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There is a naive belief that ego is essential to success. It's as ingrained in our cultural myth-making as the image of the starving artist or the strung-out but brilliant musician. And maybe we like these myths because they make for good movies or good excuses for our own lack of success. The Big Swinging Dick mentality might seem glamorous and special, but in reality, it's about as helpful as ... well ... a big swinging dick. (Like, constantly swinging, as in it would never stop swinging. You understand how that would be inconvenient, right?)

These beliefs persist because most of us never actually have to interact with these assholes. If we did, we'd see two things. Firstly, ego is almost always a liability and not an asset. Ask Kanye West. His ego might tell him he's the greatest rapper alive, but it's also told him he's a brilliant fashion designer -- a delusion that's cost him about $53 million which he apparently doesn't have. Secondly, the "stubborn individualism" we like to highlight in certain maverick personalities and eccentric billionaires is usually closer to malignant sociopathy and selfishness than it is the principled creativity that the Oscar-winning movies try to make it out to be.

But you don't have to take my word for it (though I did write a book about it). Let's look at the actual history. Here are five profoundly successful people, and how their enormous egos either killed them, cost them billions, ensured humiliating defeats, or generally turned them into insufferable asshats whom everyone hated.

Steve Jobs


The two-sentence version of Steve Jobs for most people is: "Visionary genius starts Apple Computers and then is foolishly fired by the 'suits' who came in to run the place. He proves them all wrong by coming back -- after a brief stopover starting Pixar -- and turning Apple into the world's most valuable company."

It's the Hero's Journey, and proof that The Man always tries to keep creatives down. Except this is totally wrong. If you'd been in charge of Apple, you'd have fired Steve Jobs, too. Not because he was an asshole or acting (as one board member put it) like a "petulant brat," but because the Macintosh division, which he was in charge of, missed its sales target by 90 percent. You can suck at being a good person or you can suck at your job, but you can't do both -- I don't care how smart you are. And Jobs became increasingly terrible, because he was a walking egomaniacal dickhead.

Kinda makes you feel stupid for wasting all those perfectly good apples, huh?

A short list of examples. Jobs was asked specifically "to behave" by Apple's CEO before a meeting with Bill Glavin, the vice chairman of Xerox. Jobs started (and then immediately ended) that meeting by telling Xerox, "You guys don't have any clue what you're doing." He told said that Mick Jagger was "on drugs. Either that or he's brain damaged" because he didn't know who Jobs was ... in 1984. On a trip to Italy, Steve told the Apple general manager there that "You don't deserve to be able to sell the Mac." On another occasion, Jobs told a woman organizing an Apple press event -- after she pulled a miracle by finding, at midnight, the right type of lilies he demanded -- that her suit was "disgusting." This coming from the guy who would eventually choose a mock turtleneck and a pair of dad jeans as his official uniform, like he was perpetually on his way to Parents Weekend at his kid's mime school.

But even if he wasn't mean, his approach didn't really work. A marketing chief for Apple once described Jobs's leadership style as "management by character assassination." "[Jobs] was not the world's greatest manager," his biographer, Walter Isaacson, has said. "In fact, he could have been one of the world's worst managers." The problem was that, despite Jobs's utter and complete certainty that he was right, he was often wrong. For instance, there was the time he became convinced that all the machines in one of Apple's factories should be painted certain colors. He spent hours obsessing over the colors. He ignored warnings that repainting this high-performance machinery would damage it and overrode the manufacturing director. Guess what? It broke the most expensive machine (they renamed it "Steve's Folly"). The director quit.

At least he didn't demand that it all be done in glass.

The reason Jobs's story isn't as sad as some is that he was able to conquer some of these demons and came back to run Apple in a somewhat sane manner. He made billions as a result. But he still couldn't help himself. He was notorious for parking in handicap parking spaces at the front of Apple. Hey, Steve, you're worth billions of dollars. Why not just pull up to the front and have a valet park for you? Or build yourself an office around a parking spot? Or, I don't know, walk? There was also the time he berated a poor old lady at a Whole Foods for not making a smoothie to his liking. Look, I hate overpaying for juice and waiting in line too, but the bigger question here is, why are you getting your own smoothies, anyway?! Why can't you feel any empathy for someone not quite as brilliant as you?

That inability to listen or follow basic common sense came back in a nasty way for Jobs when he tried in vain to cure his own cancer with "acupuncture sessions, drinking special fruit juices, visiting 'spiritualists' and using other treatments he found on the internet." Sadly, the problem with ego is that it tells us we know better even when we don't. Fatally so.



