Brian Chesky on the Trap of Being a People-Pleasing CEO

On the How I Built This podcast, Chesky argued that the skills required to launch a company are distinct from those needed to lead one. While he spent his youth building and designing—a lifelong apprenticeship for a founder—the actual role of CEO proved counterintuitive. He specifically warned that conventional management advice, such as hiring experts and stepping back, can be a death sentence for a young firm.

Instead, Chesky advocates for a hands-on approach with workers who are smart and hungry, rather than those who are simply experienced but disconnected from the company’s vision. Early in his career, his desire to be liked and his tendency to defer to older, more seasoned employees often led to strategic missteps. He noted that managing expenses and profitability are relatively simple tasks, but fostering a cohesive culture where employees operate correctly in the CEO's absence remains the most demanding challenge of the job.