Losing money, mygo, what does it mean that I really lost money?

[Boys' Love/GBC] [Male Protagonist Harem]
Jin Zhaozhi transmigrated with a money-losing system.
As a time traveler, he was well aware of the money-losing system's tricks. No matter how outrageous his investments were, he would always end up making money in unexpected ways, or failing and being ridiculed by the system.
What if he did the opposite, investing only in popular projects, turning the tide and making money proactively?
"Girl bands should go all in on LiveHose during their prime. Invest in the area surrounding this SPCE LiveHose!"
"Toyokawa Properties announces development of a villa area around the port area? No wonder it's the confidence of an old-generation chaebol. Bands can't make as much money as real estate. I'm going all in on Toyokawa Properties stock!"
"veMjic is a truly ingenious band project, and their lineup is top-notch. A nationwide tour? We'll take out a loan and go all in! We'll book every single Mjic band concert in the Kansai region!"
In the end, Jin Zhaozhi watched as he and the Toyokawa Group accumulated debts, then became rich overnight, then accumulated debts again, and then became rich overnight once more... He and the money-losing system fell into deep thought.
The money-losing system: "No, you're really losing money?"
Jin Zhaozhi: "Never mind that. The key thing now is that I suspect the Toyokawa family also has a money-losing system."