Career
Chesky moved to Los Angeles following graduation from RISD to work for 3DID as an industrial designer.[18] He designed toys, guitars, medical equipment, and other items at 3DID. Chesky became disillusioned with the job and long commutes, particularly after being part of a team that worked on the Pureflush toilet seat for the television show American Inventor. He reduced his hours at 3DID in 2007 to work on furniture designs.[19]
In October 2007, he moved to San Francisco to live with RISD classmate Joe Gebbia.[6] Chesky did not have enough money to pay his rent, and they opened their house to short-term renters as a bed and breakfast, providing air mattresses for guests to sleep on and Pop-Tarts for breakfast during the Industrial Designers Society of America conference, when hotel rooms were scarce. The business became Airbnb.[20][6]
Gebbia and Chesky asked Nathan Blecharczyk to work on a new website for the company, then known as Airbed & Breakfast. The site launched before 2008's South by Southwest (SXSW) in Austin, Texas, and generated two bookings, one of which was Chesky. He met Michael Seibel at SXSW, who would later connect him with Y Combinator and led to significant investment for Airbnb. The company re-launched again before the 2008 Democratic National Convention in Denver, Colorado. It was featured in TechCrunch, driving so much traffic to the company website that it crashed.[21] Chesky and his partners targeted microblogs to advertise the service, which led to a trickle-up to larger Denver-area publications including the Denver Post, then national publications including The New York Times. The strategy led to 800 room listings and 80 guest bookings.
Chesky and Gebbia had US$20,000 in debt each after the Democratic National Convention. They developed and designed election-themed cereal boxes to generate funds. They purchased 1,000 boxes of commercial cereals and repackaged them as "Obama O's" and "Cap'n McCains". Sales of the rebranded cereal generated between US$20,000–US$30,000 and allowed the two to pay most of their debts.[22][23]
In early 2009, Chesky, Gebbia, and Blecharczyk enrolled in a Y Combinator startup course. The course provided US$20,000 in seed money and training from Paul Graham, among others, in exchange for a six-percent stake in the company. Sequoia Capital partner Greg McAdoo invested US$585,000 in what was now known as Airbnb at the end of the course. The company continued to operate out of Chesky's and Gebbia's apartment, with Chesky eventually moving out to live in locations for rent on the platform. He assumed the title of chief executive officer of Airbnb in fall 2010. In 2011, Chesky and the cofounders decided against purchasing Wimdu, a rival firm heavily funded by Rocket Internet. Instead, Airbnb purchased Accoleo, a German imitator, and began a rapid expansion in Europe.
Chesky wrote blog posts about Airbnb's efforts to rectify issues after a host's house was vandalized in 2011. He was criticized for his handling of the situation after his comments were publicly contradicted by the victim. This led to Chesky writing a public message acknowledging his failure, the expansion of the Airbnb customer service team, and the creation of a fund for hosts should similar situations arise in the future. According to journalist Leigh Gallagher, Chesky considered the moment a "rebirth" for Airbnb.
During the coronavirus pandemic, Airbnb underwent significant restructuring, eliminating several departmental divisions and laying off approximately 1,900 employees.[24] The company offered severance packages that included extended health care benefits and published a directory of affected employees.[25] Chesky also took a more direct role in daily operations, involving senior leadership in broader company projects.[24]
In December 2020, Airbnb became a public company via an initial public offering. Fortune ranked Chesky No. 43 on its "100 Most Powerful People in Business" in 2024.[26]
