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

Airbnb’s CEO spent 6 months living in his company’s rentals—and found the core problem with his business

Trey Williams
By
Trey Williams
Trey Williams
Down Arrow Button Icon
Trey Williams
By
Trey Williams
Trey Williams
Down Arrow Button Icon
May 4, 2023, 9:50 AM ET
Airbnb CEO Brian Chesky.
Airbnb CEO Brian Chesky.Courtesy of Airbnb

Brian Chesky found himself in the same boat as millions of Americans during the pandemic: working from home, joining daily Zoom calls, and suddenly struck by the realization that he could do his work from anywhere.

Recommended Video

Joining the digital nomad movement—which picked up steam as travel and lockdown restrictions loosened—didn’t just allow the Airbnb CEO to work from somewhere other than his San Francisco home office; it sparked an idea that helped him fall back in love with the core business and understand the customer experience, he says. And he hopes it will help re-engage Airbnb’s users.

“Last year, I started living in Airbnbs, and I stayed in like a dozen and a half over the course of six months. It became this one-year journey of becoming the ultimate guest, only living in Airbnbs from one house to the other,” Chesky told Fortune in a recent video call, his dog Sophie roaming behind him. “And when I started staying in homes, I started noticing variability.”

Some hosts asked him to sign rental agreements, imposed “giant” cleaning fees, and even gave him a list of chores to perform before checking out. He questioned the need for these requests. “I’d ask them, ‘Why are you doing all of this?'” Chesky says. They didn’t always know he ran the company.

“The worst 10% of guest and host experiences were making it worse for everyone,” he continues. “And the whole point of our platform is to take those things off the table.”

Chesky’s endeavor to understand the experiences of hosts and guests mimics a pattern seen among other prominent CEOs. Often, executives in the corner office drift further from their employees and the core part of their business as they scale and diversify product and service offerings. 

Two Harvard Business School professors authored a study on how CEOs spend their time and found that, on average, just 6% of their time is spent with frontline teams and 3% with customers. They spend 72% of their time in meetings.

“CEOs face a real risk of operating in a bubble and never seeing the actual world their workers face,” the authors write. “Spending time with the rank and file and with savvy external frontline constituencies is an indispensable way to gain reliable information on what is really going on in the company and in the industry.”

Chesky himself admits to being distracted pre-pandemic with all the shiny new things Airbnb had in the pipeline.

However, the idea of a frontline CEO is not unique to Airbnb, especially as companies reevaluate their post-pandemic business model amid cultural and inflationary pressures. Laxman Narasimhan, who took over as CEO of Starbucks in March, said in a letter to employees that he planned to take barista shifts once a month. And Uber CEO Dara Khosrowshahi got behind the wheel and moonlighted as a driver during the pandemic, which led him to “reevaluate every single assumption that we’ve made,” he told the Wall Street Journal.

Airbnb is launching more than 50 new features and improvements this week, resulting from Chesky’s experiences as a guest and host and months of digging into customer complaints via social media, its support line, and conversations with platform users.

Among the improvements Chesky is most excited about is Airbnb Rooms, “an all-new take on the original Airbnb,” the corporate tagline reads. Airbnb has more or less become the go-to place for entire vacation rentals. But Chesky and his team now want to encourage room rentals as a low-cost option to house rentals. The cost of Airbnb rentals has increased, and social media is littered with user complaints about the prices. Cue the Airbnb room, which costs an average of $67 a night, Chesky says, compared to the $153 average daily rate across all Airbnbs on the platform. One hurdle the company must overcome is convincing guests to cohabitate with a stranger in their home. In response, Airbnb is adding hosts’ mini-profiles to listings as well as security information, inclulding whether a room has a lock and a 24/7 safety line.

Courtesy of Airbnb

Chesky and his team hope the new offering will make Airbnb more appealing than a hotel. In addition, the company plans to roll out a total pricing feature after guests and hosts complained that fees didn’t show up until booking, and it will unveil tools to help hosts keep their pricing competitive.

“To make a change, you have to touch the product, the policies, the service across all these different touch points,” Chesky says. “A lot of this came from my firsthand experience and just looking at the product and booking with fresh eyes. It’s building a product for the person you were when you started the company.”

This round of new features is the most expansive Airbnb has done, Chesky said during a recent press event in New York City, and he expects some 300 million guests to use the platform this year. But Chesky acknowledges there’s more to fix.

He says he hopes people see the changes, see that he’s listening, and keep flagging updates they’d like to see.

“You always want to work on something new, but when you have a service like ours, and so many people use it, it’s easy to forget what they actually want. You have to have their permission to do new things,” Chesky says. “A good lesson is: Fall back in love with your core business. Get into the nitty-gritty. I spent the last couple of years just doing the thankless job, improving things, being a glorified customer support agent.”

“I finally feel like I found how I want to run the company.”

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
Trey Williams
By Trey Williams
Twitter icon
See full bioRight Arrow Button Icon

Latest in Leadership

Nicholas Thompson
C-SuiteBook Excerpt
I took over one of the most prestigious media firms while training for an ultramarathon. Here’s what I learned becoming CEO of The Atlantic
By Nicholas ThompsonDecember 13, 2025
20 hours ago
Lauren Antonoff
SuccessCareers
Once a college dropout, this CEO went back to school at 52—but she still says the Gen Zers who will succeed are those who ‘forge their own path’
By Preston ForeDecember 13, 2025
22 hours ago
Asiathe future of work
The CEO of one of Asia’s largest co-working space providers says his business has more in common with hotels
By Angelica AngDecember 12, 2025
1 day ago
Donald Trump
HealthHealth Insurance
‘Tragedy in the making’: Top healthcare exec on why insurance will spike to subsidize a tax cut to millionaires and billionaires
By Nick LichtenbergDecember 12, 2025
2 days ago
three men in suits, one gesturing
AIBrainstorm AI
The fastest athletes in the world can botch a baton pass if trust isn’t there—and the same is true of AI, Blackbaud exec says
By Amanda GerutDecember 12, 2025
2 days ago
Brainstorm AI panel
AIBrainstorm AI
Creative workers won’t be replaced by AI—but their roles will change to become ‘directors’ managing AI agents, executives say
By Beatrice NolanDecember 12, 2025
2 days ago

Most Popular

placeholder alt text
Success
Apple cofounder Ronald Wayne sold his 10% stake for $800 in 1976—today it’d be worth up to $400 billion
By Preston ForeDecember 12, 2025
2 days ago
placeholder alt text
Economy
Tariffs are taxes and they were used to finance the federal government until the 1913 income tax. A top economist breaks it down
By Kent JonesDecember 12, 2025
2 days ago
placeholder alt text
Success
40% of Stanford undergrads receive disability accommodations—but it’s become a college-wide phenomenon as Gen Z try to succeed in the current climate
By Preston ForeDecember 12, 2025
2 days ago
placeholder alt text
Economy
The Fed just ‘Trump-proofed’ itself with a unanimous move to preempt a potential leadership shake-up
By Jason MaDecember 12, 2025
1 day ago
placeholder alt text
Success
Apple CEO Tim Cook out-earns the average American’s salary in just 7 hours—to put that into context, he could buy a new $439,000 home in just 2 days
By Emma BurleighDecember 12, 2025
2 days ago
placeholder alt text
Economy
For the first time since Trump’s tariff rollout, import tax revenue has fallen, threatening his lofty plans to slash the $38 trillion national debt
By Sasha RogelbergDecember 12, 2025
2 days ago
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • 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
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 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.