Airbnb CEO: “IT WAS SO DARK WE NEARLY DIED!”. I Was Lonely, Deeply Sad & Wanted To Be Loved! [INSPIRING!] Brian Chesky

If you enjoyed hearing about the highs and lows of creating the world’s biggest brands, I recommend you listen to my conversation with Spotify founder, Daniel Ek, here: https://www.youtube.com/watch?v=w_35cUaU_NA
Is being an artist the secret behind running a Fortune 500 company?
In this new episode Steven sits down again with the co-founder and CEO of Airbnb, Brian Chesky.
Brian created ‘Airbed and Breakfast’ in 2007 with his college friend Joe Gebbia as a scheme to pay their rent. Cut to 2020, when Airbnb became a public company, with its initial public offering reaching $100 billion, one of the highest in history. Brian has been named by Forbes as one of America's Richest Entrepreneurs Under 40, and one of Time’s 100 Most Influential People.
In this conversation Brian and Steven discuss topics, such as:

His difficult childhood

Always feeling like an outsider and different

How his art teacher changed his life

The way industrial design shaped his career as a CEO

Always wanting to design his own world

Wanting to escape his childhood

His work addiction

Working as a way of finding love

How success is isolating

What no one told him about success

The need to fight to be connected with people

Why success won't fix you

How Obama changed his life

The life changing impact of one text message

His biggest regret

The impact of Walt Disney upon him

How creativity changes the world

Airbnb initially just being a way to pay the rent

How creativity beats data

Why more companies need creativity and heart

Why company culture is everything

The importance of leaders as examples

How your worst moments define you

Airbnb’s fight for survival

What he learned about true happiness

The world’s loneliness pandemic


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The Diary of a CEO with Steven Bartlett is a podcast hosted by Steven Bartlett, the CEO of the social media management company, Social Chain. The podcast features Bartlett's reflections on his experiences as a CEO, as well as interviews with other business leaders and entrepreneurs. The show provides insights into the challenges and opportunities of running a successful business, as well as the personal journeys of its guests. The Diary of a CEO is known for its honest and candid discussions on the realities of being a CEO, and is aimed at helping listeners understand the inner workings of successful businesses.

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I was a broke, university dropout, at 18 I built an industry leading social media marketing company, and at 27 I resigned as CEO. At 28 I co-founded Flight Story – a marketing and communications company, and thirdweb - a software platform, making it easy to build web3 applications. I then launched private equity fund, Flight Fund, to accelerate the next generation of European unicorns. During this time I decided to launch 'The Diary Of A CEO' podcast with the simple mission of providing an unfiltered journey into the remarkable stories and untold dimensions of the world’s most influential people, experts and thinkers.

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• No. of episodes: 701
• Latest episode: 2025-07-14
• Business Society & Culture

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