Core Insights - Airbnb's IPO in December 2020 was one of the most successful in history, with shares opening at $144.71, a 113% increase from the initial offering price of $68, leading to a valuation of approximately $103 billion [1][2] - The company's market capitalization at debut surpassed the combined market caps of the three largest U.S. hotel chains: Marriott ($43 billion), Hilton ($39 billion), and Hyatt ($8 billion) [2] - Despite the financial success, CEO Brian Chesky described the moment as one of the saddest periods of his life, feeling isolated and disconnected from others [2][4] Company Background - Airbnb was founded in 2008 by Brian Chesky, Joe Gebbia, and Nathan Blecharczyk, who initially shared a close familial bond [5] - Chesky's intense focus on work led to feelings of guilt when spending time with friends and family, contributing to his sense of isolation [5][6] Impact of the Pandemic - The COVID-19 pandemic severely impacted Airbnb, causing an 80% drop in sales within eight weeks, yet the company made a remarkable recovery with its IPO [7] - Chesky experienced peak loneliness during this period, emphasizing the disconnect that can accompany success [7] Mentorship and Personal Growth - Chesky developed a mentorship relationship with former President Barack Obama, who provided advice on maintaining personal connections [8][9] - Following the IPO, Chesky reflected on his friendships and recognized the importance of reconnecting with old friends, which he found transformative [10][11]