractor, and Trump himself mostly got rich through sweetheart eminent domain deals,
http://michellemalkin.com/2011/04/22/donald-trumps-eminent-domain-empire/
where property was seized by the government and handed over to cronies like him to be turned into casinos. Moreover, the "brilliant job creator" basically had to file for bankruptcy in the 90's.
So now he compensates for it by doing sleazy reality shows and making a public spectacle of himself with meaningless stunts like this. Good thing some people are impressed.