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The 24 Most Surprising Things About The World’s Top CEOs

Here are 25 of the strangest and most surprising things about some of the world’s biggest CEOs.

When we think of a CEO of the major companies that define the world, it’s easy to imagine that they were always these successful people. That even when they were children, they were already little titans of industry. But many of the most successful CEOs in the world come from surprising places or have unique traits we'd never expect. While some of them always wanted to change the world, others came into success more by surprise than anything else. Some of them have very specific dietary and health routines to keep themselves centered, mentally and physically. And some of them have just lived the kind of normal trials of society that we could otherwise never imagine them having to go through.

These CEOs, across a wide berth of fields and industries, all share one thing in common, and it's that they’ve all got something weird and unexpected about them that makes them even more interesting beyond their wealth and status. Some of them are cool, and some of them are just so weird. But hey, when they've got the success, they might as well enjoy it. Here are 25 of the strangest and most surprising things about some of the world’s biggest CEOs.

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24 Jeff Bezos (Amazon) Was A Summer Camp Counselor

via: The Verge

Jeff Bezos is one of the big names in business today, with his ownership of Amazon making him one of the most ubiquitous CEOs in the world. Bezos has been building to this day, and has been trying to be a leader his whole life. Just look at his teenage job as a summer camp counselor for a program he started. Teaming up with his then-girlfriend, the pair managed to set up a 10-day summer camp that even had the Lord of the Rings books as the required reading, which was quite well-played for the teenage Bezos.

23 Mark Cuban (Shark Tank) Was A Disco Dance Instructor

via: Entrepreneur

Mark Cuban has his fingers in a whole lot of pies, from basketball to stocks to straight up entertainment. That last one shouldn’t be all that surprising, though, as Cuban has always had a bit of a performer in him. He’s been dancing his entire life, and was even a disco dance instructor through high school and college. Cuban eventually appeared on Dancing With the Stars, so at least he got to bring that passion to the stage for the world to see at least once.

22 Elon Musk (Tesla) Was Less Than Kind To A McLaren F1

via: Inverse

With Tesla Motors, Elon Musk is poised to irrevocably change the automotive industry forever. But that doesn’t mean he wasn’t dumb and young just like the rest of us. After making his fortune in 1999 at the age of 28, Musk bought a McLaren F1, one of the most valuable cars in the world. And then roughly months later, he crashed it trying to show off to PayPal co-founder Peter Thiel. The craziest thing was that he didn’t even have insurance on the thing!

21 Eric Schmidt (Alphabet Inc) Has A Personal Club

via: Wired

Former Google head honcho (and current chairman to Alphabet Inc.) Eric Schmidt is controversial in the world of finance thanks to his commitment to having fun, no matter what. He’s had a number of famous relationships over the years, and that was even before he went all out and set up his own personal club in downtown Manhattan. He had the whole place soundproofed, and even has a secondary club that doubles as a yacht.

20 Larry Ellison (Oracle) Put $1 Billion On His Credit Card

via: Wall Street Journal

What do you do when you’re the fifth wealthiest person on the entire planet? If you’re Larry Ellison, co-founder of computer technology company Oracle, then you go big. Seriously, this dude owns multiple islands, even in the Hawaiian area. And if you’re curious what kind of money the super wealthy are dealing with, then look no further than his credit card. Documents revealed that he pushed his card PAST his spending limit of $1 billion. Seriously.

19 Charlie Cheever (Quora) Loves StarCraft 2

via: Youtube

Video games can easily take over someone's life. And just because someone becomes wealthy and powerful doesn’t mean they can avoid that kind of allure. Just look at Charlie Cheever, one of the founders of Quora, and his over-the-top commitment to sci-fi strategy game StarCraft 2. He can be found in many online forums of the game, and has proven to be quite good at it too. Clearly he has the time to really invest into it.

18 Sergey Brin (Google) Is Super Into Working Out

via: Bloomberg

Staying healthy and in shape is vital no matter what profession you end up in. Google co-founder Sergey Brin especially knows that, as he’s become famously stringent about his workout routine. Seriously, he’s easier to find in the gym instead of his own office. Even among the rest of the employees at Google, he’s famously become one of the biggest fitness lovers within the company. Hey, it’s that kind of attitude that helped get Google started in the first place.

