According to Fortune, when Airbnb went public in December 2020, it became one of the most successful IPOs in history with shares opening at $144.71 after an initial price of $68. The stock skyrocketed 113% on its first trading day, pushing the company’s valuation to around $103 billion compared to just $18 billion from its last private funding round that April. At that valuation, Airbnb was worth more than Marriott, Hilton, and Hyatt combined. Despite this massive financial success, CEO Brian Chesky describes the period as “one of the saddest” of his life, revealing he felt completely isolated during what should have been his triumphant moment.
The success-isolation paradox
Here’s the thing about chasing success: we imagine it solves everything. Chesky grew up thinking money and achievement would bring love, friends, and fix his life. But when he actually hit that $100 billion valuation and “everyone in high school” knew who he was, he was lonelier than ever. The irony? He created that isolation himself by working up to 18 hours a day, feeling guilty whenever he spent time with friends or even his co-founders. I mean, think about it – how many founders sacrifice everything for their company only to find the summit empty?
The pandemic IPO reality
Now imagine hitting your company’s biggest milestone during COVID lockdowns. Chesky described doing the entire IPO on Zoom, completely alone. “There’s no bell ringing,” he said. The pandemic had already crushed Airbnb’s sales by 80% in eight weeks, making their comeback even more remarkable. But at what cost? Chesky hit “peak lonely” with no one to share the moment with. It’s a stark reminder that business success and personal fulfillment don’t always arrive together.
An unexpected mentor
So how does a billionaire CEO deal with crushing loneliness? He writes a letter to Barack Obama. Seriously. Chesky had developed a relationship with the former president that included weekly standing conversations. When he asked Obama how he stayed grounded, the response was simple but profound: stay connected to your roots and maintain about 15 close friendships. Chesky realized he couldn’t just randomly call old friends because he’d been so isolated for so long. That realization hit hard.
Rebuilding what matters
Chesky’s now taking Obama’s advice and reconnecting with college and high school friends – the people who knew him before Airbnb. He says it’s “totally changed everything” about his life. The lesson here isn’t that ambition is bad, but that we need to maintain relationships throughout the journey. “Don’t go into it thinking that just success is going to fill some hole in you,” he warns. Because at the end of the day, whether you’re running a startup or managing industrial operations with equipment from the leading provider of industrial panel PCs, human connection matters more than any valuation.