In 480 BC, the Persian Emperor Xerxes began his famous invasion of Greece. Given his resources -- an army of some 2.5 million men held in complete obedience -- and his disorganized and puny enemy, he probably should have been able to make quick work of the bickering city states in the region. A betting man at the time would have guessed that we'd all be speaking Persian for the rest of history. But Xerxes lost. Not just lost, but in one critical battle, his entire army was humiliated by a grand total of 300 warriors who belonged to a weird military cult called "Sparta." And then he lost again at Salamis, where he fell for a ridiculous ruse by the Athenian general Themistocles, who fooled Xerxes into thinking he was actually on his side (egoists think everyone loves them). Then he lost at Plataea and limped home in complete failure (but not before getting his ass kicked a fourth time at Mycale).

He probably didn't even get to enjoy the lovely views.

One story makes it clear that Xerxes's real enemy wasn't the Greeks, but his own raging, delusional ego. As he crossed the Hellespont, a waterway separating Europe and Asia now known as the Dardanelles, the waters surged up and destroyed the bridges his engineers had spent days building. In response, Xerxes thought it would be appropriate to throw chains into the river, and ordered it be given 300 lashes and branded with hot irons. As his men delivered his punishment, they were ordered to harangue the river. "You salt and bitter stream, your master lays this punishment upon you for injuring him, who never injured you." Oh, and he also cut off the heads of the men who built the first bridges. For good measure.

The great historian Herodotus called the display "presumptuous," which is probably an understatement. I say "fucking crazy" is more appropriate. Then again, it was part of a pattern. Shortly before this, Xerxes had written a letter to a nearby mountain in which he needed to cut a canal. "You may be tall and proud," he wrote, "but don't you dare cause me any trouble. Otherwise, I'll topple you into the sea."

Yes, you read that right: Xerxes, the emperor of Persia, threatened a mountain, spanked a river, and lectured both of them like they were children in the back of a station wagon. Don't MAKE me turn this chariot around!

To be fair, Mother Nature is far easier to control than an upset toddler.

You might remember Xerxes from the movie 300. He was considered a fool long before that. Cicero paints him as an addict who never found satisfaction despite access to unlimited pleasure (which is why he overreached so badly). Montaigne called him a fool. In a long history of tyrants in the ancient world, Xerxes is singled out by historians as being particularly stupid and immature -- he's Kim Jong-un. You wouldn't think it'd be possible to be worse than his father, but somehow the son managed. Even the actor assigned this ridiculous role in 300 felt inclined to judge the man: "He's rich, he's arrogant, he's a very unstable megalomaniac. He just wants to conquer the world. His ambition is unlimited. He wants glory; he wants victory; he wants eternal fame. Underneath all that wanting, though, he's ultimately weak and very insecure." Aeschylus's play about the invasion has a better line. After hearing what his son has been up to, Xerxes's dad asks: "Tell me, wife, does not all this mean that my son was ill in his mind?"

Um, yes, your son is sick with ego. And he destroyed your empire because of it.

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Howard Hughes


At a business lunch in 1924, Howard Hughes, Sr. stood up and then fell dead of a heart attack. He left to his son, a young Howard Hughes, Jr., a multi-million-dollar empire with a monopoly on a critical drill bit used in the oil business. Despite what the movies and myth-making might have you believe, over the next five decades, Howard Hughes proved himself to be quite possibly the worst businessman of the 20th Century ... and a colossal and deranged egomaniac as well.

Hughes started off by moving from Houston to Los Angeles and never stepping foot in his father's factory again. Trading stocks from his bedside, he lost more than $8 million in the market leading up to the Depression. He got into the movie business, whereupon his most well-known film, Hell's Angels, took over four years to make, lost $1.5 million on a budget of $4.2 million, and nearly bankrupted the tool company in the process. Then, not having learned a lesson the first time, Hughes lost another $4 million on Chrysler stock in early 1930. As you can imagine, the "responsible adults" in his life warned him against all of these moves. But he was the genius who knew better.

After all, "responsible adults" made him dress like this.

He then put all this aside to enter the aviation business, creating a defense contractor called the Hughes Aircraft Company. Howard's two contracts during World War II, worth $40 million, were massive failures at the expense of both the American taxpayers and himself. The most notable, the Hercules -- derisively referred to as the "Spruce Goose," and one of the biggest planes ever made -- took more than five years to develop, cost roughly $20 million, and flew just a single time for barely a mile, only 70 feet above the water. At his insistence and expense, it then sat in an air-conditioned hangar in Long Beach at the cost of $1 million a year for decades. Deciding to double down on the film business, Hughes purchased the movie studio RKO and proceeded to lose $22 million and 1,500 employees as he ran it into the ground over four short years. Tiring of these businesses as well, he forsook defense contracting and handed it off to those responsible adults, who managed to turn it into a real business ... almost exclusively because he wasn't there to fuck it up. The only thing Hughes really made any money off of personally was Trans World Airlines, whose stock he was forced to sell after shareholders sued him for mismanagement.

