When Airbnb CEO Brian Chesky spoke with Dax Shepard on the “Armchair Expert” podcast, he shattered a common misconception about success. Despite reaching what many would consider the pinnacle of career achievement—an Initial Public Offering (IPO) that saw Airbnb’s valuation skyrocket from $47 billion to $86.5 billion in less than 24 hours—Chesky admitted to feeling unhappy, isolated, and disappointed. For a man who had started a company intending to bring people together, the isolation he felt seemed particularly ironic.

The Journey to IPO and Emotional Toll

Brian Chesky, along with co-founders Joe Gebbia and Nathan Blecharczyk, launched Airbnb in 2008, aiming to disrupt the traditional hospitality industry. Despite the company’s meteoric rise in the following decade, Chesky still struggled with a sense of loneliness. As his co-founders’ lives changed and their families expanded, the companionship they once shared waned, leaving Chesky yearning for more personal connections.

Even as he reached the professional goal of an IPO in December 2020, Chesky found that the achievement did not fill the emotional void he had hoped it would. The moment marked “one of the saddest periods” of his life, indicating that personal fulfilment cannot solely be achieved through professional success.

The Science of Happiness: Social Fitness

Data from an ongoing Harvard University study, initiated in 1938, seems to corroborate Chesky’s personal experiences. The study reveals that career and financial achievements are not reliable predictors of contentment or overall well-being. Instead, “social fitness”—the quality and frequency of one’s relationships—stands out as a significant factor. As Marc Schulz, one of the researchers, put it, “It’s our relationships that keep us happy.”

Reinvesting in Relationships: A Shift in Strategy

Faced with this personal revelation, Chesky took steps to reinvest in his own social fitness. A prominent example is his decision to list his own San Francisco home on Airbnb, allowing guests to stay in his spare room during select weekends. This not only added a personal touch to Airbnb’s customer experience but also filled a gap in Chesky’s own life, affording him the social interactions he felt were missing.

The Launch of Airbnb Rooms and Beyond

Six months after Chesky started hosting guests in his own home, Airbnb launched a new service, Airbnb Rooms, which allows hosts to rent individual rooms in their residences. Whether directly influenced by Chesky’s own experiences or not, the feature aligns well with his newfound focus on the value of relationships. Since the announcement in early May, Airbnb’s stock has risen from $118.86 to $144.14 per share, indicating that focusing on human connection can also make good business sense.

The Unfinished Climb

In his conversation with Dax Shepard, Chesky cautioned others not to view success as an ultimate solution to personal issues. “Some of the most difficult periods in people’s lives aren’t when they fail, but when they get to the top of that mountain and realize they don’t feel any differently,” he said. It serves as a pertinent reminder that the measure of success goes beyond monetary gain or professional milestones; it’s about the relationships we cultivate along the way.