I am reminded of one of my favorite philosophical quotes - “Every body got a game plan til they get punched in the mouth”, Mike Tyson.
Let’s say you asked a company to fight the war on terror. The company would make a command decision: we can barely afford the war on drugs, how could we also fight a war on terror and institute this whole new program? We’ve got to make cuts. So we’d decide, responsibly, which was more important: looking at people naked in airports or denying educational assistance to pot smokers and generally destroying the fourth amendment. It’s a tough call, I admit, they’re both terribly attractive, but businesses make such tough calls all the time. As you are probably aware, though, pro-business forces never even seemed to think of it at the time…
What tough decision? If you get asked to fight the war on terror, you privatize security and put in minimum wage people, outsource your intelligence analysis to India, lay off most of the NSA, and then vote yourself a 50% raise for saving money. What’s tough about that?
And Trump has been mainly a (self-) promoter for the last few decades, whose true business is branding, not real estate any more.
Cain’s pizza company lost significant market value while he ran it. Pillsbury dumped it for a huge loss.
Modern corporations are not suited to build or form great political leaders. Steve Jobs and Bill Gates were great CEO’s but would have made bad presidents. Both are control freaks who manage every process and decision and push their subordinates to excel or fire them if they don’t. Presidents never get to do that to Congress.
It is one thing to “know politics” in the case of office or market politics (more accurately, politicking) as a way to get to the top or to gain influence and power; it is another to actually hold high office in a democratic regime, where once you reach the power you find it is highly constrained.

Well, what about George Soros or Warren Buffett? Would they make good politicians?
Well, there you go: George Soros and Warren Buffet. Their job performance suggests they are most likely “great” businessmen…
…who AFAIK and have shown little or no interest in actually being in elected political office, preferring to influence those who are. They know their strengths and know that those strengths are better used from outside of the government structure.

Let’s say you asked a company to fight the war on terror. The company would make a command decision: we can barely afford the war on drugs, how could we also fight a war on terror and institute this whole new program? We’ve got to make cuts. So we’d decide, responsibly, which was more important: looking at people naked in airports or denying educational assistance to pot smokers and generally destroying the fourth amendment. It’s a tough call, I admit, they’re both terribly attractive, but businesses make such tough calls all the time. As you are probably aware, though, pro-business forces never even seemed to think of it at the time…
The difference is that a company will decide to do so if it is profitable, not if it is “right”.
I think it depends on the type of “great businessman”. You don’t get a lot of “self-made men” thinking they can be good politicians. Steve Jobs would never have run for anything. What you get in politics are CEOs like Meg Whitman, the Bushes and Steve Forbes who come from the business school mentality that management is a science unto itself and can be done successfully without any direct experience with the company’s operations. It’s only natural that someone who believes a good manager can manage anything would believe him-herself to be an excellent elected official. Mitt Romney seems to be in this mold.
Ross Perot strikes me as the biggest exception to this rule. He was sorta kinda self-made, but thought he could run the world.
Fortunately, we have a real-word example of what happens when one of the Whitman types you describe tries to apply their management skills to something a bit different: Jerry Jones.

The difference is that a company will decide to do so if it is profitable, not if it is “right”.
While my disdain was surely clear in context, the point wasn’t that one was more profitable than the other, it is that governments, in general, aren’t run like businesses, and even those that pay lip service to the idea are strangely silent when their cronies’ money is on the line. Hard to eliminate the war on drugs when private prisons are so darned profitable! So there is no reason to suppose that a businessman would fare better than, say, an engineer.
I quite like the idea of a government led by engineers and scientists, actually. Oh wait… that’s China. Hmm.

What tough decision? If you get asked to fight the war on terror, you privatize security and put in minimum wage people, outsource your intelligence analysis to India, lay off most of the NSA, and then vote yourself a 50% raise for saving money. What’s tough about that?
Yeah but could you do all that with a straight face? That’s where the real skill comes into play.

I quite like the idea of a government led by engineers and scientists, actually. Oh wait… that’s China. Hmm.
No, that’s Technocracy!

No, that’s Technocracy!
Not exactly. Technocracy isn’t just a government composed of engineers, it’s a government set up by engineers. So even if engineers won every seat in Congress, it wouldn’t be Technocracy. In Technocracy there would be no Congress, just some sort of expert panel whose members were chosen based on their technical qualifications. As far as I know, Chinese government officials “just happen to be” engineers. They’re in the government because of their loyalty to the Communist Party, not because of their technical qualifications.