Adam Neumann and the Art of Failing Up

Adam Neumann stood on the 57th floor of the Woolworth Building, the neo-Gothic skyscraper that was once the tallest in the world. It was late on a Friday night in 2013, and the WeWork founder and chief executive had just made a move to add the top 30 floors to his rapidly expanding real estate dealings.

Mr. Neumann and three employees had already enjoyed a few drinks when he decided to bring them to tour his latest coup. In the gutted-out space, they tossed beer bottles into empty elevator shafts, listening to them clink on the way down. Then, Mr. Neumann told them all to follow him out to the ledge. No guardrails. No enclosures. Just four inebriated start-up executives teetering on the edge of death.