5 Bizarre Habits Of Highly Successful CEOs

CEOs. They're not like you and me. They're ambitious. They're trailblazers. They're gutsy, sexy, mysterious, powerful, adventurous and absolutely Wait, you say. One of these things is not like the others. Who says CEOs are weird? I do. You don't stand out from the pack by being normal. The difference is that some CEOs hide their strangeness better than others. Personally, I prefer the ones that let their freak flag fly. At least you don't have to wonder how weird they are, they just come out and show you.

Of course, most of the CEOs of this world aren't all that odd. Some are just a little more driven, more type A personality, more tightly wound. But surely at least one of them is, if not a Patrick Bateman-level mass murderer, hiding some skeletons in their closet. Hopefully metaphorically.

The CEOs on that list do not fit that description. They don't hide their oddness. They let it all hang out. Some literally (I'm looking at you, Andrew Mason). And while we can't approve of all of their behavior we can at least understand that once you've achieved so much you start looking for other challenges. Even if those challenges put you in dire physical risk or make your employees wonder when you'll end up in a padded cell.

Here is a list of five CEOs with five habits that will genuinely surprise you, and leave you with a greater understanding of why you're not a millionaire business mogul. You're just not weird enough. So put on your tinfoil hat, make sure your underwear is on over your pants, and start reading.


5 Underwear Yoga

Who: Andrew Mason, Groupon

I am sorry to report that the CEO who posted a 9 minute video of himself doing yoga in their underwear was not one of The Richest's sexiest CEOs. No, this was Andrew Mason, possibly the strangest CEO of the modern tech era.

Andrew Mason – ousted CEO of Groupon – does some pretty odd stuff. The most shocking wasn't his plan to present Mayor Bloomberg with a pony. It wasn't turning down a 6 billion dollar acquisition deal from Google in Groupon's early infancy. It wasn't even his insistence on talking about miniature dollhouses if Dealbook wanted to interview him. Nope, the most shocking thing he did (in public) was upload a video of himself doing yoga in his underwear in front of a Christmas tree we can only hope was in his own home.

4 Mealtime Treasure Hunts


Who: Howard Hughes, RKO Pictures

You may know Howard Hughes as the man played by Leonardo DiCaprio in the film The Aviator. Leo, fine actor that he is, did a great job of creating empathy for a man who was by all accounts one of the strangest and most obsessive of all the bizarre American business magnates.

Most of his odd behavior is no laughing matter, stemming from a severe case of obsessive compulsive disorder. Life is just not enjoyable when you can't eat peas without sorting them by size. But before his mental health declined to the point of morbitidy he was … odd. A favorite weird behavior of Howard's was one that might be fun for a child: He'd have the Beverly Hills Hotel staff leave his meals hidden in tree limbs, corners and nooks and crannies so he would have to hunt for them. That actually might make mealtime a lot more enjoyable.

3 Elephant Hunting

Bob Parsons, GoDaddy

GoDaddy web hosting catches a lot of flack for their questionable business practices and treatment of their customers but it is Bob Parsons, CEO of GoDaddy, is doing his duty to divert the negative attention from his company by redirecting all the hate straight onto himself. By killing elephants in Africa. And videotaping it.

Yes, the self-made millionaire with the commercials for a web hosting company that features buxom girls that have absolutely nothing to do with web hosting made a movie of himself murdering “problem” elephants, butchering them and feeding them to starving Zimbabweans. Zimbabweans wearing GoDaddy gear. Evidently Bob thought it would be good publicity for his company to show loyal customers feasting on the flesh of an endangered species. Yikes.

Bob is the epitome of a man who would rather have bad attention than no attention, hopping from one public relations nightmare to another with astounding rapidity. He even backed out of an IPO because it would have required a short media blackout. Good on you, Mr. Parsons. Stand on your principles. Your terrifying, terrifying principles.

2 Jousting


Sandy Lerner, Cisco Systems

Of all the hobbies on this list, this is in my opinion the most “CEO” of them all. It incorporates several things that you might assume CEOs would be into: Historical artifacts, horses, land, risk, competition and money. Of course it also involves potentially grievous injury and far too much sweat for most computer nerds but you can't have it all.

The CEO who enjoys this hobby – and even breeds the shire horses she (yes, she) uses to joust – is none other than Sandy Lerner, founder of Cisco Systems and Urban Decay cosmetics. So, let's see, Sandy – a 59 year old woman, computer nerd and cosmetics enthusiast – is officially tougher than all of us. I am a little embarrassed, but at least I know who I would hire to command my order of knights should I ever get that lordship I've been after.

1 Being A Superhero

Richard Branson, Virgin

OK, so he doesn't dress in tights and a cape (as far as I know, and what you do in the privacy of your own home is your own business) but he does have a host of insanely cool adventures as his recreational resume. His real hobby is starting very successful companies, but the hobby I am referring to here is hot air ballooning. And not just regular hot air ballooning. Trans-Atlantic hot air ballooning.

Not content to explore space and the sea, Virgin founder and multiple-private-island-owning Richard Branson was the first person ever to float, party-favor-like across the ocean from one continent to another in a hot air balloon. The feat had previously been pulled off in balloons filled with gas.

Admittedly it doesn't take all that much effort to get where you're going when you're in an aircraft that has no controls save up and down, but it most definitely takes guts and more spare time than almost anyone else with an income has.


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