"That we have made a hero out of Howard Hughes," a young Joan Didion once wrote, "tells us something interesting about ourselves ..." She's right. It tells us that we're idiots and we pick bad heroes.

We're really good at coming up with funny nicknames for dumb shit, though.

Hughes was, among many things, a preposterous racist who believed that black people were dirty and carried diseases (and should be segregated accordingly). He didn't talk to movie star Ava Gardner for a month and a half when he found out her childhood friend was black. He was corrupt and shadowy figure who gave loads of illegal cash to Nixon (fear of the exposure of these bribes were partly responsible for the Watergate break-in). He invested in his first Las Vegas casino not because people love gambling, but because he was too lazy to vacate the hotel room he was squatting in. He staffed his company almost entirely with sycophants (usually Mormons), whom he would harangue with weird multi-page memos about Kleenex and not looking him in the eye. Then we're supposed to excuse all this because he may have had a mental illness?

There is a strong argument that Hughes' mental decline was the result of repeated head trauma ... which he caused because he was reckless and selfish. Like a plane crash near Culver City, California in which he nearly died, but which could have completely avoided if only he followed the Air-Force-approved flight plan (the pilot error, which he denied, is called a "crushing blow to Hughes' ego" by his biographers). Or a car accident after a night of drinking in Hollywood in which he killed an old man. CTE is a real disease, but it's hard to sympathize with someone who gave it to themselves by being incredibly unsafe. And even if Hughes did have it, being a drug addict certainly didn't help anything. Consuming massive, borderline lethal, amounts of codeine for decades, as well as Valium and Librium (taking them, as one biographer wrote, at "ten times the normal dose"), usually doesn't help anything.

No matter how many reminders Vegas posts.

Hughes believed that he was lucid and in control of the things he thought mattered, and bested plenty of saner people. God forbid a journalist would call him a mere "millionaire." "Goddammit," he replied, "I'm a BILLIONAIRE." Except he was probably only that rich because he never paid any taxes. In an impressive streak, Hughes once evaded paying any personal income taxes for 17 consecutive years. He would even later go as far as to create a medical foundation as a tax dodge which one biographer called "an outrageous parody." Oh, and why did he leave California in 1966? To escape state taxes.

So when Hughes died on a plane in 1976, malnourished and hooked on codeine, surrounded by hangers-on who were bleeding him of money and genius, it wasn't some accident. It was the result of a lifetime of selfish, indulgent, terrible decisions.

John DeLorean


As bad as Howard Hughes was, it'd be hard to find a bigger cult hero who was actually a huge asshole than John DeLorean. For starters, the man was preposterously vain. As one of his biographers would mock him, "probably no words in the Bible would have more significance to a contrite DeLorean than the admonition from the preacher in Ecclesiastes, 'Vanity of vanities; all is vanity.'" One of his frat brothers (yes, of course he was in a frat) recalls: "He was very vain about his looks. Whenever he passed a mirror, he glanced over to see himself, or tried to comb down his hair." His home was filled with mirrors, and he went through extensive facial surgery. At one point, he tried to introduce a fake space in his name -- becoming De Lorean -- to bolster his bogus claims of French ancestry.

In his mind, he's the sexy blonde.

This is a dude who actually collaborated on a book called On A Clear Day You Can See General Motors. It was a great line, but probably a bit premature for a guy who hadn't even launched a single car yet. Especially because seeing General Motors and actually beating them are entirely different things. Especially when his management style, as one employee described it, was "chasing colored balloons" -- going from one ridiculous distraction to the next. DeLorean seemed to be convinced that marketing would be all it'd take to beat the biggest car company in the world.

Which is why he wasn't concerned with making cars that worked, and let's not dance around the fact that the DeLoreans were terrible when they came out. They didn't work. Cost per unit was massively overbudget. The company hadn't secured enough dealers to sell them, and they couldn't deliver cars to the dealers they had signed up. The launch was a disaster. The DeLorean Motor Company never recovered.

The letters the company received speak for themselves. One person wrote from Long Island: "I am embarrassed to be the owner of a DeLorean ... When the headlights don't turn off, I am embarrassed. When the signal lights don't work, I am endangered. When the fuel gauge doesn't work, I get stuck." That the car you buy will work as expected is a pretty usual prerequisite -- unless you buy a DeLorean. As one delighted customer wrote, "the car is of no use to me because I cannot be sure when it will run." But that's not simply cherry picking from unsatisfied consumers. One of the company's executives said that "car companies average three or four claims for each produced car in the course of a year. But the DeLorean was pulling three or four claims per car per month." [Emphasis mine.]

Erin Cadigan/iStock
Almost all of them involved problems with the flux capacitor.

