I guess the point Randymarsh is making is that Trump could and should have done rather a lot more with his start-up capital than he has actually achieved. If, as has been reported, Trump could have made (far) more of his starting millions by doing exactly nothing other than allow stock index tracking to take its natural course rather than work hard to invest, then doesn't that suggest that his "clever" investments were not quite so clever as he keeps saying? I guess it's true that he could just as easily have invested badly and lost everything, and there's no way I'd describe a billionaire from any starting position as unsuccessful, but all the same it's a point worth making. Trump attempts to sell himself as basically bigger than Jesus, and makes outrageous lies about his success or net worth, or pretty much anything else about him.
And anyway, the litany of failures along the way is quite a significant list -- often overlooked by his admirers, perhaps overemphasised by his detractors, but still worth noting. Of particular import is Trump University, that is basically a fraud case waiting to explode in Trump's face assuming the wheels of American justice turn properly.
We can't let him get away with this. Maybe calling him stupid is unfair, but on the other hand he lies instead about having "one of the highest IQs" out there (even if this is true after all, who cares? IQ as a measure is overrated) -- and calling anyone who challenges him "stupid and insecure" to boot? Maybe the man is no fool, but how can you take seriously the claims of someone boasting about their vocabulary in the first place, let alone when he does so with "I know the best words"? Maybe his hands aren't tiny, but on the other hand how can a man stand up and boast about having "no problem" with the size of what's inside his pants and not think that the entire election is a joke when that becomes a part of the debate?
Put another way, Donald Trump does and says everything that TTT and others profess to hate whenever "liberal lefties" do it. He is dismissive, pompous, rude, arrogant, self-absorbed, obsessed with minutiae (literally, in the case of his hands), and contemptuous of his detractors. When left-wing people are accused of this, whether justified or not, it's as an insult. When Trump does it, they lap it up. It's sickening to see just how hypocritical Trump's supporters are about his behaviour. Even more so in America, where he shows contempt for various parts of the constitution (in particular Due Process, freedom of expression, etc etc).
I could draw more attention to it but then even in typing the above I know I'm wasting my time. TTT won't care (he has said so); others will just ignore it and/ or divert attention by focusing on Clinton's own flaws instead. I don't envy the choice America has to make in November, but in any reasonable assessment Clinton is merely a bad candidate. Trump wouldn't even register on the same scale.