30 Weirdest CEOs of All Time, Ranked
These weirdest CEOs stand out for having behaviors or habits deemed crazy, eccentric and, at times, undeniably controversial.
30 Craziest CEOs of All Time, Ranked
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Being a CEO is a demanding job. A CEO needs to be able to inspire and engage with their staff and get the best work out of people, whether they’re running a small startup or a multinational corporation.
They are expected to drive profits, increase business and answer to a board of directors and often to shareholders. If they’re in charge of a startup, they may feel pressure from investors to produce revenue.
Not surprisingly, CEOs are usually people who can disrupt traditions, create change, take risks and try new things. However, sometimes people in these positions can take disruption, risky behavior or trying new ideas too far, and their actions just seem plain crazy to the rest of us. These are the 30 weirdest CEOs who stand out for having behaviors or habits deemed crazy, eccentric and, at times, undeniably controversial.
30. Indra Nooyi
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Birth date: Oct. 28, 1955
Company: PepsiCo
Years as CEO: 2006 - 2018
Why She’s One of the Weirdest CEOs
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Indra Nooyi was the CEO of PepsiCo, one of the largest food and beverage multinationals, until 2018. During Nooyi’s time with the company, she almost doubled total revenue, expanded the company’s international markets and increased the range of healthy foods.
Nooyi grew up in India in a family that prized education. Each night, her mother asked all her children to imagine what they would do if they were a president or prime minister, then write an essay and read it after dinner. This rather unusual habit is something that she credits to her success and ability to lead.
29. Aaron Levie
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Birth date: Dec. 27, 1985
Company: Box
Years as CEO: 2005 - 2021
Why He’s One of the Weirdest CEOs
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Aaron Levie is the co-founder of the cloud-based content management and collaboration platform, Box. As a teenager, while learning about computers in school, Levie also worked as a professional magician. He said that performing magic taught him crucial lessons in leadership.
For example, doing magic and making a business presentation have a lot in common as both activities need to build suspense and engage people in a story to be successful. Running a startup needs to capture people’s imagination and convince them that a founder’s vision is possible.
28. Warren Buffett
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Birth date: Aug. 30, 1930
Company: Berkshire Hathaway
Years as CEO:1965 - 2021
Why He’s One of the Weirdest CEOs
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Warren Buffett, known as the “Oracle of Omaha'' is one of the most successful stock market investors of all times. He is the CEO of the multinational conglomerate, Berkshire Hathaway.
Buffett bought his first stock at 11 and was paying taxes by the age of 13. He is reputed to have read 600 to 1,000 pages daily when he started out in business, and now, at 90, still spends 80 percent of his day reading and thinking.
27. Michael Kors
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Birth date: Aug. 9, 1959
Company: Michael Kors
Years as CEO: 1997 - 2011
Why He’s One of the Weirdest CEOs
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Michael Kors is an American fashion designer. After dropping out of design school, Kors began selling his clothes at Bergdorf Goodman and Saks Fifth Avenue. When his company went bankrupt in 1993, he worked for the House of Celine as a designer and relaunched his own company.
Kors went on to build a multibillion-dollar empire that has since gone public. He has been a celebrity judge on “Project Runway.” Kors’ famous quirk is that he wears the same all-black clothes to work every day: crewneck, suit and loafers. This lets him focus his energy on making other, more eccentric fashion decisions.
26. Laura Alber
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Birth date: Sept. 7, 1968
Company: Williams-Sonoma
Years as CEO: 1995 - 2021
Why She’s One of the Weirdest CEOs
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Laura Alber has been the CEO of Williams Sonoma, the chain of homewares, kitchen and cooking stores for more than 25 years. Alber admits to being both professionally and personally obsessed by food. She reads a lot about health and diet, and her favorite book is “The Corporate Athlete” by Jack Groppel.
Alber spends a lot of time on the weekend doing meal prep for the week ahead, making portion sizes and freezing them. She brings her lunch to work every day. Alber also cuts up apples, celery and carrots and brings them to the office as small meals over the course of the day.
