Why Did Fast Success Make Airbnb Sloppy?

Brian Chesky says fast success made Airbnb sloppy because the company forgot how hard the first product was to create. The team iterated 30 versions of the website before Airbnb worked, then expected everything else to work. Teams got funding, and employees were expected to invent the next great thing. Many good employees could not have started Airbnb, so asking them to start the next Airbnb was too much. Money, resources, and pressure to expand fed hubris, overconfidence, and indulgence. With no money, founders stay disciplined, say no, live inside constraints, and stay principled. The first time they ride a rocket ship, judgment can go down. They start thinking they can do everything, thinking gets sloppy, and they throw money at ideas to see what sticks.

Companies with fast success expand too quickly into other things. The new efforts do not stick, and the quality stays low. The same pattern hit Airbnb, the adolescence of a company. Growing pains followed. The company outgrew the founders, and chaos followed. People got a new manager every few months. Airbnb did everything and nothing well. The company got diluted, then wayward, as bureaucracy set in and the work calcified. As dysfunction grew, stepping away felt like the answer, on the belief that the founder must be the problem. The best leadership is presence, not absence, and leaving made the problems worse.

The castle became a prison: a beautiful company, the founder locked at the top, with no clear way out. The repair took five or six years.