The Business World’s Craziest CEOs

“You have enemies? Good. That means you’ve stood up for something, sometime in your life.”

Changing the world means changing the status quo. In every situation, there are people that benefit from the status quo. You can bet that they will be fighting back.

On the other hand, we’ve all met arrogant people who attach undue importance to themselves and confront others over trivial matters.

That’s the thing about some of the ‘crazy CEO’s. It’s difficult to really assess their true worth. At times, they appear to be visionaries heralding a new era for the world, and at other times they simply appear to be immature and arrogant.

The truth is that they are a mixture of both. The qualities that give them their self-confidence, energy and audacity often leads them towards arrogance and even insecurity. The key question then becomes- where does the balance tip? Towards genius and changemaker or arrogant and aggressive?

Two sides of the same coin?

Rahul Yadav is the latest enigma that has divided opinion, but he is by no means the only one. Let’s take a look at three other famous crazy CEO’s.

The most powerful developer in the greatest real estate market of the world is synonymous with wealth, power and success, and the phrase “You’re fired.” His businesses decisions have sometimes been questionable- he has filed for corporate bankruptcy four times, but he’s always bounced back. According to Forbes, he is worth $4.1 Billion at the time this article was written. Whatever you might have to say about his political beliefs, he is definitely a businesses genius.

The other side of his personality comes out when you talk about bankruptcy and his personal worth, as writer Timothy L. O’Brien found out. When in his book ‘Trump Nation’, O’Brien estimated Trump’s net worth to be between $150-$250 million, Trump took the removal of his billionaire status extremely hard. So hard, that he sued O’Brien and his book publisher for defamation, asking for $5 Billion in damages. That’s right, $5 Billion.

We might even have given Trump the benefit of the doubt, if not for when he personally replied to tweets detailing Trump’s bankruptcy. The tweets were simply about an old article by three users with less than 100 followers, and were receiving no notice. For the record, Trump had 2 million followers, and with his reply, he probably brought a million times more attention to the matter than it would have received in the first place.

Here’s what O’Brien thinks- “I think it’s very important to him, psychologically and emotionally, to be considered fabulously wealthy, because I think he sees it as part of a pecking order and a symbol of his arrival,” as reported in this article of The Atlantic.

The latest entrepreneurial star has seen his enemies grow almost as quickly as his company. But when accused of everything from compromising passenger safety to breaking regulations and sabotaging opponent’s businesses and even misogyny, one of Kalanick’s early investors simply has this to say-

“It’s hard to be a disrupter and not be an ass****.”

To be fair to Kalanick- he is up against an extremely regulated sector- that of taxi’s and personal transportations, and for a man who aims to build the world’s largest transportation company- completely following the rules would probably mean killing the dream before it began.

There’s no denying Kalanick’s mission is one the world desperately needs- i.e., fixing a transportation system that, depending upon the place to place, ranges from irritating to extremely annoying to completely broken.

But is he guilty of being too focused on growth? Opinions will vary, but most will agree that distributing compromising information about a critical journalist is taking things a bit too far.

For a full list of Uber’s controversies, read this article.

How can we write a post on ‘crazy CEO’s without talking about the original ‘crazy one’?

Steve Jobs has become one of the most romanticized individuals of this decade, so much so that it threatens to distort his real story. It’s often reported to be one of an unyielding genius who could be extremely mean and compromise the best of his relations for business goals.

The truth is, however, that the Steve Jobs that was fired from Apple, while being a genius visionary, was too unfocused, immature and whimsical to be a truly great business leader- like he became during his second innings. He used to keep shifting focus, both with specifications decided within projects like he did with the first NeXT computer and between projects. He would completely ignore the opinion of others, and often be too extravagant, as with NeXT’s office and brochure (he spent $100,000 dollars on that and the logo). He would pick fights with business leaders, throw tantrums, scream tirades at employees and journalists, all the time walking barefoot. He was the definition of the crazy CEO’s, a man who weighed the balance on both sides.

It was his years at NeXT and Pixar that he acquired the qualities that would help him in the most successful second innings in business history, and change the world as we know it.

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