Brian Chesky on the three errors that defined his early CEO years

Chesky, speaking on the "How I Built This" podcast, described himself as a "naturally terrible CEO" during the company's formative years. The first major error was an over-reliance on experienced executives hired from larger corporations. By deferring to their resumes rather than his own intuition, Chesky allowed management strategies ill-suited for a scaling startup to take root. He realized too late that leaders who are accustomed to managing established businesses often struggle when tasked with the creative, hands-on building required at an earlier stage.

His second struggle involved a conflict-averse nature that bordered on being a people pleaser. Chesky found it difficult to hold underperforming colleagues accountable, often taking on their tasks himself rather than initiating necessary, uncomfortable performance conversations. This hesitation stemmed from a desire to be liked rather than effectively managed. Finally, he failed to say "no" enough, allowing competing priorities to fragment the company's focus. Without a singular, decisive vision, he found that teams would drift toward divergent goals, leaving him to spend years correcting the strategic misalignment caused by subordinates acting on their own agendas.