Explaining Donald Trump

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If writing about music is like dancing about architecture, then explaining about Trump is like sneezing about hermeneutics.

I believe it to be the general opinion across the land that anyone who thinks he can explain Donald Trump has probably just escaped from an Institution for the Criminally Insane.

From where I sit it appears to be the case that the entire world — not just the American corner of it — has taken sides on the matter of Donald Trump. I therefore consider it my sworn duty as Your Humble Blogger to Explain Donald Trump to both the traumatized Trump-​haters of the world and the enraptured Trump-​lovers of the world. Not only that, but I’m going to assert, only semi-​facetiously, that I can explain Trump by focusing on merely two of his characteristics.

The reason I can claim to do so is that, as it happens, I’m observing the Trump phenomenon from a rare vantage point. After forty years of working with wealthy families I’ve had the – I was going to say “pleasure,” but instead I’ll say the “opportunity” — to come to know a very, very few people like Donald Trump. By that I mean men and women who have built gigantic fortunes in one lifetime, typically north of $1 billion.

In other words, these folks aren’t ordinary people like the rest of us, and they aren’t ordinary wealthy people, and they aren’t even ordinary entrepreneurs. They are what I’ll call “mega entrepreneurial personalities” (MEPs). Whether or not “the rich are different,” these people are certainly different. They typically possess personalities so large they wouldn’t fit in, well, Trump Tower.

MEPs didn’t get where they are by being modest wallflowers. They have, instead, levels of self-​confidence that border on the deranged. They represent an infinitesimally small percentage of the human population, and most people live entire lifetimes without ever bumping into one of them. Which is perhaps why Trump’s behavior seems so inexplicable to so many people.

To understand the MEP phenomenon, let’s begin with Teddy Roosevelt’s famous advice to “speak softly and carry a big stick.” That certainly seems like sound counsel, and it well describes the sort of President Americans typically want to see in office.

Roosevelt’s advice makes sense if you happen to be, say, the head of a powerful nation, like the US. It makes sense if you happen to be a general leading a powerful army, like Eisenhower. It makes sense if you happen to be the CEO of a huge corporation, like Tim Cook. But what if you’re just one person trying to make your way in the world? You can speak softly if you want, but if you do no one will hear you. Since you aren’t carrying a big stick, something else about you had better be big, and what that thing is, is the Mega Entrepreneurial Personality.

MEPs therefore aren’t shy, retiring violets. If we think of a bunch of antonyms for “shy,” our MEPs will be all of them: loud, aggressive, bold, egotistical, self-​absorbed, audacious. They know they are starting out life carrying a very small, almost invisible stick, and so the last thing they want to do is to “speak softly.” MEPs decidedly do not speak softly.

But rather than prattle on in general about MEPs and their nature, let’s examine a representative sampling of Mega Entrepreneurial Personality characteristics and how they operate in the real world.

  • MEPs are, for example, extremely high-​energy folks. A typical day for an MEP might begin with a 6:30 a.m. power breakfast. Throughout the day MEPs might make or take forty or fifty phone calls, most of them extremely brief. They will attend twenty meetings, some lasting only a few minutes. They’ll arrive home at seven, just in time to host a fundraiser for some fancy charity. Naturally, many important people will attend the event, so dealmaking will go on into the wee hours. At 6:30 the next morning — actually, later that same morning — it will start all over again. A typical MEP’s schedule would put most of us in the hospital.
  • MEPs possess chutzpah with a capital “C” — Chutzpah. Imagine that you somehow came into possession of a wooden-​looking live-​action children’s TV show based on stock footage from, of all things, a Japanese TV series. What would you do with it? If you are like most of us, the answer is “nothing.” Maybe we’d show it to our neighbors for laughs on home movie night. If we were entrepreneurial types, we might take a deep breath and show the thing to a local TV station, suggesting that they might put it on at some ungodly hour when only eight-​year-​old boys are watching TV — say, seven on Sunday morning. But if you were Haim Saban you would take your show straight to Rupert Murdoch. Murdoch’s programming people wouldn’t stop laughing at you long enough to tell you to get lost, but they would eventually realize that life is simply too short to say no to Haim Saban. They run the show at some ungodly hour and the damn thing instantly becomes a mega-​hit. Saban parlays the popularity of Power Rangers into a half ownership in what became the Fox Family Channel which, a few years later, was sold to Disney for something like $5 billion. Meanwhile, the rest of us are back in Poughkeepsie watching home movies.
  • MEPs have a searing, almost supernatural ability to identify the weaknesses of their opponents. When Donald Trump speaks of “Low Energy Jeb,” or “Little Marco,” or “Crooked Hillary,” he is being outrageous and rude. But he has also zeroed in on exactly the Achilles Heels of those candidates. I have no idea whether this ability is innate in MEPs or whether, more likely, it developed over many years of having to compete as individuals against bigger and stronger adversaries. But it’s there and it’s almost universal among the MEPs I’ve known.
    • I’ll continue with my exploration of MEP traits next week.

      Next up: Explaining Donald Trump, Part II


Greg Curtis

Gregory Curtis is the founder and Chairman of Greycourt & Co., Inc., a wealth management firm. He is the author of three investment books, including his most recent, Family Capital. He can be reached at . Please note that this post is intended to provide interested persons with an insight on the capital markets and is not intended to promote any manager or firm, nor does it intend to advertise their performance. All opinions expressed are those of Gregory Curtis and do not necessarily represent the views of Greycourt & Co., Inc., the wealth management firm with which he is associated. The information in this report is not intended to address the needs of any particular investor.

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