These Billionaire Founders Famously Hate Being a CEO: ‘Like Staring Into the Abyss and Eating Glass’
From Tesla CEO Elon Musk to former Asana CEO Dustin Moskovitz, here are the CEOs who have spoken out about the downsides of the position.
Key Takeaways
- Facebook co-founder and former Asana CEO Dustin Moskovitz admitted earlier this week that being a CEO was “exhausting.”
- Moskovitz isn’t the only CEO to express his dislike for the role — Elon Musk famously compared starting a company to “staring into the abyss and eating glass.”
- Airbnb CEO Brian Chesky said that he experienced “depths of loneliness” as a CEO that were hard to put into words.
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 , Moskovitz said that he didn’t intend to be CEO of Asana when he 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 and 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 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 “” 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 , and most of his fortune is tied to his ownership of the companies he leads, including a in Tesla and a in SpaceX.
Emad Mostaque, the co-founder and former CEO of Stability AI, stepped down from the CEO position in March 2024 to pursue . When asked about his departure that month, Mostaque told the that “being a CEO sucks.”
“Elon was right,” Mostaque, who has a net worth of , 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 , 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 , according to the Bloomberg Billionaires Index.
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A 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 . According to data from executive recruiting firm Challenger, Gray & Christmas, a record 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, .
Key Takeaways
- Facebook co-founder and former Asana CEO Dustin Moskovitz admitted earlier this week that being a CEO was “exhausting.”
- Moskovitz isn’t the only CEO to express his dislike for the role — Elon Musk famously compared starting a company to “staring into the abyss and eating glass.”
- Airbnb CEO Brian Chesky said that he experienced “depths of loneliness” as a CEO that were hard to put into words.
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 , Moskovitz said that he didn’t intend to be CEO of Asana when he 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.”