17 Aaron Levie (Box) Loves Magic Tricks

via: Business Insider

Box CEO Aaron Levie is younger than many of the people on this list, but that doesn’t make him any less of an important figure in the current world of business. Levie has transitioned into a pretty solid role at his company, and has been using the freedom that job allows to indulge in his passion for magic tricks. Seriously, this is a guy worth nine figures, and he will straight-up wow you with you some card tricks at a party.

16 Susan Wojcicki (YouTube) Comes From A Family Of Teachers

via: Recode

Susan Wojcicki is one of the most powerful women in the tech world at the moment, but she didn’t come from Silicon Valley origins. She graduated from Harvard University with a B.A. in both Literature and History, and probably double majored because of the impact her parents had on her. Raised by two teachers, Wojcicki was encouraged in her youth to explore every kind of subject she was ever interested in, helping turn into the kind of person who has helped transform YouTube into a massive presence online.

15 Dick Costolo (Twitter) Was A Stand-Up Comedian

via: Business Insider

Dick Costolo is one of the heads of Twitter, a.k.a. one of the absolute biggest and most prolific websites currently online. Come on, you know it, don’t pretend like you don’t know what Twitter is. You know what it is. But what you probably didn’t know what that Costolo is that he previously worked as a stand-up comedian and improv actor. You can even find his material online. What a huge career jump he made, and I am sure he is glad that he decided to pursue a different path.

14 Les Moonves (CBS) Was A Bit-Actor

via: Vulture

Before he moved behind the camera and become one of the most prolific heads in entertainment (currently serving as the CEO of CBS), Moonves had his eyes on the world of entertainment his entire life. Before taking the reins of the company himself, he was just a bit player in a handful of television shows during the 1970s. Never finding that big break he was looking for, Moonves decided to move into production instead, and made a real name for himself.

13 Sumner Redstone (Viacom) Had A Fascinating Past

via: Vulture

Sumner Redstone is one of the heads of Viacom, one of the biggest media companies in the entire world. But before that, he also had one of the absolute coolest jobs possible. Namely, he was an actual spy during World War II. He helped break secret code to help the Allies push to victory in the Pacific, and spoke out against the unjust internment of families during that period. It's obvious that Redstone brought his invaluable life experience to his professional life, and is a huge success because of that.

12 Richard Plepler (HBO) Got His Start Pitching Benjamin Netanyahu By Chance

via: Winter Is Coming

Richard Plepler worked his way up through sheer charm and intelligence, and nothing speaks to that more than how he got his first documentary made. The HBO founder recognized Israeli Prime Minister Benjamin Netanyahu at a restaurant. He went to the man and pitched him a documentary about the Israeli/Palestinian conflict. If anything, Richard Plepler has shown us all that we have to take advantage of any opportunity that comes our way, because we never know what will happen!

11 John Mackey (Whole Foods) Was A Total Hippie

via: Business Ethics Magazine

John Mackey, co-CEO of Whole Foods, is shy about his unexpected past as a stereotypical hippie before becoming a massively powerful CEO. He dropped out of a B.A. in Philosophy and Religion according to Time Magazine, and reminisced about his time living as a member of a commune. Eventually fed up with the way business was typically handled, he opened the first Whole Foods alongside his girlfriend in 1978 (originally called Safer Way before a name change in 1980).

10 Steve Ells (Chipotle) Has A Degree In Art History

via: Business Insider

Steve Ells loves art. It’s a major passion of his, and has been since his college days. He even got his college degree in the study of it. But worried about his potential job prospects after leaving school, the future founder of Chipotle went to the Culinary Institute as a potential backup job. He launched the Mexican food chain three years later, and credits his time raising funds for the new company as his true “MBA” training for business.

