Many a company was stuck with a datacenter unit that was unresponsive to the company's needs, and people migrated to AWS to avoid dealing with them. This straight out happened in front of my eyes multiple times. At the same time, you also end up in AWS, or even within AWS, using tools that are extremely expensive, because the cost-benefit analysis for the individuals making the decision, who often don't know very much other than what they use right now, are just wrong for the company. The executive on top is often either not much of a technologist or 20 years out of date, so they have no way to discern the quality of their staff. Technical disagreements? They might only know who they like to hang out with, but that's where it ends.
So for path dependent reasons, companies end up making a lot of decisions that in retrospect seem very poor. In startups if often just kills the company. Just don't assume the error is always in one direction.