don't take this as a defense of trump, I would not invest my money in one of his enterprises...but here's how I look at his business record. First of all trump has a lot of money and a lot of business ventures, and he can afford to takes risks. Next, he pushes the envelope in his dealings. He's willing to "throw a lot of things against the wall" to see what sticks, uses a lot of debt (other people's money) - to include to suppliers/investors - and then uses available laws to exit and write off his losses...and then move to another venture. I doubt he loses sleep at night when suppliers or investors are left holding the bag.
In no small way, this is how he's running the government. he signs a lot of executive orders or dictates other actions to see what will happen. He is sued a lot, and has no problem with that (he's got a whole department of lawyers paid by the taxpayers). When he wins that's great, and when he loses he just moves on to another EO or dictate. He initiates and manages chaos seemingly as part of his management style.
There is no question in my mind that he and his family are benefiting financially from his office. While I don't think that's what a government official should do, in fact, they all seem to do it. But Trump has mastered the technique to a degree seldom, if ever, seen before.
Got your "trump watch" yet, It's the best watch ever made, never been one like it before