The 10 Biggest CEO Facepalm Moments

The 10 Biggest CEO Facepalm Moments

CEO Facepalm moments
CEO Facepalm moments

Sometimes powerful and accomplished people do really, really stupid things. Things so stupid, you have no choice but to bury your face deep in your palm and hope it’s all a dream. These are facepalm moments, and for years, some of the world’s most prominent CEOs and business leaders have been hard at work making them for us.

From faking your own death in a plane crash to issuing threats against your critics, here are ten lessons in how to kill your career in a single moment. You might have to look away in disbelief a few times.

Emil Michael (Uber) threatening his critics and their families

Some companies hire publicists to manage their image and communicate with the media in a carefully crafted way, but here’s another strategy: just say whatever comes into your mind, at any time, especially when you’re angry. That’s what Emil Michael, VP Business of Uber, has done with really remarkable results. In response to mounting criticism of Uber’s business model, Michael threatened to spend a million dollars to hire opposition researchers and journalists to dig up dirt on journalists’ personal lives and families, thus giving them “a taste of their own medicine.” In an age of digital communication, when anyone can take to Yelp and Twitter to express an opinion, this worked out really well for Michael and his critics were immediately silenced. In totally unrelated news, Uber is looking for a publicist.

Michael Jeffries (Abercrombie & Fitch) saying his clothes are only for attractive people

Abercrombie & Fitch is known for its controversial advertising and labour practices, which include marketing sexualized clothing to pre-teens and hiring “brand models” to work in their stores. They also raised eyebrows recently for only offering women’s shirts in size L or smaller and pants up to size 10. When asked what the deal was, Jeffries threw gasoline on the fire by saying his brand’s clothes were only meant for thin, attractive, popular people. Haters can hate, but we think it’s actually very selfless of him to run a store that he can’t even go into.

Anthony Noto (Twitter) failing at using Twitter

Twitter is really complicated, right? For example, you can write a regular tweet, which is public, or you can send a direct message, which is private. Wait, we’re already lost, so we’ll just explain this in layman’s terms. Anthony Noto, CFO of Twitter, recently sent out the wrong kind of tweet during talks about buying another company and accidentally went public about private M&A activity. In his defense, Twitter is hard to learn and it’s not like he works for them or anything.

John Mackey (Whole Foods) posting on Yahoo under a thinly-veiled pseudonym

Have you ever liked your own haircut so much, you actually called yourself cute in a public forum? John Mackey of Whole Foods sure has! Between 1999 and 2006, Mackey posted in Yahoo stock market forums under the alias Rahodeb, an anagram for Deborah, his wife’s name. Rahodeb was an especially active critic of Wild Oats, one of his competitors, who he lambasted repeatedly for their poor business practices and slumping revenue. On the other hand – shockingly – he only had nice things to say about Whole Foods, as well as his own hairdo in a photo that came out with a quarterly report. Rahodeb’s identity was revealed in an antitrust lawsuit following Whole Foods’ acquisition of Wild Oats in 2007. An aggregation of his comments shows that he even claimed to be George W. Bush at one point.

Gavin McInnes (Vice) – pretty much any time he talks

You know your drunk uncle who makes inappropriate comments at family holiday dinners? Imagine starting a company with him, and you have Gavin McInnes of Vice. Always one for stirring up controversy, he’s on record saying things like feminists are “miserable” and the US should “close the borders now and let everyone assimilate to a Western, white, English-speaking way of life.” McInnes became a liability for Vice’s co-founders as the media company exploded in popularity across the 2000s, forcing them to cut ties and all but erase him from their history. Recently he was also ousted from Rooster, an advertising company he co-founded, for publishing an essay championing transphobia. This means he’s on the job market!

Dov Charney (American Apparel) let’s say… gratifying himself in front of an interviewer

American Apparel’s eccentric founder is well known today as one of the worst CEOs of all time, having drummed up countless sexual harassment allegations while running his company’s revenue into the ground. But there was a time when he was regarded as a lamplight for humane business practices, when American Apparel was at the forefront of a movement to increase the quality of manufacturing jobs and bring them back to North America. This all changed completely in a Jane Magazine interview from 2004, where Charney repeatedly masturbated in front of the journalist and received oral sex from a female employee. It was the key moment that shifted the discourse about American Apparel away from fair labor and toward Charney’s antics, and it was the beginning of the end of his career.

Marcus Schrenker (Financial adviser) faking his own death

Anyone who has ever watched a B-level detective movie knows that faking your own death is a fool proof way to solve all of your problems. That’s why the financial adviser Markus Schrenker, when he faced prosecution for fraud, decided to stage a plane crash. After making a fake distress call, he bailed out of his private turboprop Piper Meridian and let it descend into the Florida wilderness while he parachuted to safety. It might have worked if he hadn’t then bone-headedly checked into a hotel, pulled his motorcycle out of a storage facility, and e-mailed his neighbor. Now he’s in jail serving four years for the crash and ten years for securities fraud.

Ernest Saunders (Guinness) faking Alzheimer’s disease

Ernest Saunders was one of the Guinness 4, who manipulated the company’s stock prices in order to help them buy another distilling company. After he was sentenced to five years in prison (soon reduced to two and a half), Saunders began developing the symptoms of Alzheimer’s disease. A judge deemed him too unhealthy to serve his sentence and had him released. Then, like magic, the symptoms disappeared and he returned to his normal self. Pretty miraculous for a disease that has no cure.

Sumner Redstone (Viacom) pushing a teen girl band on everyone

Of all the facepalm moments, this one might be the most cringe worthy. Apparently Sumner Redstone, Executive Chairman of Viacom, has a thing for teen pop bands. This much became clear when he forced MTV to air a reality show about the Electric Barbarellas and then went on a witch hunt against anyone who said he was artificially propping up the band. This included leaving journalists threatening voicemails and offering a reward for information on his detractors. All this for a band that his granddaughter should care about, not him. You’d think the head of Viacom would have more important things to worry about.

Tony Hayward (BP) going yachting during the Gulf oil spill

As millions upon millions of gallons of oil spilled into the Gulf of Mexico, BP CEO Tony Hayward thought it was a good to go yacht racing around the Isle of Wight. This angered officials on the other side of the Atlantic who were working tirelessly to clean up the spill, not least presidential chief of staff Rahm Emanuel, who said the incident was just one in a long line of Hayward’s PR gaffes. When trying to save face, Hayward just made things worse by saying, “There’s no one who wants this thing over more than I do, I’d like my life back.” Though intended as a sympathetic statement, his concern with himself in a time of crisis just showed how out of touch he was. Understandably, he has since been replaced by Lord Browne of Madingley.

Also, here’s a video of Steve Ballmer dancing to Fergie

Enjoy!