25. Tim Kendall
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Birth date: Jan. 11, 1970
Company: Moment App
Years as CEO: 2018 - 2021
Why He’s One of the Weirdest CEOs
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Tim Kendall is the CEO of Moment, an app that helps both adults and children learn to use smartphones and apps in a healthier way. Kendall formerly worked at Facebook and Pinterest. His jobs involved persuading people to spend more time online.
However, Kendall became convinced that the world was facing an epidemic of screen addiction with dire consequences. He quit his job at Pinterest, deleted his Facebook app and invested $7 million in Moment to persuade people to spend less time on their phones. Kendall is also known for taking five-minute ice baths in the morning — because why not?
24. Sara Blakely
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Birth date: Feb. 27, 1971
Company: Spanx
Years as CEO: 2000 - 2021
Why She’s One of the Weirdest CEOs
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Sara Blakely is the founder and owner of Spanx, a shapewear company that sells underwear, leggings, swim and maternity wear. She is also the world’s youngest self-made billionaire. Blakely wanted a footless slimming garment that wouldn’t show under clothing, so she cut the feet off a pair of pantyhose to make her first prototype. Blakely thought up the company name Spanx while driving in her car.
Every morning, she goes for an hour-long drive on her way to work. Blakely actually lives only minutes from her office, so she uses her “fake commute” as her creative thinking time.
23. Jason Kingsley
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Birth date: December 1964
Company: Rebellion Developments
Years as CEO: 1992 - 2021
Why He’s One of the Weirdest CEOs
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During the week, Jason Kingsley runs one of the U.K.’s largest gaming companies, Rebellion Developments, which he started and owns with his brother. The company is known for producing computer games Alien vs. Predator and 2000AD.
On the weekends, Kingsley loves to joust, the sport of medieval European knights, which involves riding on horseback, wearing armor and charging at opponents with a weapon called a lance. He says he runs his company, and his life, by the traditional knight’s code of honor: bravery, honesty and kindness. Kingsley keeps a stable of 13 horses and owns custom suits of armor that cost $35,000.
22. Clark Benson
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Birth date: Unknown
Company: Ranker
Years as CEO: 2009 - 2021
Why He’s One of the Weirdest CEOs
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Clark Benson is a serial entrepreneur in the tech industry. He set up Ranker (his fifth startup) in 2009, as a digital media company that crowd-sources rankings for a wide range of topics. Ranker uses the data it compiles to sell advertising on its site.
Benson is known for his quirky habit of bringing in an on-call stylist to cut his hair and trim his eyebrows during work meetings — to make the most of his limited time. He also likes to walk around barefoot at work.
21. Craig Cooper
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Birth date: May 9, 1963
Company: CardieX
Years as CEO: 2017 - 2021
Why He’s One of the Weirdest CEOs
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Craig Cooper is a serial entrepreneur, venture capitalist, fitness author and the host of TV show “Adventure Capitalists.” He co-founded companies such as Boost Mobile, Softbank Capital Technology Fund, NRG-Asia Pacific and EBT Mobile (China).
Cooper is a men’s health writer and author who is passionate about outdoor sports and is an active investor in digital health and wellness technologies. He is known for some unusual health habits: He eats five cans of sardines daily, takes 22-minute naps and falls asleep at exactly 10:24 p.m. each night.
20. Bill Gates
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Birth date: Oct. 28, 1955
Company: Microsoft
Years as CEO: 1975 - 2000
Why He’s One of the Weirdest CEOs
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Bill Gates is a computer programmer, entrepreneur, author and philanthropist who co-founded Microsoft, the world’s largest software company for personal computers. When Microsoft started, Gates memorized the license plates of all his employees, so he could look out into the parking lot and tell who was working and at what time.
Gates also has the habit of rocking when he is working; the more focused he is on the work, the more he rocks. He reads a lot of books, about 50 a year, and he will always finish reading a book he’s started, even if he dislikes it.
19. Andrew Mason
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Birth date: Nov. 30, 1980
Company: Groupon
Years as CEO: 2008 - 2013
Why He’s One of the Weirdest CEOs
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Andrew Mason is the founder and former CEO of Groupon. Groupon is a site that offers virtual discount coupons on a wide variety of goods and services.
He once released a Christmas video of himself doing yoga in his underwear. As a stunt, Mason announced that he was setting up a scholarship fund called Grouspawn for the first two babies born to couples who used Groupon on their first date. He stirred up controversy with a Super Bowl ad that appeared to make light of the situation of people in Tibet.
