In December 2020, Airbnb made a remarkable debut on the Nasdaq Stock Market, opening at $144.71 per share. The event marked one of the most successful initial public offerings (IPOs) in history, with shares soaring 113% above the initial price of $68. This significant leap in share value propelled the firm’s valuation to an astounding $103 billion, a stark contrast to its $18 billion valuation after the last private funding round in April that same year.

Airbnb’s entry into the market was so astounding, its debut market capitalization surpassed the combined market caps of Marriott International, Hilton Worldwide, and Hyatt Hotels, the nation’s three largest hotel chains, valued at $43 billion, $39 billion, and $8 billion respectively. Yet, amidst this monumental success, Airbnb’s CEO, Brian Chesky, found himself grappling with unexpected emotions. Far from the joy and satisfaction one might expect, Chesky described this period as "one of the saddest" of his life, a sentiment that offers a sobering look into the often overlooked personal cost of business success.

Airbnb’s IPO Success: A Bittersweet Achievement for CEO Brian Chesky

In December 2020, Airbnb made a remarkable entry into the Nasdaq Stock Market with an opening share price of $144.71, marking one of the most successful Initial Public Offerings (IPOs) in history. The rental platform’s stocks soared on their debut day, rising 113% above the initial public offering price of $68. Consequently, the firm’s valuation jumped to around $103 billion, a significant leap from the $18 billion valuation after the firm’s last private funding round in April of the same year.

To put this into perspective, Airbnb’s debut market capitalization surpassed the combined market caps of the nation’s three largest hotel chains: Marriott International, Hilton Worldwide, and Hyatt Hotels, valued at $43 billion, $39 billion, and $8 billion, respectively. However, amidst this financial success, Airbnb’s CEO, Brian Chesky, described this moment as "one of the saddest periods" of his life.

The Price of Success

Growing up, Chesky had always sought success, believing that it would earn him adoration and solve all his problems. However, when Airbnb hit the $100 billion valuation and everyone knew of his accomplishments, he found himself lonelier than ever. This isolation was largely self-inflicted as he had devoted himself entirely to his work.

Chesky, along with co-founders Joe Gebbia and Nathan Blecharczyk, started Airbnb in 2008. The trio initially shared a familial bond, but as the company grew, Chesky felt a growing sense of guilt and obligation towards the company, often sidelining his personal relationships.

Rising from the Pandemic

Despite the COVID-19 pandemic’s detrimental effect on global tourism causing Airbnb’s sales to plummet by 80% in just eight weeks, the company came back stronger with a successful IPO. However, Chesky confessed that he was at his loneliest during this period, isolated and conducting the entire IPO process over Zoom.

Lessons from a Mentor

During his lonely peak, Chesky turned to former US President Barack Obama, with whom he had developed a close mentor-mentee relationship. Obama’s advice to him was to stay connected to his roots, which were his past relationships. This advice made Chesky reflect on his isolation and the need to reconnect with his friends.

A New Chapter

Chesky admitted that he hadn’t anticipated the loneliness that accompanies success. He now seeks fulfillment by reconnecting with his college and high school friends. While it’s unclear whether he has rekindled his relationships with his Airbnb co-founders, he claims that reconnecting with his childhood friends has significantly improved his life.

In conclusion, Airbnb’s IPO success story serves as a reminder that success isn’t solely defined by financial achievements. It’s equally important to maintain personal relationships and a work-life balance. As Chesky’s experience shows, the pursuit of success can sometimes lead to unexpected places, and being at the top can feel lonely if one doesn’t build and maintain strong personal connections along the journey.