In an era where the “grindset” ethos—marked by punishingly early wake-ups, ice baths, and unwavering adherence to corporate norms—has become a widely accepted blueprint for success, Airbnb CEO Brian Chesky is charting a distinctly different course.
He’s not just tweaking the playbook; he’s rewriting significant portions of it, advocating for a leadership style that prioritizes personal well-being alongside corporate achievement.
“Don’t apologize for how you want to run your company,” Chesky recently advised in an interview with the Wall Street Journal.
For the head of the $84.8 billion short-term rental giant, this philosophy translates into embracing late-night productivity and decisively cutting down on traditionally accepted, yet often tedious, executive duties.
The email exile and the end of early starts
One of the most significant departures from the corporate script for Chesky has been his relationship with email.
“Emailing was the thing about my job that I hated the most before the pandemic,” he confessed.
While much of the business world has seen a resurgence of pre-2019 office life—complete with five-day workweeks, team-building events, and casual office chatter—email has not made a similar comeback in Chesky’s routine.
He now rarely touches them, deeming them a significant annoyance.
Instead, the Airbnb chief prefers more direct and immediate forms of communication while on the clock, favoring calls and texts, as reported by the WSJ.
This isn’t the only entrenched office tradition Chesky has jettisoned. The dreaded 9 a.m. meeting is also a relic of the past for him.
As a self-professed night owl who finds his peak productivity in the later hours, Chesky has instituted a 10 a.m. start time for meetings, and not a minute sooner.
“When you’re CEO,” Chesky quipped, “you can decide when the first meeting of the day is.”
Night owl productivity: Chesky’s ‘5-to-9 after his 9-to-5’
The 43-year-old co-founder of Airbnb doesn’t subscribe to the “early bird gets the worm” adage.
His energy surges in the evening, particularly after his workout routine, which typically concludes around 9:30 p.m.
From 10 p.m. onwards, he hits his stride, often working until he falls asleep around 2:30 a.m.
In picture: Airbnb CEO Brian Chesky (Source: LinkedIn)
“If I had a girlfriend, that would probably change,” Chesky candidly remarked. “But I don’t, so I’ll enjoy this.”
This late-to-bed, late-to-rise schedule naturally dictates a later start to his formal workday.
Chesky is not alone in this preference; a growing cohort of high-achieving leaders are rejecting the 5 a.m. club and tailoring their sleep patterns to complement their demanding careers.
Musician and entrepreneur Will.i.am, for instance, manages his tech venture during standard business hours but then re-engages with his creative pursuits, working until 9 p.m.
“Work-life balance is not for the architects that are pulling visions into reality,” Will.i.am told Fortune.
Those words don’t compute to the mindset of the materializers.
Chesky’s unconventional approach, while potentially surprising to some in the tech world, is inspiring others.
Whitney Wolfe Herd, founder and former CEO of Bumble, shared with the Wall Street Journal, “Chesky always said to me that being a public-company CEO doesn’t have to be miserable, and I thought he was crazy.”
However, Chesky’s philosophy resonated, and upon her return to Bumble this year, Wolfe Herd felt better equipped for the role.
“He really taught me how to be a CEO again,” she stated.
This movement towards personalized leadership styles is gaining traction. Nvidia CEO Jensen Huang, who helms a $2.8 trillion chip company, eschews traditional corporate hierarchy.
He has famously eliminated one-on-one meetings, opting instead for larger group discussions with his leadership team to foster open collaboration and rapid information flow.
“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,” Huang explained last year.
Similarly, Whole Foods CEO Jason Buechel actively counters the always-on executive culture by fully utilizing his paid time off.
He champions the importance of rest and relaxation, asserting that neglecting earned vacation can be detrimental to mental health.
“I highly prioritize PTO,” Buechel recently told Fortune. “So I do use all of my allocation each year.”
These examples underscore a growing trend among top executives: a conscious effort to redefine success, not by a rigid set of rules, but by what genuinely works for them and their organizations.
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