Brian Chesky

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
December 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
November 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
Success

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
November 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
October 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
October 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
October 22, 2025
Chesky
AI

Chesky says OpenAI tools not ready for ChatGPT tie-up with Airbnb app

By Natalie Lung and Bloomberg
October 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 Royle
August 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
July 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
June 4, 2025
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
May 15, 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
May 15, 2025
Filmmaker Ryan Coogler
Success

Multimillionaire ‘Sinners’ director was $200,000 deep in student debt and ‘making no money’ around the filming of ‘Creed’

By
April 28, 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
March 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
January 17, 2025

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