The ‘grindset’ routine of 3 a.m. wake-ups, cold plunges, and strict adherence to the corporate playbook has become normalized as the path to success. But Airbnb CEO Brian Chesky has been unapologetically doing things differently.
“Don’t apologize for how you want to run your company,” Chesky told The Wall Street Journal last year. For the $74 billion short-term rental boss, that looks like staying up late and cutting down on traditional but tedious duties.
“[Emailing] was the thing about my job that I hated the most before the pandemic,” Chesky said. Although much of the corporate world has returned to what it was like in 2019—with five days in office, team bonding activities, and watercooler gossip—emailing is one thing that hasn’t made a comeback with the CEO.
Chesky no longer bothers with pesky emails; they were a huge annoyance, and he rarely touches them anymore. Instead, Chesky communicates while he’s on the clock and prefers to call and text, the WSJ reported. And that’s not the only office tradition he’s done away with. For Chesky, 9 a.m. meetings are a thing of the past.
As someone who hits productivity strides in the wee hours of the morning, Chesky pushes early meetings back to 10 a.m.—and no earlier.
“When you’re CEO,” Chesky said, “you can decide when the first meeting of the day is.”
Chesky didn’t immediately respond to Fortune‘s request for comment.
The Airbnb CEO’s 5-to-9 after his 9-to-5
The 44-year-old Airbnb co-founder also doesn’t believe the early bird catches the worm—he gets his energy in the nighttime, after his workout routine that wraps up around 9:30 p.m. He hits his peak productivity at 10 p.m., lasting until he falls asleep around 2:30 a.m.
“If I had a girlfriend, that would probably change,” Chesky explained. “But I don’t, so I’ll enjoy this.”
A 2:30 a.m. bedtime means no meetings at the crack of dawn the next day—10 a.m. is the earliest he’ll go. And Chesky isn’t the only high-power leader isn’t the only one who works late hours in striving for success. Fortune has interviewed dozens of CEOs who are rejecting the 5 a.m. club, and making their sleep pattern work with a high-flying career.
For one, musician and entrepreneur Will.i.am runs his tech venture between 9 a.m. to 5 p.m., but then jumps back into the grind to work on his creative business until 9 p.m.
“Work-life balance is not for the architects that are pulling visions into reality,” Will.i.am told Fortune last year. “Those words don’t compute to the mindset of the materializers.”
Other CEOs shaping their role to fit their lifestyle
This type of executive behavior would shock other tech leaders, but some are finding inspiration in the way he moves.
“[Chesky] always said to me that being a public-company CEO doesn’t have to be miserable,” Whitney Wolfe Herd, founder and CEO of Bumble, told WSJ last year. “And I thought he was crazy.”
Chesky’s philosophy stuck with her, and in her return to Bumble, she felt ready to take on the task: “He really taught me how to be a CEO again.”
And there’s a growing number of leaders writing their own rules and going against the grindset grain.
Nvidia CEO Jensen Huang is running a $4.5 trillion chip company, but despises the idea of corporate hierarchy. That’s why he’s totally scrapped one-on-one meetings, and only gathers for large conversations with the rest of leadership. Huang wants everyone to be on the same page and collaborate for the best business outcomes. It’s a breather from the rigid structure of most corporations.
“In that way, our company was designed for agility. For information to flow as quickly as possible. For people to be empowered by what they are able to do, not what they know,” the tech entrepreneur said in 2024.
Whole Foods CEO Jason Buechel also balances his intense schedule of incessant meetings and travel by using all of his paid time off. While most executives always feel the need to be at the helm, he drives home the importance of rest and relaxation. If someone doesn’t take their hard-earned days off, Beuchel believes that can be destructive to mental health.
“I highly prioritize PTO,” Buechel told Fortune in 2024. “So I do use all of my allocation each year.”
A version of this story was published on Fortune.com on May 15, 2025.
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