It's only fitting that the DeLorean Motor Company had but one success story: Back To The Future. The DeLorean was a perfect car for that movie. It had a futuristic, industrial feel to it. The gull wings gave it the impression of being able to fly. And the fact that none of the shit in the damn thing ever worked gave Doc Brown that much more room to operate, because he had few critical functions to work around. There's no way he would have been able to retrofit any other car with a time machine that ran on plutonium. Only that tin can of a vehicle would work. And even then, when push came to shove, he still needed a bolt of lightning to generate the 1.21 gigawatts of electricity necessary to get the goddamn thing up to freeway speed.

I suppose all of this isn't so terrible on its face. Plenty of creative people have overreached with ambitious projects and failed. Nothing wrong with that. But as the bad news began to pile up and the picture made clear and public, how do you think DeLorean the man responded? Was it with resigned acceptance? Did he acknowledge the errors his disgruntled employees were making public for the first time? Was he able to reflect, even slightly, on the mistakes and decisions that had brought him, his investors, and his employees so much trouble?

Did he realize the toy version of his car is worth more than a real one?

Of course not. Instead, he put in motion a series of events that would end in a $60 million drug deal and his subsequent arrest. That's right; he figured the best way to save his company would be to secure financing through an illegal shipment of 220 pounds of cocaine. But he was acquitted! It was entrapment! his supporters like to argue. This is rather implausible when you watch the video of him holding up a baggie of cocaine, saying with giddy excitement, "This stuff is as good as gold." Yeah, you're an idiot, DeLorean -- sorry, De Lorean -- and your cars sucked too.

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Donald Trump


In 1990, a mediocre businessman (but shrewd marketer) from New York City named Donald Trump gave an interview in Playboy in which he claimed that America needed a bigger ego -- one like his. His fear was that America was being "outegotized" by Saudi Arabia, West Germany, and Japan. To think, just 30 years later, America would get all this swagger back when Trump ran for president, claiming that having hosted an "incredible" Miss Universe pageant in Russia was legitimate foreign policy experience qualifying him to possess nuclear codes.

In the intervening decades, Trump has not only turned his idea of ego into parody, but also into a runaway train of fraud, failure, and shamelessness. From being so desperate for media attention that he pretended to be his own publicist under the name John Barron, to creating Trump "University," which is currently being sued for "not just ... fraud, false advertising, and unfair business practices, but also [for] having used such tactics against vulnerable seniors in ways that violated special "financial elder abuse" statutes in California and Florida." Vulnerable seniors, Donald? Come on, man! You've already cornered the market on vulnerable younger Eastern European women. Can't you leave some demographic undisturbed?

"You! You are the one I am going to fuck over next!"

The failures ... there have been so many failures. There were Trump Steaks, about which the CEO of the only store carrying them said, "we literally sold almost no steaks." Trump Magazine, which also flopped. Trump Airlines. And the four bankruptcies in Atlantic City, New York, and Indiana. Like Jobs, his certainty works, except when it doesn't. Like the 2006 prophetic statement from a man who considers himself a real estate visionary: "I think it's a great time to start a mortgage company." Nailed it.

Trump's supporters brush all these aside. "He's very rich, you know," they say (or rather, Trump says this himself, pretending to be a spokesperson). But the reality is that Trump is a liar. He has claimed to be worth $1.7 billion and $5 billion on the same goddamn day! Gawker actually has an impressive timeline of his inflated net worth, and when Gawker has legitimate criticism of you, that's saying something. In any case, it's incredibly important to Trump that you know that he's a billionaire. Except he might not actually be. One of his biographers was sued by Trump (for billions) for saying that "Three people with direct knowledge of Donald's finances, people who had worked closely with him for years, told me that they thought his net worth was somewhere between $150 million and $250 million." That case was thrown out.

Of course, lying comes quite naturally to Trump, maybe moreso than it does for other egomaniacs. PolitiFact analyzed 77 of his statements last year, and you know how many it found false? Three out of four! Just think, by this standard, a one-hour speech from him has about 45 minutes of pure lies. But what's most impressive is that he's so delusional that he doesn't even think he's lying. He literally lives in a world where he is entitled to his own facts.

And his own phallic symbols.

But, you might reply, how has this cost him anything? He's still rich. He might well be president very soon. I believe that is quite possible. And I believe Andrew Sullivan when he calls this an "extinction-level event." In this sense, Donald Trump and his ego will win only in the Charlie Sheen sense, and the tragic, ignominious end is written all over his bloated orange face. And when it happens, we all lose with him ... because we're doing to die in World War III or in a new depression that will make Herbert Hoover look like a great president.

Ryan Holiday is the bestselling author of Ego is the Enemy and three other books. His monthly reading recommendations which go out to 50,000+ subscribers are found here.

Check out the biggest egos of Hollywood in The 5 Most Hilarious Actor Meltdowns Behind Famous Movies, and read about the greatest egomaniac of them all in 10 Stories About Donald Trump You Won't Believe Are True.

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