The Bizarre Habits of 9 Highly Obsessive CEOs

By Diane Bullock and Jonah Loeb  NOV 13, 2012 12:00 PM

The bizarre rules and regulations set by Abercrombie & Fitch CEO Michael Jeffries for his corporate jet got us thinking about other overly particular corporate leaders. Turns out Jeffries is part of a long tradition.


MINYANVILLE ORIGINAL You don’t get to the top of the corporate heap without having to cope with an eccentricity or two. Over the years, we’ve seen more than a few folks in the Fortune 500 dip a toe into the brackish waters of Lake OCD. Allow Minyanville to take you on a little visit to our favorite business leaders who we’ve committed -- pin-striped straight jackets and all -- to the corporate cuckoo’s nest.
Michael Jeffries, CEO of Abercrombie & Fitch
It’s perfectly reasonable for a company manual that outlines the policies and procedures of the entire organization to run several dozen pages. A bit over-the-top, however, is a 47-page rule book by which employees assigned to the corporate jet must abide. The “Aircraft Standards” set by Abercrombie & Fitch (NYSE:ANF) CEO Michael Jeffries for his Gulfstream G550 are not only oddly obsessive, but some actually border on fetishistic.

Exposed in the wake of an age-discrimination lawsuit filled last month by the plane’s former pilot, the Abercrombie enchiridion mandates that attendants (often male models) abide by a strict dress code of Abercrombie polo shirts, jeans, boxer briefs, flip-flops, and the brand’s cologne, spritzed periodically during the flight. Unless the temperature dips below 50 degrees, outerwear is prohibited. But don’t think Jeffries’ staff is ever off the hook from having to bare a little hairless chest. Though jackets are permitted, they are to to be fastened at the “fourth button from the bottom,” with the last button left open.  

Only when it comes to staffers’ hands does Jeffries insist on formal dress. White gloves must be worn when setting tables for meals -- with the exception of the flatware, which is to be handled with black gloves.

And, lest you think Abercrombie & Fitch shareholders don’t have a stable of unstable on their hands, consider that Phil Collins’ “Take Me Home” is the required soundtrack during boarding on all return flights, a five-point procedure is laid out for the seating of Jeffries’ dogs, and one -- and only one -- response may be uttered by a crew member when responding to a request made by him or his partner, Matthew Smith: “No problem.”

With the company’s stock losing half its value over the past year, the board may want to re-rethink his annual $200,000 personal flying budget, which had already been trimmed from $4 million. For a cost-cutting compromise, how about downsizing to just one pair of gloves... in gray?
Walt Disney, Co-Founder and Former President of The Walt Disney Company

Leave it to a depressive to create the happiest place on Earth.  

In 1956, the year after opening Disneyland (NYSE:DIS), Walt Disney opened up to the Saturday Evening Post about his self-described 1931 “nervous breakdown” and “crack-up.”

“I kept expecting more from my artists than they were giving me,” Disney said “and all I did all day long was pound, pound, pound. Costs were going up. Somehow, each new picture we finished cost more to make than we figured it would earn.”

Disney’s doctor diagnosed him with “an acute attack of perfectionism.”

But five years after his admitted “emotional tailspin,” Disney still hadn’t entered recovery mode when it came to the unrealistically lofty and confusing demands he continued to make of employees.

In 1936, Disney animator Berny Wolf suffered weeks of undue stress over a few-second throwaway gag of three pelicans doing a Jimmy Durante impression in the Silly Symphonies cartoon short “Elmer Elephant.” During one infamously grueling sweatbox session, Disney seemed to expect Wolf to intuit what he was thinking when he criticized him saying, “You should know better than that.”

Twelve pencil tests later -- and with none of the project crew, including director Wilfred Jackson, being able to make heads or tails of Disney’s discontent -- Wolf took a guess that the birds were facing the wrong direction and traced and re-shot them so the action flowed the other way. On the 13th try, he took it to back to the sweatbox.

"I got it in the reel and Walt looked at it and at me and said, Finally, finally!" Wolf said in Walt's People - Volume 9: Talking Disney With the Artists Who Knew Him (Xlibris, 2010). “You would just want to die.”
Howard Hughes, Founder of Hughes Aircraft Company, Former Owner of Trans World Airlines, RKO Pictures

When Time magazine names you second in its list of the Top 10 Most Reclusive Celebrities, you’ve probably wrestled with more than your share of demons. And when it comes to bat-crazy billionaires, Minyanville thinks Howard Hughes set the bar.

For the accomplished entrepreneur, innovator, engineer, and filmmaker, multiple talents also, unfortunately, meant multiple psychological disorders. Throughout his 71 years, Hughes produced and directed Oscar-winning films, founded Hughes Aircraft Company, and acquired Trans World Airlines and RKO Pictures. He had a finger in just about every pie in America from the mid-1920s to the mid-1960s and was almost single-handedly responsible for the city of Las Vegas as we know it. But he also likely suffered from obsessive-compulsive disorder, bipolar disorder, and symptoms of paranoid schizophrenia.

