Loss leading only works when
- it leads to a situation that allows you to prevent competitors from selling to your customers (gilded age railroad and pipeline industries are great examples). Then you can eventually raise prices and not lose back any market share.
- or when it allows you to remarket to customers and make back the difference (selling a single console at a loss to sell a whole library of high margin videos games, or selling jet engines at a loss to lock in 30-year maintenance contracts).