Earlier quoted context omitted.
Let's be honest here. If you had as much money as Mcclure, would you waste as much time trying to please people by bending over backwards with perfect grammar, lack of slang, and an apologetic tone? Everyone starts writing to please other people through resumes, cover letters, thank-you cards, and apologies. But once you have enough money like Mcclure, you can say "Fuck you" when you want to and not worry about losin…
Yes, I would. It doesn't take that much more effort. Your argument is that he's too busy for punctuation to be worth his time? What about people who are more wealthy than him who manage to do so? What would you think if Warren Buffett wrote like this? He's acting like the kids in junior high who thought they were being rebellious by shopping at Hot Topic and dressing punk. He's just replaced one style for another. He…
But my whole point is that there's more people like him that don't feel like writing perfectly. As you just admitted, it takes extra effort to write for your audience instead of writing for yourself. And why would he bother to hire an assistant to edit it? That also takes effort.
Warren Buffet obviously has the choice to behave in the same manner. He also has the choice to be reckless like Larry Ellison and fly jet fighters, or be like the Koch brother's and spend millions on libertarian think-tanks to anger a large democratic populace. Or conversely, why does Buffet choose to anger countless libertarians by saying he and other billionaires should pay a higher tax rate than his secretary? If he was a truly wise businessman, he would refrain from political statements like that.
My point is that wealth makes people more confident in revealing their idiosyncrasies. Whether or not you like their true personality is another story. Amusingly and relatedly I've lost over 20 karma points for telling what people don't want to hear even though I do not support Dave McClure's behavior.