A longtime germaphobe, Hughes actually had enough wealth to outsource his compulsive habits to employees. His compulsive rituals were delegated to servants who were forced to wrap his spoon handles in tissue paper and cellophane. Retrieving his hearing aid from the bathroom cabinet was a process that required no less than 45 tissues as well as a hand-washing with a brand new bar of soap.  

Hughes’ mental illnesses worsened with age and have been at least partially blamed on trauma he sustained from near-fatal crashes during test flights of his own self-built planes. Toward the end of his life, he hid from public life inside expensive hotel penthouses and spent four months in a dim studio screening room where he subsisted on chocolate bars and milk and stored his urine inside the empty bottles. When he died in 1976 of kidney failure -- triggered by a combination of dehydration and a daily diet of 20-30 aspirin -- he was an unkempt and emaciated 94-pound billionaire without the presence of mind to even leave a proper will.
Frank Rosenthal, Former CEO of the Stardust, Fremont, Marina, and Hacienda Casinos

Money? Check. Murder? Check. Muffins? Checkmate!

Stardust Resort and Casino’s Frank Lawrence "Lefty" Rosenthal took an obsessive approach to quality control that was immortalized by Robert De Niro’s portrayal in the 1995 Scorsese classic Casino. In a famous scene, the persnickety resort owner and mob boss (fictitiously named “Ace”) frets over the unequal blueberry distribution between his and an associate’s muffins. Ace marches into the kitchen and demands the chef fill each individual muffin tin with the same number of blueberries.  

Baker: Do you know how long that's going to take?
Ace: I don't care how long it takes. Put an equal amount in each muffin.

Throughout the 1970s, Rosenthal ruled his Las Vegas enterprises with an iron fist (or, if you were a casino cheat, a rubber mallet) but he knew all of his workers by name -- even if they didn’t always measure up to his standards.  

“You need manpower and brain power. It was difficult to find good employees in that state [Nevada],” Rosenthal said in an interview with Player. “So if you demand 16 ounces to the pound you are challenged. You are criticized as being a perfectionist.”
Donald Trump, Chairman and President of The Trump Organization, Founder of Trump Entertainment Resorts

Given his paranoid fixation with our commander-in-chief’s birthplace, it’s not necessarily a stretch to learn that Donald Trump suffers from other obsessive tendencies. The NBC (NASDAQ:GE) reality star and occasional real estate developer, who once claimed that, as a supposed foreign-born citizen, Barack Obama has perpetrated “one of the greatest scams in the history of politics, and in history period” may be, clinically speaking, a few tartines short of a picnic.

It’s true; The Donald has OCD. The disease manifests in a phobia of germs. He once distributed bottles of hand sanitizer to reporters at a press conference, refuses to touch elevator buttons, and avoids shaking hands with people. He’s especially palms-off with teachers, whose filthy desks are a veritable cesspool of “17,000 germs per square inch.”

Tragically, it appears Mr. Trump’s condition is worsening. In the midst of the Sandy Storm, the unprecedented weather event that pummeled parts of the Northeast earlier this month, Trump seemed to be suffering from his own mental hurricane.  He intensified his attacks on Barack Obama -- this time questioning the legitimacy of the president’s educational history. In a homemade video posted on his Facebook (NASDAQ:FB) page, Trump said the the third day of the storm’s aftermath was a “very, very sad day” since Obama failed to meet his noon deadline to produce his college and passport application records in exchange for $5 million in charity.

Maybe he’ll find a mental health clinic that could use the donation.

Marissa Mayer, CEO of Yahoo

In all likelihood, Yahoo (NASDAQ:YHOO) wasn’t going to get its mojo back with a leader that procrastinated her way through her first quarter with the company. Sure, new CEO Marissa Mayer may fall in the more fastidious quadrants of the Myers-Briggs. In fact she could even be accused of having some control issues.

According to an article in BGR, the former Google (NASDAQ:GOOG) executive began imposing her “Googirl” work ethic on her new employees as soon as she took the helm. Product designers have been forced to produce at a far faster pace than they’ve been accustomed. Mayer allegedly only approved a team’s new unit pitch if they could get it to market months ahead of their proposed schedule. She then gave them “exactly one week to figure out how to get the product out by the end of the year,” or else they’d all be fired.

This is, after all, the same person who engineered the perfect cupcake recipe by way of her own meticulously researched and logged spreadsheet data -- and then repeated the process for frosting.

Perhaps a bit overbearing for some people’s tastes, Mayer has insisted she personally sign off on every new company hire and on holding weekly “FYI meetings” that help her keep an eye on them.

If her first earnings call as Yahoo’s CEO is any indication, there’s a method to Mayer’s micromanaging. The company beat analysts’ forecasts of $0.25 a share, reporting a rise in third-quarter earnings by 66% to 35 cents-per-share on $1.09 billion in revenue.

