The Exchange

They did what? The wacky antics of some well-known CEOs

The Exchange
Outrageous CEO Moments - John Legere
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John Legere

The life of a corporate CEO can be challenging, filled with endless responsibilities and the kind of pressure the rest of us can’t even imagine. The image of the buttoned-down, stressed-out CEO persists for a reason.

But that doesn’t mean all CEOs fit the mold. Some executives buck the trend by embracing a more casual attitude, cultivating an outsider image or simply by dropping a few “f bombs” during their public appearances.

For example, T-Mobile (TMUS) CEO John Legere raised eyebrows on Tuesday when he crashed competitor AT&T’s launch party at the Consumer Electronics Show in Las Vegas, complete with a bright-pink T-Mobile t-shirt. He was escorted out by security after about 15 minutes when a CNET reporter tweeted a photo of Legere at the event. Later, Legere told tech news site Re/code that he simply “wanted to hear [rapper] Macklemore,” who was performing at the party.

Legere has also made headlines for his unique personal style – he eschews the usual suit-and-tie, opting instead for jeans, that pink T-Mobile t-shirt and sneakers with bright pink laces – as well as actively embracing social media and trolling the competition in all media. All qualify as very non-CEO-like activities.

But Legere is far from alone when it comes to outrageous CEO behavior. Consider these other contenders for the title of world’s nuttiest CEO.

John Mackey – Whole Foods

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In 2007 it was revealed that Whole Foods (WFM) CEO and co-founder John Mackey had been posting under a pseudonym -- in his case “Rahodeb,” a variation on his wife Deborah’s name -- on the Yahoo Finance message board associated with his company’s stock for the better part of seven years, sometimes talking up Whole Foods, sometimes taking aim at his rivals and sometimes making more ... cryptic ... comments. “I like Mackey’s haircut. I think he looks cute!” read one Rahodeb post from April 28, 2000.

Things got complicated for Mackey when the Federal Trade Commission discovered his online antics while researching the grocer’s then-proposed acquisition of its smaller competitor, Wild Oats, and tried to use his comments about the company against him (Whole Foods eventually won out, acquiring Wild Oats later that year.) “I posted on Yahoo! under a pseudonym because I had fun doing it,” Mackey later admitted. “I never intended any of those postings to be identified with me.”

Andrew Mason – Groupon

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No one ever accused Groupon (GRPN) founder Andrew Mason of being a typical CEO. After all, while in charge of the fast-growing ecommerce company, he wrote reams of poetry on his personal blog, posted a video of himself doing yoga in his underwear and, most jarringly for a chief executive, turned down a $6 billion acquisition offer from Google (GOOG) in 2010. Even his farewell memo to staff, following his 2013 dismissal, was ... different.

“After four and a half intense and wonderful years as CEO of Groupon, I've decided that I'd like to spend more time with my family,” Mason wrote. “Just kidding - I was fired today.”

And he isn’t slowing down yet. Four months after being fired, Mason released an album of original rock songs titled “Hardly Workin.’” A typical line: “If you’re seeking business wisdom / You don’t need no MBA / Look no further than the beauty / That surrounds us every day.” Yes, it’s available on iTunes.

Tim Armstrong – AOL

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AOL’s (AOL) local news network, Patch, has had a rough run of late, hemorrhaging more than $300 million since it was acquired in 2009, cutting its total number of sites by one-third last fall and becoming the subject of shutdown rumors in late 2013. That stress boiled over in August when, on a conference call with some 1,000 Patch and AOL employees, CEO Tim Armstrong fired Patch’s creative director, Abel Lenz, at what appeared to be the drop of a hat. “Abel, put that camera down right now!,” Armstrong can be heard saying on the call recording, right in the middle of his presentation on Patch’s long-term prospects. “Abel, you’re fired. Out!”

Armstrong was apparently upset that Lenz was taking photographs during what was supposed to be a confidential, internal meeting. The CEO later apologized for the public outburst: “I am writing you to acknowledge the mistake I made last Friday during the Patch all-hands meeting when I publicly fired Abel Lenz. I am the CEO and leader of the organization, and I take that responsibility seriously.”

Lenz, however, remained fired.

Steve Ballmer – Microsoft

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And what list of wacky CEO antics would be complete without a mention of outgoing Microsoft (MSFT) CEO Steve Ballmer, the king of over-the-top, extra-emotional outbursts dating back to his earliest days with the company. (His car salesman-inspired videos for the various versions of Windows, for example, are must-see-TV.)

It’s an impressive body of work, but it was all leading up to his legendary 2013 retirement speech. At Seattle’s KeyArena in front of some 13,000 Microsoft employees, Ballmer cried, danced and yelled his way through a high-energy farewell. He high-fived his way off the stage to the strains of Michael Jackson’s “Wanna Be Startin’ Somethin’” – which was apparently played at Microsoft’s first employee meeting in 1983 – and “(I’ve Had) The Time of My Life,” better known as “that song from ‘Dirty Dancing.’”

Soak it in, Steve. Soak. It. In.

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