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Brian Chesky

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Late Apple cofounder Steve Jobs
Success
Former Apple exec had lunch with his boss Steve Jobs for 15 years—he says the late founder’s ‘insatiable curiosity’ taught him to never coast on his expertise
By Emma BurleighFebruary 25, 2026
Airbnb CEO Brian Chesky
Success
Airbnb CEO says AI is ‘the best thing that ever happened to’ his company—he warns other founders: ‘If you don’t disrupt yourself, someone else will’
By Emma BurleighFebruary 17, 2026
Demis Hassabis, chief executive officer of Google DeepMind
Success
The CEO of Google DeepMind juggles another job as the founder of a multibillion-dollar startup by starting a second workday at 10 p.m.
By Emma BurleighFebruary 12, 2026
Sam Darnold #14 of the Seattle Seahawks
Success
Super Bowl champion Sam Darnold says his plumber dad played with him every day after work, no matter how tough his day was—and that taught him resilience
By Emma BurleighFebruary 9, 2026
Airbnb CEO Brian Chesky
Success
Airbnb’s Brian Chesky says CEOs don’t have to be ‘miserable’—that’s why he got rid of emails and banned meetings before 10 a.m.
By Emma BurleighFebruary 7, 2026
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
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Success
Billionaire TikTok founder is now the richest person in all of Asia, with a $105 billion net worth—he's gained $92 billion since 2019 thanks to AIplaceholder alt text
By Emma BurleighSeptember 17, 2026
Personal Finance
Current price of oil as of September 17, 2026placeholder alt text
By Joseph HostetlerSeptember 17, 2026
Arts & Entertainment
Ed Sheeran asked Patriots owner Robert Kraft for $2 million aid donation after Macklemore was dropped from his tour for pro-Palestine commentsplaceholder alt text
By Marco Quiroz-GutierrezSeptember 18, 2026
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