• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises

2

Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that

3

Nearly 50,000 Lake Tahoe residents have to find a new power source after their energy source looks to redirect lines to data centers

1

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises

2

Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that

3

Nearly 50,000 Lake Tahoe residents have to find a new power source after their energy source looks to redirect lines to data centers
LeadershipCommentary

Airbnb CEO: This is the biggest risk I’ve ever taken

By
Brian Chesky
Brian Chesky
Down Arrow Button Icon
By
Brian Chesky
Brian Chesky
Down Arrow Button Icon
October 28, 2014, 12:47 PM ET
Airbnb CEO Brian Chesky Interview

Today Fortune launched the Fortune 40 Under 40 Insider Network, one of several online communities where the biggest names in business answer timely career and leadership questions. This week, we ask: What’s the biggest risk you’ve ever taken? Our first answer comes from Airbnb CEO Brian Chesky.

When I graduated from the Rhode Island School of Design, I got a job at a small industrial design firm in LA. I loved it at first – I had a job that paid well, and some of my designs even ended up on store shelves.

But I felt unfulfilled designing products that would eventually end up in landfills, and wanted to build something that would last. I worked with a few entrepreneurs in LA, and it struck me that even though I was the designer, they were the ones that were creating something meaningful. I asked myself, ‘what’s the difference between them and me? Why can’t I do the same thing?’ That’s when I realized — they had taken a risk, and I hadn’t.

Then one day, I got a call from my college friend, Joe Gebbia. He had been telling me that I should move to San Francisco ever since we graduated, but this call triggered something for me, and I finally decided to take the risk. Everyone has one or two moments in their life when they make a decision and it changes their life forever. Almost every decision in my life I’ve now made is a chain reaction from the moment I decided to move to San Francisco.

So I packed all of my possessions into the back of my old Honda Civic, and set off for to a city where it turned out I couldn’t even afford my first month’s rent. It was a risky decision, but finding a way to pay the rent is what ultimately led us to blow up a few air mattresses and rent out our living room to three strangers who needed a place to stay for the weekend. We called it the AirBed and Breakfast, an idea that eventually became Airbnb.

In our society, we’re conditioned to avoid taking risks at all the wrong times. Right after college, we’re told to do the safe thing, check all the right boxes, and keep our heads down. It’s assumed that once we find our footing or get a stable job, then we can try to swing for the fences.

But that’s not how life works, and it’s the wrong way to think about risk. Inevitably, things change as you get older. You might start a family. You might run into unexpected obstacles along the way. And with each day that passes, taking risks will feel scarier, and seem harder, than ever before.

So my advice is, don’t wait. There will always be plenty of reasons to play it safe. But more often than not, the most exciting times in your life will be the times when you take a risk – when you follow that gnawing feeling in your gut instead of the safe, cautious path suggested by others.

For me, it’s made all the difference.

Brian Chesky is CEO of Airbnb.

About the Author
By Brian Chesky
See full bioRight Arrow Button Icon

Latest in Leadership

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

texas
North AmericaHousing
The new American Dream doesn’t live in a big city. It lives in Celina, Texas
By Nick LichtenbergMay 15, 2026
4 hours ago
Harrison Ford wearing a bow tie
SuccessWealth
Before ‘Star Wars’ made him a multimillionaire, Harrison Ford struggled to make ends meet—so he spent 15 years working a trades side-gig
By Preston ForeMay 15, 2026
5 hours ago
Under Armour CEO Kevin Plank says micromanagement is ‘underestimated.’ Steve Jobs and Elon Musk would agree
C-Suitesuccess
Under Armour CEO Kevin Plank says micromanagement is ‘underestimated.’ Steve Jobs and Elon Musk would agree
By Sydney LakeMay 15, 2026
6 hours ago
jensen
Travel & LeisureChina
‘It’s so good’: Jensen Huang enjoys Beijing delicacies on trip with Trump
By The Associated PressMay 15, 2026
7 hours ago
lori
Commentarymental health
I run Valvoline Instant Oil Change and work with young people every day. They’re in crisis—and we all have to try to help
By Lori FleesMay 15, 2026
9 hours ago
michael
CommentaryEducation
AI is wiping out entry-level jobs. Here’s how colleges can fill the gap
By Michael HansenMay 15, 2026
10 hours ago

Most Popular

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
3 days ago
Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that
Success
Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that
By Preston ForeMay 13, 2026
2 days ago
Nearly 50,000 Lake Tahoe residents have to find a new power source after their energy source looks to redirect lines to data centers
Travel & Leisure
Nearly 50,000 Lake Tahoe residents have to find a new power source after their energy source looks to redirect lines to data centers
By Catherina GioinoMay 12, 2026
3 days ago
Current price of oil as of May 14, 2026
Personal Finance
Current price of oil as of May 14, 2026
By Joseph HostetlerMay 14, 2026
1 day ago
The airplane fuel shortage is a myth propagated by airlines who want to cancel unprofitable flights, says private jet CEO
Energy
The airplane fuel shortage is a myth propagated by airlines who want to cancel unprofitable flights, says private jet CEO
By Jim EdwardsMay 14, 2026
2 days ago
Steve Jobs used a 'beer test' for interviews at Apple—if he didn’t want to drink with you, you didn’t get the job
Success
Steve Jobs used a 'beer test' for interviews at Apple—if he didn’t want to drink with you, you didn’t get the job
By Orianna Rosa RoyleMay 14, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.