Click through to the next page for Steve Jobs, Martha Stewart and Nikola Tesla.

Nikola Tesla, CEO and Founder, Tesla Electric Light & Manufacturing
Before there were Abercrombie jets, before there was a Magic Kingdom, before The Donald…there was Tesla. An Austrian-born Serb who died penniless despite being one of the greatest scientists and inventors of all time, Tesla has become a sort of cult figure in pop culture.
Tesla’s long-standing feud with Thomas Edison and his tragic life story make him an easy figure to idealize, and there’s good reason to admire him; in his prime working years from about 1884 to 1930, he invented everything from the spark plug to the airplane turbine engine to the remote-control boat. His high-voltage and high-frequency experiments at Colorado Springs in 1899 were and still are some of the most ambitious and ingenious scientific projects ever performed.
In reality, though, Tesla was -- as an employer and as a person -- truly bizarre.
His obsessive-compulsive disorder, quite pronounced in his later years, gave him a hatred of round objects and of hair and an obsession with the number three. He was, at 6-feet 2-inches tall and 142 pounds, almost skeletally thin, and his dislike for overweight people caused him to fire a secretary who had put on a few extra pounds. Perhaps it’s just as well for the world that Tesla remained celibate his entire life.
Oh, and he never slept more than two hours at a time. And he sometimes saw blinding flashes of light accompanied by visions. And he fell in love with a pigeon. Nikola Tesla is that rare figure of such simultaneous brilliance and insanity -- think Michael Jackson -- that any really weird story about him is probably true.
Steve Jobs, Former CEO of Apple
Under the leadership of Steve Jobs, CEO of Apple (NASDAQ:AAPL) from 1997 to 2011, the company went from a PC also-ran to an international superbusiness on the back of beautiful, innovative products like the iPod, iPhone, and iPad. One of his first major hits was the iMac, an all-in-one desktop computer that came in vibrant colors like blue, green, and orange.
Know what else came in orange? Steve Jobs.
The Apple CEO was famously weird about his eating habits and once reportedly ate so many carrots in such a short time period that his skin turned a vibrant orange. He would often eat only one kind of food for weeks and lecture his friends and family about the virtues of his current diet, only to abandon it for another obsession shortly afterward. Jobs even claimed that his fruit-only diet made it necessary for him to bathe only once a week, a notion that may not have been shared by Apple employees.
By the end of his life, Jobs had even realized that refraining from food could induce periods of euphoria and would fast even when his ailing body required nutrition. His perfectionism may have created some of the most iconic product lines in the history of consumer goods, but it also made him an intense, demanding, and, well, orange person.
His strangeness didn’t stop with his diet, either. Jobs’ employees reported that he often demanded impossible amounts of work from them with little to no recognition of their physical or emotional limitations, simply refusing to take “I can’t do that” for an answer. To be fair, he never balked at that kind of work himself, often staying up for entire days at a time coding. Jobs even worked himself literally into the ground, leaving four years' worth of product plans to Apple when he died in October of 2011.
Crazy or not, Jobs’ approach worked. Upon hearing that Bill Gates had remarked that Apple’s business model only worked because it had Steve Jobs, Jobs snapped that Microsoft’s (NASDAQ:MSFT) model only worked because it “[didn’t] mind making crappy products.”
Martha Stewart, Chairwoman of Martha Stewart Living Omnimedia
Martha Stewart, home and living guru to millions and convicted white-collar criminal, is almost certainly a robot. The Jersey City native has turned her knack for decorating into a multi-billion-dollar company, Martha Stewart Living Omnimedia (NYSE:MSO), through the kind of hard work and merciless commitment that can build and ruin nations.
Stewart is always—always—in control. Her list of personal (not professional) employees is in the dozens, from drivers to stable hands (for her many horses) to personal assistants. Countless women have struggled in vain to maintain the kind of focus and excellence that Stewart never deviates from. Even when she was in prison for securities fraud, Stewart (because sometimes the world is just filled with delights) went by the name “M. Diddy” and, according to some reports, created and ran a baked-goods black market while behind bars.
Yes. Exactly like you hoped against hope that she would.
Despite (or probably because of) this all-around perfection, Stewart is a terrifying boss. According to reports posted on Gawker and elsewhere, no ink other than red or black may be used in her offices, every employee’s desk must be entirely clear at the end of each day, and nobody is allowed to have any personal items like, you know, coffee mugs or photos of loved ones.

The terror in the air hasn't produced stellar results for investors, mind you. Last week Omnimedia reported a $50.7 million quarterly loss and total revenue of $43.5 million, a 17% drop in revenue compared to the same quarter last year. The company is planning to layoff about 12% of its workforce.
In Martha Stewart’s world, the only loved one is Martha Stewart. That’s how her whole operation works, and that’s probably why it works.
No positions in stocks mentioned.