Top 3 Craziest CEOs Ever


From Dov Charney to John Mackey, these CEOs show us that not all business leaders aren’t cut out to be role models!

After a massive round of firings and failed changes to Twitter’s core functioning, Elon Musk has announced that he will step down from his position as the Chief Executive Officer (CEO). His only condition for doing so? Finding someone foolish enough to take over. Since he started working as the company’s CEO, it has lost 60% of its share value and is clearly on a downward spiral.

While Musk’s story is undoubtedly unusual, he isn’t the only one in history to have done wacky things after becoming a CEO. Here is a list of some of the craziest CEO stories that should serve as a red flag to anyone in the business world.

Dov Charney

Image courtesy of Wikimedia Commons

The founder and former CEO of the clothing retailer American Apparel, Dov Charney, had a dramatic fall from grace when he danced naked in front of his female employees in 2014. This, however, wasn’t the only “crazy” thing that Charney had done. He was known to walk around the American Apparel factory in his underwear and allegedly masturbated in front of a female journalist. He has also been embroiled in multiple accusations of sexual harassment, using ethnic slurs and misusing company funds during his tenure.

After he was removed from the CEO position, Charney went on to create another clothing business called Los Angeles Apparel. Everything about Los Angeles Apparel was similar to his previous venture, from the business’s name to the clothes it made. Since starting afresh, Charney has continued to do controversial things, such as manufacturing Kanye West’s “White Lives Matter” t-shirts

As of 2022, Chaney had to file for bankruptcy because of an unsettled payment worth US$30 million. He owes the money to a hedge fund involved with his previous venture, American Apparel, which has gone through its own bankruptcies and has been converted to an online shop in 2022. 

Andrew Mason

Image courtesy of Wikimedia Commons

Another strange CEO worth mentioning is Andrew Mason, the founder and former CEO of the e-commerce website Groupon. Unlike Charney, Mason hasn’t had any sexual harassment accusations made against him. However, he did indeed release an album where the song “My Door Is Always Open” includes sexual harassment innuendos. 

Mason has done other mind-boggling things as well, such as releasing a nine-minute video doing yoga in his underwear and wearing a guerilla suit to work on multiple occasions. He also created a scholarship called Groupspwan, which funded the college education of children whose parents used Groupon on their first dates. To prove that you had actually used Groupon, the couple had to send in a picture of them on the date featuring the coupon and the day’s newspaper. Groupon even set up a team of investigators to verify that the couple’s claims were legitimate. 

In 2011, the company released a problematic Super Bowl advertisement mocking the struggle of the Tibetan people. The ad starts off by praising Tibet’s beauty and then takes a very unsavory turn. It goes from “…their very culture is in jeopardy” to “but they still whip up an amazing fish curry” and then finally promotes Groupon’s service. 

In 2013, Mason was fired from the CEO position—not for any of the crazy things he did, but for Groupon’s less-than-stellar financial performance. He then went on to create an app called Detor, which offered audio tours to cities that was acquired by audio equipment manufacturer Bose.  

John Mackey

Image courtesy of Wikimedia Commons

Finally, this list would be incomplete without John Mackey, the co-founder and CEO of the American grocery store chain Whole Foods. In 2007, Mackey was identified as an internet troll going by the name “Rahodeb”. As Rahodeb, Mackey regularly posted positive comments about Whole Foods on Yahoo! Finance bulletin boards all the while bashing the company’s rivals. He later went on to say that he had no intent to be identified as the troll and that he had fun with his internet persona.

Besides hurling hate toward Whole Foods’ competitors, Mackey has also made multiple other controversial statements. In 2009, he wrote an op-ed saying that he was against Obamacare (an affordable healthcare act in the U.S.). This got him into a lot of trouble with the American public, with some even calling for a boycott of Whole Foods. He has doubled down over the years, saying that instead of needing health insurance, people should be focusing on improving their diet and lifestyle. 

As of 2022, Mackey is as problematic as ever, making statements like “the young people don’t seem like they want to work” and that “socialists are taking over” when discussing the labor shortage in America.

From sexual misconduct and wacky behavior to controversial comments, these CEOs have all done different things to earn their spot on this list. While only two of the three people on this list were fired from their positions, these stories should serve as a warning sign to all founder-CEOs who feel like they are invincible. CEOs need to realize that their actions aren’t their own but rather represent their company at large. Thus, they need to be cautious about everything they say or do. Make sure to remember these stories, look for the right role models and be mindful of your actions if you currently run your own business or intend to do so in the future.

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Header image courtesy of Envato Elements 


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