I worked on something back then that had to interface with payment networks. All the payment networks had software for Windows to accomplish this that you could run under NT, while under Linux you had to implement your own connector -- which usually involved interacting with hideous old COBOL systems and/or XML and other abominations. In many cases you had to use dialup lines to talk to the banks. Again, software was available for Windows NT but not Linux.
Our solution was to run stuff to talk to banks on NT systems and everything else on Linux. Yes, those NT machines had banks of modems.
In the late 90s using NT for something to talk to banks is not necessarily a terrible idea seen through the lens of the time. Linux was also far less mature back then, and we did not have today's embarrassment of riches when it comes to Linux management and clustering and orchestration software.
If you're a tech leader and confuse Linux boxes for mainframes then I don't think it's hindsight that makes you look foolish. It's that you do not, in fact, understand what you're talking about or how to talk about it - which is your job as a tech leader.
Yeah Elon has gotten annoying (my god has he been insufferable lately) but his companies have done genuine good for the human race. It's really hard for me to think of any of the other recently made billionaires who have gotten rich off of something other than addicting devices, time-wasting social media and financial schemes.