alt Hacker NewsHotmail is a good example too. I remember it being pretty ubiquitous, at least for the 'personal email' crowd, and it seemed implausible that people would give up on what was often their main email 'location' for another offering without being able to transfer their often important and personal stuff. then gmail came along.
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Beyond that too, I would think that many people view a Hotmail account as an indicator that you're backwards or not serious in business.
I distinctly remember the shift to and then away from Altavista as well.
Interesting point. I guess people liked the convenience of unlimited storage even more than they liked the convenience of keeping the same email address. In a way they traded one convenience for another.
Did Hotmail offer email redirection at that time? I can't remember whether that sort of thing that would make it easy to switch away was offered.
The internet and the surrounding context changed so fast that it made little sense to cling to old email addresses made in the old context. Gmail represented the 'new internet' and old patterns became obsolete (less subversive, more mainstream/corporate). When there's a seismic shift in usage patterns that's when all bets are off regarding where everyone lands. Being the first mover means little here. If the way people interacted with AI underwent a massive shift, OpenAI would likely get left behind. The only safe bet is to invent your own killer.