Jack Ma, whose company Alibaba (NYSE: BABA) recently IPO’d for 25 Billion, opened up about the pressures of having an unthinkable sum of money. Ma says that he feels uncomfortable being under constant pressure and having an overwhelming responsibility to all his new shareholders. He yearns for the simple days when he made twenty bucks a month. Putting aside the Horatio Alger on steroids levels of amazingness to Jack Ma’s story, if I were a shareholder, this sense of unease around money would worry me. Have you ever heard of another CEO speaking with such trepidation? Every time Mark Zuckerberg opens his mouth, it’s to say something with force, conviction and confidence. He may dress like that dad trying to look a little too cool as he drops his daughter off at kindergarten, but when it comes to interviews, he brings the heat. He talks about wanting to “make big bets that excite and amaze people.” You think Mark Zuckerberg loses a wink of sleep over being in charge of allocating billions and billions of dollars? Not likely. Similarly, Steve Jobs built Apple (NYSE: AAPL) into the largest company on earth with the use of aggression, tenacity and by never letting pressure get to him. He abandoned his own daughter in the pursuit of improving his company, for crying out loud. Pretty awful guy, but he was not being paid to be a father. He was being paid to lead a company. He was ultra confident, to the point that he assumed he knew better than the consumer. According to Jobs, “People don’t know what they want until you show it to them.” Take my money, please. Google (NASDAQ: GOOG) is another company where there is no talk of the CEOs being unsure of how to spend their money. They are boldly shooting for the moon with projects like the Google LunarXPRIZE, Calico, and the self driving car project. So what if they spy on everything we do and are the leading candidate of all tech companies to develop a Skynet-like product that will destroy the world? As of this moment, I’d trust Larry and Sergey with my money. They are certainly not afraid to be billionaires. Finally, there is good ol’ Jeff Bezos. The New York times runs a scathing article that paints him as the overseer of a Gulag-like corporation, and he doesn't even bat an eye. He lashed back at the article and doubled down on his positions. Another possible sociopath, but another guy who is ultra driven and has no problem making big, bold proclamations. Amazon (NASDAQ: AMZN) stock seems to be on a never-ending upward surge, so the results speak for themselves. There is no direct correlation between companies who have brash, uber-confident CEOs and the performance of that company's stock. This is just one man’s opinion. But, having been in many professional basketball teams’ locker rooms, I can say with certainty that it never goes well when you have a meek, quiet coach. You need to know that your leader is totally fearless. I’ve seen coaches try to take someone out of the game, only to change their mind after getting a death stare from their star player. It was sad. When you’re the leader of an organization, you should never be left looking like a bully just took your lunch money. I’m not saying Jack Ma has reached that point, but you’re definitely not getting my hard earned dollars when you sound so unsure about yourself.