'Winging it'
Trump has had several large business failures over the years, and with the benefit of hindsight there are some contributing factors that stand out -
1) Ego driven overreach, hubris. This has been a personality trait throughout Trump's life.
2) Getting into businesses that were outside his expertise. Manhattan real estate is Trump's forte and that's what he was always most interested in. When he got into the Atlantic City casino business (and the airline business), he was entering areas outside of his expertise and he didn't have a strong innate interest in them, and didn't fully understand the dynamics.
3) Loss of key advisors - in 1989, 3 of Trump's closest business advisors were killed in a helicopter crash, and he wasn't able to adequately replace them.
These are 3 key areas which will likely determine whether or not Trump's presidency is a success - his ego, his lack of expertise and possible lack of interest, and the quality of his advisors.
Let's hope there's more to Trump than the veneer, and he gets good advisors around him. I think Gingrich would be a good guy to have around - he knows how the government works and is smart enough to get quickly up to speed on the current foreign policy realm. Gingrich may have some baggage as a Washington insider, but you have to have an experienced guy in there somewhere, and he would also be reassuring to the Deep State. Gingrich is usually the smartest guy in the room, and could help keep the Donald out of trouble, and Trump is clearly going to need the help.
