The biggest issues you mentioned are related to the content, which can be solved in 2 ways, curated (in progress via DVMs) and purple pilling.

Purple pilling is opportunistic, if nostr was around during covid it would be bigger. Do you think it's easier to drag creators here from a place like Twitter, or is it easier to get folks from rumble, minds etc?

Do you think we need to get content creators the ability to x post so it fits into their existing workflows and then as they see value allow them to create pay walled content, or do we need/want pay walled content?

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not an expert - (expressed views n points) -

whichever way possible it fine - "make-it-easy-but--somewhat-secure" will helpful long run - lot of #press feeds pours into nostr via bridges of general web content now + bot alerts / tips rss

I personally think cross posting functionality is needed. Get someone from Twitter signed up, they don't have to use nostr, but just post the content. They log in 3 months later and see all their sats