These Billionaire Founders Famously Hate Being a CEO

Earlier this week, Facebook co-founder and former Asana CEO Dustin Moskovitz admitted that being a CEO was “exhausting” and ill-suited to his personality — and he’s far from the only CEO to speak of the pitfalls of the role.

In an interview published on Monday with Stratechery, Moskovitz said that he didn’t intend to be CEO of Asana when he co-founded the workplace productivity platform in 2008.

“By personality, I don’t like to manage teams, and it wasn’t my intention when we started Asana,” Moskovitz explained. “One thing led to another, and I was CEO.”

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Moskovitz began serving as Asana’s CEO in October 2010 and retired from the role in July. He told Stratechery that, in the 15 years he worked as CEO, he had to “put on” a “face” every day that was different from his true introverted nature.

Moskovitz, who is worth $12 billion according to the Bloomberg Billionaires Index, isn’t the only CEO to express his dislike for the role. Elon Musk, the founder and CEO of at least three companies, including Tesla, SpaceX and xAI, famously compared starting a company to “staring into the abyss and eating glass” in an interview in April 2013.

In the interview, Musk explained that CEOs must constantly face the possibility of failure (“the abyss”) while dealing with the most painful and difficult problems (“the glass”). Musk is the richest person in the world, with a net worth of $458 billion, and most of his fortune is tied to his ownership of the companies he leads, including a 15.73% stake in Tesla and a 42% stake in SpaceX.

Related: Elon Musk Reveals His Tactics for Building Successful Companies, Including Sleeping Under His Desk and ‘Working Every Waking Hour’

Emad Mostaque, the co-founder and former CEO of Stability AI, stepped down from the CEO position in March 2024 to pursue decentralized AI initiatives. When asked about his departure that month, Mostaque told the New York Times that “being a CEO sucks.”

“Elon was right,” Mostaque, who has a net worth of $1.1 billion, said at the time. “It is like looking into the abyss and chewing glass.”

In January 2024, Airbnb co-founder and CEO Brian Chesky shared his thoughts about the emotional challenges of leadership on X, writing that although he didn’t feel lonely as a founder working beside his two co-founders, “the depths of loneliness” he experienced as a CEO “are difficult to put into words.”

Chesky is worth $10.2 billion, according to the Bloomberg Billionaires Index.

Related: Airbnb’s CEO Says He Personally Manages 40 to 50 Employees as Direct Reports: ‘A Lot of Work’

A June 2022 survey conducted by Deloitte found that nearly 70% of C-suite executives across the U.S., U.K., Canada and Australia wanted to quit their jobs. The survey, which polled 1,050 C-suite leaders, revealed that two out of five executives described themselves as constantly overwhelmed, with 36% saying they were exhausted.

CEO resignations have more recently reached all-time highs. According to data from executive recruiting firm Challenger, Gray & Christmas, a record 1,358 chief executives stepped down in the first half of this year, a 9% increase from the 1,250 CEOs who left their posts during the same period last year and the highest year-to-date total on record.

“CEO turnover continues to climb in 2025, reflecting the immense pressures leaders face,” Andy Challenger, workplace and labor expert at Challenger, Gray & Christmas, said in a statement.

Earlier this week, Facebook co-founder and former Asana CEO Dustin Moskovitz admitted that being a CEO was “exhausting” and ill-suited to his personality — and he’s far from the only CEO to speak of the pitfalls of the role.

In an interview published on Monday with Stratechery, Moskovitz said that he didn’t intend to be CEO of Asana when he co-founded the workplace productivity platform in 2008.