Need we go on? These and other antics eventually got him fired from Groupon.
18. Elon Musk
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Birth date: June 28, 1971
Company: Tesla Motors, SpaceX
Years as CEO: 2008 - 2021
Why He’s One of the Weirdest CEOs
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Elon Musk has been called “the greatest mind of modern times” and a “real-life Tony Stark.” He is an engineer and serial entrepreneur who co-founded PayPal, Tesla Motors, SpaceX, NeuralLink, OpenAI and The Boring Company. Musk breaks his day up into five-minute intervals in order to be more productive. He also ignores most of his phone calls.
Musk is infamous for posting bizarre tweets on Twitter and for backing the crypto coin, Doge, that started as a joke. He is also well-known for offering multimillion-dollar prizes for new technologies that aid climate change and space exploration. So, crazy, but also quite forward-thinking.
17. John Mackey
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Birth date: Aug. 15, 1953
Company: Whole Foods
Years as CEO:2010 - 2021
Why He’s One of the Weirdest CEOs
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John Mackey co-founded Whole Foods, the natural grocery chain, in 1980 with three other friends. The company is credited with taking healthy eating mainstream in America.
For seven years, Mackey wrote anonymous posts on a Yahoo finance message board, praising himself and Whole Foods and attacking competitors. Even when his identity was revealed, Mackey continued to post his messages and pretend he wasn’t the writer. In 2017, after Amazon bought the company, Mackey announced that he didn’t need to earn money (his net worth is $75 million), and his salary from that point on was $1 a year.
16. Greg Glassman
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Birth date: July 22, 1956
Company: Crossfit
Years as CEO: 2000 - 2020
Why He’s One of the Weirdest CEOs
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Greg Glassman and then-wife Lauren developed CrossFit as an intense fitness regime. The system became a world-wide craze, and the CrossFit program is licensed to over 14,000 gyms worldwide. CrossFit is worth as much as $4 billion.
In June 2020, Glassman posted a tweet on Twitter saying “Floyd-19” drawing a reference to the shooting of George Floyd by police officers and COVID-19 and implying that the country was overreacting to both events. Reaction was swift. The company lost sponsors, endorsements and business, and Glassman was widely criticized. He apologized and later stepped down as CEO.
15. Bob Parsons
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Birth date: Nov. 27, 1950
Company: GoDaddy
Years as CEO: 1997 - 2011
Why He’s One of the Weirdest CEOs
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Bob Parsons is an American entrepreneur who started the BigDaddy group of companies. BigDaddy is the largest and most popular web hosting site. The company was especially known for its racy SuperBowl ads.
What’s more, Parsons has a passion for motorbikes, golf and big-game hunting. He started an online controversy when he posted a video of himself shooting an African elephant that he said was a “problem elephant” destroying crops and that he was helping poor farmers. Conservation and nonprofit groups criticized his actions, stating that there were better ways of handling the situation and accused him of animal cruelty.
14. John Schnatter
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Birth date: Nov. 23, 1961
Company: Papa John’s
Years as CEO: 1985 - 2017
Why He’s One of the Weirdest CEOs
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John Schnatter started the Papa John’s pizza restaurant in 1985 and grew the company to become America’s third-largest pizza chain. Schnatter is an avid football fan, and Papa John’s was a longtime NFL and Super Bowl Sponsor.
In 2017, Schnatter ignited controversy when he blamed NFL player protests over racism for declining pizza sales. Schatter stepped down as CEO but remained chairman of the board. Six months later, he triggered another controversy by continuing to criticize NFL players and using the N-word in a conference call. Papa Johns lost sponsorships, and Schnatter was forced to resign.
13. Marissa Mayer
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Birth date: May 30, 1975
Company: Yahoo
Years as CEO: 2012 - 2017
Why She’s One of the Weirdest CEOs
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Marissa Mayer was Google’s first female software engineer. In her time with the search engine company, she helped develop G-mail, Chrome, Google Maps, Google Earth and Street View. Mayer can be obsessive. She worked 130-hour weeks at Google and would sleep at her desk. Mayer is also rarely without her laptop to maximize her work time.
