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Brian Chesky

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Despite Airbnb CEO Brian Chesky and Steve Jobs praising micromanagers, a new survey ranks them among the most annoying coworkers
Success
Despite Airbnb CEO Brian Chesky and Steve Jobs praising micromanagers, a new survey ranks them among the most annoying coworkers
By Orianna Rosa RoyleFebruary 1, 2026
Airbnb CEO says Steve Jobs taught him that obsessing over details isn’t about control—it’s about helping people think bigger and move faster. But Gen Z doesn’t agree
Success
Airbnb CEO says Steve Jobs taught him that obsessing over details isn’t about control—it’s about helping people think bigger and move faster. But Gen Z doesn’t agree
By Orianna Rosa RoyleJanuary 23, 2026
Photo of Brian Chesky
Success
Airbnb CEO Brian Chesky says he went to ‘night school’ for an hour every day with Barack Obama and even turned in homework
By Preston ForeDecember 15, 2025
Brian Chesky says Airbnb’s successful IPO was ‘one of the saddest periods’ of his life—then Barack Obama gave him one piece of advice
Success
Brian Chesky says Airbnb’s successful IPO was ‘one of the saddest periods’ of his life—then Barack Obama gave him one piece of advice
By Orianna Rosa RoyleNovember 10, 2025
After selling his business for $532 million, this millennial says a life of leisure was surprisingly ‘boring’, so he’s choosing to go back to work
Arts & Entertainment
After selling his business for $532 million, this millennial says a life of leisure was surprisingly ‘boring’, so he’s choosing to go back to work
By Orianna Rosa RoyleNovember 9, 2025
Airbnb CEO Brian Chesky
Success
Airbnb CEO Brian Chesky says employers need to hire Gen Z even if ‘AI can do the interns’ work’—or one day, the bots will outnumber bosses
By Emma BurleighOctober 30, 2025
Left: Apple CEO Tim Cook. Right: Ex-PepsiCo CEO Indra Nooyi.
Success
The CEOs of Apple, Airbnb, and PepsiCo agree on one thing: life as a business leader is incredibly lonely
By Emma BurleighOctober 29, 2025
Airbnb cofounder and CEO Brian Chesky
Success
Airbnb CEO Brian Chesky challenges founders with a critical question if they aspire to emulate his success
By Emma BurleighOctober 22, 2025
Chesky
AI
Chesky says OpenAI tools not ready for ChatGPT tie-up with Airbnb app
By Natalie Lung and BloombergOctober 21, 2025
Brian Chesky
Success
Airbnb CEO Brian Chesky says he’s still in founder mode—he personally handpicks staff, treats them as direct reports, and decides who stays
By Jessica Coacci and Orianna Rosa RoyleAugust 26, 2025
Airbnb’s CEO studied Steve Jobs’s playbook to slash bureaucracy and build his $84 billion empire. Inside Brian Chesky’s 5-step hiring strategy to cut red tape
Leadership
Airbnb’s CEO studied Steve Jobs’s playbook to slash bureaucracy and build his $84 billion empire. Inside Brian Chesky’s 5-step hiring strategy to cut red tape
By Meredith HoJuly 18, 2025
Brian Chesky speaks into a microphone
Success
Airbnb CEO Brian Chesky says his dad did him ‘a service’ by never complimenting him—it’s a lesson he’s kept while building the $82 billion giant
By Preston ForeJune 4, 2025
Airbnb’s new app for ‘services’ is getting shot down by critics — here’s why CEO Brian Chesky should be thrilled
Tech
Airbnb’s new app for ‘services’ is getting shot down by critics — here’s why CEO Brian Chesky should be thrilled
By Allie GarfinkleMay 14, 2025
Will.i.am nods his hat standing behind a yellow SXSW background.
Success
Black Eyed Peas frontman Will.i.am reveals his biggest investment mistake: turning down Airbnb founder Brian Chesky and losing out on millions
By Preston ForeMarch 13, 2025
The founder of activist short-seller Hindenburg Research, Nate Anderson.
Success
Founders keep saying they learned the same life lesson after extraordinary career success: ‘I had isolated myself’
By Emma BurleighJanuary 17, 2025
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