Brian Chesky isn’t your typical tech tycoon, but he definitely stands amongst them.
Born in 1981 in Niskayuna, New York, Chesky was interested in drawing, painting and design growing up. In 1999 he started at the Rhode Island School of Design, and, in 2004, he came away with a Bachelor of Fine Arts in industrial design.
In his time at the design school he met Joe Gebbia, who would go on to be a very important figure in his future.
After a stint in LA working as an industrial designer for $40,000 a year, he found himself living in San Francisco with Gebbia, with the pair struggling to pull together rent each month.
In 2007, the Industrial Designers Society of America held a conference in the city and hotels citywide booked out, leaving conference-goers desperate for rooms. The pair saw an opportunity.
They went out and bought three air mattresses and put them for rent in their apartment as Airbed and Breakfast. Three people took up the offer… and the rest? It’s history.
A few months after their initial trial with the air mattresses, Chesky and Gebbia linked up with Harvard graduate and technical architect Nathan Blecharczyk and together the trio founded Airbnb. Chesky "gravitated naturally to the role of leader” and became the leader and CEO.
To get funding, the trio went an unconventional route.
They created special-edition cereals called “Obama O’s” and “Cap’n McCains,” based on the presidential candidates at the time, and not only did it earn them recognition, it got them a place in Y Combinator.
Over the past decade, Airbnb has become one of Silicon Valley's biggest success stories; it is one of the biggest organizations in the world listed on the Nasdaq-100, with a market cap of $104.51 billion.
Although the pandemic hit Airbnb particularly hard, the company has fought to recover and, in 2020, it went public at a $100 billion valuation and with the share price more than doubling to upwards of $144.
Chesky, who although handing over the day-to-day operations of the company, remains CEO of Airbnb and is the company’s largest individual shareholder. It’s estimated he owns around 15%.
That stake in the $100 billion dollar company has given Chesky a net worth of around $13.5 billion, making him one of the Valley’s richest people. In 2016, he, along with his other two co-founders, signed on to Warren Buffett and Bill and Melinda Gates’ Giving Pledge, pledging to donate more than half of their wealth within their lifetimes.
What companies does he own?
Because Chesky is one of Airbnb’s largest individual shareholders, by proxy he owns parts of all Airbnb’s subsidiary companies. Airbnb has made 24 acquisitions and 18 investments since its founding in 2008. Most of these relate to accommodation and payment services Airbnb used for expansion.
Its 18 investments include:
- OYO: An Indian-based booking platform and global budget hotel chain. According to TechCrunch, Airbnb invested an undisclosed amount between $150 and $200 million.
- Zeus Living: An accommodation platform for business travelers. Airbnb invested in Zeus Living's Series B with several investors totaling $55 million.
- OneTrust: A privacy management software platform to operationalize data privacy compliance and privacy. Airbnb invested in OneTrust's Series C with several investors totaling $300 million.
- Tiqets: A cultural and travel experiences booking platform. Airbnb invested in Tiqets' Series C with several investors totaling $60 million.
- Resy: A New York-based hospitality tech company acquired by American Express. Airbnb invested in Resy's Series A with several investors totaling $13 million.
Its 24 acquisitions include:
In 2017, Airbnb acquired Luxury Retreats, a service that focuses on high-end homes, for around $200 million. A source told TechCrunch that Airbnb was “deeply interested in the company because of their extremely talented team with deep experience in the luxury segment. Their capability in luxury is unrivaled and complimentary to the capabilities at Airbnb.” Homes on the platform include a villa owned by Francis Ford-Coppola in Puglia, Italy; and Richard Branson’s Necker Island.
In 2019, Airbnb acquired HotelTonight, a hotel-booking service focused on last-minute trips, for around $400 million. Together, Airbnb said HotelTonight and Airbnb would offer guests more choices and make it easier for the “world’s best boutique and independent hotels to connect with Airbnb’s global network of guests.” “We want Airbnb to be the place where travelers plan all of their trips, whether they are booking one year or one day in advance,” said Airbnb President of Homes Greg Greeley at the time. “The HotelTonight team has a tremendous passion for helping guests and rich industry expertise. We are more than thrilled to have them on board.”
In 2017, Airbnb acquired London startup Accomable to expand its housing stock opportunities for people with disabilities. The deal included adding Accomable’s more than 1,000 house and apartment listings that can accommodate guests with physical disabilities to the Airbnb website. Airbnb said it hired Accomable’s founders and most of its seven-person staff to build out Airbnb’s wheelchair-accessible housing inventory and provide more complete and accurate information to disabled travelers, who often rely on a hotel emailing pictures of a room to determine whether it is accessible.
In 2016, Airbnb acquired Proprly, a property management service that managed cleaning, guest check-in, and other aspects of the rental process on behalf of hosts. Although it eventually shut down the service, the purchase showed Airbnb could have been looking into building out more in-house services for years. As it stands, Airbnb has opted out of offering cleaning and management services itself, preferring to partner with other providers. However, its acquisition of property management software company Luckey could point to a pivot to expanded services.
Airbnb acquired property management software company Luckey in late-2018. The short-term rentals company was based in Paris and started by Aurélien Malfait, David Barbe, and Félix Malfait. The acquisition hinted that Airbnb could be looking to expand into property management services, and it came at a time the company was battling with local regulators in Paris — one of its most lucrative markets. According to Business Insider, Luckey's team joined Airbnb but remained an independent business unit and has continued operating its service, which was rebranded as "Luckey by Airbnb."
In a move that well-positioned Airbnb to deal with the new post-pandemic work from anywhere trend, the company acquired Urbandoor in 2019. Urbandoor is a global online marketplace where professionals can find furnished and serviced apartments tailored to their needs for extended business trips, relocations, and other longer-term stays. It brings together technologists, entrepreneurs, real estate and hospitality professionals to connect guests with furnished apartment options that meet their needs, Airbnb said during the announcement. Guests looking to book longer trips – often business travelers – choose to stay in serviced apartments because they offer amenities such as gyms, pools and concierge services. “Bringing more of these places to stay to Airbnb will strengthen Airbnb for Work’s engagement with the more than 500,000 companies who use Airbnb for Work to help manage their business travel,” the company said.
Chesky has had a major role in all of the company’s acquisitions, overseeing the future strategic direction and planning for growth. In 2021, he shared his vision with James Manyika, who chairs the McKinsey Global Institute.
“I think this is the first at-bat of the first inning for Airbnb," Chesky said in an interview with Manyika. "The company is 13 years old. You don’t raise your 13-year-old to be a good 14-year-old. You raise your 13-year-old to be a great adult with a long career over many decades. That is how we are thinking about Airbnb.”
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