One of Meyer’s hobbies is making cupcakes. She became obsessed with making the perfect ones and bought a number of cookbooks to find the best recipe. After testing numerous ones, making separate spreadsheets for both ingredients and frosting, Mayer created her own version.
12. Jeff Bezos
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Birth date: Jan. 12, 1964
Company: Amazon
Years as CEO: 1994 - 2021
Why He’s One of the Weirdest CEOs
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Jeff Bezos is famous for starting an online bookstore in his garage that grew into Amazon, one of the world’s largest online retailers. He won’t allow PowerPoint to be used in meetings, requiring employees to read memos instead. Bezos won’t allow more people in a meeting or on a team than can be fed by two pizzas. He is famous for forwarding customer complaints to staff with just a question mark added.
Bezos spends $1 billion annually on his space exploration company, Blue Origin, and calls it his most important work. And wait for it — he’s building a 10,000-year clock on his ranch in Texas.
11. Mark Zuckerberg
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Birth date: May 14, 1984
Company: Facebook
Years as CEO: 2004 - 2021
Why He’s One of the Weirdest CEOs
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Mark Zuckerberg is the founder of Facebook, the social media network that he set up while still in college. One of Zuckerberg’s best known quirks is that he wears the same grey T-shirt and jeans to work every day to cut down on his decision-making.
When Zuckerberg wants to interview a new employee for Facebook, he takes them for a walk in the woods near company headquarters and then asks if they want to join Facebook. Zuckerberg decided that he would only eat meat if he had killed the animal himself. He has slaughtered chickens, pigs and goats (something that doesn’t entice us to go on a walk with him in the woods).
10. Steve Jobs
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Birth date: Feb. 24, 1955
Company: Apple
Years as CEO: 1996 - 2011
Why He’s One of the Weirdest CEOs
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Steve Jobs and Steve Wozniak started Apple in 1976 to make affordable personal computers. After leaving and returning to Apple, Jobs oversaw the development of the iPod, iPad and iPhone.
Jobs was a fruitarian, eating just fruit, vegetables, nuts and seeds. He only bathed once a week, claiming that he didn’t smell due to his diet. Jobs also wore exactly the same thing every day — a black turtleneck, blue jeans and sneakers — to minimize his decision-making and save mental energy for his work.
Why He’s One of the Weirdest CEOs
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Jack Dorsey co-founded Twitter and business payment company Square. He is known for his extreme generosity: He gave a third of his Twitter shares to employees and $1 billion in Square stock to COVID-19 relief and other charitable causes.
Dorsey’s strange habits revolve around health. Dorsey follows an extreme form of intermittent fasting and only eats one meal a day at dinnertime. He meditates for up to two hours every day and uses a near-infrared light bulb at work, as he believes it promotes cellular regeneration. Dorsey also likes to alternate 15-minute saunas with three-minute ice baths.
8. Peter Thiel
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Birth date: Oct. 11, 1967
Company: PayPal
Years as CEO: 1999 - 2002
Why He’s One of the Weirdest CEOs
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Peter Thiel is an entrepreneur, hedge fund manager and venture capitalist who co-founded PayPal, Palantir Technologies and Founders Fund, a venture capital firm that has invested in Airbnb, Stripe and SpaceX. He was the first outside investor in Facebook.
Thiel also set up the Thiel Foundation to fund research in artificial intelligence and life extension because is obsessed with biotechnologies that can extend life. He wants to live to 120 and experiments on himself with life-extension biohacks. Thiel takes small amounts of Human Growth Hormones, which stimulates cell repair, and injects himself with blood from young people, a procedure called parabiosis. And, yes, you read that right.
7. Matt Harrigan
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Birth date: Unknown
Company: PacketSled Inc.
Years as CEO: 2013 - 2016
Why He’s One of the Weirdest CEOs
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Matt Harrigan is well known in the cyber-security community and is credited with inventing a technique known as network penetration testing. He set up a cyber-security business called PacketSled in 2013.
Harrigan is best-known for his rant on Facebook, in which he threatened to shoot then-President Trump. His comments went viral after they were posted on Twitter and Reddit. Harrigan received death threats and his home address was posted on the internet. He later regretted his comments, cooperated with the Secret Service’s investigation and resigned as CEO of his company.
