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

The One Thing Every Entrepreneur Can Learn From Brian Chesky

By
Anthony Soohoo
Anthony Soohoo
Down Arrow Button Icon
By
Anthony Soohoo
Anthony Soohoo
Down Arrow Button Icon
November 5, 2015, 4:15 PM ET
Courtesy of Dot &Bo.

The Leadership Insider network is an online community where the most thoughtful and influential people in business contribute answers to timely questions about careers and leadership. Today’s answer to the question “What’s the most important lesson you’ve learned in your career?” is by Anthony Soohoo, cofounder and CEO, Dot & Bo.

From a very young age, many of us are conditioned to believe that failure is something to fear. While the end goal of any endeavor is without a doubt success, society tends to highlight incredible business stories while sweeping aside any hardships the entrepreneur may have faced along the way. If there’s one thing I’ve learned during my time in the tech and media industry at Apple (AAPL), Yahoo (YHOO), CBS Interactive (CBS) and co-founder and CEO of Dot & Bo, it’s that embracing and acknowledging failure is just as critical as success.

Growing up, I watched my parents work tirelessly, facing numerous hardships while raising a family. Their resilience and confidence taught me to look for the light in any seemingly dark situation. Finding the positive within your own failure affords you a moment of clarity — a chance to reflect, improve, and make things better. In the now widely circulated “7 Rejections” Medium post, Airbnb co-founder and CEO Brian Chesky brought to light how his team was turned down by prominent investors on their quest to raise capital. While this is just a snapshot of the numerous rejections they likely encountered, I’ll bet that Chesky was initially devastated to fail, but he might also say that it was a profoundly deeper learning experience than if Airbnb was simply handed funding right off the bat.

See also: Why It Pays To Be Nice at Work

When I got together with my co-founders in 2013, we spent a good portion of our time testing out several concepts before launching Dot & Bo. Initially, each idea and mock up we developed for the company was completely and utterly wrong. During the first five months of building the company, we essentially failed every single day. From our merchandise mix to our marketing messages to hiring people that just weren’t a fit, the experience was one big “aha” moment that something wasn’t working. However, embracing those struggles redefined our vision of moving beyond a company that sold furniture, to creating a brand that would inspire and enable people to create their dream living spaces. Here are two of the most important lessons I learned:

If you’re going to experience failure, try to make sure it’s big flop versus a minor mishap
If we had only failed on a small scale, we might have believed it to be a fluke and steered the company down the wrong path. While some of the initial concepts we had explored were completely wrong, over time we became smarter about our products. Failing fast and hard enables you to quickly navigate the ever-evolving entity that is your business.

Never stop trying to fail
If failure is the prerequisite of success, businesses can no longer afford not to encourage risk taking. At Dot & Bo, we believe in launching projects quickly and iterating rapidly on those that show signs of success, while acknowledging initiatives that fall flat. Continuous feedback is helpful in assisting your team to grow both professionally and personally.Whether you’re building an ecommerce company or a niche brick-and-mortar store, every mistake you make is an opportunity to grow and reflect on how to improve. After all, the best success stories typically have a healthy dash of hardship in them, right?

Read all responses to the Leadership Insider question: “What’s the most important lesson you’ve learned in your career?”

The key to a successful career change: start a blog by Peter Thomson, marketing director of SeedInvest.

The secret to dealing with difficult coworkers by Clark Valberg, CEO of InVision.

The best way to plan for a successful career? Forget the plan by Stephen Cannon, CEO of Mercedes-Benz USA.

About the Author
By Anthony Soohoo
See full bioRight Arrow Button Icon

Latest in Commentary

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 Commentary

Hong Kong is the hub for China’s AI IPOs. It can be so much more than that
CommentaryHong Kong
Hong Kong is the hub for China’s AI IPOs. It can be so much more than that
By Brian Wong and Tony ChanMay 3, 2026
5 hours ago
jason corso
Commentarydisruption
AI models are choking on junk data
By Jason CorsoMay 3, 2026
13 hours ago
blake
CommentaryHousing
I spent a decade selling homes to the ultra-wealthy. What I saw explains the housing market’s nepo problem
By Blake O'ShaughnessyMay 3, 2026
15 hours ago
Can the ‘blue economy’ deliver on its promise? Investors are starting see the ocean as an asset worth protecting
CommentaryConservation
Can the ‘blue economy’ deliver on its promise? Investors are starting see the ocean as an asset worth protecting
By Natalie Sum Yue ChungMay 2, 2026
1 day ago
old
Commentaryaffordability
The American household just took an 81% margin cut. Wall Street hasn’t priced it in
By Katica RoyMay 2, 2026
2 days ago
dario
CommentaryAnthropic
Anthropic’s most powerful AI model just exposed a crisis in corporate governance. Here’s the framework every CEO needs.
By Jeffrey Sonnenfeld, Stephen Henriques, Dan Kent and Holden LeeMay 2, 2026
2 days ago

Most Popular

Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
Personal Finance
Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
By Fatima Hussein and The Associated PressMay 1, 2026
3 days ago
America got rich and got sad. A top economist says 2020 broke something that hasn't healed
Economy
America got rich and got sad. A top economist says 2020 broke something that hasn't healed
By Nick LichtenbergMay 3, 2026
15 hours ago
Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
Economy
Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
By Jacqueline MunisMay 2, 2026
1 day ago
China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
North America
China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
By Jake AngeloApril 30, 2026
3 days ago
I spent a decade selling homes to the ultra-wealthy. What I saw explains the housing market's nepo problem
Commentary
I spent a decade selling homes to the ultra-wealthy. What I saw explains the housing market's nepo problem
By Blake O'ShaughnessyMay 3, 2026
15 hours ago
Sam Altman says the quiet part out loud, confirming some companies are ‘AI washing’ by blaming unrelated layoffs on the technology
AI
Sam Altman says the quiet part out loud, confirming some companies are ‘AI washing’ by blaming unrelated layoffs on the technology
By Sasha RogelbergMay 3, 2026
14 hours 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.