In the 1960s, the CEO of Ampex wanted his employees to take LSD to improve their creativity. The board of directors said "No" and then had to fire him after they discovered he had snuck off anyway on a mountain hike with 7 or 8 engineers and given them LSD.
2. Walt Bettinger, the CEO of Charles Schwab often conducts interviews over breakfast, asking the cook ahead of time to slightly mess up the candidate's order. He judges their reaction as a test of their character.
3. Michael O'Leary, the CEO of Ryanair airlines, has his own taxicab company with just one cab so that he can legally use the bus lanes and avoid traffic jams.
4. When Steve Madden was convicted of fraud and forced to resign as CEO of his own company, he created a new position for himself that paid $700,000 per year while he was in prison.
5. Travis Kalanick, the billionaire founder and CEO of Uber claims that he was the #2 ranked Wii Tennis player in the world.
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Mary Barra, the CEO of GM changed the workplace dress code from a complicated 10-page document to two words: "Dress appropriately."
7. Robert Hohman, the CEO and the co-founder of Glassdoor quit his job as a president of the Hotwire website to do nothing but play World of Warcraft for a year and only founded the company after hitting the maximum level in the game.
8. Mike Jeffries, the former CEO of Abercrombie & Fitch went on record as saying he does not want fat or unattractive people wearing his clothes or employed at his company.
9. As of June 2020, the CEOs of Microsoft (Satya Nadella), Adobe (Shantanu Narayen), and MasterCard (Ajaypal Singh Banga) all went to the same high school (Hyderabad Public School, Begumpet) in India.
10. Michael O'Leary, the CEO of low budget airline Ryanair wanted to charge passengers £1 to use the onboard toilets. The policy was never implemented because it violated EU regulations.
Reed Hastings, the CEO of Netflix offered to form a partnership with Blockbuster in the late 90s and the CEO of Blockbuster (John Antioco) laughed in his face.
12. Todd Davis, the CEO of Life Lock (identity theft protection) posted his social security number to the public to show the effectiveness of his company. His identity was stolen 13 times.
13. Sidney Weinberg, the CEO of Goldman Sachs started from as a janitor's assistant in the company, where his responsibilities included brushing the firm’s partners’ hats and wiping the mud from their overshoes making $3/week.
14. Dick Fuld, the former CEO of Lehman Brothers, got punched in the face and knocked out cold in the Lehman Brothers gym, the same night the Bank announced its bankruptcy.
15. Marissa Mayer, the CEO of Yahoo, circumvented her own rule disallowing employees to work from home by bringing her home to work--and building a nursery by her office.
Aaron Feuerstein, who was the owner and CEO of Malden Mills, which burned down in 1995. After this happened, he supported his 3,000 employees for 6 months using his personal savings. It ended up costing him $25 million to do the right thing.
17. Former Citigroup CEO Vikram Pandit apologized for Citigroup's board of directors' misuse of bailout money on increasing his salary, condemned their purchase of a private jet plane, and worked for 2 years for only $1 a year until they returned to profitability.
18. In 2001, a former Disney CEO Michael Eisner thought "Finding Nemo" was so terrible, that he postponed contract negotiations with Pixar until after the release in hopes of getting a better deal. "Finding Nemo" went on to gross over $868 million.
19. Michael Christopher Woodford, the CEO of Olympus was fired when he discovered that $1.6 billion of the company's money had been paid to the yakuza.
20. Jack Dorsey, the CEO of Twitter, launched his tech career by writing open-source software to route delivery trucks from the Internet.
21Frederick W. Smith
Frederick W. Smith, the CEO, founder, and chairman of FedEx has separately killed two people in motor vehicle accidents: one in a hit and run (for which he was released on $250 bond), and another where he lost control, causing the vehicle to flip, killing the passenger.
22. Trip Adler, the CEO of Scribd, earned the company’s first $17 in revenue by playing the saxophone outside Scribd’s office at Christmas time.
23. John Lasseter, the former CEO of Pixar was fired from Disney for promoting computer animation.
24. Chip Bergh, the CEO of Levis, recommends that you never wash your jeans.
25. Steve Ells, the CEO of Chipotle's got paid $25.1 million in 2013 and over 75% of Chipotle's investors voted against his proposed pay increase in 2014, making it the least popular pay-increase proposal among the largest 3000 companies in the US.