6. Eddie Lampert
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Birth date: July 19, 1962
Company: Sears
Years as CEO: 2013 - 2019
Why He’s One of the Weirdest CEOs
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Eddie Lampert was a hedge fund manager who took over as CEO of Sears, the iconic American retailer, which was struggling financially. Lampert ran the company remotely from his homes in Connecticut and Florida. He wanted to compete with Amazon for online sales but refused to invest in Sear’s web business.
Lampert broke the company up into 30 smaller businesses and forced unit heads to compete for company resources. He wouldn’t modernize stores, despite the fact that customers were leaving the brand in droves. Finally, in 2018, Sears filed for bankruptcy, closing its stores and laying off thousands of workers.
5. Jason Russell
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Birth date: Oct. 12, 1978
Company: Invisible Children Inc.
Years as CCO: 2004 - 2014
Why He’s One of the Weirdest CEOs
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Jason Russell was a founder of Invisible Children, a charity set up to raise awareness of war crimes committed by the Lord’s Resistance Army (LRA), an African rebel Christian militia. The charity’s founders were filmmakers and activists who made a viral documentary about the LRA.
The charity was accused of exaggerating its effectiveness and misrepresenting the work it was doing in Africa. Jason Russell, who suffers from bi-polar disorder had a public breakdown which was captured on video and went viral. The charity was formally shutdown in 2014.
4. David Green
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Birth date: Nov. 13, 1941
Company: Hobby Lobby
Years as CEO: 1970 - 2021
Why He’s One of the Weirdest CEOs
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David Green started Hobby Lobby, the arts and crafts chain, with a $600 loan. Green believes that religion and business shouldn’t be separated. Hobby Lobby sued the U.S. government over Obamacare coverage and won an exemption from having to provide contraception to workers. He was criticized for laying off thousands of workers during the pandemic and saying that God would look after them.
Green spent $500 million helping to establish the Museum of the Bible. The museum was unknowingly involved in antiquities looting and smuggling and was fined $3 million by the U.S. government. The museum returned thousands of artifacts lacking proper documentation to Iraq and Egypt.
3. Elizabeth Holmes
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Birth date: Feb. 3, 1984
Company: Theranos
Years as CEO: 2003 - 2018
Why She’s One of the Weirdest CEOs
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Elizabeth Holmes founded the medical technology company, Theranos, to develop more efficient diagnostic blood testing. She claimed that Theranos had developed a simple finger-prick test that could easily and cheaply detect dozens of diseases, including cancer. Investors flocked to the startup, and the company was valued at $9 billion.
However, media investigations revealed widespread fraud and deception at the company. After sanctions by federal authorities, Theranos ceased operations, and Holmes was charged with fraud and conspiracy charges. Company investors lost over $1 billion. In Holmes’ latest twist, she is pregnant and will give birth in July 2021, postponing her trial.
2. Dov Charney
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Birth date: Jan. 31, 1969
Company: American Apparel
Years as CEO: 2003 - 2014
Why He’s One of the Weirdest CEOs
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Dov Charney is a Canadian entrepreneur who moved to the U.S. and started American Apparel as a wholesale business. The company grew to be the largest American clothing manufacturer and is credited with setting the early 2000 trends for hoodies, high waist jeans and sunglasses. American Apparel was also known for its risque ads with models in provocative poses.
Charney had a reputation as a sexual creep and for sexual harassment of his staff. Five former employees filed lawsuits against him, and he was fired by the company that he had founded. American Apparel filed for bankruptcy in 2017 and closed all its stores.
1. Adam Neumann
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Birth date: April 25, 1979
Company: WeWork
Years as CEO: 2010 - 2019
Why He’s One of the Weirdest CEOs
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Adam Neumann was a co-founder of WeWork, global co-working spaces where people could work, socialize and create community. Neumann was a highly charismatic founder with an overinflated sense of self-worth, who told people that he wanted to be the president of the world, live forever and become history’s first trillionaire.
The company culture was stressful and divisive, and Neumann’s financial decisions drove the company into debt. In addition, he spent millions on himself. When WeWork tried to go public, investors discovered that the company had been privately overvalued by a factor of six, and the IPO was cancelled. Neumann was forced to resign.
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