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The ‘grindset’ routine of 3 am wake upcold immersion, and strict adherence to the corporate playbook has become normalized as the path to success. but Airbnb CEO Brian Chesky doesn’t apologize for doing things differently.
“Don’t apologize for how you run your company,” Chesky said the Wall Street Journal last year. For the $74 billion short-term rental employer, that’s like staying up late and cutting back on traditional but grueling duties.
“(Emailing) was the thing about my job that I hated the most before the pandemic,” Chesky said. Although most of the corporate world is back to how it was in 2019—with five days at the office, team bonding events, and watercoolers gossip—Emailing is something that has never gotten back to the CEO.
Chesky no longer bothers with pesky emails; they were a great annoyance, and he seldom touched them. However, Chesky talks while he is 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 early morning hours, Chesky pushes early meetings back to 10 a.m.—and no earlier.
“If you’re the CEO,” Chesky says, “you get to decide when the first meeting of the day is.”
Chesky didn’t answer right away luckThis is a request for comment.
Airbnb CEO’s 5-to-9 after his 9-to-5
The 44-year-old Airbnb co-founder also doesn’t believe that the early bird can catch the worm—he gets his energy at night, after his exercise routine that ends around 9:30 p.m.
“If I had a girlfriend, maybe it would change,” Chesky explained. “But I’m not, so I’m going to enjoy it.”
A 2:30 a.m. bedtime meant no dawn meetings the next day—10 a.m. was the earliest he would go. And Chesky is not the only high-powered leader not the only one working late hours to strive for success. luck Interview dozens of CEOs who rejected the 5 am club, and made their sleep pattern work with a long career.
For one, musician and entrepreneur Will.i.am runs his tech venture between 9 a.m. and 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 architects who pull visions of reality,” Will.i.am told luck last year. “Those words do not compute the thought of the materializers.”
Some CEOs shape their role to fit their lifestyle
This type of executive behavior is surprising to some technology leaders, but others find inspiration in the way he operates.
“(Chesky) always told me that being a CEO of a public company doesn’t have to be miserable,” Whitney Wolfe Herd, founder and CEO of Bumble, SPOKE WSJ last year. “And I thought he was crazy.”
Chesky’s philosophy stuck with him, and when he returned to Bumble, he felt ready to take on the task: “He really taught me how to be a CEO again.”
And there are more and more leaders who write their own rules and go against the grindset grain.
Nvidia CEO Jensen Huang runs a $4.5 trillion chip company, but despises the idea of corporate hierarchy. That’s him completely dismissed one-on-one meetings, and only gather for larger conversations with other leaders. Huang wants everyone to be on the same page and work together for the best business outcome. It’s a breather from the rigid structure of most corporations.
“In that way, our company is designed for agility. For information to flow as quickly as possible. SAYS in 2024.
Whole Foods CEO Jason Buechel also balances his hectic schedule of non-stop meetings and travel by using up all his paid vacation time. While most executives often feel the need to be at the helm, he drives home the importance of rest and relaxation. If a person doesn’t rest on their days when they’re tired, Beuchel believes it can harm mental health.
“I put the PTO first,” Buechel SPOKE luck in 2024. “That’s why I use all my allocation every year.”
A version of this story was published on Fortune.com on May 15, 2025.
