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    Home»Startups»These billionaire founders hate becoming CEOs
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    These billionaire founders hate becoming CEOs

    PineapplesUpdateBy PineapplesUpdateOctober 22, 2025No Comments5 Mins Read
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    These billionaire founders hate becoming CEOs
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    key takeaways

    • Facebook co-founder and former Asana CEO Dustin Moskowitz admitted earlier this week that being a CEO was “exhausting.”
    • Moskowitz isn’t the only CEO to express his dislike of this role – Elon Musk famously compared starting a company to “staring into the abyss and eating glass.”
    • Brian Chesky, CEO of Airbnb, said that as a CEO he experienced a “depth of loneliness” that was difficult to put into words.

    Earlier this week, Facebook co-founder and former Asana CEO Dustin Moskowitz admitted that being a CEO was “exhausting” and not a good fit for his personality — and he’s far from the only CEO to talk about the pitfalls of the role.

    In an interview published on Monday with stratcherryMoskowitz said when he did not intend to become CEO of Asana co-founding Workplace Productivity Forum in 2008.

    “Personality-wise, I don’t like managing teams, and that was not my intention when we started Asana,” Moskowitz explained. “One thing led to another, and I became CEO.”

    RELATED: Instead of cuts, this $28 billion design company’s response to AI is to hire more people

    Moskowitz joins Asana as CEO in October 2010 And retired From the role in July. He told Stratechery that, in his 15 years of working as a CEO, he had to put up a “face” every day that was different from his true introverted nature.

    These billionaire founders hate becoming CEOs
    Dustin Moskowitz, co-founder of Facebook and former co-founder and CEO of Asana. Photo by Ryan Anson/Bloomberg via Getty Images

    Moskowitz, for what it’s worth $12 billion He’s not the only CEO to express his dislike of the role, according to the Bloomberg Billionaires Index. Elon Musk, founder and CEO of at least three companies, including Tesla, SpaceX and XAI, has compared starting a company to “staring into the abyss and eating glassIn an interview in April 2013.

    In the interview, Musk explained that CEOs constantly face the possibility of failure (“the abyss”) when dealing with the most painful and difficult problems (“the glass”). Musk is the richest person in the world, what is his net worth $458 billionAnd much of their fortune is tied to ownership of the companies they lead, including 15.73% stake in tesla and a 42% stake At SpaceX.

    RELATED: Elon Musk reveals his strategy for building successful companies, including sleeping under desk and ‘working every waking hour’

    Stability AI co-founder and former CEO Imad Mostaq resigned as CEO in March 2024 to move on. Decentralized AI InitiativeWhen Mostak was asked about his departure that month, he explained new York Times That “being a CEO sucks.”

    “Elon was right,” Mostack, whose net worth is $1.1 billionIt was said at that time. “It’s like looking into the abyss and chewing glass.”

    In January 2024, Brian Chesky, co-founder and CEO of Airbnb, shared his thoughts about the emotional challenges of leadership on xWriting that although he did not feel alone as a founder while working with his two co-founders, as a CEO he experienced a “depth of loneliness” that is “hard to put into words.”

    Cheski is worth $10.2 billionAccording to the Bloomberg Billionaires Index.

    RELATED: Airbnb CEO says he personally manages 40 to 50 employees as direct reports: ‘A lot of work’

    A June 2022 survey A survey conducted by Deloitte found that nearly 70% of C-suite executives in the US, UK, Canada and Australia wanted to leave their jobs. The survey, which surveyed 1,050 C-suite leaders, revealed that two in five executives described themselves as constantly overwhelmed, while 36% said they were exhausted.

    The CEO has recently resigned reached all-time highAccording to data from executive recruiting firm Challenger, Gray & Christmas, a record 1,358 chief executives The number of CEOs who stepped down in the first half of this year is a 9% increase compared to the 1,250 CEOs who stepped down during the same period last year and the highest ever on record.

    “CEO turnover is set to continue to rise in 2025, reflecting the enormous pressures leaders face,” said Andy Challenger, workplace and labor expert at Challenger, Gray & Christmas. said in a statement,

    key takeaways

    • Facebook co-founder and former Asana CEO Dustin Moskowitz admitted earlier this week that being a CEO was “exhausting.”
    • Moskowitz isn’t the only CEO to express his dislike of this role – Elon Musk famously compared starting a company to “staring into the abyss and eating glass.”
    • Brian Chesky, CEO of Airbnb, said that as a CEO he experienced a “depth of loneliness” that was difficult to put into words.

    Earlier this week, Facebook co-founder and former Asana CEO Dustin Moskowitz admitted that being a CEO was “exhausting” and not a good fit for his personality — and he’s far from the only CEO to talk about the pitfalls of the role.

    In an interview published on Monday with stratcherryMoskowitz said when he did not intend to become CEO of Asana co-founding Workplace Productivity Forum in 2008.

    The remainder of this article is locked.

    Connect with Entrepreneur, For access today.

    Billionaire CEOs Founders hate
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