Here is the answer to the first question from a book excerpt on alternet.org.
From the moment of his birth, Trump was set up for success. The large inheritance left to him by his father, coupled with the contributions and the protections of society and the US government made his ascension to the Forbes 400 list almost inevitable. Nevertheless, Trump fails to recognize this phenomenon and continues to express his belief that he did it alone.
Read the article to find out the details leading to that conclusion.
Then check out the remaining 21 questions David Cay Johnston has for Trump about his suspicious business practices (also at alternate.org).
Here are some examples.
18. You say that your experience as a manager will allow you to run the federal government much better than President Obama or Hilary Clinton. On Fortune Magazine’s 1999 list of the 496 most admired companies, your casino company ranked at the bottom – worst or almost worst in management, use of assets, employee talent, long-term investment value, and social responsibility. Your casino company later went bankrupt.
Why should voters believe your claims that you are a competent manager?
6. Trump Tower is not a steel girder high rise, but 58 stories of concrete.
Why did you use concrete instead of traditional steel girders?
7. Trump Tower was built by S&A Concrete, whose owners were "Fat" Tony Salerno, head of the Genovese crime family, and Paul "Big Paul" Castellano, head of the Gambinos, another well-known crime family.
If you did not know of their ownership, what does that tell voters about your management skills?
These are questions not being asked by the lame-stream media. Instead, we get a diet of poll numbers showing Trump to be the driver of the Republican clown car.
Elizabeth Warren blew up the myth of self-made millionaires quite some time ago. Trump is an example of that mythology. Now we need the press to lean real hard on Trump and his bogus claims about his management skills. Johnston's 21 questions would be a good starting point.