This can be earned in about 20-30 seconds in the game. Just start a game, on local mode, living board or classic board, it doesn't matter, classic rules, 1 controller for all, press
to select your token, press
again to select the other token, for the guest (you
) and after this, press
to start the game. Throw the dice and after your turn, throw the dice for the guest and after you've bought the first property for the guest, press
and
. This way, the guest player will go bankrupt and you'll win the game earning you this achievement