Brian Chesky’s career journey is marked by innovation and perseverance. After graduating from RISD, he moved to San Francisco in 2007 and, alongside his classmate Joe Gebbia, co-founded Airbnb when they turned their apartment into a makeshift bed and breakfast. This creative solution to the lack of hotel rooms during a design conference led to the company’s inception. Known for his hands-on leadership, Chesky’s customer-focused approach and marketing stunts, such as selling “Obama O’s” and “Cap’n McCains” cereals, helped secure early investment and mentorship. In 2020, Airbnb went public, solidifying Chesky’s place in the business world.

Early Life and Background
Brian Chesky was born on August 29, 1981, in Niskayuna, New York, to Deborah and Robert Chesky. His father is of Polish descent, and his mother is of Italian heritage. Growing up, Chesky developed a passion for ice hockey, which was his first hobby, but he later became interested in art, particularly influenced by Leonardo da Vinci. He also developed an interest in landscape architecture and urban planning after observing the redesign of his parents’ backyard. Chesky has a younger sister, Allison, and enjoys hobbies such as sketching and bonsai.

Education
Chesky graduated from Niskayuna High School in 1999 and went on to attend the Rhode Island School of Design (RISD), where he earned a Bachelor of Fine Arts in Industrial Design in 2004. At RISD, he was deeply influenced by the works of Charles and Ray Eames, as well as Walt Disney. He also served as the captain of the RISD hockey team and was a competitive bodybuilder. During his time at RISD, Chesky designed the unofficial mascot, Scrotie.

Career Journey

• Early Career and Move to San Francisco
  • After graduating from RISD, Chesky moved to Los Angeles to pursue a career as an industrial designer.
  • In 2007, he relocated to San Francisco to live with his RISD classmate, Joe Gebbia.
  • Faced with financial struggles and unable to pay rent, Chesky and Gebbia opened their apartment to short-term renters during a design conference, offering air mattresses and Pop-Tarts.
• The Birth of Airbnb
  • This short-term rental idea grew into Airbnb, which Chesky co-founded with Gebbia and Nathan Blecharczyk.
  • The initial offering was an air mattress rental service for conference-goers, which quickly became popular.
  • The concept evolved into the global home-sharing platform Airbnb, with Chesky taking on the role of CEO.
• Leadership at Airbnb
  • Known for a hands-on leadership style, Chesky was deeply involved in the company’s operations and focused on customer-driven innovation.
  • His experiences as both a guest and a host on Airbnb helped shape the platform’s development.
  • Chesky’s leadership was described as “founder mode,” emphasizing direct engagement with all aspects of the business.
• Securing Early Funding
  • To fund the startup, Chesky and his co-founders created a creative marketing campaign, selling special-edition cereals called “Obama O’s” and “Cap’n McCains” during the 2008 U.S. presidential election.
  • This stunt caught the attention of Y Combinator founder Paul Graham, leading to $20,000 in funding and mentorship for the company.
• Airbnb’s Public Debut
  • Under Chesky’s leadership, Airbnb expanded rapidly and achieved global success.
  • In December 2020, Airbnb went public through an initial public offering (IPO), marking a major milestone in Chesky’s career and the company’s growth.

Recognition and Achievements
Chesky’s success has earned him numerous accolades and recognition. In 2015, he was included in Forbes‘ list of America’s Richest Entrepreneurs Under 40 and was featured in Time‘s list of the 100 most influential people. The same year, President Barack Obama appointed him as a Presidential Ambassador for Global Entrepreneurship. In 2017, Fortune named Chesky one of the “World’s Greatest Leaders,” and he received an honorary doctorate from RISD. He was also awarded Bay Area Executive of the Year in 2018 by American City Business Journals. In 2022, Chesky was featured among the 100 Most Powerful People in Global Hospitality by the International Hospitality Institute.

Philanthropy and Giving Back
Chesky has made a significant impact through his philanthropic efforts. In 2016, he joined the Giving Pledge, a group of billionaires committed to donating the majority of their wealth to charitable causes. In 2020, Chesky donated $10 million to nonprofit organizations supporting frontline workers during the coronavirus pandemic. In 2022, he was ranked No. 20 on The Chronicle of Philanthropy’s list of the 50 most prolific philanthropists in the U.S. Additionally, Chesky pledged $100 million over five years to the Obama Foundation to launch the Voyager Scholarship, a program designed to support students pursuing careers in public service. This scholarship provides financial aid, mentorship, and opportunities for real-world experiences.

Chesky’s journey from industrial designer to a leading figure in global hospitality highlights his visionary leadership, commitment to innovation, and dedication to giving back to the community.