Bringing someone "onchain" is such a bad framing. It's as bad as the early days of the web where we tried to bring people "online". The reality with the web is the thing that worked was friends just trying to chat or email or share a website with their friends. It wasn't about being online, it was about the end result.

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I think people had to be comfortable with the online thing before the next step was possible

Yeah because I had to use a modem and connect through an ISP. Similar to how someone now knows they are “onchain” because they have to use a wallet and deal with all that

What does being comfortable mean? I was around then. I didn't know how any of it worked I just knew I could connect and go look at my friends site or chat with them.