Before Airbnb grew into a platform with more than 9 million listings worldwide, its entire inventory consisted of three inflatable air beds inside CEO Brian Chesky's San Francisco apartment. Chesky had quit his job, packed his belongings into a Honda Civic for a cross-country move, and found himself unable to pay rent. When he noticed that local hotels were fully booked because of the Industrial Designers Society of America's International Design Conference in San Francisco, a business was born.

"We called it the air-bed-and-breakfast," Chesky told Fortune in 2017 at a World's Greatest Leaders event.

Chesky and Airbnb cofounder Joe Gebbia were drawn to the idea of earning money and meeting new people through their makeshift accommodations, and they opened their home to three guests. "What if you could book someone's home the way you could book a hotel anywhere in the world?" Chesky said of the inspiration. The pair launched Airbnb in 2008 together with Gebbia's former roommate Nathan Blecharczyk.

The path there was an unlikely one for Chesky, whose parents were social workers in upstate New York—he was born in Albany—and who urged him to pursue a high-paying career. To their chagrin, he enrolled instead at the Rhode Island School of Design.

"I'm going to become an artist," Chesky recalls telling his mother, to which she responded: "You somehow managed to pick the only job in the world that pays less than a social worker. You'll get paid nothing."

Today, Chesky has less to worry about. Airbnb, which went public in December 2020, carries a market capitalization of $112 billion, above its level from before the pandemic—which at one point threatened the company's very survival. Airbnb lost 80% of its business in the first months of the pandemic, and Chesky reorganized the company in a scramble to stay alive.

Creativity as a double-edged sword

Chesky's creativity is what created—and later saved—Airbnb, but it also meant business veterans did not initially take him seriously. His design background proved a hindrance for the budding startup: while seeking $150,000 to fund an estimated 10% of the company, Chesky met with more than 20 potential investors, and every one of them turned him down.

"Joe and I were designers, and as far as they were concerned, designers didn't start companies," Chesky said. "We didn't look like a tech founder, which is ridiculous because I don't think you should ever hire somebody because they look like something else. You want a new thing."

Investor interest finally materialized after Airbnb began designing presidential-candidate-themed cereal boxes, which caught the attention of Paul Graham, founder of Y Combinator, a Silicon Valley startup accelerator known for backing early-stage founders.

"Creative companies are companies that tap into a sense of imagination," Chesky told Time. "That they might come up with new breakthrough ideas, that people that were only beholden to near-term measurable outcomes won't ever have."

Regulatory pressure and a new guest policy

Success at Airbnb has been a double-edged sword, with explosive growth forcing the company to refocus at times. During the pandemic, Chesky told Fortune in 2023, he opened his own home as an Airbnb listing to better understand the host experience, and he lived in various Airbnbs across the United States for six months. There he discovered inconsistent and unnecessary practices among hosts, including complicated rent agreements.

The company continues to face headwinds from waves of short-term rental regulation in New York and across Europe, where cities are implementing phase-outs, prohibiting rentals shorter than 30 days, or declining to renew tourist apartment licenses. In the U.S., housing advocates have fought against Airbnb, according to the AP, arguing that short-term rentals have essentially become hotels. Airbnb has pushed back against the regulations, contending that short-term rental bans would limit affordable accommodations for travelers. The measures highlight how short-term rentals have become a policy flashpoint where local housing concerns and traveler demand intersect in major destinations.

Last month, Airbnb introduced a new "reasonable house rules and requests" policy, under which the company stopped asking guests to "complete tasks that require significant effort or time, or would typically be performed by a cleaner," such as stripping the bed, washing and putting away dishes, or taking trash offsite. The policy will go into effect on rentals booked on or after Nov. 20. It has drawn pushback from hosts threatening to boycott the platform or raise cleaning fees, while coming as a pleasant surprise to customers. Because hosts supply the listings behind Airbnb's more than 9 million offerings, how the rollout lands with hosts and guests alike is a detail to watch once bookings made on or after Nov. 20 begin operating under the new rules.

A version of this story was published on Fortune.com on Jan. 24, 2024.