9 Jack Ma (Alibaba) Was Turned Down By KFC

VIA: Time

Jack Ma is one of the eighteen founders of Alibaba, one of the absolute largest wholesale online stores in the world. But before he was helping create a company that deals in commerce with people all across the globe, Jack Ma had a lot more difficulty keeping a roof over his head. While learning English and selling whatever he could think of to get by, he was even turned down for a job working for a Kentucky Fried Chicken establishment. That is pretty surprising in retrospect, right? That manager has to be so angry at themselves.

8 Sean Parker (Facebook) Got The LOTR Costume Designer For His Wedding

via: Quartz

Sean Parker has been one of the biggest names in tech ever since he helped found Napster back in the early 2000s. But his recent wedding had maybe his most unexpected and over the top antics – namely, what happened during his recent wedding. He got the costume designer from the Lord of the Rings films to come and design the outfits for everyone who was attending the wedding. The only person who got to show up in normal clothes, surprisingly enough, was Bono from U2.

7 Craig Cooper (Boost Mobile) Eats A Whole Lot Of Sardines

via: CNBC

Craig Cooper from Boost Mobile is incredibly alpha male, even for the high intensity world of finance. The man is committed to his running routine, surfing out during the best waves of the day, and also to feeding his slightly strange love of sardines. Seriously, the man goes out of his way to make sure he has sardines every day. It’s a whole thing he does, and a major part of what he eats to remain in good physical shape. There’s liking something, and then there’s Cooper's love for those little fish.

6 Shigeru Miyamoto (Nintendo) Likes To Measure Things For Fun

via: Muzli -Design Inspiration

Shigeru Miyamoto is responsible for a lot of great childhood memories all around the world. He turned his childhood fantasies into the video games that entertained generations, and is still running strong as the face and heart of the Nintendo video game company. But instead of playing his games for fun, he has a different hobby – namely, measuring things in rooms. Just random things around the room, to see if he can guess it accurately from sight.

5 Indra Nooyi (Pepsi) Wrote Speeches For Her Family Game Night

via: Fortune

When most of us think back to family game night, we remember things like monopoly or charades. But Pepsi CEO Indra Noovi actually had a way more serious variant of that common pastime. Instead of playing random games, she and her siblings would write speeches about what they would do if they were in control of the world, and their mother would vote on her favorite. It helped motivate Noovi, and made her the woman she is today.

4 Jason Kingsley (Rebellion) Likes To Joust

via: My Life In Pixels

Rebellion is a highly profitable gaming company based in Britain that has put together some truly fantastic series. He’s also very into the fantastical settings in general, if his main hobby isn’t enough of proof. The CEO is actually an avid medieval fanboy, and even goes out jousting when he has the free time. Like, full-on jousting. Like, the man rides a horse in metal armor and tries to hit another guy (also riding a horse in metal armor) with a long stick.

3 Laura Alber (Williams-Sonoma) Cooks Her Food Weeks In Advance

via: CNBC

Laura Alber is one of the most successful women in the fitness world, playing a major role for multiple companies in the area. But she takes that with her home from the office too. She goes to great lengths to set up her meals in advance to make sure they’re all healthy and delicious. To that end, she usually cooks her meals over the weekend and freezes them for the coming weeks. She actually sees it as a personal means of relaxation, which is probably for the best.

2 Mark Parker (Nike) Has A Sketch Notebook

via: Youtube

The human brain can be divided into two halves, with each half focusing on a different aspect of thought. Nike CEO Mark Parker really believes in the divide between the two, and makes sure to address both sides while he’s at work. The CEO has been spotted during meetings with a notebook, in which he doesn’t just take notes but also draws a bunch of sketches and free-form thoughts. Who knew all those doodles we drew in high school were for a good cause?

1 Many Of Them Have Appeared On The Simpsons

via: Youtube

The Simpsons has been on television for over thirty years at this point, which is incredible. And in that time, a whole host of famous people from across all walks of life have appeared in the animated sitcom. And that includes some of the most successful people in the world. Mark Cuban, Richard Branson, Jeff Bezos and a whole lot of the other wealthiest people in the world have visited Springfield at one point or another. Keep an eye out next time you watch the show!

References:, BusinessInsider, Fortune, Time, Observer, IndependentVanityFair, Forbes

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The 24 Most Surprising Things About The World’s Top CEOs