The problem is that the free market only really works when all information is available to all parties and there's low switching cost. So it works decently for commodities, but no business ever wants to sell a commodity. In fact most business advice I've seen is about how to get away from selling commodified products into a free market and instead sell opaquely differentiated products to a locked-in market with high switching costs and barriers to entry.

Peter Thiel: "Competition is for losers."

Yes. This is why you should immediately start interviewing when you observe this kind of behavior coming from management.

Eventually, yes. Unless they sell to another company and the technical debt goes into the trash with the company's product.

On the other hand, "the market can remain irrational longer than you can remain solvent."

Perhaps, but there is nothing free market about financial services.