I think the best known example for this is Hollywood Accounting, which is how a $19m movie with $150m worldwide can 'lose money'.

https://www.techdirt.com/articles/20121018/01054720744/holly...

I've also seen this happen in real estate. You can make a ton of profit, but if your on-paper amortizations outweigh your in-real-life profit then you on-paper lose money even though in the real world you're richer than you were before.