He doesn't win or lose anything. He's just trying to break even on his mattress promotions. If he wins the bet then all those winnings go to paying refunds on the mattresses. If he loses then he keeps the huge surge of mattress sales he had for the promotion. He makes money by selling you other furniture while in the store not covered by the mattress promotion. At minimum he has the $100+ delivery fee that is not part of the promotion.
Plus the obscene amount of free advertising he gets from national and local media. Without knowing his cost structure, it seems to be a pretty brilliant business model.
