Craziest CEOs of All Time

by Sasha Konikovo about a year ago in business wars

From a CEO who had a complete meltdown at a press conference to the owner of the "rainbow gulag," here is our list of the craziest CEOs of all time.

Craziest CEOs of All Time

One of the most commonly-cited trivia pieces about mental illness is that CEOs and business owners are far more likely to be psychopaths than the average person. Some stats suggest that as many as 1 in 5 CEOs are psychopathic or sociopathic in nature.

Truth be told, there have been a *lot* of really psycho, downright unstable CEOs throughout the years. Some are so crazy, they'd make Patrick Bateman from American Psycho seem like a stand-up guy.

It's hard to really believe the depths that CEOs will go to when they go off the deep end. This list will show you how deep the CEO rabbit hole goes, by highlighting the insanity of the craziest CEOs of all time.

Dov Charney (American Apparel)

Oh, man. Hang on tight, folks. This isn't going to be a nice way to kick off a list. Dov Charney isn't just one of the craziest CEOs of all time; he's also one of the rape-iest CEOs in the fashion industry.

Dov Charney made headlines when he founded upscale clothing company, American Apparel. Known for their edgy marketing and sexy models, it was the darling of the hipster world for a good while.

Then, the rumors started to swirl.

People began to talk about Charney's erratic behavior. Models claimed that he would grope them, sexually assault them, expect them to have sex with him, and even masturbate during business meetings. What's really insane is that Charney was cavalier about his behavior.

He straight up told an interviewer from Jane magazine that he and a model "put on a show" for a female business intern. He also paraded around the office in his underwear and posted the footage on the company site.

Eventually, his sex-fueled antics grew to be too much, and he was removed from his position by the board of directors. (And nothing of value was lost.)

John Mackey (Whole Foods)

To a point, it's hard to imagine Whole Foods being owned by anyone but a hipster. However, John Mackey is far from the typical peace-loving, artisan coffee-sipping denizen of his own grocery store. He's actually a pretty angry bloke.

Back in 2000, Mackey actually created a Yahoo troll account called "Rahodeb" that literally did nothing but praise his company and attack any competitors.

He even started to offer tips on how to save money at Whole Foods, and started to praise his own leadership. Eventually, people called him out for being a spambot—and even a PR agency pointed it out.

Cue the meltdown that made him one of the craziest CEOs of all time.

Rather than deny that it was him, or just admit that he was being a twerp, Mackey decided to claim that he was George W. Bush. Yes, the president. Then, he continued to troll... for another seven years, despite people all knowing it was him.

Bob Parsons (GoDaddy)

At the very least, we can say that Mackey is pretty humorous. Not all of the craziest CEOs of all time can be described that way. Bob Parsons, for example, is one of the most disgustingly cruel people on this list.

His idea of having fun is going to Africa, getting people to wear GoDaddy gear, and then shooting elephants while videotaping it. Yep, he thinks it's fun to shoot an endangered species. To add salt to the wound, he uploaded the video of his "vacation" to YouTube—and also added footage of them ripping the elephant's body apart.

He also has shot videos of leopard hunts, but has since given those up. Enjoying animal cruelty like that has to be a sign of something seriously wrong with your head.

John Schnatter (Papa John's)

Better ingredients, better pizza... not much better mental health, though. John Schnatter, founder of Papa John's, quickly made a point to prove himself to be one of the craziest CEOs of all time.

His erratic behavior was well-known throughout the industry, as was his addiction to plastic surgery. Schnatter recently stepped down from his fast food mega-chain after he ended up railing against Colin Kaepernick's peaceful protest in the NFL.

He was known for being a tough boss, often pacing about stores eyeing every employee carefully. A lot of employees claimed that Schnatter made them nervous.

After making a series of pretty costly PR mistakes involving the NFL, Schnatter stepped down from his role as CEO in 2017.

Thomas Edison (Edison Labs)

You'd never guess it, but the Wizard of Menlo Park was actually pretty unstable. Along with being insanely cruel to Nikola Tesla and stiffing him out of money, Edison was also known for having a certain level of paranoia and delusion.

His most famous "quirk" was believing in "little people" who were as tiny as atoms that lived inside your brain. He believed these little people worked to control and record your memories, and that a loss of little people meant you'd get Alzheimer's.

