The We That Didn’t Work at WeWork

Adam Neumann and Masayoshi Son were negotiating a possible $20 billion check when Mr. Son pulled up an image of Yoda on his iPad.

It was summer 2018 and Mr. Son’s tech conglomerate, SoftBank Group Corp., had already pumped over $4 billion into WeWork, the shared office space startup Mr. Neumann co-founded eight years earlier. Now Mr. Neumann was trying to get Mr. Son to buy a majority stake in WeWork. It would have been the largest acquisition ever of a startup, part of a bid to turbocharge a three-pronged strategy to dominate global real estate.