"You think money means you're successful?"
If people give you lots money in return for you providing them with some form of good or service, then yes, your successful.
"Usually it means you were lucky."
Very occasionally. Like if you have a really strong streak at a high-stakes table, or win the lottery. But most of those people wind up even poorer than they were before they won.
"Or that your lazy ass never worked a day because your daddy was rich."
It happens, but it's rare. In the book "The Millionaire Next Door," the authors determined that 80%-90% of millionaires were first-generation wealthy. And in fact you were more likely to find millionaires in middle class and blue-collar neighborhoods, because wealth accumulation wasn't so much a function of how much you earned as it was how much you saved.
"Trump has money (not a billionaire) but he has been a failure at everything he ever touched."
Trump is a socialite first and foremost. He has been since at least the 1980s. I went back and re-watched the TV show "Just Shoot Me." One of the main characters (Jack Gallo) has an ongoing feud with DJT in the series. This was before The Apprentice, and certainly before the presidency.
As for his inheritance, had he simply hired a good financial advisor and spent his days playing golf, he'd probably be far richer today. But for rich people money is not nearly the social feedback that power is. You can't buy yourself an Air Force One or White House. You have to convince the voters to give it to you.