He even tried to create a device to talk to them. Yep. Might be a bit over-the-top, all things considered.

Steve Jobs (Apple)

Steve Jobs was basically the Willy Wonka of the tech world, but there's a side to him that many never knew. Among coworkers and contemporaries, Jobs was known for being excessively cruel and icy. But, you can be an asshole without being crazy, right?

What made Jobs one of the craziest CEOs of all time was his obsession with his body. That same perfectionism he applied to Apple also applied itself to his eating. More specifically, he was known for being extremely eating disordered and would only eat certain foods.

When he was diagnosed with cancer, he refused treatment until it was too late for him to recover. Earlier on, he asked doctors to supply him with five different oxygen masks so he could choose the most aesthetically pleasing one.

From what we've heard, his legendarily icy demeanor gave his closest coworkers feelings that their company couldn't care less about them. Whether that's true or not, it's safe to say that workplace stress must have been through the roof with him as chief.

Jason Russell (Invisible Children, Inc.)

It may seem a bit strange to see a nonprofit leader on a list of the craziest CEOs of all time, but the truth is that we can't ignore that time Russell snapped. Though he was most well-known for Kony 2012, the documentary that went viral and highlighted the atrocities that happened to child soldiers, the fame he incurred was just too much for him.

Due to the pressures he faced with his newfound Kony fame, he ended up having a nervous meltdown that cost him everything. TMZ released a video of him stripping naked and masturbating in public for reasons unknown.

Believe it or not, his breakdown didn't make him "crazy." It was actually caused due to extreme exhaustion and stress due to his demanding schedule. He was detained for a psych evaluation, and word is that he's feeling better now.

Eddie Lampert (Sears)

If there's one company that has a seriously long record for being able to stay afloat, it's Sears. Ever since the 19th century, Sears Roebuck has been one of the top sellers of family appliances in America.

However, it's no secret that Sears has fallen behind on hard times—and to a point, that's partly because the board of directors made the decision to hire one of the craziest CEOs of all time to be their new CEO. Eddie Lampert, though talented, is definitely a man who has issues.

Most recently, Lampert's long rant caused stocks to plunge after calling the fact that his company is showing signs of struggling "unfair." The entire rant, which was reported by Reuters, blamed the media for not reporting what he wanted them to say.

His tirade against mainstream media landed Sears in hot water and the company stock plummeted. Maybe the kitchen's too hot for Mr. Lampert? Maybe they need a new Chief Executive Officer?

Well, at least Lampert's oration skills would get him a good spot on the Republican Party's politician roster. Speaking of Republicans...

Donald Trump (Trump Hotels)

You knew that this would end up on this list. Love him or hate him, Donald Trump has proven that he's not all there. At the very least, we have caught him lying about his health and showing that he doesn't fully understand what it means to be a president.

At most, he's shown himself to be suffering from Narcissistic Personality Disorder as defined in the DSM-IV. He's caused us to flirt with potential nuclear war, annihilated trade agreements, and more. This makes anyone wonder if Donald Trump is going to jail—or the psych ward.

Matt Harrigan (PacketSled Inc)

While you might recognize most of the names on this list, chances are that you don't know PacketSled Inc. This is because it's a startup—and despite its obscurity, has managed to seal its claim to fame for having one of the craziest CEOs of all time.

You see, some CEOs are known for unhinged rants. Others are known for being rapey. Few CEOs, even when they are totally unbalanced, would be as crazy as to threaten to assassinate the president on Facebook.

And yet, that's exactly what Harrigan did. He threatened to do kill President Trump, and even claimed he'd use a sniper rifle to shoot him. Oh, and he also said, "Bring it, Secret Service!"

As you can imagine, it went over about as well as you'd expect.

Yes, Secret Service was involved. Yes, he was investigated. No, he didn't get jail time. He claimed it was a joke. Somehow, we don't think the feds were laughing.

business wars
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Sasha Konikovo

Born in the Ukraine and currently a citizen of New York City, Sasha Konikovo has become obsessed with makeup, fashion, and anything that keeps her svelte figure looking sharp. She hopes to marry a billionaire and have a lifestyle like Paris Hilton soon enough.

See all posts by Sasha Konikovo