Well I don't know about specific examples, but it's a phenomenon that has been observed in many areas over decades, thus the funny saying.

After crossing 40 years of age, and working for a while now, I believe it's also because of politics. You might think the goal is to deliver the best possible product, but territory grabs within companies are important, and done by people that don't have enough skill other than territory grabs. E.g. look at Trump and his behavior. No skills other than having his way, and then he gets to decide.

Of the technical reason, for sure we underestimate how much faster technology gets. Fred Brooks had this example in his Mythical Man Month book, how the os/360 got the option of a disk drive instead of mag tape, but the result was worse because everyone assumed it was much faster than it really was.