I think you might be being a bit harsh to the 90s era internet companies when you talk about them not seeing the potential of ideas like YouTube, Google, Squarespace, Paypal, etc. I mean, technology was more limited back then, and Youtube wasn’t really too plausible a concept til Adobe Flash came along and made cross browser compatible web video a possibility.
Squarespace may have been a difficult concept to bring about then too, because browser compatibility with HTML and CSS was all over the place. Nowadays, you can make a site work in most browsers and have them look… mostly like they’re supposed to in each one. In the 90s and early 00s, you had to basically code different sites for Internet Explorer and Netscape Navigator.
Technology and art evolves, and what’s possible with each does too. Early TV shows and films were nothing like what we have today, and were often basically glorified special effect demos or the equivalent of a radio show where you can see the presenter. Early games on Atari era systems were nothing like todays games, and in some cases, basically tried to map real world concepts to extremely basic gameplay.
Should makers of VR software go for more interesting stuff than virtual rollercoasters or ‘death simulators’? Sure, but the medium still needs to evolve a bit to get to the point where it can handle some more unique ideas and possibilities. And like every other medium, the early attempts at utilising it will be obvious concepts that don’t really push it to its limits.