30 Weirdest CEOs of All Time, Ranked

Britta Pedersen / AP Photo
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

Why She’s One of the Weirdest CEOs

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

Birth date: Dec. 27, 1985
Company: Box
Years as CEO: 2005 – 2021
Why He’s One of the Weirdest CEOs

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.