The point is precisely that being super fixated on Microsoft as a monopoly producing relatively trash-quality products is a static worldview. It is the case that Microsoft monopoly did not in any shape or form preclude a measly search startup and a beleaguered Cupertino company from surpassing it to the slightest (mind you, Windows is still the dominant desktop OS, which compared to what it meant in the 90s is immaterial; people rarely think about writing Windows apps anymore: they write web, iOS and Android apps.) This is the whole point of Thiel's thesis. The contemporary version of this world transition we are witnessing is from search to chatbot.
Meanwhile Microsoft by pushing the "trash" products actually served the industry at large well in other ways: it provided a consistent standard base to widely deploy PCs and applications.
Aside: the "competition is for losers" tagline is not from Thiel himself: apparently the publisher came up with a punchy line, and I think that refers to his broader ideology. What I brought up is a very specific observation in his thesis that high margin monopolies are actually good from the perspective of society in a dynamic world where it does not merely translate rent-seeking long-term.
Apple and Google succeeded not by beating Microsoft at its game, but by playing a different game, which happened due to technological revolutions they capitalized on. Apple has a fair claim to partially engendering some of the revolutions; esp. mobile computing. As you said, Window is still the dominant desktop operating system. Who knows what better operating systems people could have been using all this time?
Aside: the "competition is for losers" tagline is not from Thiel himself: apparently the publisher came up with a punchy line, and I think that refers to his broader ideology. What I brought up is a very specific observation in his thesis that high margin monopolies are actually good from the perspective of society in a dynamic world where it does not merely translate rent-seeking long-term.