The above is a graph I modified from a Rogers technology adoption curve
Good point about the tools but of course this topic also includes vision and 'selling'. I think that by 2000 many folks had enough vision to understand how the internet was impacting content delivery. This covers the first two groups above, the geeks and the visionaries.
And typically, there is a 'selling' period where the geeks and the visionaries have to convince and get 'buy-in' by others in an organization. In the early 2000s common sense and the 'handwriting on the wall' was that the internet was certainly a paradigm shift in how we all access and used information in our lives. In other words the pragmatists joined the geeks and the visionaries and by 2008 most forward facing organizations were well underway with transitioning into the internet age. That was over a decade ago and as we approach 95%+ internet adoption now in 2020 I think it is appropriate to use the phase 'behind the curve' for our hobby.
I fully understand not being on a 'bleeding edge' with tech, it is risky and costly. But I would also think that many companies and organization would like to think of themselves as leaders and not followers. Hopefully our hobby will lead by visionaries and not by laggards.